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Available in 24 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-24" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">24 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Mol%C3%A8cula_amfip%C3%A0tica" title="Molècula amfipàtica – Catalan" lang="ca" hreflang="ca" data-title="Molècula amfipàtica" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Amfifil" title="Amfifil – Danish" lang="da" hreflang="da" data-title="Amfifil" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%91%CE%BC%CF%86%CE%AF%CF%86%CE%B9%CE%BB%CE%BF%CF%82" title="Αμφίφιλος – Greek" lang="el" hreflang="el" data-title="Αμφίφιλος" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Mol%C3%A9cula_anfif%C3%ADlica" title="Molécula anfifílica – Spanish" lang="es" hreflang="es" data-title="Molécula anfifílica" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Molekula_anfifiliko" title="Molekula anfifiliko – Basque" lang="eu" hreflang="eu" data-title="Molekula anfifiliko" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A2%D9%85%D9%81%DB%8C%D9%81%DB%8C%D9%84%DB%8C" title="آمفیفیلی – Persian" lang="fa" hreflang="fa" data-title="آمفیفیلی" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Amphiphile" title="Amphiphile – French" lang="fr" hreflang="fr" data-title="Amphiphile" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Anfip%C3%A1tico" title="Anfipático – Galician" lang="gl" hreflang="gl" data-title="Anfipático" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%89%E0%A4%AD%E0%A4%AF%E0%A4%B8%E0%A4%82%E0%A4%B5%E0%A5%87%E0%A4%A6%E0%A5%80" title="उभयसंवेदी – Hindi" lang="hi" hreflang="hi" data-title="उभयसंवेदी" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-ig mw-list-item"><a href="https://ig.wikipedia.org/wiki/Amphiphile" title="Amphiphile – Igbo" lang="ig" hreflang="ig" data-title="Amphiphile" data-language-autonym="Igbo" data-language-local-name="Igbo" class="interlanguage-link-target"><span>Igbo</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Amfifilik" title="Amfifilik – Indonesian" lang="id" hreflang="id" data-title="Amfifilik" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Anfifilico" title="Anfifilico – Italian" lang="it" hreflang="it" data-title="Anfifilico" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Amfipati%C5%A1kumas" title="Amfipatiškumas – Lithuanian" lang="lt" hreflang="lt" data-title="Amfipatiškumas" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-lmo mw-list-item"><a href="https://lmo.wikipedia.org/wiki/Amfifileg" title="Amfifileg – Lombard" lang="lmo" hreflang="lmo" data-title="Amfifileg" data-language-autonym="Lombard" data-language-local-name="Lombard" class="interlanguage-link-target"><span>Lombard</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Amfifiel" title="Amfifiel – Dutch" lang="nl" hreflang="nl" data-title="Amfifiel" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E4%B8%A1%E8%A6%AA%E5%AA%92%E6%80%A7%E5%88%86%E5%AD%90" title="両親媒性分子 – Japanese" lang="ja" hreflang="ja" data-title="両親媒性分子" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Amfifil" title="Amfifil – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Amfifil" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Mol%C3%A9cula_anfip%C3%A1tica" title="Molécula anfipática – Portuguese" lang="pt" hreflang="pt" data-title="Molécula anfipática" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Amfifil" title="Amfifil – Romanian" lang="ro" hreflang="ro" data-title="Amfifil" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Amfipaattinen" title="Amfipaattinen – Finnish" lang="fi" hreflang="fi" data-title="Amfipaattinen" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Amfifil" title="Amfifil – Swedish" lang="sv" hreflang="sv" data-title="Amfifil" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Amfifil" title="Amfifil – Turkish" lang="tr" hreflang="tr" data-title="Amfifil" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a 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srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fd/Phospholipid.svg/377px-Phospholipid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fd/Phospholipid.svg/502px-Phospholipid.svg.png 2x" data-file-width="290" data-file-height="176" /></a><figcaption><a href="/wiki/Phospholipid" title="Phospholipid">Phospholipids</a>, such as this <a href="/wiki/Glycerophospholipid" title="Glycerophospholipid">glycerophospholipid</a>, have amphipathic character.</figcaption></figure> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Phospholipids_aqueous_solution_structures.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Phospholipids_aqueous_solution_structures.svg/250px-Phospholipids_aqueous_solution_structures.svg.png" decoding="async" width="250" height="307" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Phospholipids_aqueous_solution_structures.svg/375px-Phospholipids_aqueous_solution_structures.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Phospholipids_aqueous_solution_structures.svg/500px-Phospholipids_aqueous_solution_structures.svg.png 2x" data-file-width="331" data-file-height="407" /></a><figcaption>Cross-section view of the structures that can be formed by <a href="/wiki/Phospholipids" class="mw-redirect" title="Phospholipids">biological amphiphiles</a> in aqueous solutions. Unlike this illustration, micelles are usually formed by non-biological, single-chain, amphiphiles, soaps or detergents, since it is difficult to fit two chains into this shape</figcaption></figure> <p>In <a href="/wiki/Chemistry" title="Chemistry">chemistry</a>, an <b>amphiphile</b> (from <a href="/wiki/Greek_language" title="Greek language">Greek</a> <i> </i>αμφις<i> (amphis)</i> 'both' and <i> </i>φιλíα<i> (<a href="/wiki/Philia" title="Philia">philia</a>)</i> 'love, friendship'), or <b>amphipath</b>, is a <a href="/wiki/Chemical_compound" title="Chemical compound">chemical compound</a> possessing both <a href="/wiki/Hydrophilic" class="mw-redirect" title="Hydrophilic">hydrophilic</a> (<i>water-loving</i>, <a href="/wiki/Chemical_polarity" title="Chemical polarity">polar</a>) and <a href="/wiki/Lipophilic" class="mw-redirect" title="Lipophilic">lipophilic</a> (<i>fat-loving</i>, nonpolar) properties.<sup id="cite_ref-openstax_1-0" class="reference"><a href="#cite_note-openstax-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Such a compound is called <b>amphiphilic</b> or <b>amphipathic</b>. Amphiphilic compounds include <a href="/wiki/Surfactants" class="mw-redirect" title="Surfactants">surfactants</a> and <a href="/wiki/Detergent" title="Detergent">detergents</a>. The <a href="/wiki/Phospholipid" title="Phospholipid">phospholipid</a> amphiphiles are the major structural component of <a href="/wiki/Cell_membrane" title="Cell membrane">cell membranes</a>. </p><p>Amphiphiles are the basis for a number of areas of research in chemistry and biochemistry, notably that of <a href="/wiki/Lipid_polymorphism" title="Lipid polymorphism">lipid polymorphism</a>. </p><p>Organic compounds containing hydrophilic groups at both ends of the molecule are called <a href="/wiki/Bolaamphiphile" title="Bolaamphiphile">bolaamphiphilic</a>. The <a href="/wiki/Micelle" title="Micelle">micelles</a> they form in the aggregate are <a href="/wiki/Prolate" class="mw-redirect" title="Prolate">prolate</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Structure">Structure</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amphiphile&action=edit&section=1" title="Edit section: Structure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Lipophilic" class="mw-redirect" title="Lipophilic">lipophilic</a> group is typically a large <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbon</a> <a href="/wiki/Moiety_(chemistry)" title="Moiety (chemistry)">moiety</a>, such as a long chain of the form CH<sub>3</sub>(CH<sub>2</sub>)<sub>n</sub>, with n > 4. </p><p>The <a href="/wiki/Hydrophilic" class="mw-redirect" title="Hydrophilic">hydrophilic</a> group falls into one of the following categories:<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. (June 2021)">citation needed</span></a></i>]</sup> </p> <ol><li>charged groups <ul><li><a href="/wiki/Anionic" class="mw-redirect" title="Anionic">anionic</a>. Examples, with the lipophilic part of the molecule represented by <i>R</i>, are: <ul><li><a href="/wiki/Carboxylate" title="Carboxylate">carboxylates</a>: RCO<sub>2</sub><sup>−</sup></li> <li><a href="/wiki/Sulfate" title="Sulfate">sulfates</a>: RSO<sub>4</sub><sup>−</sup></li> <li><a href="/wiki/Sulfonate" title="Sulfonate">sulfonates</a>: RSO<sub>3</sub><sup>−</sup></li> <li><a href="/wiki/Phosphate" title="Phosphate">phosphates</a> (the charged <a href="/wiki/Functional_group" title="Functional group">functional group</a> in <a href="/wiki/Phospholipid" title="Phospholipid">phospholipids</a>)</li></ul></li> <li><a href="/wiki/Cationic" class="mw-redirect" title="Cationic">cationic</a>. Examples: <ul><li><a href="/wiki/Ammonium" title="Ammonium">ammoniums</a>: RNH<sub>3</sub><sup>+</sup></li></ul></li></ul></li> <li>polar, uncharged groups. Examples are <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohols</a> with large R groups, such as diacyl glycerol (DAG), and <a href="/w/index.php?title=Oligo_ethylene_glycol&action=edit&redlink=1" class="new" title="Oligo ethylene glycol (page does not exist)">oligo ethylene glycol</a> with long alkyl chains.</li></ol> <p>Often, amphiphilic species have several lipophilic parts, several hydrophilic parts, or several of both. <a href="/wiki/Protein" title="Protein">Proteins</a> and some block <a href="/wiki/Copolymer" title="Copolymer">copolymers</a> are such examples.<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. (June 2021)">citation needed</span></a></i>]</sup> </p><p>Amphiphilic compounds have lipophilic (typically <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbon</a>) structures and hydrophilic polar functional groups (either ionic or uncharged).<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. (June 2021)">citation needed</span></a></i>]</sup> </p><p>As a result of having both lipophilic and hydrophilic portions, some amphiphilic compounds may dissolve in water and to some extent in <a href="/wiki/Apolar" class="mw-redirect" title="Apolar">non-polar</a> <a href="/wiki/Solvent" title="Solvent">organic solvents</a>. </p><p>When placed in an immiscible biphasic system consisting of aqueous and organic solvents, the amphiphilic compound will partition the two phases. The extent of the hydrophobic and hydrophilic portions determines the extent of partitioning.<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. (June 2021)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="Biological_role">Biological role</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amphiphile&action=edit&section=2" title="Edit section: Biological role"><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:The_lipid_and_lipid_bilayer.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/79/The_lipid_and_lipid_bilayer.png/220px-The_lipid_and_lipid_bilayer.png" decoding="async" width="220" height="260" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/7/79/The_lipid_and_lipid_bilayer.png 1.5x" data-file-width="300" data-file-height="354" /></a><figcaption>The lipid bilayer, the material that makes up cell membranes.</figcaption></figure> <p><a href="/wiki/Phospholipid" title="Phospholipid">Phospholipids</a>, a class of amphiphilic molecules, are the main components of <a href="/wiki/Biological_membrane" title="Biological membrane">biological membranes</a>. The amphiphilic nature of these molecules defines the way in which they form membranes. They arrange themselves into <a href="/wiki/Lipid_bilayer" title="Lipid bilayer">lipid bilayers</a>, by forming a sheet composed of two layers of lipids. Each layer forms by positioning their lypophilic chains to the same side of the layer. The two layers then stack such that their lyphphilic chains touch on the inside and their polar groups are outside facing the surrounding aqueous media. Thus the inside of the bilayer sheet is a non-polar region sandwiched between the two polar sheets.<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>Although <a href="/wiki/Phospholipid" title="Phospholipid">phospholipids</a> are the principal constituents of biological membranes,<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> there are other constituents, such as <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a> and <a href="/wiki/Glycolipid" title="Glycolipid">glycolipids</a>, which are also included in these structures and give them different physical and biological properties.<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. (June 2021)">citation needed</span></a></i>]</sup> </p><p>Many other amphiphilic compounds, such as <a href="/wiki/Pepducin" title="Pepducin">pepducins</a>, strongly interact with biological membranes by insertion of the hydrophobic part into the lipid membrane, while exposing the hydrophilic part to the aqueous medium, altering their physical behavior and sometimes disrupting them.<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. (June 2021)">citation needed</span></a></i>]</sup> </p><p>Aβ proteins form antiparallel β sheets which are strongly amphiphilic,<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> and which aggregate to form toxic oxidative Aβ fibrils. Aβ fibrils themselves are composed of amphiphilic 13-mer modular β sandwiches separated by reverse turns. Hydropathic waves optimize the description of the small (40,42 aa) plaque-forming (aggregative) Aβ fragments.<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> </p><p><a href="/wiki/Antimicrobial_peptide" class="mw-redirect" title="Antimicrobial peptide">Antimicrobial peptides</a> (AMPs) are another class of amphiphilic molecules, a <a href="/wiki/Big_data" title="Big data">big data</a> analysis showed that amphipathicity best distinguished between AMPs with and without anti-gram-negative bacteria activities. The higher amphipathicity, the better chances for AMPs possessing antibacterial and antifungal dual activities.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Examples">Examples</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amphiphile&action=edit&section=3" title="Edit section: Examples"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>There are several examples of molecules that present amphiphilic properties: </p><p><a href="/wiki/Hydrocarbon" title="Hydrocarbon">Hydrocarbon</a>-based <a href="/wiki/Surfactant" title="Surfactant">surfactants</a> are an example group of amphiphilic compounds. Their polar region can be either <a href="/wiki/Ion" title="Ion">ionic</a>, or non-ionic. Some typical members of this group are: <a href="/wiki/Sodium_dodecyl_sulfate" title="Sodium dodecyl sulfate">sodium dodecyl sulfate</a> (<a href="/wiki/Anion" class="mw-redirect" title="Anion">anionic</a>), <a href="/wiki/Benzalkonium_chloride" title="Benzalkonium chloride">benzalkonium chloride</a> (<a href="/wiki/Cation" class="mw-redirect" title="Cation">cationic</a>), <a href="/wiki/Cocamidopropyl_betaine" title="Cocamidopropyl betaine">cocamidopropyl betaine</a> (<a href="/wiki/Zwitterion" title="Zwitterion">zwitterionic</a>), and <a href="/wiki/1-octanol" class="mw-redirect" title="1-octanol">1-octanol</a> (long-chain alcohol, non-ionic).<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. (June 2021)">citation needed</span></a></i>]</sup> </p><p>Many biological compounds are amphiphilic: <a href="/wiki/Phospholipid" title="Phospholipid">phospholipids</a>, <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a>, <a href="/wiki/Glycolipid" title="Glycolipid">glycolipids</a>, <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acids</a>, <a href="/wiki/Bile_acid" title="Bile acid">bile acids</a>, <a href="/wiki/Saponin" title="Saponin">saponins</a>, local anaesthetics, etc.<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. (June 2021)">citation needed</span></a></i>]</sup> </p><p><a href="/wiki/Soap" title="Soap">Soap</a> is a common household amphiphilic surfactant compound. Soap mixed with water (polar, hydrophilic) is useful for cleaning oils and fats (non-polar, lipiphillic) from kitchenware, dishes, skin, clothing, etc. </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=Amphiphile&action=edit&section=4" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Amphoterism" title="Amphoterism">Amphoterism</a></li> <li><a href="/wiki/Abiogenesis#Possible_role_of_bubbles" title="Abiogenesis">Bubbles in abiogenesis</a></li> <li><a href="/wiki/Emulsion" title="Emulsion">Emulsion</a></li> <li>Free <a href="/wiki/Surface_energy" title="Surface energy">surface energy</a></li> <li><a href="/wiki/Surfactant" title="Surfactant">Surfactant</a></li> <li><a href="/wiki/Lipid_polymorphism" title="Lipid polymorphism">Lipid polymorphism</a></li> <li><a href="/wiki/Sodium_dodecyl_sulfate" title="Sodium dodecyl sulfate">Sodium dodecyl sulfate</a></li> <li><a href="/wiki/Wetting" title="Wetting">Wetting</a></li> <li><a href="/wiki/Viral_envelope" title="Viral envelope">Viral envelope</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=Amphiphile&action=edit&section=5" 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-openstax-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-openstax_1-0">^</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="CITEREFBetts" class="citation book cs1">Betts, J. Gordon. "3.1 The cell membrane". <a rel="nofollow" class="external text" href="https://openstax.org/books/anatomy-and-physiology/pages/3-1-the-cell-membrane"><i>Anatomy & physiology</i></a>. OpenStax. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-947172-04-3" title="Special:BookSources/978-1-947172-04-3"><bdi>978-1-947172-04-3</bdi></a><span class="reference-accessdate">. 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Retrieved <span class="nowrap">2020-06-02</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=The+Lipid+Chronicles&rft.atitle=Structure+of+a+Membrane&rft.date=2011-11-05&rft_id=http%3A%2F%2Fwww.samuelfurse.com%2F2011%2F11%2Fthe-structure-of-a-membrane%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAmphiphile" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSchubertBehlLesleyBrack1995" class="citation journal cs1">Schubert, D; Behl, C; Lesley, R; Brack, A; Dargusch, R; Sagara, Y; Kimura, H (14 March 1995). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC42408">"Amyloid peptides are toxic via a common oxidative mechanism"</a>. <i>Proceedings of the National Academy of Sciences of the United States of America</i>. <b>92</b> (6): 1989–93. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1995PNAS...92.1989S">1995PNAS...92.1989S</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1073%2Fpnas.92.6.1989">10.1073/pnas.92.6.1989</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC42408">42408</a></span>. <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/7892213">7892213</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Proceedings+of+the+National+Academy+of+Sciences+of+the+United+States+of+America&rft.atitle=Amyloid+peptides+are+toxic+via+a+common+oxidative+mechanism&rft.volume=92&rft.issue=6&rft.pages=1989-93&rft.date=1995-03-14&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC42408%23id-name%3DPMC&rft_id=info%3Apmid%2F7892213&rft_id=info%3Adoi%2F10.1073%2Fpnas.92.6.1989&rft_id=info%3Abibcode%2F1995PNAS...92.1989S&rft.aulast=Schubert&rft.aufirst=D&rft.au=Behl%2C+C&rft.au=Lesley%2C+R&rft.au=Brack%2C+A&rft.au=Dargusch%2C+R&rft.au=Sagara%2C+Y&rft.au=Kimura%2C+H&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC42408&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAmphiphile" class="Z3988"></span></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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPhillips2015" class="citation journal cs1">Phillips, J.C. (20 May 2015). "Thermodynamic description of Beta amyloid formation using physicochemical scales and fractal bioinformatic scales". <i>ACS Chemical Neuroscience</i>. <b>6</b> (5): 745–50. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fcn5001793">10.1021/cn5001793</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/25702750">25702750</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=ACS+Chemical+Neuroscience&rft.atitle=Thermodynamic+description+of+Beta+amyloid+formation+using+physicochemical+scales+and+fractal+bioinformatic+scales&rft.volume=6&rft.issue=5&rft.pages=745-50&rft.date=2015-05-20&rft_id=info%3Adoi%2F10.1021%2Fcn5001793&rft_id=info%3Apmid%2F25702750&rft.aulast=Phillips&rft.aufirst=J.C.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAmphiphile" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChien-Kuo_WangLing-Yi_ShihKuan_Y._Chang2017" class="citation journal cs1">Chien-Kuo Wang; Ling-Yi Shih; Kuan Y. Chang (2017-11-22). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6150348">"Large-scale analysis of antimicrobial activities in relation to amphipathicity and charge reveals novel characterization of antimicrobial peptides"</a>. <i>Molecules</i>. <b>22</b> (11): 2037. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.3390%2Fmolecules22112037">10.3390/molecules22112037</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6150348">6150348</a></span>. <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/29165350">29165350</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Molecules&rft.atitle=Large-scale+analysis+of+antimicrobial+activities+in+relation+to+amphipathicity+and+charge+reveals+novel+characterization+of+antimicrobial+peptides&rft.volume=22&rft.issue=11&rft.pages=2037&rft.date=2017-11-22&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6150348%23id-name%3DPMC&rft_id=info%3Apmid%2F29165350&rft_id=info%3Adoi%2F10.3390%2Fmolecules22112037&rft.au=Chien-Kuo+Wang&rft.au=Ling-Yi+Shih&rft.au=Kuan+Y.+Chang&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6150348&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAmphiphile" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a 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(equation)</a></li> <li><a href="/wiki/Apparent_molar_property" title="Apparent molar property">Apparent molar property</a></li> <li><a href="/wiki/Miscibility_gap" title="Miscibility gap">Miscibility gap</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Concentration" title="Concentration">Concentration</a><br />and related quantities</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/Molar_concentration" title="Molar concentration">Molar concentration</a></li> <li><a href="/wiki/Mass_concentration_(chemistry)" title="Mass concentration (chemistry)">Mass concentration</a></li> <li><a href="/wiki/Number_density" title="Number density">Number concentration</a></li> <li><a href="/wiki/Volume_fraction" title="Volume fraction">Volume concentration</a></li> <li><a href="/wiki/Equivalent_concentration" title="Equivalent concentration">Normality</a></li> <li><a href="/wiki/Molality" title="Molality">Molality</a></li> <li><a href="/wiki/Mole_fraction" title="Mole fraction">Mole fraction</a></li> <li><a href="/wiki/Mass_fraction_(chemistry)" title="Mass fraction (chemistry)">Mass fraction</a></li> <li><a href="/wiki/Natural_abundance" title="Natural abundance">Isotopic abundance</a></li> <li><a href="/wiki/Mixing_ratio" title="Mixing ratio">Mixing ratio</a></li> <li><a href="/wiki/Ternary_plot" title="Ternary plot">Ternary plot</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Solubility" title="Solubility">Solubility</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Solubility_equilibrium" title="Solubility equilibrium">Solubility equilibrium</a></li> <li><a href="/wiki/Total_dissolved_solids" title="Total dissolved solids">Total dissolved solids</a></li> <li><a href="/wiki/Solvation" title="Solvation">Solvation</a></li> <li><a href="/wiki/Solvation_shell" title="Solvation shell">Solvation shell</a></li> <li><a href="/wiki/Enthalpy_change_of_solution" title="Enthalpy change of solution">Enthalpy of solution</a></li> <li><a href="/wiki/Lattice_energy" title="Lattice energy">Lattice energy</a></li> <li><a href="/wiki/Raoult%27s_law" title="Raoult's law">Raoult's law</a></li> <li><a href="/wiki/Henry%27s_law" title="Henry's law">Henry's law</a></li> <li><a href="/wiki/Solubility_table" title="Solubility table">Solubility table (data)</a></li> <li><a href="/wiki/Solubility_chart" title="Solubility chart">Solubility chart</a></li> <li><a href="/wiki/Miscibility" title="Miscibility">Miscibility</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Solvent" title="Solvent">Solvent</a></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/Category:Solvents" title="Category:Solvents">Category</a>)</li> <li><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">Acid dissociation constant</a></li> <li><a href="/wiki/Protic_solvent" title="Protic solvent">Protic solvent</a></li> <li><a href="/wiki/Polar_aprotic_solvent" title="Polar aprotic solvent">Polar aprotic solvent</a></li> <li><a href="/wiki/Inorganic_nonaqueous_solvent" title="Inorganic nonaqueous solvent">Inorganic nonaqueous solvent</a></li> <li><a href="/wiki/Solvation" title="Solvation">Solvation</a></li> <li><a href="/wiki/List_of_boiling_and_freezing_information_of_solvents" title="List of boiling and freezing information of solvents">List of boiling and freezing information of solvents</a></li> <li><a href="/wiki/Partition_coefficient" title="Partition coefficient">Partition coefficient</a></li> <li><a href="/wiki/Chemical_polarity" title="Chemical polarity">Polarity</a></li> <li><a href="/wiki/Hydrophobe" title="Hydrophobe">Hydrophobe</a></li> <li><a href="/wiki/Hydrophile" title="Hydrophile">Hydrophile</a></li> <li><a href="/wiki/Lipophilicity" title="Lipophilicity">Lipophilic</a></li> <li><a class="mw-selflink selflink">Amphiphile</a></li> <li><a href="/wiki/Lyonium_ion" title="Lyonium ion">Lyonium ion</a></li> <li><a href="/wiki/Lyate_ion" title="Lyate ion">Lyate ion</a></li></ul> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Amphiphile&oldid=1249577935">https://en.wikipedia.org/w/index.php?title=Amphiphile&oldid=1249577935</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" 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