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id="toc-1,2-Dicarbonyls-sublist" class="vector-toc-list"> <li id="toc-1,2-Dialdehyde" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#1,2-Dialdehyde"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>1,2-Dialdehyde</span> </div> </a> <ul id="toc-1,2-Dialdehyde-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-1,2-Diketones" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#1,2-Diketones"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.2</span> <span>1,2-Diketones</span> </div> </a> <ul id="toc-1,2-Diketones-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-1,2-Ketoaldehydes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#1,2-Ketoaldehydes"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.3</span> <span>1,2-Ketoaldehydes</span> </div> </a> <ul id="toc-1,2-Ketoaldehydes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-1,2-Diesters_and_diacids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#1,2-Diesters_and_diacids"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.4</span> <span>1,2-Diesters and diacids</span> </div> </a> <ul id="toc-1,2-Diesters_and_diacids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-α-Keto-_and_formylcarboxylic_acids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#α-Keto-_and_formylcarboxylic_acids"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.5</span> <span>α-Keto- and formylcarboxylic acids</span> </div> </a> <ul id="toc-α-Keto-_and_formylcarboxylic_acids-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-1,3-Dicarbonyls" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#1,3-Dicarbonyls"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>1,3-Dicarbonyls</span> </div> </a> <button aria-controls="toc-1,3-Dicarbonyls-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle 1,3-Dicarbonyls subsection</span> </button> <ul id="toc-1,3-Dicarbonyls-sublist" class="vector-toc-list"> <li id="toc-1,3-Dialdehydes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#1,3-Dialdehydes"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>1,3-Dialdehydes</span> </div> </a> <ul id="toc-1,3-Dialdehydes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-1,3-Diketones" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#1,3-Diketones"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>1,3-Diketones</span> </div> </a> <ul id="toc-1,3-Diketones-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-1,3-Diesters_and_diacids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#1,3-Diesters_and_diacids"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>1,3-Diesters and diacids</span> </div> </a> <ul id="toc-1,3-Diesters_and_diacids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-β-Keto-esters" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#β-Keto-esters"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.4</span> <span>β-Keto-esters</span> </div> </a> <ul id="toc-β-Keto-esters-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-1,4-Dicarbonyls" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#1,4-Dicarbonyls"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>1,4-Dicarbonyls</span> </div> </a> <button aria-controls="toc-1,4-Dicarbonyls-sublist" 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class="vector-toc-link" href="#1,4-Diesters_and_diacids"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>1,4-Diesters and diacids</span> </div> </a> <ul id="toc-1,4-Diesters_and_diacids-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-1,5-Dicarbonyls" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#1,5-Dicarbonyls"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>1,5-Dicarbonyls</span> </div> </a> <button aria-controls="toc-1,5-Dicarbonyls-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle 1,5-Dicarbonyls subsection</span> </button> <ul id="toc-1,5-Dicarbonyls-sublist" class="vector-toc-list"> <li id="toc-1,5-Dialdehydes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#1,5-Dialdehydes"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>1,5-Dialdehydes</span> </div> </a> <ul id="toc-1,5-Dialdehydes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-1,5-Diketones" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#1,5-Diketones"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>1,5-Diketones</span> </div> </a> <ul id="toc-1,5-Diketones-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-1,5-Diesters_and_diacids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#1,5-Diesters_and_diacids"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3</span> <span>1,5-Diesters and diacids</span> </div> </a> <ul id="toc-1,5-Diesters_and_diacids-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Hydration_and_cyclization" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Hydration_and_cyclization"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Hydration and cyclization</span> </div> </a> <ul id="toc-Hydration_and_cyclization-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Safety" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Safety"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Safety</span> </div> </a> <ul id="toc-Safety-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" 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class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"><span class="mw-redirectedfrom">(Redirected from <a href="/w/index.php?title=Diketone&redirect=no" class="mw-redirect" title="Diketone">Diketone</a>)</span></div></div> <div id="mw-content-text" 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">Molecule containing two adjacent C=O groups</div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Dicarbonyl_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/12/Dicarbonyl_structure.png/152px-Dicarbonyl_structure.png" decoding="async" width="152" height="290" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/12/Dicarbonyl_structure.png/228px-Dicarbonyl_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/12/Dicarbonyl_structure.png/304px-Dicarbonyl_structure.png 2x" data-file-width="316" data-file-height="602" /></a><figcaption>General structure of 1,2-, 1,3-, and 1,4-dicarbonyls</figcaption></figure> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, a <b>dicarbonyl</b> is a <a href="/wiki/Molecule" title="Molecule">molecule</a> containing two <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a> (<style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">C=O</span>) <a href="/wiki/Functional_group" title="Functional group">groups</a>. Although this term could refer to any <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> containing two carbonyl groups, it is used more specifically to describe molecules in which both carbonyls are in close enough proximity that their <a href="/wiki/Reactivity_(chemistry)" title="Reactivity (chemistry)">reactivity</a> is changed, such as 1,2-, 1,3-, and 1,4-dicarbonyls. Their properties often differ from those of monocarbonyls, and so they are usually considered functional groups of their own. These compounds can have symmetrical or unsymmetrical <a href="/wiki/Substituent" title="Substituent">substituents</a> on each carbonyl, and may also be functionally symmetrical (di<a href="/wiki/Aldehyde" title="Aldehyde">aldehydes</a>, di<a href="/wiki/Ketone" title="Ketone">ketones</a>, di<a href="/wiki/Ester" title="Ester">esters</a>, <i>etc.</i>) or unsymmetrical (keto-esters, <a href="/wiki/Keto-acid" class="mw-redirect" title="Keto-acid">keto-acids</a>, <i>etc.</i>). </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="1,2-Dicarbonyls"><span id="1.2C2-Dicarbonyls"></span>1,2-Dicarbonyls</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Dicarbonyl&action=edit&section=1" title="Edit section: 1,2-Dicarbonyls"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="1,2-Dialdehyde"><span id="1.2C2-Dialdehyde"></span>1,2-Dialdehyde</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Dicarbonyl&action=edit&section=2" title="Edit section: 1,2-Dialdehyde"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div><p> The only 1,2-dialdehyde is <a href="/wiki/Glyoxal" title="Glyoxal">glyoxal</a>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CHO)<sub class="template-chem2-sub">2</sub></span>. Like many alkyldialdehydes, glyoxal is encountered almost exclusively as its hydrate and oligomers thereof. These derivatives often behave equivalently to the <a href="/wiki/Aldehyde" title="Aldehyde">aldehydes</a> since hydration is reversible. Glyoxal condenses readily with <a href="/wiki/Amine" title="Amine">amines</a>. Via such reactions, it is a precursor to many <a href="/wiki/Heterocyclic_compound" title="Heterocyclic compound">heterocycles</a>, e.g. <a href="/wiki/Imidazole" title="Imidazole">imidazoles</a>.</p><figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Diacetyl.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ad/Diacetyl.svg/140px-Diacetyl.svg.png" decoding="async" width="140" height="164" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ad/Diacetyl.svg/210px-Diacetyl.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/ad/Diacetyl.svg/280px-Diacetyl.svg.png 2x" data-file-width="205" data-file-height="240" /></a><figcaption><a href="/wiki/Diacetyl" title="Diacetyl">Diacetyl</a>, the simplest diketone</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="1,2-Diketones"><span id="1.2C2-Diketones"></span>1,2-Diketones</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Dicarbonyl&action=edit&section=3" title="Edit section: 1,2-Diketones"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The principal diketone is <a href="/wiki/Diacetyl" title="Diacetyl">diacetyl</a>, also known as 2,3-butanedione, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>C(O)C(O)CH<sub class="template-chem2-sub">3</sub></span>. 1,2-Diketones are often generated by oxidation (dehydrogenation) of the <a href="/wiki/Diol" title="Diol">diols</a>:<sup id="cite_ref-Ullmann_1-0" class="reference"><a href="#cite_note-Ullmann-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {RCH(OH)CH(OH)R -> RC(O)C(O)R + 2 H2}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mtext>RCH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>OH</mtext> <mo stretchy="false">)</mo> </mrow> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>OH</mtext> <mo stretchy="false">)</mo> </mrow> <mtext>R</mtext> <mo stretchy="false">⟶</mo> <mtext>RC</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>O</mtext> <mo stretchy="false">)</mo> </mrow> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>O</mtext> <mo stretchy="false">)</mo> </mrow> <mtext>R</mtext> <mo>+</mo> <mn>2</mn> <mspace width="thinmathspace" /> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {RCH(OH)CH(OH)R -> RC(O)C(O)R + 2 H2}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/1be13f20dfef02014a3828ca316c5d97546c1666" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:47.28ex; height:3.009ex;" alt="{\displaystyle {\ce {RCH(OH)CH(OH)R -> RC(O)C(O)R + 2 H2}}}"></span></dd></dl> <p>2,3-Butanedione, <a href="/wiki/2,3-pentanedione" class="mw-redirect" title="2,3-pentanedione">2,3-pentanedione</a>, and 2,3-hexanedione are found in small amounts in various foods. They are used as aroma components in alcohol-free beverages and in baked goods.<sup id="cite_ref-Ullmann_1-1" class="reference"><a href="#cite_note-Ullmann-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Benzil" title="Benzil">Benzil</a>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(PhCO)<sub class="template-chem2-sub">2</sub></span>, is the corresponding diphenyl derivative. </p><p>A distinctive feature of 1,2-diketones is the long C-C bond linking the carbonyl groups. This bond distance is about 1.54 Å, compared to 1.45 Å for the corresponding bond in <a href="/wiki/1,3-butadiene" class="mw-redirect" title="1,3-butadiene">1,3-butadiene</a>. The effect is attributed to repulsion between the partial positive charges of the carbonyl carbon atoms.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>1,2-Diketones condense with many bifunctional nucleophiles, such as <a href="/wiki/Urea" title="Urea">urea</a> and <a href="/wiki/Thiourea" title="Thiourea">thiourea</a> to give heterocycles. Condensation with aromatic amines gives <a href="/wiki/Diimine" title="Diimine">diketimine</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(RC=NAr)<sub class="template-chem2-sub">2</sub></span>). </p><p>In the cases of <a href="/wiki/1,2-Cyclohexanedione" title="1,2-Cyclohexanedione">1,2-cyclohexanedione</a> and <a href="/wiki/1,2-Cyclopentanedione" title="1,2-Cyclopentanedione">1,2-cyclopentanedione</a>, the <a href="/wiki/Enol" title="Enol">enol</a> is about 1-3 kcal/mol more stable than the diketo form.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/O-quinone" class="mw-redirect" title="O-quinone">ortho-Quinone</a>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">4</sub>H<sub class="template-chem2-sub">4</sub>(CO)<sub class="template-chem2-sub">2</sub></span>, is the parent of a large family of 1,2-diketones. </p> <div class="mw-heading mw-heading3"><h3 id="1,2-Ketoaldehydes"><span id="1.2C2-Ketoaldehydes"></span>1,2-Ketoaldehydes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Dicarbonyl&action=edit&section=4" title="Edit section: 1,2-Ketoaldehydes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Methylglyoxal.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f3/Methylglyoxal.png/164px-Methylglyoxal.png" decoding="async" width="164" height="104" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f3/Methylglyoxal.png/246px-Methylglyoxal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f3/Methylglyoxal.png/328px-Methylglyoxal.png 2x" data-file-width="355" data-file-height="225" /></a><figcaption><a href="/wiki/Methylglyoxal" title="Methylglyoxal">Methylglyoxal</a>, a well-known 2-oxoaldehyde</figcaption></figure> <p>A well-known compound of this class is <a href="/wiki/Methylglyoxal" title="Methylglyoxal">methylglyoxal</a>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>C(O)CHO</span>, also known as pyruvaldehyde. These compounds are also known as <b>2-oxoaldehydes</b><sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> or α-ketoaldehydes. </p> <div class="mw-heading mw-heading3"><h3 id="1,2-Diesters_and_diacids"><span id="1.2C2-Diesters_and_diacids"></span>1,2-Diesters and diacids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Dicarbonyl&action=edit&section=5" title="Edit section: 1,2-Diesters and diacids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Oxalic_acid" title="Oxalic acid">Oxalic acid</a> and its esters define this family of compounds. The diacid is produced industrially by oxidation of waste sugars. It occurs naturally (as the conjugate base), notably in members of the plant species <i>Oxalis</i>. Condensation of the diesters with <a href="/wiki/Diamine" title="Diamine">diamines</a> gives cyclic diamides. </p> <div class="mw-heading mw-heading3"><h3 id="α-Keto-_and_formylcarboxylic_acids"><span id=".CE.B1-Keto-_and_formylcarboxylic_acids"></span>α-Keto- and formylcarboxylic acids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Dicarbonyl&action=edit&section=6" title="Edit section: α-Keto- and formylcarboxylic acids"><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:Ketocarboxylic_Acids_General_Formulae_V.1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Ketocarboxylic_Acids_General_Formulae_V.1.svg/220px-Ketocarboxylic_Acids_General_Formulae_V.1.svg.png" decoding="async" width="220" height="362" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Ketocarboxylic_Acids_General_Formulae_V.1.svg/330px-Ketocarboxylic_Acids_General_Formulae_V.1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/65/Ketocarboxylic_Acids_General_Formulae_V.1.svg/440px-Ketocarboxylic_Acids_General_Formulae_V.1.svg.png 2x" data-file-width="376" data-file-height="618" /></a><figcaption>Important keto-acids: <a href="/wiki/Pyruvic_acid" title="Pyruvic acid">pyruvic acid</a> (top), <a href="/wiki/Acetoacetic_acid" title="Acetoacetic acid">acetoacetic acid</a>, and <a href="/wiki/Levulinic_acid" title="Levulinic acid">levulinic acid</a> (bottom).</figcaption></figure> <p>α-Keto-acids and -esters are well known. <a href="/wiki/Pyruvic_acid" title="Pyruvic acid">Pyruvic acid</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>C(O)CO<sub class="template-chem2-sub">2</sub>H</span>) is the parent α-ketoacid. Its conjugate base, pyruvate (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>C(O)CO<span class="template-chem2-su"><span>−</span><span>2</span></span></span>), is a component of the <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">citric acid cycle</a> and product of glucose metabolism (<a href="/wiki/Glycolysis" title="Glycolysis">glycolysis</a>). The corresponding aldehyde-acid is <a href="/wiki/Glyoxalic_acid" class="mw-redirect" title="Glyoxalic acid">glyoxalic acid</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">HC(O)CO<sub class="template-chem2-sub">2</sub>H</span>). </p> <div class="mw-heading mw-heading2"><h2 id="1,3-Dicarbonyls"><span id="1.2C3-Dicarbonyls"></span>1,3-Dicarbonyls</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Dicarbonyl&action=edit&section=7" title="Edit section: 1,3-Dicarbonyls"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="1,3-Dialdehydes"><span id="1.2C3-Dialdehydes"></span>1,3-Dialdehydes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Dicarbonyl&action=edit&section=8" title="Edit section: 1,3-Dialdehydes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The parent 1,3-dialdehyde is <a href="/wiki/Malondialdehyde" title="Malondialdehyde">malondialdehyde</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">2</sub>(CHO)<sub class="template-chem2-sub">2</sub></span>), a β-dicarbonyl. Like most dialdehydes, it is rarely encountered as such. Instead it is handled almost exclusively as its hydrate, methyl acetal, and oligomers thereof. These derivatives often behave like the parent. Many 2-substituted derivatives are known. They are often prepared by alkylation of the <a href="/wiki/Enolate" title="Enolate">enolate</a> of malondialdehyde. </p> <div class="mw-heading mw-heading3"><h3 id="1,3-Diketones"><span id="1.2C3-Diketones"></span>1,3-Diketones</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Dicarbonyl&action=edit&section=9" title="Edit section: 1,3-Diketones"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>1,3-Diketones are also called β-diketones. An important member is <a href="/wiki/Acetylacetone" title="Acetylacetone">acetylacetone</a>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>C(O)CH<sub class="template-chem2-sub">2</sub>C(O)CH<sub class="template-chem2-sub">3</sub></span>. <a href="/wiki/Dimedone" title="Dimedone">Dimedone</a> is a cyclic 1,3-diketone. <a href="/wiki/1,3-Indandione" title="1,3-Indandione">1,3-Indandione</a> is the cyclic 1,3-diketone fused to a benzene ring. Acetylacetone is prepared industrially by the thermal rearrangement of isopropenylacetate.<sup id="cite_ref-Ullmann_1-2" class="reference"><a href="#cite_note-Ullmann-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Another cyclic 1,3-diketone is <a href="/wiki/2,2,4,4-Tetramethylcyclobutanedione" title="2,2,4,4-Tetramethylcyclobutanedione">2,2,4,4-tetramethylcyclobutanedione</a>, which is a precursor to a useful <a href="/wiki/Diol" title="Diol">diol</a>. </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {CH2(CH3)COC(O)Me -> MeC(O)CH2C(O)Me}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mtext>COC</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>O</mtext> <mo stretchy="false">)</mo> </mrow> <mtext>Me</mtext> <mo stretchy="false">⟶</mo> <mtext>MeC</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>O</mtext> <mo stretchy="false">)</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>O</mtext> <mo stretchy="false">)</mo> </mrow> <mtext>Me</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {CH2(CH3)COC(O)Me -> MeC(O)CH2C(O)Me}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/8b1333292bb65cb02ff7887688f02d21134e8c76" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:49.194ex; height:3.009ex;" alt="{\displaystyle {\ce {CH2(CH3)COC(O)Me -> MeC(O)CH2C(O)Me}}}"></span></dd></dl> <p>1,3-Diketones often <a href="/wiki/Tautomer" title="Tautomer">tautomerize</a> to an <a href="/wiki/Enol" title="Enol">enol</a> and ketol. They usually exist predominantly in the enol form <sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (March 2024)">citation needed</span></a></i>]</sup>. The percent enol in <a href="/wiki/Acetylacetone" title="Acetylacetone">acetylacetone</a>, <a href="/wiki/1,1,1-Trifluoroacetylacetone" title="1,1,1-Trifluoroacetylacetone">trifluoroacetylacetone</a>, and <a href="/wiki/Hexafluoroacetylacetone" title="Hexafluoroacetylacetone">hexafluoroacetylacetone</a> are 85, 97, and 100%, respectively (neat, 33 °C).<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> Cyclic 1,3-diketones, such as <a href="/wiki/1,3-Cyclohexanedione" title="1,3-Cyclohexanedione">1,3-cyclohexanedione</a> and <a href="/wiki/Dimedone" title="Dimedone">dimedone</a>, similarly exist significantly in the enol form. </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:AcacH.svg" class="mw-file-description" title="Scheme 1. Tautomerism of 2,4-pentanedione"><img alt="Scheme 1. Tautomerism of 2,4-pentanedione" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/75/AcacH.svg/300px-AcacH.svg.png" decoding="async" width="300" height="72" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/75/AcacH.svg/450px-AcacH.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/75/AcacH.svg/600px-AcacH.svg.png 2x" data-file-width="512" data-file-height="123" /></a></span></dd></dl> <p>Like other diketones, 1,3-diketones are versatile precursors to heterocycles. The conjugate base derived from 1,3-ketones can serve as <a href="/wiki/Ligand" title="Ligand">ligand</a> s to form <a href="/wiki/Metal_acetylacetonates" title="Metal acetylacetonates">metal acetylacetonate coordination complexes</a>. In the <a href="/wiki/DeMayo_reaction" title="DeMayo reaction">DeMayo reaction</a> 1,3-diketones react with alkenes in a photochemical <a href="/wiki/Pericyclic_reaction" title="Pericyclic reaction">pericyclic reaction</a> to form (substituted) 1,5-diketones. </p><p>Classically, 1,3-diketones are prepared by the <a href="/wiki/Claisen_condensation" title="Claisen condensation">Claisen condensation</a> of a ketone with an ester. </p> <div class="mw-heading mw-heading3"><h3 id="1,3-Diesters_and_diacids"><span id="1.2C3-Diesters_and_diacids"></span>1,3-Diesters and diacids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Dicarbonyl&action=edit&section=10" title="Edit section: 1,3-Diesters and diacids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Malonic_acid" title="Malonic acid">Malonic acid</a> and its esters are the parent members of this class of dicarbonyls. Also common are the 2-substituted derivatives with the formula <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RCH(CO<sub class="template-chem2-sub">2</sub>R)<sub class="template-chem2-sub">2</sub></span>, which arise by C-alkylation of the conjugate base (the enolate) <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NaCH(CO<sub class="template-chem2-sub">2</sub>R)<sub class="template-chem2-sub">2</sub></span>. </p> <div class="mw-heading mw-heading3"><h3 id="β-Keto-esters"><span id=".CE.B2-Keto-esters"></span>β-Keto-esters</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Dicarbonyl&action=edit&section=11" title="Edit section: β-Keto-esters"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>β-Keto-esters arise readily by the condensation of a pair of esters. A well known example is <a href="/wiki/Ethyl_acetoacetate" title="Ethyl acetoacetate">ethyl acetoacetate</a> (although it is prepared by ethanolysis of <a href="/wiki/Ketene" title="Ketene">ketene</a>). </p> <div class="mw-heading mw-heading2"><h2 id="1,4-Dicarbonyls"><span id="1.2C4-Dicarbonyls"></span>1,4-Dicarbonyls</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Dicarbonyl&action=edit&section=12" title="Edit section: 1,4-Dicarbonyls"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="1,4-Dialdehydes"><span id="1.2C4-Dialdehydes"></span>1,4-Dialdehydes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Dicarbonyl&action=edit&section=13" title="Edit section: 1,4-Dialdehydes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Succinaldehyde" title="Succinaldehyde">Succinaldehyde</a> (CH<sub>2</sub>CHO)<sub>2</sub> is the simplest and parent 1,4-dialdehyde. The aromatic derivative is <a href="/wiki/Phthalaldehyde" title="Phthalaldehyde">phthalaldehyde</a>. </p> <div class="mw-heading mw-heading3"><h3 id="1,4-Diketones"><span id="1.2C4-Diketones"></span>1,4-Diketones</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Dicarbonyl&action=edit&section=14" title="Edit section: 1,4-Diketones"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:P-Benzochinon.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e4/P-Benzochinon.svg/53px-P-Benzochinon.svg.png" decoding="async" width="53" height="133" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e4/P-Benzochinon.svg/80px-P-Benzochinon.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e4/P-Benzochinon.svg/106px-P-Benzochinon.svg.png 2x" data-file-width="70" data-file-height="176" /></a><figcaption><a href="/wiki/1,4-Benzoquinone" title="1,4-Benzoquinone">1,4-Benzoquinone</a> is a cyclic 1,4-doubly unsaturated diketone.</figcaption></figure> <p>Diketones with two methylene groups separating the carbonyl groups, also called γ-diketones, typically coexist with their <a href="/wiki/Enolization" class="mw-redirect" title="Enolization">enol</a> <a href="/wiki/Tautomer" title="Tautomer">tautomers</a>. The preeminent member is <a href="/wiki/Acetonylacetone" class="mw-redirect" title="Acetonylacetone">acetonylacetone</a>. 1,4-Diketones are useful precursors to heterocycles via the <a href="/wiki/Paal%E2%80%93Knorr_synthesis" title="Paal–Knorr synthesis">Paal–Knorr synthesis</a>, which gives <a href="/wiki/Pyrrole" title="Pyrrole">pyrroles</a>: </p> <dl><dd><span class="mw-default-size" typeof="mw:File"><a href="/wiki/File:Paal-Knorr_Pyrrole_Synthesis.svg" class="mw-file-description" title="Dehydration of 1,4-diketones gives furans."><img alt="Dehydration of 1,4-diketones gives furans." src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Paal-Knorr_Pyrrole_Synthesis.svg/331px-Paal-Knorr_Pyrrole_Synthesis.svg.png" decoding="async" width="331" height="94" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Paal-Knorr_Pyrrole_Synthesis.svg/497px-Paal-Knorr_Pyrrole_Synthesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Paal-Knorr_Pyrrole_Synthesis.svg/662px-Paal-Knorr_Pyrrole_Synthesis.svg.png 2x" data-file-width="331" data-file-height="94" /></a></span></dd></dl> <p>This reactivity is the basis of the <a href="/wiki/Neurotoxicity" title="Neurotoxicity">neurotoxicity</a> of γ-diketones.<sup id="cite_ref-tox_6-0" class="reference"><a href="#cite_note-tox-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> 1,4-Diketones are also precursor to <a href="/wiki/Furan" title="Furan">furans</a> and <a href="/wiki/Thiophene" title="Thiophene">thiophenes</a>. The condensation of 1,4-diketones (and related substrates) with <a href="/wiki/Hydrazine" title="Hydrazine">hydrazines</a> afford dihydropyridazines, which can be converted to <a href="/wiki/Pyridazine" title="Pyridazine">pyridazines</a>. </p><p><a href="/wiki/P-quinone" class="mw-redirect" title="P-quinone"><i>para</i>-quinone</a>, C<sub>4</sub>H<sub>4</sub>(CO)<sub>2</sub>, is the parent of a large family of 1,4-diketones. </p> <div class="mw-heading mw-heading3"><h3 id="1,4-Diesters_and_diacids"><span id="1.2C4-Diesters_and_diacids"></span>1,4-Diesters and diacids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Dicarbonyl&action=edit&section=15" title="Edit section: 1,4-Diesters and diacids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Succinic_acid" title="Succinic acid">Succinic acid</a> and its esters are the parent members of this family of 1,4-dicarbonyls. Succinic acid is notable as a component in the <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">citric acid cycle</a>. It forms a cyclic acid anhydride, <a href="/wiki/Succinic_anhydride" title="Succinic anhydride">succinic anhydride</a>. Unsaturated members include <a href="/wiki/Maleic_acid" title="Maleic acid">maleic</a> and <a href="/wiki/Fumaric_acid" title="Fumaric acid">fumaric acids</a> and their esters. </p> <div class="mw-heading mw-heading2"><h2 id="1,5-Dicarbonyls"><span id="1.2C5-Dicarbonyls"></span>1,5-Dicarbonyls</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Dicarbonyl&action=edit&section=16" title="Edit section: 1,5-Dicarbonyls"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="1,5-Dialdehydes"><span id="1.2C5-Dialdehydes"></span>1,5-Dialdehydes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Dicarbonyl&action=edit&section=17" title="Edit section: 1,5-Dialdehydes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Glutaraldehyde" title="Glutaraldehyde">Glutaraldehyde</a> (CH<sub>2</sub>)<sub>3</sub>(CHO)<sub>2</sub> is the simplest and parent 1,5-dialdehyde. It hydrates readily. The aromatic analogue is <a href="/wiki/Isophthalaldehyde" title="Isophthalaldehyde">isophthalaldehyde</a>.<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-heading3"><h3 id="1,5-Diketones"><span id="1.2C5-Diketones"></span>1,5-Diketones</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Dicarbonyl&action=edit&section=18" title="Edit section: 1,5-Diketones"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>These diketones have three methylene groups separating the carbonyl groups. </p> <div class="mw-heading mw-heading3"><h3 id="1,5-Diesters_and_diacids"><span id="1.2C5-Diesters_and_diacids"></span>1,5-Diesters and diacids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Dicarbonyl&action=edit&section=19" title="Edit section: 1,5-Diesters and diacids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Glutaric_acid" title="Glutaric acid">Glutaric acid</a> (CH<sub>2</sub>)<sub>3</sub>(CO<sub>2</sub>H)<sub>2</sub> is the parent 1,5-diacid. </p> <div class="mw-heading mw-heading2"><h2 id="Hydration_and_cyclization">Hydration and cyclization</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Dicarbonyl&action=edit&section=20" title="Edit section: Hydration and cyclization"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:SuccinaldehydeHydrate.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0a/SuccinaldehydeHydrate.png/122px-SuccinaldehydeHydrate.png" decoding="async" width="122" height="51" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0a/SuccinaldehydeHydrate.png/183px-SuccinaldehydeHydrate.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0a/SuccinaldehydeHydrate.png/244px-SuccinaldehydeHydrate.png 2x" data-file-width="544" data-file-height="228" /></a><figcaption>2,5-Dihydroxytetrahydrofuran, the hydrated form of <a href="/wiki/Succinaldehyde" title="Succinaldehyde">succinaldehyde</a>.</figcaption></figure> <p>Small aldehydes tend to hydrate. Hydration is prevalent for dialdehydes. Glyoxal forms a series of cyclic hydrates. <a href="/wiki/Succinaldehyde" title="Succinaldehyde">Succinaldehyde</a> hydrates readily to give 2,5-dihydroxytetrahydrofuran. The aromatic <a href="/wiki/Phthalaldehyde" title="Phthalaldehyde">phthalaldehyde</a> also forms hydrated. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Orthophthalaldehyde_and_hydrated_forms_001.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/88/Orthophthalaldehyde_and_hydrated_forms_001.png/400px-Orthophthalaldehyde_and_hydrated_forms_001.png" decoding="async" width="400" height="107" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/88/Orthophthalaldehyde_and_hydrated_forms_001.png/600px-Orthophthalaldehyde_and_hydrated_forms_001.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/88/Orthophthalaldehyde_and_hydrated_forms_001.png/800px-Orthophthalaldehyde_and_hydrated_forms_001.png 2x" data-file-width="1829" data-file-height="488" /></a><figcaption></figcaption></figure> <p>Similar hydration and cyclization equilibria apply to maleic dialdehyde,<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Glutaraldehyde" title="Glutaraldehyde">glutaraldehyde</a>, and <a href="/wiki/Adipaldehyde" title="Adipaldehyde">adipaldehyde</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Safety">Safety</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Dicarbonyl&action=edit&section=21" title="Edit section: Safety"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A number of dicarbonyl compounds are bioactive. Diacetyl is known to cause the lung disease <a href="/wiki/Obliterative_bronchiolitis" class="mw-redirect" title="Obliterative bronchiolitis">bronchiolitis obliterans</a> in those individuals exposed to it in an occupational setting.<sup id="cite_ref-:04_10-0" class="reference"><a href="#cite_note-:04-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Dialdehydes, e.g. glutaraldehyde and malonaldehyde, are fixatives or sterilizers. </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=Dicarbonyl&action=edit&section=22" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Triketone" title="Triketone">Triketone</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Dicarbonyl&action=edit&section=23" title="Edit section: References"><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"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-Ullmann-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ullmann_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ullmann_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Ullmann_1-2"><sup><i><b>c</b></i></sup></a></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="CITEREFHardo_SiegelManfred_Eggersdorfer2007" class="citation encyclopaedia cs1">Hardo Siegel; Manfred Eggersdorfer (2007). "Ketones". <i><a href="/wiki/Ullmann%27s_Encyclopedia_of_Industrial_Chemistry" title="Ullmann's Encyclopedia of Industrial Chemistry">Ullmann's Encyclopedia of Industrial Chemistry</a></i>. 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