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Cinnamic acid
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{{Chembox |Verifiedfields = changed |Watchedfields = changed |verifiedrevid = 476994181 |Name = Cinnamic acid |ImageFile = Zimtsäure - Cinnamic acid.svg |ImageName = Skeletal formula of trans-cinnamic acid |ImageFile1 = Cinnamic acid 3D ball.png |ImageName1 = Ball-and-stick model of the trans-cinnamic acid molecule |ImageFile2 = Cinnamic acid.jpg |ImageName2 = Sample of the compound cinnamic acid in powder form |PIN = (2''E'')-3-Phenylprop-2-enoic acid |SystematicName = Cinnamic acid |OtherNames = ''trans''-Cinnamic acid<br>Phenylacrylic acid<ref>{{cite EB1911|wstitle=Cinnamic Acid|volume=6|page=376|short=1}}</ref><br>Cinnamylic acid<br>3-Phenylacrylic acid<br />(''E'')-Cinnamic acid<br>Benzenepropenoic acid<br>Isocinnamic acid |Section1={{Chembox Identifiers |IUPHAR_ligand = 3203 |ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |ChemSpiderID = 392447 |ChEMBL_Ref = {{ebicite|correct|EBI}} |ChEMBL = 27246 |InChI = 1/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+ |ChEBI_Ref = {{ebicite|correct|EBI}} |ChEBI = 35697 |SMILES = O=C(O)\C=C\c1ccccc1 |InChIKey = WBYWAXJHAXSJNI-VOTSOKGWBT |StdInChI_Ref = {{stdinchicite|correct|chemspider}} |StdInChI = 1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+ |StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |StdInChIKey = WBYWAXJHAXSJNI-VOTSOKGWSA-N |CASNo_Ref = {{cascite|correct|CAS}} |CASNo = 140-10-3 |UNII_Ref = {{fdacite|changed|FDA}} |UNII = U14A832J8D |PubChem = 444539 |KEGG_Ref = {{keggcite|correct|kegg}} |KEGG = C00423 |Gmelin = 3731 |Beilstein = 1905952 |EINECS = 205-398-1 |3DMet = B00108 }} |Section2={{Chembox Properties |C=9 | H=8 | O=2 |Appearance = White monoclinic crystals |Odor = Honey-like<ref name="flavornet.org">{{cite web|url=http://www.flavornet.org/info/140-10-3.html|title=Cinnamic acid|website=flavornet.org}}</ref> |Solubility = 500 mg/L<ref name="GESTIS-IOSH">{{GESTIS|ZVG=25910}}</ref> |Density = 1.2475 g/cm<sup>3</sup><ref name="GESTIS-IOSH"/> |MeltingPtC = 133 |MeltingPt_ref = <ref name="GESTIS-IOSH"/> |BoilingPtC = 300 |BoilingPt_ref = <ref name="GESTIS-IOSH"/> |pKa = 4.44 |MagSus = {{val|-7.836e-5|u=cm<sup>3</sup>/mol}} }} |Section3={{Chembox Hazards |NFPA-H = 1 |NFPA-F = 1 |NFPA-R = 0 |GHSPictograms = {{GHS07}} |GHSSignalWord = Warning |HPhrases = {{H-phrases|315|319|335}} |PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}} |FlashPt = > |FlashPtC = 100 |FlashPt_ref = <ref name="GESTIS-IOSH"/> }} |Section4={{Chembox Related |OtherCompounds = [[Benzoic acid]], [[Phenylacetic acid]], [[Phenylpropanoic acid]] }} }} '''Cinnamic acid''' is an [[organic compound]] with the formula [[phenyl|C<sub>6</sub>H<sub>5</sub>]]-CH=CH-[[Carboxylic acid|COOH]]. It is a white crystalline compound that is slightly [[soluble]] in water, and freely soluble in many organic solvents.<ref name="Merck-1996"/> Classified as an unsaturated [[carboxylic acid]], it occurs naturally in a number of plants. It exists as both a [[Cis–trans isomerism|''cis'' and a ''trans'' isomer]], although the latter is more common.<ref name="Garbe-2012"/>
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