3,4-Dihydroxycinnamic acid<br />''trans''-Caffeate<br />3,4-Dihydroxy-''trans''-cinnamate<br/>(''E'')-3-(3,4-dihydroxyphenyl)-2-propenoic acid<br />3,4-Dihydroxybenzeneacrylicacid<br />3-(3,4-Dihydroxyphenyl)-2-propenoic acid"},"Section1":{"wt":"{{Chembox Identifiers\n| IUPHAR_ligand = 5155\n| Beilstein = 1954563\n| ChEBI_Ref = {{ebicite|correct|EBI}}\n| ChEBI = 16433\n| DrugBank_Ref = {{drugbankcite|correct|drugbank}}\n| DrugBank = DB01880\n| SMILES = O=C(O)\\C=C\\c1cc(O)c(O)cc1\n| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}\n| ChemSpiderID = 600426\n| PubChem = 689043\n| ChEMBL_Ref = {{ebicite|correct|EBI}}\n| ChEMBL = 145\n| EC_number = 206-361-2\n| UNII_Ref = {{fdacite|correct|FDA}}\n| UNII = U2S3A33KVM\n| KEGG_Ref = {{keggcite|correct|kegg}}\n| KEGG = C01197\n| InChI = 1/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+\n| InChIKey = QAIPRVGONGVQAS-DUXPYHPUBE\n| StdInChI_Ref = {{stdinchicite|correct|chemspider}}\n| StdInChI = 1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+\n| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}\n| StdInChIKey = QAIPRVGONGVQAS-DUXPYHPUSA-N\n| CASNo_Ref = {{cascite|correct|CAS}}\n| CASNo = 501-16-6 \n| CASNo1_Ref = {{cascite|correct|CAS}}\n| CASNo1 = 331-39-5\n| CASNo1_Comment = (non-specific)\n\n }}"},"Section2":{"wt":"{{Chembox Properties\n| Formula = C<sub>9</sub>H<sub>8</sub>O<sub>4</sub>\n| MolarMass = 180.16 g/mol\n| Density = 1.478 g/cm<sup>3</sup>\n| MeltingPtC = 223 to 225\n| BoilingPt = \n| LambdaMax = 327 nm and a shoulder at c. 295 nm in acidified methanol<ref>{{cite journal | title = Functional role of anthocyanins in the leaves of ''Quintinia serrata'' A. Cunn. |first1=Kevin S. |last1=Gould |first2=Kenneth R. |last2=Markham |first3=Richard H. |last3=Smith |first4=Jessica J. |last4=Goris | journal = Journal of Experimental Botany | volume = 51 | issue = 347 | pages = 1107–1115 | year = 2000 | doi = 10.1093/jexbot/51.347.1107 | pmid = 10948238| doi-access = free }}</ref>\n }}"},"Section5":{"wt":"{{Chembox Hazards\n| NFPA-H = 1\n| NFPA-F = 1\n| NFPA-R = 0\n| GHSPictograms = {{GHS|07|08}}\n| GHSSignalWord = Warning\n| HPhrases = {{H-phrases|315|319|335|351|361}}\n| PPhrases = {{P-phrases|201|202|261|264|271|280|281|302+352|304+340|305+351+338|308+313|312|321|332+313|337+313|362|403+233|405|501}}\n }}"},"Section8":{"wt":"{{Chembox Related\n| OtherCompounds = [[Chlorogenic acid]]<br/>[[Cichoric acid]]<br/>[[Coumaric acid]]<br/>[[Quinic acid]]\n }}"}},"i":0}}]}'>
Cysteinyl leukotriene receptor</span>"}]]}'>CysLTTooltip Cysteinyl leukotriene receptor
Enzyme
(inhibitors)
Others
 2D diagram of caffeic acid | |||
 3D ball-and-stick model of caffeic acid | |||
 3D space filling model of caffeic acid | |||
| Names | |||
|---|---|---|---|
| IUPAC names
3-(3,4-Dihydroxyphenyl)-2-propenoic acid 3,4-Dihydroxycinnamic acid trans-Caffeate 3,4-Dihydroxy-trans-cinnamate (E)-3-(3,4-dihydroxyphenyl)-2-propenoic acid 3,4-Dihydroxybenzeneacrylicacid 3-(3,4-Dihydroxyphenyl)-2-propenoic acid | |||
| Preferred IUPAC name
(2E)-3-(3,4-Dihydroxyphenyl)prop-2-enoic acid | |||
| Identifiers | |||
3D model (JSmol) |
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| ChemSpider | |||
| EC Number | |||
PubChem Compound ID</span>"}]]}'>CID |
EPA) |  Natural occurrenceseditCaffeic acid can be found in the bark of Eucalyptus globulus, the barley grain Hordeum vulgare, and the herb Dipsacus asperoides. It can also be found in the freshwater fern Salvinia molesta and in the mushroom Phellinus linteus. Occurrences in foodeditFree caffeic acid can be found in a variety of beverages, including brewed coffee at 63.1-96.0 mg per 100 ml and red wine at 2 mg per 100 ml. It is found at relatively high levels in herbs of the mint family, especially thyme, sage and spearmint (at about 20 mg per 100 g), and in spices, such as Ceylon cinnamon and star anise (at about 22 mg per 100 g). Caffeic acid occurs at moderate levels in sunflower seeds (8 mg per 100 g), apple sauce, apricots and prunes (at about 1 mg per 100 g). It occurs at remarkably high levels in black chokeberry (141 mg per 100 g). It is also quite high in the South American herb yerba mate (150 mg per 100 g based on thin-layer chromatography densitometry and HPLC). It is also found at lower levels in barley and rye. BiosynthesiseditCaffeic acid is biosynthesized by hydroxylation of coumaroyl ester of quinic acid (esterified through a side chain alcohol). This hydroxylation produces the caffeic acid ester of shikimic acid, which converts to chlorogenic acid. It is the precursor to ferulic acid, coniferyl alcohol, and sinapyl alcohol, all of which are significant building blocks in lignin. The transformation to ferulic acid is catalyzed by the enzyme caffeate O-methyltransferase. Caffeic acid and its derivative caffeic acid phenethyl ester (CAPE) are produced in many kinds of plants.
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| Leukotriene B4 receptor 2</span>"}]]}'>BLT2Tooltip Leukotriene B4 receptor 2 | |||
| Cysteinyl leukotriene receptor 1</span>"}]]}'>CysLT1Tooltip Cysteinyl leukotriene receptor 1 |
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|---|---|
| Cysteinyl leukotriene receptor 2</span>"}]]}'>CysLT2Tooltip Cysteinyl leukotriene receptor 2 |
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| Cysteinyl leukotriene receptor E</span>"}]]}'>CysLTETooltip Cysteinyl leukotriene receptor E |
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(inhibitors)
| Arachidonate 5-lipoxygenase</span>"}]]}'>5-LOXTooltip Arachidonate 5-lipoxygenase | |
|---|---|
| Arachidonate 12-lipoxygenase</span>"}]]}'>12-LOXTooltip Arachidonate 12-lipoxygenase | |
| Arachidonate 15-lipoxygenase</span>"}]]}'>15-LOXTooltip Arachidonate 15-lipoxygenase | |
| Leukotriene-A4 hydrolase</span>"}]]}'>LTA4HTooltip Leukotriene-A4 hydrolase | |
| Leukotriene B4 ω-hydroxylase</span>"}]]}'>LTB4HTooltip Leukotriene B4 ω-hydroxylase | |
| Leukotriene C4 synthase</span>"}]]}'>LTC4STooltip Leukotriene C4 synthase | |
| Leukotriene C4 hydrolase</span>"}]]}'>LTC4HTooltip Leukotriene C4 hydrolase | |
| Leukotriene D4 hydrolase</span>"}]]}'>LTD4Tooltip Leukotriene D4 hydrolase |
(ligands)
(blockers)
| Concentrative nucleoside transporters</span>"}]]}'>CNTsTooltip Concentrative nucleoside transporters | |
|---|---|
| Equilibrative nucleoside transporters</span>"}]]}'>ENTsTooltip Equilibrative nucleoside transporters | |
| Plasma membrane monoamine transporter</span>"}]]}'>PMATTooltip Plasma membrane monoamine transporter |
(inhibitors)
| Xanthine oxidase</span>"}]]}'>XOTooltip Xanthine oxidase | |
|---|---|
| Others |
See also: Receptor/signaling modulators