| Revision as of 12:27, 15 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 476313546 of page Cinnamic_acid for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 16:52, 23 October 2024 edit Plantsurfer (talk | contribs)Extended confirmed users40,018 editsm Renamed references using RefRenamernamed citations |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Chembox |
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{{Chembox |
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|Verifiedfields = changed |
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| Watchedfields = changed |
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|Watchedfields = changed |
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| verifiedrevid = 399517239 |
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|verifiedrevid = 476994181 |
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| Name = Cinnamic acid |
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|Name = Cinnamic acid |
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|ImageFile = Zimtsäure - Cinnamic acid.svg |
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| ImageFile = cinnamicacid2.png |
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| ImageName = Skeletal formula of the trans form |
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|ImageName = Skeletal formula of trans-cinnamic acid |
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| ImageFile1 = Cinnamic-acid-3D-balls-B.png |
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|ImageFile1 = Cinnamic acid 3D ball.png |
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|ImageName1 = Ball-and-stick model of the trans-cinnamic acid molecule |
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| ImageSize1 = 220px |
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|ImageFile2 = Cinnamic acid.jpg |
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| ImageName1 = Ball-and-stick model of the trans form |
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|ImageName2 = Sample of the compound cinnamic acid in powder form |
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| IUPACName = (])-3-phenylprop-2-enoic acid |
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|PIN = (2''E'')-3-Phenylprop-2-enoic acid |
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| OtherNames = Cinnamic Acid<br />''trans''-Cinnamic Acid<br />Phenylacrylic acid<br />Cinnamylic acid<br>3-Phenylacrylic acid<br />(E)-Cinnamic acid<br />Benzenepropenoic acid<br />Isocinnamic acid |
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|SystematicName = Cinnamic acid |
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| Section1 = {{Chembox Identifiers |
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|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 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID = 392447 |
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|IUPHAR_ligand = 3203 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChEMBL = 27246 |
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|ChemSpiderID = 392447 |
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| InChI = 1/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+ |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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|ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 35697 |
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|ChEMBL = 27246 |
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|InChI = 1/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+ |
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| SMILES = O=C(O)\C=C\c1ccccc1 |
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|ChEBI_Ref = {{ebicite|correct|EBI}} |
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| InChIKey = WBYWAXJHAXSJNI-VOTSOKGWBT |
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|ChEBI = 35697 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|SMILES = O=C(O)\C=C\c1ccccc1 |
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| StdInChI = 1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+ |
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|InChIKey = WBYWAXJHAXSJNI-VOTSOKGWBT |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = WBYWAXJHAXSJNI-VOTSOKGWSA-N |
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|StdInChI = 1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+ |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| CASNo = 140-10-3 |
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|StdInChIKey = WBYWAXJHAXSJNI-VOTSOKGWSA-N |
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| PubChem = 444539 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| KEGG = C00423 |
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|CASNo = 140-10-3 |
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|UNII_Ref = {{fdacite|changed|FDA}} |
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}} |
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|UNII = U14A832J8D |
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| Section2 = {{Chembox Properties |
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|PubChem = 444539 |
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| C=9|H=8|O=2 |
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|KEGG_Ref = {{keggcite|correct|kegg}} |
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| ExactMass = 148.05243 |
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|KEGG = C00423 |
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| Appearance = White monoclinic crystals |
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|Gmelin = 3731 |
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| Solubility = 500 mg/L<ref name=GESTIS>{{GESTIS|ZVG=25910}}</ref> |
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|Beilstein = 1905952 |
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| Density = 1.2475 g/cm<sup>3</sup><ref name=GESTIS/> |
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|EINECS = 205-398-1 |
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| MeltingPtC = 133 |
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|3DMet = B00108 |
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| Melting_notes = <ref name=GESTIS/> |
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| BoilingPtC = 300 |
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| Boiling_notes = <ref name=GESTIS/> |
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| pKa = 4.44 |
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}} |
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| Section7 = {{Chembox Hazards |
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| ExternalMSDS = |
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| EUClass = Irritant ('''Xi''') |
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| RPhrases = {{R36}} |
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| SPhrases = {{S25}} |
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| FlashPt = >{{convert|100|C|F}}<ref name=GESTIS/> |
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}} |
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}} |
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}} |
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|Section2={{Chembox Properties |
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|C=9 | H=8 | O=2 |
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|Appearance = White monoclinic crystals |
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|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> |
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|Solubility = 500 mg/L<ref name="GESTIS-IOSH">{{GESTIS|ZVG=25910}}</ref> |
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|Density = 1.2475 g/cm<sup>3</sup><ref name="GESTIS-IOSH"/> |
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|MeltingPtC = 133 |
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|MeltingPt_ref = <ref name="GESTIS-IOSH"/> |
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|BoilingPtC = 300 |
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|BoilingPt_ref = <ref name="GESTIS-IOSH"/> |
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|pKa = 4.44 |
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|MagSus = {{val|-7.836e-5|u=cm<sup>3</sup>/mol}} |
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}} |
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|Section3={{Chembox Hazards |
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|NFPA-H = 1 |
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|NFPA-F = 1 |
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|NFPA-R = 0 |
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|GHSPictograms = {{GHS07}} |
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|GHSSignalWord = Warning |
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|HPhrases = {{H-phrases|315|319|335}} |
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|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}} |
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|FlashPt = > |
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|FlashPtC = 100 |
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|FlashPt_ref = <ref name="GESTIS-IOSH"/> |
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}} |
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|Section4={{Chembox Related |
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|OtherCompounds = ], ], ] |
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}} |
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}} |
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'''Cinnamic acid''' is an ] with the formula ]-CH=CH-]. It is a white crystalline compound that is slightly ] in water, and freely soluble in many organic solvents.<ref name="Merck-1996"/> Classified as an unsaturated ], it occurs naturally in a number of plants. It exists as both a ], although the latter is more common.<ref name="Garbe-2012"/> |
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==Occurrence and production== |
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===Biosynthesis=== |
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Cinnamic acid is a central intermediate in the biosynthesis of a myriad of natural products including lignols (precursors to ] and ]), ], ], ]s, ], ], ], and ]s. Its ] involves the action of the ] ] (PAL) on ].<ref>{{cite journal|journal=Molecular Plant|year=2010|volume=3|issue=1|pages=2–20|doi=10.1093/mp/ssp106|title=Phenylpropanoid Biosynthesis|last=Vogt|first=T.|pmid=20035037|doi-access=free}}</ref> |
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===Natural occurrence=== |
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It is obtained from oil of ], or from ]s such as ].<ref name="Merck-1996">{{Merck12th}}</ref> It is also found in ].{{cn|date=June 2023}} Cinnamic acid has a ]-like odor;<ref name="flavornet.org">{{cite web|url=http://www.flavornet.org/info/140-10-3.html|title=Cinnamic acid|website=flavornet.org}}</ref> and its more volatile ethyl ester, ], is a flavor component in the essential oil of ], in which related ] is the major constituent. It is also found in wood from many diverse tree species.<ref>{{cite web |last1=Oldach |first1=Laurel |title=Forensic researchers use mass spectrometry to identify smuggled wood |url=https://cen.acs.org/analytical-chemistry/mass-spectrometry/Forensic-researchers-use-mass-spectrometry-to-identify-smuggled-wood/101/i7 |website=Chemical and Engineering News |publisher=American Chemical Society |date=February 22, 2023}}</ref> |
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===Synthesis=== |
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Cinnamic acid was first synthesized by the base-catalysed condensation of ] and ], followed by ] of the ] product.<ref name="Garbe-2012">{{Ullmann|first=Dorothea|last=Garbe|title=Cinnamic Acid|doi=10.1002/14356007.a07_099|year=2012}}</ref> In 1890, ] described the synthesis of ] via the reaction of ] with benzaldehyde in the presence of ] as base.<ref>{{cite journal|last=Claisen|first=L.|date=1890|url=https://babel.hathitrust.org/cgi/pt?id=uc1.b3481786;view=1up;seq=992|title=Zur Darstellung der Zimmtsäure und ihrer Homologen|trans-title=On the preparation of cinnamic acid and its homologues|journal=Berichte der Deutschen Chemischen Gesellschaft|volume=23|pages=976–978|doi=10.1002/cber.189002301156}}</ref> Another way of preparing cinnamic acid is by the ] reaction.<ref>{{cite book|first=L.|last=Tieze|title=Reactions and Synthesis in the Organic Chemistry Laboratory|location=Mill Vall, CA|date=1988|page=1988}}</ref> The reactants for this are benzaldehyde and ] in the presence of a weak base, followed by acid-catalyzed ]. It can also be prepared by oxidation of ], condensation of ] and sodium acetate (followed by acid hydrolysis), and the ]. The oldest commercially used route to cinnamic acid involves the ], which is given in the following scheme<ref name="Garbe-2012"/> |
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:].<ref>{{cite journal |doi=10.15227/orgsyn.005.0083|author=F. K. Thayer|title=m-Nitrocinnamic Acid|journal=Organic Syntheses|year=1925|volume=5|page=83}}</ref>]] |
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==Metabolism== |
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Cinnamic acid, obtained from autoxidation of ], is metabolized into ] in the liver.<ref name="Jana-2013">{{cite journal | vauthors = Jana A, Modi KK, Roy A, Anderson JA, van Breemen RB, Pahan K | title = Up-regulation of neurotrophic factors by cinnamon and its metabolite sodium benzoate: therapeutic implications for neurodegenerative disorders | journal = ] | volume = 8 | issue = 3 | pages = 739–55 | date = June 2013 | pmid = 23475543 | pmc = 3663914 | doi = 10.1007/s11481-013-9447-7 | url = | issn = }}</ref> |
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==Uses== |
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Cinnamic acid is used in flavorings, ], and certain ]s. A major use is as a precursor to produce ], ], and ] for the perfume industry.<ref name="Merck-1996"/> Cinnamic acid is a precursor to the sweetener ] via enzyme-catalysed amination with ].<ref name="Garbe-2012"/> Cinnamic acid can ] in non-polar solvents resulting in different ].<ref>{{cite journal | doi = 10.1186/s13065-015-0080-9 | pmid = 25798191 | pmc = 4369286 | title = 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 | journal = Chemistry Central Journal | volume = 9 | pages = 11 | year = 2015 | last1 = Bradley | first1 = J.-C. | last2 = Abraham | first2 = M. H. | last3 = Acree | first3 = W. E. | last4 = Lang | first4 = A. | last5 = Beck | first5 = S. N. | last6 = Bulger | first6 = D. A. | last7 = Clark | first7 = E. A. | last8 = Condron | first8 = L. N. | last9 = Costa | first9 = S. T. | last10 = Curtin | first10 = E. M. | last11 = Kurtu | first11 = S. B. | last12 = Mangir | first12 = M. I. | last13 = McBride | first13 = M. J. | doi-access = free }}</ref> |
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==References== |
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{{Reflist|30em}} |
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{{Hydroxycinnamic acid}} |
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{{Authority control}} |
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] |
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] |
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] |