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class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Brewery science and beer chemical composition</div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:12-hopfenwiegen.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f5/12-hopfenwiegen.jpg/220px-12-hopfenwiegen.jpg" decoding="async" width="220" height="151" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f5/12-hopfenwiegen.jpg/330px-12-hopfenwiegen.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f5/12-hopfenwiegen.jpg/440px-12-hopfenwiegen.jpg 2x" data-file-width="1280" data-file-height="879" /></a><figcaption>Weighing <a href="/wiki/Hops" title="Hops">hops</a></figcaption></figure> <p>The <a href="/wiki/Chemical_compound" title="Chemical compound">chemical compounds</a> in <a href="/wiki/Beer" title="Beer">beer</a> give it a distinctive taste, smell and appearance. The majority of compounds in beer come from the <a href="/wiki/Metabolic_pathway" title="Metabolic pathway">metabolic</a> activities of plants and <a href="/wiki/Yeast" title="Yeast">yeast</a> and so are covered by the fields of <a href="/wiki/Biochemistry" title="Biochemistry">biochemistry</a> and <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>.<sup id="cite_ref-FOOTNOTEBarth20139,89_1-0" class="reference"><a href="#cite_note-FOOTNOTEBarth20139,89-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> The main exception is that beer contains over 90% water and the mineral ions in the water (hardness) can have a significant effect upon the taste.<sup id="cite_ref-FOOTNOTEBarth201369-88_2-0" class="reference"><a href="#cite_note-FOOTNOTEBarth201369-88-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Four_main_ingredients">Four main ingredients</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Beer_chemistry&action=edit&section=1" title="Edit section: Four main ingredients"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Four main ingredients are used for making beer in the process of <a href="/wiki/Brewing" title="Brewing">brewing</a>: <a href="/wiki/Carbohydrate" title="Carbohydrate">carbohydrates</a> (from <a href="/wiki/Malt" title="Malt">malt</a>), <a href="/wiki/Hops" title="Hops">hops</a>, <a href="/wiki/Yeast" title="Yeast">yeast</a>, and <a href="/wiki/Water" title="Water">water</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Carbohydrates_(from_malt)"><span id="Carbohydrates_.28from_malt.29"></span>Carbohydrates (from malt)</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Beer_chemistry&action=edit&section=2" title="Edit section: Carbohydrates (from malt)"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The carbohydrate source is an essential part of the beer because <a href="/wiki/Yeast" title="Yeast">unicellular yeast organisms</a> convert <a href="/wiki/Carbohydrate" title="Carbohydrate">carbohydrates</a> into energy to live. Yeast <a href="/wiki/Metabolism" title="Metabolism">metabolize</a> the carbohydrate source to form a number of compounds including <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>. The process of <a href="/wiki/Brewing" title="Brewing">brewing</a> beer starts with <a href="/wiki/Malting" title="Malting">malting</a> and <a href="/wiki/Mashing" title="Mashing">mashing</a>, which breaks down the long carbohydrates in the <a href="/wiki/Barley" title="Barley">barley</a> grain into more <a href="/wiki/Monosaccharide" title="Monosaccharide">simple sugars</a>. This is important because yeast can only metabolize very short chains of sugars.<sup id="cite_ref-FOOTNOTEBarth2013144_3-0" class="reference"><a href="#cite_note-FOOTNOTEBarth2013144-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Long-carbohydrates are <a href="/wiki/Polymer" title="Polymer">polymers</a>, large branching linkages of the same molecule over and over. In the case of barley, we mostly see polymers called <a href="/wiki/Amylopectin" title="Amylopectin">amylopectin</a> and <a href="/wiki/Amylose" title="Amylose">amylose</a> which are made of repeating linkages of <a href="/wiki/Glucose" title="Glucose">glucose</a>. On very large time-scales (thermodynamically) these polymers would break down on their own, and there would be no need for the malting process.<sup id="cite_ref-FOOTNOTEJanson1996_4-0" class="reference"><a href="#cite_note-FOOTNOTEJanson1996-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> The process is normally sped up by heating up the barley grain.<sup id="cite_ref-FOOTNOTEBarth2013144_3-1" class="reference"><a href="#cite_note-FOOTNOTEBarth2013144-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> This heating process activates <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> called <a href="/wiki/Amylase" title="Amylase">amylases</a>. The shape of these enzymes, their <a href="/wiki/Active_site" title="Active site">active site</a>, gives them the unique and powerful ability to speed these degradation reactions to over 100,000 times faster. The reaction that takes place at the active site is called a <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a> reaction, which is a cleavage of the linkages between the sugars. Repeated hydrolysis breaks the long amylopectin polymers into simpler sugars that can be digested by the yeast.<sup id="cite_ref-FOOTNOTEJanson1996_4-1" class="reference"><a href="#cite_note-FOOTNOTEJanson1996-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Dextrin_skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/25/Dextrin_skeletal.svg/220px-Dextrin_skeletal.svg.png" decoding="async" width="220" height="275" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/25/Dextrin_skeletal.svg/330px-Dextrin_skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/25/Dextrin_skeletal.svg/440px-Dextrin_skeletal.svg.png 2x" data-file-width="320" data-file-height="400" /></a><figcaption>Amylopectin consists of many glucose molecules linked together either by 1,6 or 1,4 linkages.</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Hops">Hops</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Beer_chemistry&action=edit&section=3" title="Edit section: Hops"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Hops are the flowers of the hops plant <i><a href="/wiki/Humulus_lupulus" title="Humulus lupulus">Humulus lupulus</a></i>. These flowers contain over 440 essential oils, which contribute to the aroma and non-bitter flavors of beer.<sup id="cite_ref-FOOTNOTEJanson1996_4-2" class="reference"><a href="#cite_note-FOOTNOTEJanson1996-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> However, the distinct bitterness especially characteristic of pale ales comes from a family of compounds called alpha-acids (also called <a href="/wiki/Humulone" title="Humulone">humulones</a>) and beta-acids (also called <a href="/wiki/Lupulone" title="Lupulone">lupulones</a>). Generally, brewers believe that α-acids give the beer a pleasant bitterness whereas β-acids are considered less pleasant.<sup id="cite_ref-FOOTNOTEJanson1996_4-3" class="reference"><a href="#cite_note-FOOTNOTEJanson1996-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> α-acids isomerize during the boiling process in the reaction pictured. The six-member ring in the humulone isomerizes to a five-member ring, but it is not commonly discussed how this affects perceived bitterness. </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:S-Humulone_Isomerization.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a6/S-Humulone_Isomerization.svg/220px-S-Humulone_Isomerization.svg.png" decoding="async" width="220" height="57" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a6/S-Humulone_Isomerization.svg/330px-S-Humulone_Isomerization.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a6/S-Humulone_Isomerization.svg/440px-S-Humulone_Isomerization.svg.png 2x" data-file-width="512" data-file-height="132" /></a><figcaption>Humulone is an alpha-acid and one of the major flavor components of hops. Chemistry of beer often concerns the reactions of molecules such as this, and how to better control them for best flavor.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup></figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Yeast">Yeast</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Beer_chemistry&action=edit&section=4" title="Edit section: Yeast"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Ethanol_fermentation_fr.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4e/Ethanol_fermentation_fr.svg/220px-Ethanol_fermentation_fr.svg.png" decoding="async" width="220" height="478" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4e/Ethanol_fermentation_fr.svg/330px-Ethanol_fermentation_fr.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4e/Ethanol_fermentation_fr.svg/440px-Ethanol_fermentation_fr.svg.png 2x" data-file-width="520" data-file-height="1129" /></a><figcaption>Chemical structures showing ethanol fermentation</figcaption></figure> <p>In beer, the metabolic waste products of yeast are a significant factor. In aerobic conditions, the yeast will use in the <a href="/wiki/Glycolysis" title="Glycolysis">glycolysis</a> the simple sugars obtained from the <a href="/wiki/Malting_process" class="mw-redirect" title="Malting process">malting process</a>, and convert <a href="/wiki/Pyruvate" class="mw-redirect" title="Pyruvate">pyruvate</a>, the major organic product of glycolysis, into <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> and water via the <a href="/wiki/Cellular_respiration" title="Cellular respiration">cellular respiration</a>. Many homebrewers use this aspect of yeast metabolism to carbonate their beers. However, under industrial anaerobic conditions yeasts cannot use pyruvate, the end products of glycolysis, to generate energy in cellular respiration. Instead, they rely on a process called <a href="/wiki/Fermentation" title="Fermentation">fermentation</a>. Fermentation converts pyruvate into <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> through the intermediate <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Water">Water</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Beer_chemistry&action=edit&section=5" title="Edit section: Water"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Water can often play, directly or indirectly, a very important role in the way a beer tastes,<sup id="cite_ref-FOOTNOTEBarth201369-88_2-1" class="reference"><a href="#cite_note-FOOTNOTEBarth201369-88-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-FOOTNOTEJanson1996_4-4" class="reference"><a href="#cite_note-FOOTNOTEJanson1996-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> as it is the main ingredient. The <a href="/wiki/Ion" title="Ion">ion</a> species present in water can affect the <a href="/wiki/Metabolic_pathway" title="Metabolic pathway">metabolic pathways</a> of <a href="/wiki/Yeast" title="Yeast">yeast</a>, and thus the metabolites one can taste. For example, calcium and iron ions are essential in small amounts for yeast to survive, because these metal ions are usually required <a href="/wiki/Cofactor_(biochemistry)" title="Cofactor (biochemistry)">cofactors</a> for yeast <a href="/wiki/Enzyme" title="Enzyme">enzymes</a>.<sup id="cite_ref-FOOTNOTEJanson1996_4-5" class="reference"><a href="#cite_note-FOOTNOTEJanson1996-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Beer_carbonation">Beer carbonation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Beer_chemistry&action=edit&section=6" title="Edit section: Beer carbonation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In aerobic conditions, yeast turns sugars into <a href="/wiki/Pyruvate" class="mw-redirect" title="Pyruvate">pyruvate</a> then converts pyruvate into water and <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a>. This process can carbonate beers. In commercial production, the yeast works in anaerobic conditions to convert pyruvate into <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>, and does not carbonate beer. Beer is carbonated with pressurized CO<sub>2</sub>. When beer is poured, carbon dioxide dissolved in the beer escapes and forms tiny bubbles. These bubbles grow and accelerate as they rise by feeding off of nearby smaller bubbles, a phenomenon known as <a href="/wiki/Ostwald_ripening" title="Ostwald ripening">Ostwald ripening</a>. These larger bubbles lead to “coarser” foam on top of poured beer. </p> <div class="mw-heading mw-heading3"><h3 id="Nitro_beer_(CO2_replaced_by_N2_gas)"><span id="Nitro_beer_.28CO2_replaced_by_N2_gas.29"></span>Nitro beer (CO<sub>2</sub> replaced by N<sub>2</sub> gas)</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Beer_chemistry&action=edit&section=7" title="Edit section: Nitro beer (CO2 replaced by N2 gas)"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Beers can be carbonated with <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">CO<sub>2</sub></a> or made sparkling with an <a href="/wiki/Inert_gas" title="Inert gas">inert gas</a> such as <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a> (N<sub>2</sub>), <a href="/wiki/Argon" title="Argon">argon</a> (Ar), or <a href="/wiki/Helium" title="Helium">helium</a> (He). Inert gases are not as <a href="/wiki/Solubility" title="Solubility">soluble</a> in water as carbon dioxide, so they form bubbles that do not grow through <a href="/wiki/Ostwald_ripening" title="Ostwald ripening">Ostwald ripening</a>. This means that the beer has smaller bubbles and a more creamy and stable head.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> These less soluble inert gases give the beer a different and flatter texture. In beer terms, the mouthfeel is smooth, not bubbly like beers with normal carbonation. Nitro beer (for nitrogen beer) could taste less acidic than normal beer.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Aromatic_compounds">Aromatic compounds</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Beer_chemistry&action=edit&section=8" title="Edit section: Aromatic compounds"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Beers contain many aromatic substances. Up to now, chemists using advanced analytical instruments such as <a href="/wiki/Gas_chromatography" title="Gas chromatography">gas</a> and <a href="/wiki/HPLC" class="mw-redirect" title="HPLC">high performance liquid</a> <a href="/wiki/Chromatography" title="Chromatography">chromatographs</a> coupled to <a href="/wiki/Mass_spectrometry" title="Mass spectrometry">mass spectrometers</a>, have discovered over 7,700 different chemical compounds in beers.<sup id="cite_ref-ArsTech_2021_08_18_8-0" class="reference"><a href="#cite_note-ArsTech_2021_08_18-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Foam_stabilizers">Foam stabilizers</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Beer_chemistry&action=edit&section=9" title="Edit section: Foam stabilizers"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The beer foam stability depends amongst other on the presence of <a href="/wiki/Transition_metal" title="Transition metal">transition metal</a> <a href="/wiki/Ions" class="mw-redirect" title="Ions">ions</a> (<span class="chemf nowrap">Fe<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:0.8em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">2+</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sub></span></span></span>, <span class="chemf nowrap">Co<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:0.8em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">2+</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sub></span></span></span>, <span class="chemf nowrap">Ni<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:0.8em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">2+</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sub></span></span></span>, <span class="chemf nowrap">Cu<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:0.8em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">2+</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sub></span></span></span>...), macromolecules such as <a href="/wiki/Polysaccharide" title="Polysaccharide">polysaccharides</a>, <a href="/wiki/Protein" title="Protein">proteins</a>, and <a href="/wiki/Isohumulone" title="Isohumulone">isohumulone</a> compounds from <a href="/wiki/Hops" title="Hops">hops</a> in the beer. Foam stability is an important concern for the first perception of the beer by the consumer and is therefore the object of the greatest care by the brewers and the barmen in charge to serve draft beer, or to properly pour beer into a glass from the bottle (with a good head retention and without overfoaming, or gushing when opening the bottle). </p><p>Many patents for various types of beer foam stabilizers have been filed by breweries and the agro-chemical industry in the last decades. <a href="/wiki/Cobalt" title="Cobalt">Cobalt</a> salts added at low <a href="/wiki/Concentration" title="Concentration">concentration</a> (1 – 2 <a href="/wiki/Parts-per_notation" title="Parts-per notation">ppm</a>) were popular in the sixties, but raised the question of <a href="/wiki/Cobalt_poisoning" title="Cobalt poisoning">cobalt toxicity</a> in case of undetected accidental overdosage during beer production. As an alternative, organic foam stabilizers are produced by <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a> of recovered by-products of beer manufacture, such as spent grains or <a href="/wiki/Hops" title="Hops">hops</a> residues.<sup id="cite_ref-Union_Carbide_1963_9-0" class="reference"><a href="#cite_note-Union_Carbide_1963-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>Amongst the large spectrum of purified, or modified, natural <a href="/wiki/Food_additive" title="Food additive">food additives</a> available on the market, soluble <a href="/wiki/Carboxymethyl_cellulose" title="Carboxymethyl cellulose">carboxymethyl hydroxyethyl cellulose</a>,<sup id="cite_ref-Patent_CMHEC_10-0" class="reference"><a href="#cite_note-Patent_CMHEC-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Propylene_glycol_alginate" title="Propylene glycol alginate">propylene glycol alginate</a> (PGA, <a href="/wiki/Food_additive" title="Food additive">food additive</a> with <a href="/wiki/E_number" title="E number">E number</a> E405),<sup id="cite_ref-Jackson_1980_11-0" class="reference"><a href="#cite_note-Jackson_1980-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Pectin" title="Pectin">pectins</a> and <a href="/wiki/Gellan_gum" title="Gellan gum">gellan gum</a> have also been investigated as foam stabilizer. </p> <div class="mw-heading mw-heading3"><h3 id="Cobalt_salts">Cobalt salts</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Beer_chemistry&action=edit&section=10" title="Edit section: Cobalt salts"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In 1957, two brewing chemists, Thorne and Helm, discovered that the <span class="chemf nowrap">Co<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:0.8em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">2+</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sub></span></span></span> cation was able to stabilize beer foam and to avoid beer overfoaming and gushing.<sup id="cite_ref-Thorne_Helm_1957_12-0" class="reference"><a href="#cite_note-Thorne_Helm_1957-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> The addition of a tiny amount of <a href="/wiki/Cobalt" title="Cobalt">cobalt</a> ions in the range 1 – 2 mg/L (<a href="/wiki/Parts-per_notation" title="Parts-per notation">ppm</a>) was effective. Higher concentrations would be toxic and lower ones ineffective. </p><p>Cobalt is a <a href="/wiki/Transition_metal" title="Transition metal">transition metal</a> whose <a href="/wiki/Atomic_orbital" title="Atomic orbital">atomic orbitals</a> are able to interact with <a href="/wiki/Ligand" title="Ligand">ligands</a>, or <a href="/wiki/Functional_group" title="Functional group">functional groups</a> (–OH, –COOH, –NH<sub>2</sub>), attached to organic molecules naturally present in the beer, making <a href="/wiki/Macromolecule" title="Macromolecule">macromolecular</a> <a href="/wiki/Coordination_complex" title="Coordination complex">coordination complexes</a> stabilizing the beer foam. Cobalt could behave as an inter- or intra-molecular bridge between different <a href="/wiki/Polysaccharide" title="Polysaccharide">polysaccharide</a> molecules (changing their shape or size), or cause some <a href="/wiki/Conformational_change" title="Conformational change">conformational changes</a><sup id="cite_ref-Urban_2013_13-0" class="reference"><a href="#cite_note-Urban_2013-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> of different types of molecules present in solution, affecting their absolute configuration and thus the foam molecular structure and its behavior. </p><p>Thorne and Helm (1957) also formulated the hypothesis that cobalt, by being <a href="/wiki/Coordination_complex" title="Coordination complex">complexed</a> with certain nitrogenous constituents of the beer (e.g., <a href="/wiki/Amino_acid" title="Amino acid">amino acids</a> from <a href="/wiki/Malt" title="Malt">malt</a> <a href="/wiki/Protein" title="Protein">proteins</a>), might produce <a href="/wiki/Surfactant" title="Surfactant">surface-active substances</a> inactivating the <a href="/wiki/Nucleation_in_microcellular_foaming" title="Nucleation in microcellular foaming">gaseous nuclei</a> responsible for <a href="/wiki/Foam" title="Foam">overfoaming</a> and gushing.<sup id="cite_ref-Thorne_Helm_1957_12-1" class="reference"><a href="#cite_note-Thorne_Helm_1957-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p><p>Gushing is a specific problem also studied into more details by Rudin and Hudson (1958).<sup id="cite_ref-Rudin_Hudson_1958_14-0" class="reference"><a href="#cite_note-Rudin_Hudson_1958-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> These authors discovered that gushing is also promoted by other <a href="/wiki/Transition_metal" title="Transition metal">transition metal</a> <a href="/wiki/Ion" title="Ion">ions</a> such as these of <a href="/wiki/Nickel" title="Nickel">nickel</a> and <a href="/wiki/Iron" title="Iron">iron</a>, but not by <a href="/wiki/Cobalt" title="Cobalt">cobalt</a> ions. <a href="/wiki/Isohumulone" title="Isohumulone">Isohumulone</a> (an <a href="/wiki/Iso-alpha_acid" class="mw-redirect" title="Iso-alpha acid">iso-alpha acid</a> responsible for the <a href="/wiki/Taste" title="Taste">bitter taste</a> of <a href="/wiki/Hops" title="Hops">hops</a>) and its combinations with Ni, or Fe, also favor gushing, while pure Co ions or their combination with isohumulone do not exhibit gushing and overfoaming. This explains why cobalt salts were specifically selected at a concentration of 1 – 2 mg/L as anti-gushing agent for beer. Rudin and Hudson (1958) and other authors also found that Co, Ni and Fe ions preferentially concentrate in the foam itself.<sup id="cite_ref-Rudin_Hudson_1958_14-1" class="reference"><a href="#cite_note-Rudin_Hudson_1958-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>In the sixties, after approval by the <a href="/wiki/US_FDA" class="mw-redirect" title="US FDA">US FDA</a>, <a href="/wiki/Cobalt(II)_sulfate" title="Cobalt(II) sulfate">cobalt sulfate</a> was commonly used at low concentration in the USA as an additive to stabilize beer <a href="/wiki/Foam" title="Foam">foam</a> and to prevent gushing after beer is exposed to vibrations during its transport or handling. </p><p>Although <a href="/wiki/Cobalt" title="Cobalt">cobalt</a> is an essential <a href="/wiki/Micronutrient" title="Micronutrient">micronutrient</a> needed for <a href="/wiki/Vitamin_B12" title="Vitamin B12">vitamin B12</a> synthesis, excess levels of cobalt in the body can lead to <a href="/wiki/Cobalt_poisoning" title="Cobalt poisoning">cobalt poisoning</a> and must be avoided. It triggered the development of qualitative and quantitative analysis methods to accurately assay cobalt in beer in order to prevent accidental overdosage and cobalt poisoning.<sup id="cite_ref-Segel_Lautenbach_1964_15-0" class="reference"><a href="#cite_note-Segel_Lautenbach_1964-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p><p>Too high levels of cobalt are known to be responsible for the beer drinker's <a href="/wiki/Cardiomyopathy" title="Cardiomyopathy">cardiomyopathy</a>. The first issues mentioned in the literature were reported in Canada in the middle of the sixties after an accidental overdosage in the <a href="/wiki/Dow_Breweries" title="Dow Breweries">Dow Breweries</a> in <a href="/wiki/Quebec_City" title="Quebec City">Quebec City</a>. </p><p>In August 1965, a person presented to a hospital in <a href="/wiki/Quebec_City" title="Quebec City">Quebec City</a> with symptoms suggestive of <a href="/wiki/Alcoholic_cardiomyopathy" title="Alcoholic cardiomyopathy">alcoholic cardiomyopathy</a>. Over the next eight months, fifty more cases with similar findings appeared in the same area with twenty of these being fatal. It was noted that all were heavy drinkers who mostly drank beer and preferred the <a href="/wiki/Dow_Breweries" title="Dow Breweries">Dow brand</a>; thirty out of those drank more than 6 litres (12 pints) of beer per day.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Epidemiology" title="Epidemiology">Epidemiological studies</a> found that the <a href="/wiki/Dow_Breweries" title="Dow Breweries">Dow Breweries</a> had been adding <a href="/wiki/Cobalt(II)_sulfate" title="Cobalt(II) sulfate">cobalt sulfate</a> to the beer for <a href="/wiki/Foam" title="Foam">foam</a> stability since July 1965 and that the concentration added in the Quebec city brewery was ten times that of the same beer brewed in <a href="/wiki/Montreal" title="Montreal">Montreal</a> where there were no reported cases.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Storage_and_degradation">Storage and degradation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Beer_chemistry&action=edit&section=11" title="Edit section: Storage and degradation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Fluorescence_in_beer_@_450nm_illumination.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/31/Fluorescence_in_beer_%40_450nm_illumination.jpg/220px-Fluorescence_in_beer_%40_450nm_illumination.jpg" decoding="async" width="220" height="153" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/31/Fluorescence_in_beer_%40_450nm_illumination.jpg/330px-Fluorescence_in_beer_%40_450nm_illumination.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/31/Fluorescence_in_beer_%40_450nm_illumination.jpg/440px-Fluorescence_in_beer_%40_450nm_illumination.jpg 2x" data-file-width="1951" data-file-height="1357" /></a><figcaption>Organic <a href="/wiki/Aromatic_acid" title="Aromatic acid">aromatic acids</a> found naturally in beer, such as <a href="/wiki/Tryptophan" title="Tryptophan">tryptophan</a>, <a href="/wiki/Tyrosine" title="Tyrosine">tyrosine</a>, and <a href="/wiki/Phenylalanine" title="Phenylalanine">phenylalanine</a>, absorb blue light and <a href="/wiki/Fluorescence" title="Fluorescence">fluoresce</a> in green under 450 nm laser light.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup></figcaption></figure> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Beer_faults" class="mw-redirect" title="Beer faults">Beer faults</a></div> <p>A particular problem with beer is that, unlike <a href="/wiki/Wine_chemistry" title="Wine chemistry">wine</a>, its quality tends to deteriorate as it ages.<sup id="cite_ref-Guardian_2020_04_01_20-0" class="reference"><a href="#cite_note-Guardian_2020_04_01-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> A <a href="/wiki/Cat_pheromone#Cat_urine_odorants" title="Cat pheromone">cat urine smell</a> and flavor called <a href="/wiki/Ribes" title="Ribes">ribes</a>, named for the genus of the black currant, tends to develop and peak.<sup id="cite_ref-FOOTNOTEBarth2013231_21-0" class="reference"><a href="#cite_note-FOOTNOTEBarth2013231-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> A cardboard smell then dominates which is due to the release of <a href="/wiki/2-Nonenal" title="2-Nonenal">2-nonenal</a>.<sup id="cite_ref-aging_22-0" class="reference"><a href="#cite_note-aging-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> In general, chemists believe that the "off-flavors" that come from old beers are due to reactive oxygen species. These may come in the form of oxygen free <a href="/wiki/Radical_(chemistry)" title="Radical (chemistry)">radicals</a>, for example, which can change the chemical structures of compounds in beer that give them their taste.<sup id="cite_ref-aging_22-1" class="reference"><a href="#cite_note-aging-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> Oxygen radicals can cause increased concentrations of <a href="/wiki/Aldehyde" title="Aldehyde">aldehydes</a> from the <a href="/wiki/Strecker_degradation" title="Strecker degradation">Strecker degradation</a> reactions of <a href="/wiki/Amino_acid" title="Amino acid">amino acids</a> in beer.<sup id="cite_ref-wkm_23-0" class="reference"><a href="#cite_note-wkm-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p><p>Beer is unique when compared to other <a href="/wiki/Alcoholic_beverages" class="mw-redirect" title="Alcoholic beverages">alcoholic beveragess</a> because it is unstable in the final package. There are many variables and chemical compounds that affect the flavor of beer during the production steps, but also during the storage of beer. Beer will develop an off-flavor during storage because of many factors, including sunlight and the amount of oxygen in the <a href="/wiki/Headspace_technology" title="Headspace technology">headspace</a> of the bottle. Other than changes in taste, beer can also develop visual changes. Beer can become hazy during storage. This is called colloidal stability (haze formation) and is typically caused by the raw materials used during the brewing process. The primary reaction that causes beer haze is the <a href="/wiki/Polymerization" title="Polymerization">polymerization</a> of <a href="/wiki/Polyphenols" class="mw-redirect" title="Polyphenols">polyphenols</a> and binding with specific proteins. This type of haze can be seen when beer is cooled below 0 degrees Celsius. When the beer is raised to room temperature, the haze dissolves. But if a beer is stored at room temperature for too long (about 6 months) a permanent haze will form.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> A study done by Heuberger <i>et al.</i> (2012) concludes that storage temperature of beers affects the flavor stability. They found that the <a href="/wiki/Metabolite" title="Metabolite">metabolite</a> profile of room temperature and cold temperature stored beer differed significantly from fresh beer. They also have evidence to support significant beer <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidation</a> after weeks of storage, which also has an effect on the flavor of beer.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/Off-flavour" title="Off-flavour">off-flavour</a> in beer, such as a cardboard or green apple taste, is often associated with the appearance of staling <a href="/wiki/Aldehydes" class="mw-redirect" title="Aldehydes">aldehydes</a>. The Strecker aldehydes responsible for the flavor change are formed during storage of the beers. Philip Wietstock et al. performed experiments to test what causes the formation of Strecker aldehydes during storage. They found that only <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a> concentration (<a href="/wiki/Leucine" title="Leucine">leucine</a> (Leu), <a href="/wiki/Isoleucine" title="Isoleucine">isoleucine</a> (Ile), and <a href="/wiki/Phenylalanine" title="Phenylalanine">phenylalanine</a> (Phe), specifically) and dissolved <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> concentration caused Strecker aldehyde formation. They also tested <a href="/wiki/Carbohydrate" title="Carbohydrate">carbohydrate</a> and Fe<sup>2+</sup> additions. A <a href="/wiki/Linear_relationship" class="mw-redirect" title="Linear relationship">linear relationship</a> was found between Strecker aldehydes formed and total packaged oxygen. This is important for brewers to know so that they can control the taste of their beer. Wietstock concludes that capping beers with oxygen barrier crown corks will diminish Strecker aldehyde formation.<sup id="cite_ref-wkm_23-1" class="reference"><a href="#cite_note-wkm-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p><p>In another study done by Vanderhaegen <i>et al.</i> (2003), different aging conditions were tested on a bottled beer after 6 months. They found a decrease in <a href="/wiki/Volatile_organic_compound" title="Volatile organic compound">volatile</a> <a href="/wiki/Ester" title="Ester">esters</a> was responsible for a reduced fruity flavor. They also found an increase in many other compounds including carbonyl compounds, ethyl esters, Maillard compounds, <a href="/wiki/Dioxolanes" class="mw-redirect" title="Dioxolanes">dioxolanes</a>, and <a href="/wiki/Furane" class="mw-redirect" title="Furane">furanic</a> ethers.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a> compounds, as stated previously in the Wietstock experiments, will create Strecker aldehydes, which tend to cause a green apple flavor. <a href="/wiki/Ester" title="Ester">Esters</a> are known to cause fruity flavors such as pears, roses, and bananas. <a href="/wiki/Maillard_reaction" title="Maillard reaction">Maillard compounds</a> will cause a toasty, malty flavor. </p><p>A study done by Charles Bamforth and Roy Parsons (1985) also confirms that beer staling flavors are caused by various carbonyl compounds. They used <a href="/wiki/Thiobarbituric_acid" title="Thiobarbituric acid">thiobarbituric acid</a> (TBA) to estimate the staling substances after using an accelerated aging technique. They found that beer staling is reduced by scavengers of the <a href="/wiki/Hydroxyl_radical" title="Hydroxyl radical">hydroxyl radical</a> (<sup>•</sup>OH), such as <a href="/wiki/Mannitol" title="Mannitol">mannitol</a> and <a href="/wiki/Ascorbic_acid" class="mw-redirect" title="Ascorbic acid">ascorbic acid</a>. They also tested the hypothesis that soybean extracts included in the fermenting wort enhance the <a href="/wiki/Shelf_life" title="Shelf life">shelf life</a> of beer flavor.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Beer_chemistry&action=edit&section=12" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1259569809">.mw-parser-output .portalbox{padding:0;margin:0.5em 0;display:table;box-sizing:border-box;max-width:175px;list-style:none}.mw-parser-output .portalborder{border:1px solid var(--border-color-base,#a2a9b1);padding:0.1em;background:var(--background-color-neutral-subtle,#f8f9fa)}.mw-parser-output .portalbox-entry{display:table-row;font-size:85%;line-height:110%;height:1.9em;font-style:italic;font-weight:bold}.mw-parser-output .portalbox-image{display:table-cell;padding:0.2em;vertical-align:middle;text-align:center}.mw-parser-output .portalbox-link{display:table-cell;padding:0.2em 0.2em 0.2em 0.3em;vertical-align:middle}@media(min-width:720px){.mw-parser-output .portalleft{clear:left;float:left;margin:0.5em 1em 0.5em 0}.mw-parser-output .portalright{clear:right;float:right;margin:0.5em 0 0.5em 1em}}</style><ul role="navigation" aria-label="Portals" class="noprint portalbox portalborder portalright"> <li class="portalbox-entry"><span class="portalbox-image"><span class="noviewer" typeof="mw:File"><a href="/wiki/File:Projet_bi%C3%A8re_logo_v2.png" class="mw-file-description"><img alt="icon" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c4/Projet_bi%C3%A8re_logo_v2.png/28px-Projet_bi%C3%A8re_logo_v2.png" decoding="async" width="28" height="28" class="mw-file-element" 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class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Beer_chemistry&action=edit&section=13" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Citations">Citations</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Beer_chemistry&action=edit&section=14" title="Edit section: Citations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-FOOTNOTEBarth20139,89-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-FOOTNOTEBarth20139,89_1-0">^</a></b></span> <span class="reference-text"><a href="#CITEREFBarth2013">Barth 2013</a>, p. 9,89.</span> </li> <li id="cite_note-FOOTNOTEBarth201369-88-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-FOOTNOTEBarth201369-88_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-FOOTNOTEBarth201369-88_2-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><a href="#CITEREFBarth2013">Barth 2013</a>, p. 69-88.</span> </li> <li id="cite_note-FOOTNOTEBarth2013144-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-FOOTNOTEBarth2013144_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-FOOTNOTEBarth2013144_3-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><a href="#CITEREFBarth2013">Barth 2013</a>, p. 144.</span> </li> <li id="cite_note-FOOTNOTEJanson1996-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-FOOTNOTEJanson1996_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-FOOTNOTEJanson1996_4-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-FOOTNOTEJanson1996_4-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-FOOTNOTEJanson1996_4-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-FOOTNOTEJanson1996_4-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-FOOTNOTEJanson1996_4-5"><sup><i><b>f</b></i></sup></a></span> <span class="reference-text"><a href="#CITEREFJanson1996">Janson 1996</a>.</span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFMarnett2009" class="citation cs2">Marnett, Alan (6 August 2009), <a rel="nofollow" class="external text" href="http://www.benchfly.com/blog/the-chemistry-of-skunky-beer/">"The Chemistry of Skunky Beer"</a>, <i>benchfly.com</i></cite><span 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"Metabolomic profiling of beer reveals effect of temperature on non-volatile small molecules during short-term storage". <i>Food Chemistry</i>. <b>135</b> (3): 284–1289. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.foodchem.2012.05.048">10.1016/j.foodchem.2012.05.048</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/22953855">22953855</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Food+Chemistry&rft.atitle=Metabolomic+profiling+of+beer+reveals+effect+of+temperature+on+non-volatile+small+molecules+during+short-term+storage&rft.volume=135&rft.issue=3&rft.pages=284-1289&rft.date=2012-12-01&rft_id=info%3Adoi%2F10.1016%2Fj.foodchem.2012.05.048&rft_id=info%3Apmid%2F22953855&rft.aulast=Hueberger&rft.aufirst=Adam&rft.au=Broeckling%2C+Corey&rft.au=Lewis%2C+Matthew&rft.au=Salazar%2C+Lauren&rft.au=Bouckaert%2C+Peter&rft.au=Prenni%2C+Jessica&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABeer+chemistry" class="Z3988"></span></span> </li> <li id="cite_note-26"><span class="mw-cite-backlink"><b><a href="#cite_ref-26">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFVanderhaegenNevenCogheVerachtert2003" class="citation journal cs1">Vanderhaegen, Bart; Neven, Hedwig; Coghe, Stefan; Verachtert, Verstrepen; erdelinckx, Guy (2003). 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"New Procedures to Improve the Flavor Stability of Beer". <i>Journal of the ASBC</i>. <b>43</b> (197): 197–202. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1094%2FASBCJ-43-0197">10.1094/ASBCJ-43-0197</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+ASBC&rft.atitle=New+Procedures+to+Improve+the+Flavor+Stability+of+Beer&rft.volume=43&rft.issue=197&rft.pages=197-202&rft.date=1985&rft_id=info%3Adoi%2F10.1094%2FASBCJ-43-0197&rft.aulast=Bamforth&rft.aufirst=Charles&rft.au=Parsons%2C+Roy&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABeer+chemistry" class="Z3988"></span></span> </li> </ol></div> <div class="mw-heading mw-heading3"><h3 id="Sources">Sources</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Beer_chemistry&action=edit&section=15" title="Edit section: Sources"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBarth2013" class="citation cs2">Barth, Roger (2013), <i>The Chemistry of Beer: The Science in the Suds</i>, <a href="/wiki/John_Wiley_%26_Sons" class="mw-redirect" title="John Wiley & Sons">John Wiley & Sons</a>, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-11873-379-0" title="Special:BookSources/978-1-11873-379-0"><bdi>978-1-11873-379-0</bdi></a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Chemistry+of+Beer%3A+The+Science+in+the+Suds&rft.pub=John+Wiley+%26+Sons&rft.date=2013&rft.isbn=978-1-11873-379-0&rft.aulast=Barth&rft.aufirst=Roger&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABeer+chemistry" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBaxterHughes2001" class="citation cs2">Baxter, Denise; Hughes, Paul (2001), <i>Beer: Quality, Safety and Nutritional Aspects</i>, <a href="/wiki/Royal_Society_of_Chemistry" title="Royal Society of Chemistry">Royal Society of Chemistry</a>, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-85404-588-4" title="Special:BookSources/978-0-85404-588-4"><bdi>978-0-85404-588-4</bdi></a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Beer%3A+Quality%2C+Safety+and+Nutritional+Aspects&rft.pub=Royal+Society+of+Chemistry&rft.date=2001&rft.isbn=978-0-85404-588-4&rft.aulast=Baxter&rft.aufirst=Denise&rft.au=Hughes%2C+Paul&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABeer+chemistry" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHopkins2011" class="citation cs2">Hopkins, R (2011), <i>Biochemistry Applied to Beer Brewing – General Chemistry of the Raw Materials of Malting and Brewing</i>, Tobey Press, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-44654-168-5" title="Special:BookSources/978-1-44654-168-5"><bdi>978-1-44654-168-5</bdi></a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Biochemistry+Applied+to+Beer+Brewing+%E2%80%93+General+Chemistry+of+the+Raw+Materials+of+Malting+and+Brewing&rft.pub=Tobey+Press&rft.date=2011&rft.isbn=978-1-44654-168-5&rft.aulast=Hopkins&rft.aufirst=R&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABeer+chemistry" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHornsey2003" class="citation cs2">Hornsey, Ian (2003), <i>A History of Beer and Brewing</i>, Royal Society of Chemistry, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-85404-630-0" title="Special:BookSources/978-0-85404-630-0"><bdi>978-0-85404-630-0</bdi></a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=A+History+of+Beer+and+Brewing&rft.pub=Royal+Society+of+Chemistry&rft.date=2003&rft.isbn=978-0-85404-630-0&rft.aulast=Hornsey&rft.aufirst=Ian&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABeer+chemistry" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJanson1996" class="citation cs2">Janson, Lee (1996), <span class="id-lock-registration" title="Free registration required"><a rel="nofollow" class="external text" href="https://archive.org/details/brewchem1010000jans"><i>Brew Chem 101</i></a></span>, <a href="/wiki/Workman_Publishing_Company" title="Workman Publishing Company">Storey</a>, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-88266-940-3" title="Special:BookSources/978-0-88266-940-3"><bdi>978-0-88266-940-3</bdi></a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Brew+Chem+101&rft.pub=Storey&rft.date=1996&rft.isbn=978-0-88266-940-3&rft.aulast=Janson&rft.aufirst=Lee&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fbrewchem1010000jans&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABeer+chemistry" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFVerhagen2010" class="citation cs2 cs1-prop-long-vol">Verhagen, Leen (2010), "Beer Flavor", <i>Comprehensive Natural Products II: Chemistry and Biology</i>, vol. 3: Development & Modification of Bioactivity, <a href="/wiki/Elsevier" title="Elsevier">Newnes</a>, pp. 967–998, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-08045-382-8" title="Special:BookSources/978-0-08045-382-8"><bdi>978-0-08045-382-8</bdi></a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Comprehensive+Natural+Products+II%3A+Chemistry+and+Biology&rft.atitle=Beer+Flavor&rft.volume=3%3A+Development+%26+Modification+of+Bioactivity&rft.pages=967-998&rft.date=2010&rft.isbn=978-0-08045-382-8&rft.aulast=Verhagen&rft.aufirst=Leen&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABeer+chemistry" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFVerzeleDe_Keukeleire2013" class="citation cs2">Verzele, M; De Keukeleire, D (2013), <i>Chemistry and Analysis of Hop and Beer Bitter Acids</i>, <a href="/wiki/Elsevier" title="Elsevier">Elsevier</a>, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-48329-086-7" title="Special:BookSources/978-1-48329-086-7"><bdi>978-1-48329-086-7</bdi></a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Chemistry+and+Analysis+of+Hop+and+Beer+Bitter+Acids&rft.pub=Elsevier&rft.date=2013&rft.isbn=978-1-48329-086-7&rft.aulast=Verzele&rft.aufirst=M&rft.au=De+Keukeleire%2C+D&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABeer+chemistry" class="Z3988"></span></li></ul> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Beer_chemistry&action=edit&section=16" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20150725014141/http://www.acs.org/content/acs/en/events/acs-webinars1/tapping-into-the-chemistry-of-beer-and-brewing-bamforth.html">Tapping into the Chemistry of Beer and Brewing</a>—an online lecture by Charles Bamforth, Professor of Malting & Brewing Sciences at the University of California</li> <li><a rel="nofollow" class="external text" href="https://janux.ou.edu/course.chem4970.html">Chemistry of Beer</a>—an online course in the subject at the University of Oklahoma</li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl 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href="/wiki/Drunk_driving" title="Drunk driving">Drunk driving</a> <ul><li><a href="/wiki/Alcohol-related_traffic_crashes_in_the_United_States" title="Alcohol-related traffic crashes in the United States">Alcohol-related traffic crashes in the United States</a></li> <li><a href="/wiki/Drunk_driving_in_the_United_States" title="Drunk driving in the United States">Drunk driving in the United States</a></li></ul></li> <li><a href="/wiki/Moonshine" title="Moonshine">Moonshine</a> <ul><li><a href="/wiki/Bathtub_gin" title="Bathtub gin">Bathtub gin</a></li></ul></li> <li>Prison alcohol <ul><li><a href="/wiki/P%C3%A1jaro_verde" title="Pájaro verde">Pájaro verde</a></li> <li><a href="/wiki/Pruno" title="Pruno">Pruno</a></li></ul></li> <li><a href="/wiki/Public_intoxication" title="Public intoxication">Public intoxication</a></li> <li><a href="/wiki/Rum-running" title="Rum-running">Rum-running</a></li> <li><a href="/wiki/Sly-grog_shop" title="Sly-grog shop">Sly-grog shop</a></li> <li><a href="/wiki/Wine_fraud" title="Wine fraud">Wine fraud</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Alcoholism" title="Alcoholism">Alcoholism</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alcohol_and_Native_Americans" title="Alcohol and Native Americans">Alcohol and Native Americans</a></li> <li><a href="/wiki/Alcoholism_in_adolescence" title="Alcoholism in adolescence">Alcoholism in adolescence</a></li> <li><a href="/wiki/Alcoholism_in_family_systems" title="Alcoholism in family systems">Alcoholism in family systems</a></li> <li><a href="/wiki/Alcoholism_in_rural_Australia" title="Alcoholism in rural Australia">Alcoholism in rural Australia</a></li> <li><a href="/wiki/Collaborative_Study_on_the_Genetics_of_Alcoholism" title="Collaborative Study on the Genetics of Alcoholism">Collaborative Study on the Genetics of Alcoholism</a></li> <li><a href="/wiki/Disease_theory_of_alcoholism" title="Disease theory of alcoholism">Disease theory of alcoholism</a></li> <li><a href="/wiki/High-functioning_alcoholic" title="High-functioning alcoholic">High-functioning alcoholic</a> (HFA)</li> <li><a href="/wiki/Seeing_pink_elephants" title="Seeing pink elephants">Seeing pink elephants</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Chemistry</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Beverage-specific <ul><li><a class="mw-selflink selflink">Beer chemistry</a></li> <li><a href="/wiki/Wine_chemistry" title="Wine chemistry">Wine chemistry</a></li></ul></li> <li><a href="/wiki/Comparison_of_psychoactive_alcohols_in_alcoholic_drinks" title="Comparison of psychoactive alcohols in alcoholic drinks">Comparison of psychoactive alcohols in alcoholic drinks</a></li> <li><a href="/wiki/Congener_(beverages)" title="Congener (beverages)">Congener</a> <ul><li><a href="/wiki/Alcohol_congener_analysis" title="Alcohol congener analysis">Alcohol congener analysis</a></li></ul></li> <li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a> <ul><li><a href="/wiki/Blood_alcohol_content" title="Blood alcohol content">Blood alcohol content</a></li></ul></li> <li><a href="/wiki/Fusel_alcohol" title="Fusel alcohol">Fusel alcohol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Effects</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Short-term_effects_of_alcohol_consumption" title="Short-term effects of alcohol consumption">Short-term effects of alcohol consumption</a></li> <li><a href="/wiki/Long-term_effects_of_alcohol" title="Long-term effects of alcohol">Long-term effects of alcohol</a></li> <li><a href="/wiki/Pharmacology_of_ethanol" title="Pharmacology of ethanol">Pharmacology of ethanol</a></li> <li><a href="/wiki/Subjective_response_to_alcohol" title="Subjective response to alcohol">Subjective response to alcohol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Adverse effects</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Hangxiety" title="Hangxiety">Anxiety</a></li> <li><a href="/wiki/Impact_of_alcohol_on_aging" title="Impact of alcohol on aging">Aging</a></li> <li><a href="/wiki/Long-term_impact_of_alcohol_on_the_brain" title="Long-term impact of alcohol on the brain">Brain</a></li> <li><a href="/wiki/Alcohol_and_cancer" title="Alcohol and cancer">Cancer</a> <ul><li><a href="/wiki/Alcohol_and_breast_cancer" title="Alcohol and breast cancer">breast cancer</a></li></ul></li> <li><a href="/wiki/Alcohol_and_cortisol" title="Alcohol and cortisol">Cortisol</a></li> <li><a href="/wiki/Effects_of_alcohol_on_memory" title="Effects of alcohol on memory">Memory</a></li> <li><a href="/wiki/Alcohol_and_pregnancy" class="mw-redirect" title="Alcohol and pregnancy">Pregnancy</a></li> <li><a href="/wiki/Alcohol_use_and_sleep" title="Alcohol use and sleep">Sleep</a></li> <li><a href="/wiki/Alcohol_tolerance" title="Alcohol tolerance">Tolerance</a>/<a href="/wiki/Alcohol_intolerance" title="Alcohol intolerance">intolerance</a></li> <li><a href="/wiki/Alcohol_and_weight" title="Alcohol and weight">Weight</a></li> <li>Beverage-specific <ul><li>Beer: <a href="/wiki/Potomania" title="Potomania">Potomania</a></li> <li>Wine: <a href="/wiki/Red_wine_headache" title="Red wine headache">Red wine headache</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Social_issues" class="mw-redirect" title="Social issues">Social issues</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Adulterated alcohol <ul><li><a href="/wiki/Moonshine#Adulterated_moonshine" title="Moonshine">Adulterated moonshine</a></li> <li><a href="/wiki/Denatured_alcohol" title="Denatured alcohol">Denatured alcohol</a> (<a href="/wiki/List_of_methanol_poisoning_incidents" title="List of methanol poisoning incidents">List of methanol poisoning incidents</a>)</li> <li><a href="/wiki/Surrogate_alcohol" title="Surrogate alcohol">Surrogate alcohol</a></li></ul></li> <li><a href="/wiki/Alcohol_abuse" title="Alcohol abuse">Alcohol abuse</a></li> <li><a href="/wiki/Alcohol_advertising" title="Alcohol advertising">Alcohol advertising</a> <ul><li><a href="/wiki/Alcohol_advertising_on_college_campuses" title="Alcohol advertising on college campuses">on college campuses</a></li></ul></li> <li><a href="/wiki/Alcohol_and_sex" title="Alcohol and sex">Sex</a> <ul><li><a href="/wiki/Beer_goggles" title="Beer goggles">Beer goggles</a></li></ul></li> <li><a href="/wiki/Alcohol_myopia" title="Alcohol myopia">Alcohol myopia</a></li> <li><a href="/wiki/Alcohol_in_association_football" title="Alcohol in association football">Alcohol in association football</a></li> <li><a href="/wiki/Alcohol_use_among_college_students" title="Alcohol use among college students">Alcohol use among college students</a></li> <li><a href="/wiki/Binge_drinking" title="Binge drinking">Binge drinking</a> <ul><li><a href="/wiki/Austrian_syndrome" title="Austrian syndrome">Austrian syndrome</a></li> <li><a href="/wiki/Alcohol_intoxication" title="Alcohol intoxication">Alcohol intoxication</a></li> <li><a href="/wiki/Epidemiology_of_binge_drinking" title="Epidemiology of binge drinking">Epidemiology of binge drinking</a></li> <li><a href="/wiki/Holiday_heart_syndrome" title="Holiday heart syndrome">Holiday heart syndrome</a></li> <li>Problematic alcoholic products <ul><li><a href="/wiki/Alcohol_powder" title="Alcohol powder">Alcohol powder</a></li> <li><a href="/wiki/Alcopop" title="Alcopop">Alcopop</a></li> <li><a href="/wiki/Borg_(drink)" title="Borg (drink)">Borg</a></li> <li>Low-cost alcohol <ul><li><a href="/wiki/Flavored_fortified_wine" title="Flavored fortified wine">Flavored fortified wine</a></li></ul></li> <li><a href="/wiki/Alcohol_(drug)#Stimulants" title="Alcohol (drug)">Polysubstance alcoholic drinks</a> <ul><li><a href="/wiki/Caffeinated_alcoholic_drink" title="Caffeinated alcoholic drink">Caffeinated alcoholic drink</a></li> <li><a href="/wiki/Coca_wine" title="Coca wine">Coca wine</a></li> <li><a href="/wiki/Nicotini" title="Nicotini">Nicotini</a></li></ul></li></ul></li> <li><a href="/wiki/Zapoy" title="Zapoy">Zapoy</a></li></ul></li> <li><a href="/wiki/Blackout_(drug-related_amnesia)" title="Blackout (drug-related amnesia)">Blackout</a></li> <li><a href="/wiki/Blackout_Wednesday" title="Blackout Wednesday">Blackout Wednesday</a></li> <li><a href="/wiki/Drinking_game" title="Drinking game">Drinking game</a> <ul><li><a href="/wiki/List_of_drinking_games" title="List of drinking games">list</a></li> <li><a href="/wiki/Pregaming" title="Pregaming">Pregaming</a></li></ul></li> <li><a href="/wiki/Drinking_in_public" title="Drinking in public">Drinking in public</a></li> <li><a href="/wiki/Drunk_walking" title="Drunk walking">Drunk walking</a></li> <li><a href="/wiki/Drunkorexia" title="Drunkorexia">Drunkorexia</a></li> <li><a href="/wiki/Dry_drunk" title="Dry drunk">Dry drunk</a></li> <li><a href="/wiki/Dutch_courage" title="Dutch courage">Dutch courage</a></li> <li><a href="/wiki/Flaming_drink" title="Flaming drink">Flaming drink</a></li> <li><a href="/wiki/Hair_of_the_dog" title="Hair of the dog">Hair of the dog</a></li> <li><a href="/wiki/Hurtful_communication#Alcohol" title="Hurtful communication">Hurtful communication</a> <ul><li><a href="/wiki/Drunk_dialing" title="Drunk dialing">Drunk dialing</a></li> <li><a href="/wiki/In_vino_veritas" title="In vino veritas"><i>In vino veritas</i></a></li></ul></li> <li><a href="/wiki/Nightcap_(drink)" title="Nightcap (drink)">Nightcap</a></li> <li><a href="/wiki/Pantsdrunk" title="Pantsdrunk">Pantsdrunk</a></li> <li><a href="/wiki/Passive_drinking" title="Passive drinking">Passive drinking</a></li> <li>Binge drinking devices <ul><li><a href="/wiki/Beer_bong" title="Beer bong">Beer bong</a></li> <li><a href="/wiki/Yard_of_ale" title="Yard of ale">Yard of ale</a></li></ul></li> <li>Routes of administration <ul><li><a href="/wiki/Alcohol_enema" title="Alcohol enema">Alcohol enema</a></li> <li><a href="/wiki/Alcohol_inhalation" title="Alcohol inhalation">Alcohol inhalation</a></li> <li><a href="/wiki/Vodka_eyeballing" title="Vodka eyeballing">Vodka eyeballing</a></li></ul></li> <li><a href="/wiki/Sconcing" title="Sconcing">Sconcing</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">History</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Andrew_Johnson_alcoholism_debate" title="Andrew Johnson alcoholism debate">Andrew Johnson alcoholism debate</a></li> <li><a href="/wiki/Dionysian_Mysteries" title="Dionysian Mysteries">Dionysian Mysteries</a></li> <li><a href="/wiki/Dipsomania" title="Dipsomania">Dipsomania</a></li> <li><a href="/wiki/Gilbert_Paul_Jordan" title="Gilbert Paul Jordan">Gilbert Paul Jordan</a></li> <li><a href="/wiki/Gin_Craze" title="Gin Craze">Gin Craze</a></li> <li><a href="/wiki/List_of_deaths_through_alcohol" title="List of deaths through alcohol">List of deaths through alcohol</a></li> <li><a href="/wiki/Rum_ration" title="Rum ration">Rum ration</a></li> <li><a href="/wiki/Rum_Rebellion" title="Rum Rebellion">Rum Rebellion</a></li> <li><a href="/wiki/Shebeen" title="Shebeen">Shebeen</a></li> <li><a href="/wiki/Six_o%27clock_swill" title="Six o'clock swill">Six o'clock swill</a></li> <li>Illegal drinking establishments <ul><li><a href="/wiki/Nip_joint" title="Nip joint">Nip joint</a></li> <li><a href="/wiki/Speakeasy" title="Speakeasy">Speakeasy</a></li></ul></li> <li><a href="/wiki/Whiskey_Rebellion" title="Whiskey Rebellion">Whiskey Rebellion</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">General</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alcoholic_beverage" title="Alcoholic beverage">Alcoholic beverage</a></li> <li>Beer <ul><li><a href="/wiki/Beer_mile" title="Beer mile">Beer mile</a></li> <li><a href="/wiki/International_Beer_Day" title="International Beer Day">International Beer Day</a></li> <li><a href="/wiki/International_Women%27s_Collaboration_Brew_Day" title="International Women's Collaboration Brew Day">International Women's Collaboration Brew Day</a></li> <li><a href="/wiki/Women_in_brewing" title="Women in brewing">Women in brewing</a></li></ul></li> <li><a href="/wiki/Drinking_culture" title="Drinking culture">Drinking culture</a> <ul><li><a href="/wiki/Ap%C3%A9ritif_and_digestif" title="Apéritif and digestif">Apéritif and digestif</a></li> <li><a href="/wiki/Hangover_remedies" title="Hangover remedies">Hangover remedies</a></li> <li><a href="/wiki/Health_effects_of_wine" title="Health effects of wine">Health effects of wine</a> <ul><li><a href="/wiki/Wine_and_food_pairing" title="Wine and food pairing">Wine and food pairing</a></li></ul></li></ul></li> <li><a href="/wiki/Drunken_monkey_hypothesis" title="Drunken monkey hypothesis">Drunken monkey hypothesis</a></li> <li><a href="/wiki/Ladies%27_night" title="Ladies' night">Ladies' night</a></li> <li><a href="/wiki/List_of_countries_by_alcohol_consumption_per_capita" title="List of countries by alcohol consumption per capita">List of countries by alcohol consumption per capita</a> <ul><li><a href="/wiki/Alcohol_consumption_by_youth_in_the_United_States" title="Alcohol consumption by youth in the United States">Alcohol consumption by youth in the United States</a></li></ul></li> <li><a href="/wiki/List_of_substances_used_in_rituals#Alcohol" title="List of substances used in rituals">Ritual use of alcohol</a></li> <li>Whiskey <ul><li><a href="/wiki/International_whisk(e)y_day" title="International whisk(e)y day">International whisk(e)y day</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Alcohol <br />control</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Alcohol_law" title="Alcohol law">Alcohol law</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Administrative_License_Suspension" title="Administrative License Suspension">Administrative License Suspension</a> (ALS)</li> <li><a href="/wiki/Alcohol_(Minimum_Pricing)_(Scotland)_Act_2012" title="Alcohol (Minimum Pricing) (Scotland) Act 2012">Alcohol (Minimum Pricing) (Scotland) Act 2012</a></li> <li><a href="/wiki/Alcohol_exclusion_laws" title="Alcohol exclusion laws">Alcohol exclusion laws</a></li> <li><a href="/wiki/Alcohol_monopoly" title="Alcohol monopoly">Alcohol monopoly</a> <ul><li><a href="/wiki/Alcoholic_beverage_control_state" title="Alcoholic beverage control state">Alcoholic beverage control state</a></li></ul></li> <li><a href="/wiki/Alcohol_packaging_warning_messages" title="Alcohol packaging warning messages">Alcohol packaging warning messages</a></li> <li><a href="/wiki/Ban_on_caffeinated_alcoholic_drinks_in_the_United_States" title="Ban on caffeinated alcoholic drinks in the United States">Ban on caffeinated alcoholic drinks in the United States</a></li> <li><a href="/wiki/Drunk_driving_law_by_country" title="Drunk driving law by country">Drunk driving law by country</a> <ul><li><a href="/wiki/DWI_court" title="DWI court">DWI court</a></li> <li><a href="/wiki/Field_sobriety_testing" title="Field sobriety testing">Field sobriety testing</a></li> <li><a href="/wiki/Hip_flask_defence" title="Hip flask defence">Hip flask defence</a></li> <li><a href="/wiki/Ignition_interlock_device" title="Ignition interlock device">Ignition interlock device</a></li></ul></li> <li><a href="/wiki/Dry_county" title="Dry county">Dry county</a> <ul><li><a href="/wiki/List_of_dry_communities_by_U.S._state" title="List of dry communities by U.S. state">List of dry communities by U.S. state</a></li></ul></li> <li><a href="/wiki/Last_call" title="Last call">Last call</a></li> <li><a href="/wiki/Legal_drinking_age" title="Legal drinking age">Legal drinking age</a> <ul><li><a href="/wiki/Legal_drinking_age_in_the_United_States" title="Legal drinking age in the United States">Legal drinking age in the United States</a></li> <li><a href="/wiki/Shoulder_tap_(alcohol)" title="Shoulder tap (alcohol)">Shoulder tap</a></li></ul></li> <li><a href="/wiki/List_of_alcohol_laws_of_the_United_States" title="List of alcohol laws of the United States">List of alcohol laws of US</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Prohibition" title="Prohibition">Alcohol prohibition</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/List_of_countries_with_alcohol_prohibition" title="List of countries with alcohol prohibition">List of countries with alcohol prohibition</a></li> <li><a href="/wiki/Neo-prohibitionism" title="Neo-prohibitionism">Neo-prohibitionism</a></li> <li><a href="/wiki/Temperance_movement" title="Temperance movement">Temperance movement</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sobriety" title="Sobriety">Sobriety</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alcohol_detoxification" title="Alcohol detoxification">Alcohol detoxification</a></li> <li><a href="/wiki/Alcohol-free_zone" title="Alcohol-free zone">Alcohol-free zone</a> <ul><li><a href="/wiki/Dry_campus" title="Dry campus">Dry campus</a></li> <li><a href="/wiki/Open-container_law" title="Open-container law">Open-container law</a></li></ul></li> <li><a href="/wiki/Brief_intervention" title="Brief intervention">Brief intervention</a></li> <li><a href="/wiki/Designated_driver" title="Designated driver">Designated driver</a></li> <li><a href="/wiki/Drug_rehabilitation" title="Drug rehabilitation">Alcohol rehabilitation</a></li> <li><a href="/wiki/Drunk_tank" title="Drunk tank">Drunk tank</a></li> <li><a href="/wiki/Managed_alcohol_program" title="Managed alcohol program">Managed alcohol program</a></li> <li><a href="/wiki/Non-alcoholic_drink" title="Non-alcoholic drink">Non-alcoholic drink</a> <ul><li><a href="/wiki/List_of_non-alcoholic_cocktails" class="mw-redirect" title="List of non-alcoholic cocktails">List of cocktails</a></li> <li><a href="/wiki/List_of_non-alcoholic_mixed_drinks" title="List of non-alcoholic mixed drinks">List of mixed drinks</a></li> <li><a href="/wiki/Spritzer#Non-alcoholic_spritzer" title="Spritzer">Spritzer</a></li> <li><a href="/wiki/Malt_drink#Non-alcoholic_malt_drinks" title="Malt drink">Malt drinks</a></li></ul></li> <li><a href="/wiki/Teetotalism" title="Teetotalism">Teetotalism</a></li> <li><a href="/wiki/Temperance_bar" title="Temperance bar">Temperance bar</a></li> <li><a href="/wiki/Temperance_and_Good_Citizenship_Day" title="Temperance and Good Citizenship Day">Temperance and Good Citizenship Day</a></li> <li><a href="/wiki/List_of_twelve-step_groups" title="List of twelve-step groups">Twelve-step groups</a> <ul><li><a href="/wiki/Al-Anon/Alateen" title="Al-Anon/Alateen">Al-Anon/Alateen</a></li> <li><a href="/wiki/Alcoholics_Anonymous" title="Alcoholics Anonymous">Alcoholics Anonymous</a> (AA):</li> <li><a href="/wiki/Adult_Children_of_Alcoholics" class="mw-redirect" title="Adult Children of Alcoholics">Adult Children of Alcoholics</a> (ACA)</li></ul></li> <li><a href="/wiki/Sober_companion" title="Sober companion">Sober companion</a></li> <li><a href="/wiki/Sober_curious" title="Sober curious">Sober curious</a></li> <li><a href="/wiki/Sober_living_house" title="Sober living house">Sober living house</a></li> <li><a href="/wiki/Sobering_center" title="Sobering center">Sobering center</a></li> <li><a href="/wiki/Sobrietol" title="Sobrietol">Sobrietol</a></li> <li><a href="/wiki/Quit_lit_(alcohol_cessation)" title="Quit lit (alcohol cessation)">Quit lit</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Alcohol limitation</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/0-0-1-3" title="0-0-1-3">0-0-1-3</a></li> <li><a href="/wiki/Alcohol_consumption_recommendations" title="Alcohol consumption recommendations">Alcohol consumption recommendations</a></li> <li><a href="/wiki/Alcohol_education" title="Alcohol education">Alcohol education</a></li> <li><a href="/wiki/Alcohol_server_training" title="Alcohol server training">Alcohol server training</a></li> <li>Monitoring <ul><li><a href="/wiki/Breathalyzer" title="Breathalyzer">Breathalyzer</a></li> <li><a href="/wiki/Electronic_tagging#Sweat_alcohol_content_monitor" title="Electronic tagging">Sweat alcohol content monitor</a></li></ul></li> <li><a href="/wiki/Brief_intervention#FRAMES" title="Brief intervention">FRAMES</a></li> <li><a href="/wiki/Foundation_for_Advancing_Alcohol_Responsibility" title="Foundation for Advancing Alcohol Responsibility">Foundation for Advancing Alcohol Responsibility</a></li> <li>Campaigns <ul><li><a href="/wiki/Dry_January" title="Dry January">Dry January</a></li> <li><a href="/wiki/Dry_July" title="Dry July">Dry July</a></li> <li><a href="/wiki/Get_Your_Sexy_Back" title="Get Your Sexy Back">Get Your Sexy Back</a></li> <li><a href="/wiki/Ocsober" title="Ocsober">Ocsober</a></li></ul></li> <li><a href="/wiki/Liquor_license" title="Liquor license">Liquor license</a></li> <li>Low-alcohol drinks <ul><li><a href="/wiki/Fermented_tea" title="Fermented tea">Fermented tea</a></li> <li><a href="/wiki/Low-alcohol_beer" title="Low-alcohol beer">Low-alcohol beer</a></li> <li><a href="/wiki/Malt_drink#Low-alcoholic_malt_drinks" title="Malt drink">Low-alcoholic malt drinks</a></li> <li><a href="/wiki/Small_beer" title="Small beer">Small beer</a></li></ul></li> <li>Measurement <ul><li><a href="/wiki/Alcoholic_spirits_measure" title="Alcoholic spirits measure">Alcoholic spirits measure</a></li> <li><a href="/wiki/Standard_drink" title="Standard drink">Standard drink</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Addiction_medicine" title="Addiction medicine">Addiction medicine</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</a> <ul><li><a href="/wiki/Chlordiazepoxide" title="Chlordiazepoxide">Chlordiazepoxide</a></li></ul></li> <li><a href="/wiki/Disulfiram-like_drug" title="Disulfiram-like drug">Disulfiram-like drugs</a> <ul><li><a href="/wiki/Disulfiram" title="Disulfiram">Disulfiram</a></li> <li><a href="/wiki/Calcium_carbimide" title="Calcium carbimide">Calcium carbimide</a></li> <li><a href="/wiki/Cyanamide" title="Cyanamide">Cyanamide</a></li></ul></li> <li><a href="/wiki/General_anaesthetic" title="General anaesthetic">General anaesthetics</a> <ul><li><a href="/wiki/Nitrous_oxide_(medication)" title="Nitrous oxide (medication)">Nitrous oxide</a></li></ul></li> <li><a href="/wiki/Sulfonic_acid" title="Sulfonic acid">Sulfonic acids</a> <ul><li><a href="/wiki/Acamprosate" title="Acamprosate">Acamprosate</a></li> <li><a href="/wiki/Homotaurine" title="Homotaurine">Homotaurine</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Religion_and_alcohol" title="Religion and alcohol">Religion and alcohol</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Christian_views_on_alcohol" title="Christian views on alcohol">Christian views on alcohol</a> <ul><li><a href="/wiki/Alcohol_in_the_Bible" title="Alcohol in the Bible">Alcohol in the Bible</a></li></ul></li> <li><a href="/wiki/Khamr" title="Khamr">Islam and alcohol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">History</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Beer_Street_and_Gin_Lane" title="Beer Street and Gin Lane"><i>Beer Street</i> and <i>Gin Lane</i></a></li> <li><a href="/wiki/Bratt_System" title="Bratt System">Bratt System</a></li> <li><a href="/wiki/Dry_state" title="Dry state">Dry state</a></li> <li><a href="/wiki/Gin_Act_1751" title="Gin Act 1751">Gin Act 1751</a></li> <li><a href="/wiki/Medicinal_Liquor_Prescriptions_Act_of_1933" title="Medicinal Liquor Prescriptions Act of 1933">Medicinal Liquor Prescriptions Act of 1933</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Related</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Index_of_alcohol-related_articles" title="Index of alcohol-related articles">Index of alcohol-related articles</a></li> <li><a href="/wiki/Alcohol_and_spaceflight" title="Alcohol and spaceflight">Alcohol and spaceflight</a></li> <li><a href="/wiki/Gateway_drug_effect" title="Gateway drug effect">Gateway drug effect</a></li> <li><a href="/wiki/Mood_disorder" title="Mood disorder">Mood disorder</a></li> <li><a href="/wiki/Non-alcoholic_fatty_liver_disease" class="mw-redirect" title="Non-alcoholic fatty liver disease">Non-alcoholic fatty liver disease</a></li> <li><a href="/wiki/Self-medication" title="Self-medication">Self-medication</a></li> <li><a href="/wiki/Spins" title="Spins">Spins</a></li> <li><a href="/wiki/Town_drunk" title="Town drunk">Town drunk</a></li> <li><a href="/wiki/French_paradox" title="French paradox">French paradox</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow hlist" colspan="2"><div> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" 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