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acid</span></h1> <div class="tagline"></div> </div> <ul id="p-associated-pages" class="minerva__tab-container"> <li class="minerva__tab selected"> <a class="minerva__tab-text" href="/wiki/Cinnamic_acid" rel="" data-event-name="tabs.subject">Article</a> </li> <li class="minerva__tab "> <a class="minerva__tab-text" href="/wiki/Talk:Cinnamic_acid" rel="discussion" data-event-name="tabs.talk">Talk</a> </li> </ul> <nav class="page-actions-menu"> <ul id="p-views" class="page-actions-menu__list"> <li id="language-selector" class="page-actions-menu__list-item"> <a role="button" href="#p-lang" data-mw="interface" data-event-name="menu.languages" title="Language" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet language-selector"> <span class="minerva-icon minerva-icon--language"></span> <span>Language</span> </a> </li> <li id="page-actions-watch" class="page-actions-menu__list-item"> <a role="button" id="ca-watch" href="/w/index.php?title=Special:UserLogin&returnto=Cinnamic+acid" data-event-name="menu.watch" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet menu__item--page-actions-watch"> <span class="minerva-icon minerva-icon--star"></span> <span>Watch</span> </a> </li> <li id="page-actions-edit" class="page-actions-menu__list-item"> <a role="button" id="ca-edit" href="/w/index.php?title=Cinnamic_acid&action=edit" data-event-name="menu.edit" data-mw="interface" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet edit-page menu__item--page-actions-edit"> <span class="minerva-icon minerva-icon--edit"></span> <span>Edit</span> </a> </li> </ul> </nav>  <div id="mw-content-subtitle"></div> </div> <div id="bodyContent" class="content"> <div id="mw-content-text" class="mw-body-content"><script>function mfTempOpenSection(id){var block=document.getElementById("mf-section-"+id);block.className+=" open-block";block.previousSibling.className+=" open-block";}</script><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><section class="mf-section-0" id="mf-section-0"><style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <p><b>Cinnamic acid</b> is an <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> with the formula <a href="/wiki/Phenyl" class="mw-redirect" title="Phenyl">C<sub>6</sub>H<sub>5</sub></a>-CH=CH-<a href="/wiki/Carboxylic_acid" title="Carboxylic acid">COOH</a>. It is a white crystalline compound that is slightly <a href="/wiki/Soluble" class="mw-redirect" title="Soluble">soluble</a> in water, and freely soluble in many organic solvents.<sup id="cite_ref-Merck-1996_4-0" class="reference"><a href="#cite_note-Merck-1996-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Classified as an unsaturated <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a>, it occurs naturally in a number of plants. It exists as both a <a href="/wiki/Cis%E2%80%93trans_isomerism" title="Cis–trans isomerism"><i>cis</i> and a <i>trans</i> isomer</a>, although the latter is more common.<sup id="cite_ref-Garbe-2012_5-0" class="reference"><a href="#cite_note-Garbe-2012-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><table class="infobox ib-chembox"> <caption>Cinnamic acid </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Zimts%C3%A4ure_-_Cinnamic_acid.svg" class="mw-file-description" title="Skeletal formula of trans-cinnamic acid"><img alt="Skeletal formula of trans-cinnamic acid" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Zimts%C3%A4ure_-_Cinnamic_acid.svg/220px-Zimts%C3%A4ure_-_Cinnamic_acid.svg.png" decoding="async" width="220" height="121" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Zimts%C3%A4ure_-_Cinnamic_acid.svg/330px-Zimts%C3%A4ure_-_Cinnamic_acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Zimts%C3%A4ure_-_Cinnamic_acid.svg/440px-Zimts%C3%A4ure_-_Cinnamic_acid.svg.png 2x" data-file-width="234" data-file-height="129"></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Cinnamic_acid_3D_ball.png" class="mw-file-description" title="Ball-and-stick model of the trans-cinnamic acid molecule"><img alt="Ball-and-stick model of the trans-cinnamic acid molecule" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a8/Cinnamic_acid_3D_ball.png/220px-Cinnamic_acid_3D_ball.png" decoding="async" width="220" height="130" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a8/Cinnamic_acid_3D_ball.png/330px-Cinnamic_acid_3D_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a8/Cinnamic_acid_3D_ball.png/440px-Cinnamic_acid_3D_ball.png 2x" data-file-width="2000" data-file-height="1181"></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Cinnamic_acid.jpg" class="mw-file-description" title="Sample of the compound cinnamic acid in powder form"><img alt="Sample of the compound cinnamic acid in powder form" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Cinnamic_acid.jpg/220px-Cinnamic_acid.jpg" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Cinnamic_acid.jpg/330px-Cinnamic_acid.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/77/Cinnamic_acid.jpg/440px-Cinnamic_acid.jpg 2x" data-file-width="4829" data-file-height="3621"></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">(2<i>E</i>)-3-Phenylprop-2-enoic acid</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">Cinnamic acid</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><i>trans</i>-Cinnamic acid<br>Phenylacrylic acid<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><br>Cinnamylic acid<br>3-Phenylacrylic acid<br>(<i>E</i>)-Cinnamic acid<br>Benzenepropenoic acid<br>Isocinnamic acid</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=140-10-3">140-10-3</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC%28O%29%5CC%3DC%5Cc1ccccc1">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td>3DMet </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.3dmet.dna.affrc.go.jp"><a rel="nofollow" class="external text" href="http://www.3dmet.dna.affrc.go.jp/cgi/show_data.php?acc=B00108">B00108</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Beilstein_database" title="Beilstein database">Beilstein Reference</a></div> </td> <td>1905952 </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=35697">CHEBI:35697</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL27246">ChEMBL27246</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.392447.html">392447</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.004.908">100.004.908</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q164785#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20"></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>205-398-1</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Gmelin_database" title="Gmelin database">Gmelin Reference</a></div> </td> <td>3731 </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IUPHAR/BPS" class="mw-redirect" title="IUPHAR/BPS">IUPHAR/BPS</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=summary&ligandId=3203">3203</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C00423">C00423</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/444539">444539</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/U14A832J8D">U14A832J8D</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600"></span></span><span style="display:none">N</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID5022489">DTXSID5022489</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q164785#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20"></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: WBYWAXJHAXSJNI-VOTSOKGWSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: WBYWAXJHAXSJNI-VOTSOKGWBT</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">O=C(O)\C=C\c1ccccc1</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>9</sub><span title="Hydrogen">H</span><sub>8</sub><span title="Oxygen">O</span><sub>2</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002148161000000000♠"></span>148.161</span> g·mol<sup>−1</sup> </td></tr> <tr> <td>Appearance </td> <td>White monoclinic crystals </td></tr> <tr> <td><a href="/wiki/Odor" title="Odor">Odor</a> </td> <td>Honey-like<sup id="cite_ref-flavornet.org_2-0" class="reference"><a href="#cite_note-flavornet.org-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.2475 g/cm<sup>3</sup><sup id="cite_ref-GESTIS-IOSH_3-0" class="reference"><a href="#cite_note-GESTIS-IOSH-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>133 °C (271 °F; 406 K)<sup id="cite_ref-GESTIS-IOSH_3-2" class="reference"><a href="#cite_note-GESTIS-IOSH-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>300 °C (572 °F; 573 K)<sup id="cite_ref-GESTIS-IOSH_3-3" class="reference"><a href="#cite_note-GESTIS-IOSH-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>500 mg/L<sup id="cite_ref-GESTIS-IOSH_3-1" class="reference"><a href="#cite_note-GESTIS-IOSH-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">Acidity</a> (p<i>K</i><sub>a</sub>) </td> <td>4.44 </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Magnetic_susceptibility" title="Magnetic susceptibility">Magnetic susceptibility</a> (χ)</div> </td> <td><span class="nowrap"><span data-sort-value="3004216399999999999♠"></span>−7.836<span style="margin-left:0.25em;margin-right:0.15em;">×</span>10<sup>−5</sup> cm<sup>3</sup>/mol</span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-exclam.svg" class="mw-file-description" title="GHS07: Exclamation mark"><img alt="GHS07: Exclamation mark" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/50px-GHS-pictogram-exclam.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/75px-GHS-pictogram-exclam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/100px-GHS-pictogram-exclam.svg.png 2x" data-file-width="512" data-file-height="512"></a></span> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td><b>Warning</b> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H315: Causes skin irritation">H315</abbr>, <abbr class="abbr" title="H319: Causes serious eye irritation">H319</abbr>, <abbr class="abbr" title="H335: May cause respiratory irritation">H335</abbr> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P261: Avoid breathing dust/fume/gas/mist/vapours/spray.">P261</abbr>, <abbr class="abbr" title="P264: Wash ... thoroughly after handling.">P264</abbr>, <abbr class="abbr" title="P271: Use only outdoors or in a well-ventilated area.">P271</abbr>, <abbr class="abbr" title="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P302+P352: IF ON SKIN: Wash with soap and water.">P302+P352</abbr>, <abbr class="abbr" title="P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing.">P304+P340</abbr>, <abbr class="abbr" title="P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.">P305+P351+P338</abbr>, <abbr class="abbr" title="P312: Call a POISON CENTER or doctor/physician if you feel unwell.">P312</abbr>, <abbr class="abbr" title="P321: Specific treatment (see ... on this label).">P321</abbr>, <abbr class="abbr" title="P332+P313: If skin irritation occurs: Get medical advice/attention.">P332+P313</abbr>, <abbr class="abbr" title="P337+P313: If eye irritation persists: Get medical advice/attention.">P337+P313</abbr>, <abbr class="abbr" title="P362: Take off contaminated clothing.">P362</abbr>, <abbr class="abbr" title="P403+P233: Store in a well ventilated place. Keep container tightly closed.">P403+P233</abbr>, <abbr class="abbr" title="P405: Store locked up.">P405</abbr>, <abbr class="abbr" title="P501: Dispose of contents/container to ...">P501</abbr> </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_811dcee2cbfc5fb2"></span><map name="ImageMap_811dcee2cbfc5fb2"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" title="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine"><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil"><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen"><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code"></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" class="notheme mw-no-invert">1</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" class="notheme mw-no-invert">1</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" class="notheme mw-no-invert">0</span></a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>> 100 °C (212 °F; 373 K)<sup id="cite_ref-GESTIS-IOSH_3-4" class="reference"><a href="#cite_note-GESTIS-IOSH-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><a href="/wiki/Benzoic_acid" title="Benzoic acid">Benzoic acid</a>, <a href="/wiki/Phenylacetic_acid" title="Phenylacetic acid">Phenylacetic acid</a>, <a href="/wiki/Phenylpropanoic_acid" title="Phenylpropanoic acid">Phenylpropanoic acid</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600"></span></span><span style="display:none">N</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=476994181&page2=Cinnamic+acid">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600"></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table> <div id="toc" class="toc" role="navigation" aria-labelledby="mw-toc-heading"><input type="checkbox" role="button" id="toctogglecheckbox" class="toctogglecheckbox" style="display:none"><div class="toctitle" lang="en" dir="ltr"><h2 id="mw-toc-heading">Contents</h2><span class="toctogglespan"><label class="toctogglelabel" for="toctogglecheckbox"></label></span></div> <ul> <li class="toclevel-1 tocsection-1"><a href="#Occurrence_and_production"><span class="tocnumber">1</span> <span class="toctext">Occurrence and production</span></a> <ul> <li class="toclevel-2 tocsection-2"><a href="#Biosynthesis"><span class="tocnumber">1.1</span> <span class="toctext">Biosynthesis</span></a></li> <li class="toclevel-2 tocsection-3"><a href="#Natural_occurrence"><span class="tocnumber">1.2</span> <span class="toctext">Natural occurrence</span></a></li> <li class="toclevel-2 tocsection-4"><a href="#Synthesis"><span class="tocnumber">1.3</span> <span class="toctext">Synthesis</span></a></li> </ul> </li> <li class="toclevel-1 tocsection-5"><a href="#Metabolism"><span class="tocnumber">2</span> <span class="toctext">Metabolism</span></a></li> <li class="toclevel-1 tocsection-6"><a href="#Uses"><span class="tocnumber">3</span> <span class="toctext">Uses</span></a></li> <li class="toclevel-1 tocsection-7"><a href="#References"><span class="tocnumber">4</span> <span class="toctext">References</span></a></li> </ul> </div> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(1)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="Occurrence_and_production">Occurrence and production</h2><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Cinnamic_acid&action=edit&section=1" title="Edit section: Occurrence and production" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div><section class="mf-section-1 collapsible-block" id="mf-section-1"> <div class="mw-heading mw-heading3"><h3 id="Biosynthesis">Biosynthesis</h3><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Cinnamic_acid&action=edit&section=2" title="Edit section: Biosynthesis" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div> <p>Cinnamic acid is a central intermediate in the biosynthesis of a myriad of natural products including lignols (precursors to <a href="/wiki/Lignin" title="Lignin">lignin</a> and <a href="/wiki/Lignocellulose" class="mw-redirect" title="Lignocellulose">lignocellulose</a>), <a href="/wiki/Flavonoids" class="mw-redirect" title="Flavonoids">flavonoids</a>, <a href="/wiki/Isoflavonoids" class="mw-redirect" title="Isoflavonoids">isoflavonoids</a>, <a href="/wiki/Coumarin" title="Coumarin">coumarins</a>, <a href="/wiki/Aurones" class="mw-redirect" title="Aurones">aurones</a>, <a href="/wiki/Stilbenes" class="mw-redirect" title="Stilbenes">stilbenes</a>, <a href="/wiki/Catechin" title="Catechin">catechin</a>, and <a href="/wiki/Phenylpropanoid" title="Phenylpropanoid">phenylpropanoids</a>. Its <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthesis</a> involves the action of the <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> <a href="/wiki/Phenylalanine_ammonia-lyase" title="Phenylalanine ammonia-lyase">phenylalanine ammonia-lyase</a> (PAL) on <a href="/wiki/Phenylalanine" title="Phenylalanine">phenylalanine</a>.<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-heading3"><h3 id="Natural_occurrence">Natural occurrence</h3><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Cinnamic_acid&action=edit&section=3" title="Edit section: Natural occurrence" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div> <p>It is obtained from oil of <a href="/wiki/Cinnamon" title="Cinnamon">cinnamon</a>, or from <a href="/wiki/Balsam" title="Balsam">balsams</a> such as <a href="/wiki/Storax" class="mw-redirect" title="Storax">storax</a>.<sup id="cite_ref-Merck-1996_4-1" class="reference"><a href="#cite_note-Merck-1996-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> It is also found in <a href="/wiki/Shea_butter" title="Shea butter">shea butter</a>.<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 2023)">citation needed</span></a></i>]</sup> Cinnamic acid has a <a href="/wiki/Honey" title="Honey">honey</a>-like odor;<sup id="cite_ref-flavornet.org_2-1" class="reference"><a href="#cite_note-flavornet.org-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> and its more volatile ethyl ester, <a href="/wiki/Ethyl_cinnamate" title="Ethyl cinnamate">ethyl cinnamate</a>, is a flavor component in the essential oil of <a href="/wiki/Cinnamon" title="Cinnamon">cinnamon</a>, in which related <a href="/wiki/Cinnamaldehyde" title="Cinnamaldehyde">cinnamaldehyde</a> is the major constituent. It is also found in wood from many diverse tree species.<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="Synthesis">Synthesis</h3><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Cinnamic_acid&action=edit&section=4" title="Edit section: Synthesis" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div> <p>Cinnamic acid was first synthesized by the base-catalysed condensation of <a href="/wiki/Acetyl_chloride" title="Acetyl chloride">acetyl chloride</a> and <a href="/wiki/Benzaldehyde" title="Benzaldehyde">benzaldehyde</a>, followed by <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a> of the <a href="/wiki/Acid_chloride" class="mw-redirect" title="Acid chloride">acid chloride</a> product.<sup id="cite_ref-Garbe-2012_5-1" class="reference"><a href="#cite_note-Garbe-2012-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> In 1890, <a href="/wiki/Rainer_Ludwig_Claisen" title="Rainer Ludwig Claisen">Rainer Ludwig Claisen</a> described the synthesis of <a href="/wiki/Ethyl_cinnamate" title="Ethyl cinnamate">ethyl cinnamate</a> via the reaction of <a href="/wiki/Ethyl_acetate" title="Ethyl acetate">ethyl acetate</a> with benzaldehyde in the presence of <a href="/wiki/Sodium" title="Sodium">sodium</a> as base.<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> Another way of preparing cinnamic acid is by the <a href="/wiki/Knoevenagel_condensation" title="Knoevenagel condensation">Knoevenagel condensation</a> reaction.<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> The reactants for this are benzaldehyde and <a href="/wiki/Malonic_acid" title="Malonic acid">malonic acid</a> in the presence of a weak base, followed by acid-catalyzed <a href="/wiki/Decarboxylation" title="Decarboxylation">decarboxylation</a>. It can also be prepared by oxidation of <a href="/wiki/Cinnamaldehyde" title="Cinnamaldehyde">cinnamaldehyde</a>, condensation of <a href="/wiki/Benzal_chloride" title="Benzal chloride">benzal chloride</a> and sodium acetate (followed by acid hydrolysis), and the <a href="/wiki/Perkin_reaction" title="Perkin reaction">Perkin reaction</a>. The oldest commercially used route to cinnamic acid involves the <a href="/wiki/Perkin_reaction" title="Perkin reaction">Perkin reaction</a>, which is given in the following scheme<sup id="cite_ref-Garbe-2012_5-2" class="reference"><a href="#cite_note-Garbe-2012-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Zimts%C3%A4ure_nach_Perkin.svg" class="mw-file-description"><noscript><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/20/Zimts%C3%A4ure_nach_Perkin.svg/450px-Zimts%C3%A4ure_nach_Perkin.svg.png" decoding="async" width="450" height="137" class="mw-file-element" data-file-width="992" data-file-height="301"></noscript><span class="lazy-image-placeholder" style="width: 450px;height: 137px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/2/20/Zimts%C3%A4ure_nach_Perkin.svg/450px-Zimts%C3%A4ure_nach_Perkin.svg.png" data-width="450" data-height="137" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/20/Zimts%C3%A4ure_nach_Perkin.svg/675px-Zimts%C3%A4ure_nach_Perkin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/20/Zimts%C3%A4ure_nach_Perkin.svg/900px-Zimts%C3%A4ure_nach_Perkin.svg.png 2x" data-class="mw-file-element"> </span></a><figcaption>Synthesis of cinnamic acid via the <a href="/wiki/Perkin_reaction" title="Perkin reaction">Perkin reaction</a>.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup></figcaption></figure></dd></dl> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(2)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="Metabolism">Metabolism</h2><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Cinnamic_acid&action=edit&section=5" title="Edit section: Metabolism" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div><section class="mf-section-2 collapsible-block" id="mf-section-2"> <p>Cinnamic acid, obtained from autoxidation of <a href="/wiki/Cinnamaldehyde" title="Cinnamaldehyde">cinnamaldehyde</a>, is metabolized into <a href="/wiki/Sodium_benzoate" title="Sodium benzoate">sodium benzoate</a> in the liver.<sup id="cite_ref-Jana-2013_11-0" class="reference"><a href="#cite_note-Jana-2013-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(3)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="Uses">Uses</h2><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Cinnamic_acid&action=edit&section=6" title="Edit section: Uses" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div><section class="mf-section-3 collapsible-block" id="mf-section-3"> <p>Cinnamic acid is used in flavorings, <a href="/wiki/Indigo_dye#Chemical_synthesis" title="Indigo dye">synthetic indigo</a>, and certain <a href="/wiki/Pharmaceutical" class="mw-redirect" title="Pharmaceutical">pharmaceuticals</a>. A major use is as a precursor to produce <a href="/wiki/Methyl_cinnamate" title="Methyl cinnamate">methyl cinnamate</a>, <a href="/wiki/Ethyl_cinnamate" title="Ethyl cinnamate">ethyl cinnamate</a>, and <a href="/wiki/Benzyl_cinnamate" title="Benzyl cinnamate">benzyl cinnamate</a> for the perfume industry.<sup id="cite_ref-Merck-1996_4-2" class="reference"><a href="#cite_note-Merck-1996-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Cinnamic acid is a precursor to the sweetener <a href="/wiki/Aspartame" title="Aspartame">aspartame</a> via enzyme-catalysed amination with <a href="/wiki/Phenylalanine" title="Phenylalanine">phenylalanine</a>.<sup id="cite_ref-Garbe-2012_5-3" class="reference"><a href="#cite_note-Garbe-2012-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Cinnamic acid can <a href="/wiki/Dimer_(chemistry)" class="mw-redirect" title="Dimer (chemistry)">dimerize</a> in non-polar solvents resulting in different <a href="/wiki/Free-energy_relationship" title="Free-energy relationship">linear free energy relationships</a>.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(4)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="References">References</h2><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Cinnamic_acid&action=edit&section=7" title="Edit section: References" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div><section class="mf-section-4 collapsible-block" id="mf-section-4"> <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-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</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 class="citation encyclopaedia cs1"><span class="cs1-ws-icon" title="s:1911 Encyclopædia Britannica/Cinnamic Acid"><a class="external text" href="https://en.wikisource.org/wiki/1911_Encyclop%C3%A6dia_Britannica/Cinnamic_Acid">"Cinnamic Acid" </a></span>. <i><a href="/wiki/Encyclop%C3%A6dia_Britannica_Eleventh_Edition" title="Encyclopædia Britannica Eleventh Edition">Encyclopædia Britannica</a></i>. Vol. 6 (11th ed.). 1911. p. 376.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Cinnamic+Acid&rft.btitle=Encyclop%C3%A6dia+Britannica&rft.pages=376&rft.edition=11th&rft.date=1911&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACinnamic+acid" class="Z3988"></span></span> </li> <li id="cite_note-flavornet.org-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-flavornet.org_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-flavornet.org_2-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.flavornet.org/info/140-10-3.html">"Cinnamic acid"</a>. <i>flavornet.org</i>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=flavornet.org&rft.atitle=Cinnamic+acid&rft_id=http%3A%2F%2Fwww.flavornet.org%2Finfo%2F140-10-3.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACinnamic+acid" class="Z3988"></span></span> </li> <li id="cite_note-GESTIS-IOSH-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-GESTIS-IOSH_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-GESTIS-IOSH_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-GESTIS-IOSH_3-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-GESTIS-IOSH_3-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-GESTIS-IOSH_3-4"><sup><i><b>e</b></i></sup></a></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://gestis.dguv.de/data?name=025910&lang=en">Record </a> in the <a href="/wiki/GESTIS_Substance_Database" title="GESTIS Substance Database">GESTIS Substance Database</a> of the <a href="/wiki/Institute_for_Occupational_Safety_and_Health_of_the_German_Social_Accident_Insurance" title="Institute for Occupational Safety and Health of the German Social Accident Insurance">Institute for Occupational Safety and Health</a> </span> </li> <li id="cite_note-Merck-1996-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-Merck-1996_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Merck-1996_4-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Merck-1996_4-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBudavari1996" class="citation cs2">Budavari, Susan, ed. 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(1988). <i>Reactions and Synthesis in the Organic Chemistry Laboratory</i>. Mill Vall, CA. p. 1988.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Reactions+and+Synthesis+in+the+Organic+Chemistry+Laboratory&rft.place=Mill+Vall%2C+CA&rft.pages=1988&rft.date=1988&rft.aulast=Tieze&rft.aufirst=L.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACinnamic+acid" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_book" title="Template:Cite book">cite book</a>}}</code>: CS1 maint: location missing publisher (<a href="/wiki/Category:CS1_maint:_location_missing_publisher" title="Category:CS1 maint: location missing publisher">link</a>)</span></span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFF._K._Thayer1925" class="citation journal cs1">F. K. Thayer (1925). "m-Nitrocinnamic Acid". <i>Organic Syntheses</i>. <b>5</b>: 83. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.005.0083">10.15227/orgsyn.005.0083</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Syntheses&rft.atitle=m-Nitrocinnamic+Acid&rft.volume=5&rft.pages=83&rft.date=1925&rft_id=info%3Adoi%2F10.15227%2Forgsyn.005.0083&rft.au=F.+K.+Thayer&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACinnamic+acid" class="Z3988"></span></span> </li> <li id="cite_note-Jana-2013-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-Jana-2013_11-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJanaModiRoyAnderson2013" class="citation journal cs1">Jana A, Modi KK, Roy A, Anderson JA, van Breemen RB, Pahan K (June 2013). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3663914">"Up-regulation of neurotrophic factors by cinnamon and its metabolite sodium benzoate: therapeutic implications for neurodegenerative disorders"</a>. <i><a href="/wiki/Journal_of_Neuroimmune_Pharmacology" title="Journal of Neuroimmune Pharmacology">Journal of Neuroimmune Pharmacology</a></i>. <b>8</b> (3): 739–55. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs11481-013-9447-7">10.1007/s11481-013-9447-7</a>. <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/PMC3663914">3663914</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/23475543">23475543</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+Neuroimmune+Pharmacology&rft.atitle=Up-regulation+of+neurotrophic+factors+by+cinnamon+and+its+metabolite+sodium+benzoate%3A+therapeutic+implications+for+neurodegenerative+disorders&rft.volume=8&rft.issue=3&rft.pages=739-55&rft.date=2013-06&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3663914%23id-name%3DPMC&rft_id=info%3Apmid%2F23475543&rft_id=info%3Adoi%2F10.1007%2Fs11481-013-9447-7&rft.aulast=Jana&rft.aufirst=A&rft.au=Modi%2C+KK&rft.au=Roy%2C+A&rft.au=Anderson%2C+JA&rft.au=van+Breemen%2C+RB&rft.au=Pahan%2C+K&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3663914&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACinnamic+acid" class="Z3988"></span></span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBradleyAbrahamAcreeLang2015" class="citation journal cs1">Bradley, J.-C.; Abraham, M. H.; Acree, W. E.; Lang, A.; Beck, S. N.; Bulger, D. A.; Clark, E. A.; Condron, L. N.; Costa, S. T.; Curtin, E. M.; Kurtu, S. B.; Mangir, M. I.; McBride, M. J. (2015). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4369286">"Determination of Abraham model solute descriptors for the monomeric and dimeric forms of <i>trans</i>-cinnamic acid using measured solubilities from the Open Notebook Science Challenge"</a>. <i>Chemistry Central Journal</i>. <b>9</b>: 11. <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/10.1186%2Fs13065-015-0080-9">10.1186/s13065-015-0080-9</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/PMC4369286">4369286</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/25798191">25798191</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemistry+Central+Journal&rft.atitle=Determination+of+Abraham+model+solute+descriptors+for+the+monomeric+and+dimeric+forms+of+trans-cinnamic+acid+using+measured+solubilities+from+the+Open+Notebook+Science+Challenge&rft.volume=9&rft.pages=11&rft.date=2015&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4369286%23id-name%3DPMC&rft_id=info%3Apmid%2F25798191&rft_id=info%3Adoi%2F10.1186%2Fs13065-015-0080-9&rft.aulast=Bradley&rft.aufirst=J.-C.&rft.au=Abraham%2C+M.+H.&rft.au=Acree%2C+W.+E.&rft.au=Lang%2C+A.&rft.au=Beck%2C+S.+N.&rft.au=Bulger%2C+D.+A.&rft.au=Clark%2C+E.+A.&rft.au=Condron%2C+L.+N.&rft.au=Costa%2C+S.+T.&rft.au=Curtin%2C+E.+M.&rft.au=Kurtu%2C+S.+B.&rft.au=Mangir%2C+M.+I.&rft.au=McBride%2C+M.+J.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4369286&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACinnamic+acid" class="Z3988"></span></span> </li> 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id='mw-data-after-content'> <div class="read-more-container"></div> </div> <div id="p-lang"> <h4>Languages</h4> <section> <ul id="p-variants" class="minerva-languages"></ul> <ul class="minerva-languages"><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%AD%D9%85%D8%B6_%D8%A7%D9%84%D8%B3%D9%8A%D9%86%D8%A7%D9%85%D9%8A%D9%83" title="حمض السيناميك – Arabic" lang="ar" hreflang="ar" data-title="حمض السيناميك" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%B3%DB%8C%D9%86%D8%A7%D9%85%DB%8C%DA%A9_%D8%A7%D8%B3%DB%8C%D8%AF" title="سینامیک اسید – South Azerbaijani" lang="azb" hreflang="azb" data-title="سینامیک اسید" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%9A%D0%B0%D0%BD%D0%B5%D0%BB%D0%B5%D0%BD%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Канелена киселина – Bulgarian" lang="bg" hreflang="bg" data-title="Канелена киселина" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/%C3%80cid_cin%C3%A0mic" title="Àcid cinàmic – Catalan" lang="ca" hreflang="ca" data-title="Àcid cinàmic" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Kyselina_sko%C5%99icov%C3%A1" title="Kyselina skořicová – Czech" lang="cs" hreflang="cs" data-title="Kyselina skořicová" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Kanelsyre" title="Kanelsyre – Danish" lang="da" hreflang="da" data-title="Kanelsyre" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Zimts%C3%A4ure" title="Zimtsäure – German" lang="de" hreflang="de" data-title="Zimtsäure" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9A%CE%B9%CE%BD%CE%B1%CE%BC%CF%89%CE%BC%CE%B9%CE%BA%CF%8C_%CE%BF%CE%BE%CF%8D" title="Κιναμωμικό οξύ – Greek" lang="el" hreflang="el" data-title="Κιναμωμικό οξύ" 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/%C3%81cido_cin%C3%A1mico" title="Ácido cinámico – Spanish" lang="es" hreflang="es" data-title="Ácido cinámico" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Cinamata_acido" title="Cinamata acido – Esperanto" lang="eo" hreflang="eo" data-title="Cinamata acido" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%B3%DB%8C%D9%86%D8%A7%D9%85%DB%8C%DA%A9_%D8%A7%D8%B3%DB%8C%D8%AF" title="سینامیک اسید – Persian" lang="fa" hreflang="fa" data-title="سینامیک اسید" 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/Acide_cinnamique" title="Acide cinnamique – French" lang="fr" hreflang="fr" data-title="Acide cinnamique" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EA%B3%84%ED%94%BC%EC%82%B0" title="계피산 – Korean" lang="ko" hreflang="ko" data-title="계피산" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%B4%D5%A1%D6%80%D5%B9%D5%B6%D5%A1%D5%A9%D5%A9%D5%B8%D6%82" title="Դարչնաթթու – Armenian" lang="hy" hreflang="hy" data-title="Դարչնաթթու" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%B8%E0%A4%BF%E0%A4%A8%E0%A4%BE%E0%A4%AE%E0%A4%BF%E0%A4%95_%E0%A4%85%E0%A4%AE%E0%A5%8D%E0%A4%B2" title="सिनामिक अम्ल – Hindi" lang="hi" hreflang="hi" data-title="सिनामिक अम्ल" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Asam_sinamat" title="Asam sinamat – Indonesian" lang="id" hreflang="id" data-title="Asam sinamat" 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/Acido_cinnamico" title="Acido cinnamico – Italian" lang="it" hreflang="it" data-title="Acido cinnamico" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%97%D7%95%D7%9E%D7%A6%D7%AA_%D7%A7%D7%99%D7%A0%D7%9E%D7%95%D7%9F" title="חומצת קינמון – Hebrew" lang="he" hreflang="he" data-title="חומצת קינמון" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-jv mw-list-item"><a href="https://jv.wikipedia.org/wiki/Asem_sinamat" title="Asem sinamat – Javanese" lang="jv" hreflang="jv" data-title="Asem sinamat" data-language-autonym="Jawa" data-language-local-name="Javanese" class="interlanguage-link-target"><span>Jawa</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Kan%C4%93%C4%BCsk%C4%81be" title="Kanēļskābe – Latvian" lang="lv" hreflang="lv" data-title="Kanēļskābe" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Cinamono_r%C5%ABg%C5%A1tis" title="Cinamono rūgštis – Lithuanian" lang="lt" hreflang="lt" data-title="Cinamono rūgštis" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Fah%C3%A9jsav" title="Fahéjsav – Hungarian" lang="hu" hreflang="hu" data-title="Fahéjsav" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%A6%D0%B8%D0%BC%D0%B5%D1%82%D0%BD%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Циметна киселина – Macedonian" lang="mk" hreflang="mk" data-title="Циметна киселина" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Kaneelzuur" title="Kaneelzuur – Dutch" lang="nl" hreflang="nl" data-title="Kaneelzuur" 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/%E3%82%B1%E3%82%A4%E7%9A%AE%E9%85%B8" title="ケイ皮酸 – Japanese" lang="ja" hreflang="ja" data-title="ケイ皮酸" 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-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Kwas_cynamonowy" title="Kwas cynamonowy – Polish" lang="pl" hreflang="pl" data-title="Kwas cynamonowy" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/%C3%81cido_cin%C3%A2mico" title="Ácido cinâmico – Portuguese" lang="pt" hreflang="pt" data-title="Ácido cinâmico" 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/Acid_cinamic" title="Acid cinamic – Romanian" lang="ro" hreflang="ro" data-title="Acid cinamic" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9A%D0%BE%D1%80%D0%B8%D1%87%D0%BD%D0%B0%D1%8F_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Коричная кислота – Russian" lang="ru" hreflang="ru" data-title="Коричная кислота" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Kyselina_%C5%A1koricov%C3%A1" title="Kyselina škoricová – Slovak" lang="sk" hreflang="sk" data-title="Kyselina škoricová" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Cimetova_kislina" title="Cimetova kislina – Slovenian" lang="sl" hreflang="sl" data-title="Cimetova kislina" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Cimetna_kiselina" title="Cimetna kiselina – Serbian" lang="sr" hreflang="sr" data-title="Cimetna kiselina" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Cinaminska_kiselina" title="Cinaminska kiselina – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Cinaminska kiselina" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi badge-Q17559452 badge-recommendedarticle mw-list-item" title="recommended article"><a href="https://fi.wikipedia.org/wiki/Kanelihappo" title="Kanelihappo – Finnish" lang="fi" hreflang="fi" data-title="Kanelihappo" 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/Kanelsyra" title="Kanelsyra – Swedish" lang="sv" hreflang="sv" data-title="Kanelsyra" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%9A%E0%AE%BF%E0%AE%A9%E0%AF%8D%E0%AE%A9%E0%AE%AE%E0%AE%BF%E0%AE%95%E0%AF%8D_%E0%AE%85%E0%AE%AE%E0%AE%BF%E0%AE%B2%E0%AE%AE%E0%AF%8D" title="சின்னமிக் அமிலம் – Tamil" lang="ta" hreflang="ta" data-title="சின்னமிக் அமிலம்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%81%E0%B8%A3%E0%B8%94%E0%B8%8B%E0%B8%B4%E0%B8%99%E0%B8%99%E0%B8%B2%E0%B8%A1%E0%B8%B4%E0%B8%81" title="กรดซินนามิก – Thai" lang="th" hreflang="th" data-title="กรดซินนามิก" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9A%D0%BE%D1%80%D0%B8%D1%87%D0%BD%D0%B0_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Корична кислота – Ukrainian" lang="uk" hreflang="uk" data-title="Корична кислота" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E8%82%89%E6%A1%82%E9%85%B8" title="肉桂酸 – Chinese" lang="zh" hreflang="zh" data-title="肉桂酸" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li></ul> </section> </div> <div class="minerva-footer-logo"><img src="/static/images/mobile/copyright/wikipedia-wordmark-en.svg" alt="Wikipedia" width="120" height="18" style="width: 7.5em; height: 1.125em;"/> </div> <ul id="footer-info" class="footer-info hlist hlist-separated"> <li id="footer-info-lastmod"> This page was last edited on 23 October 2024, at 16:52<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Content is available under <a class="external" rel="nofollow" href="https://creativecommons.org/licenses/by-sa/4.0/deed.en">CC BY-SA 4.0</a> unless otherwise noted.</li> </ul> <ul id="footer-places" class="footer-places hlist hlist-separated"> <li id="footer-places-privacy"><a 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