| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 23:04:56 UTC |
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| Update Date | 2020-03-13 16:34:15 UTC |
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| BMDB ID | BMDB0003501 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | 3,4-Dihydroxy-trans-cinnamate |
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| Description | Caffeic acid, also known as caffeate, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. Caffeic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Caffeic acid exists in all living species, ranging from bacteria to humans. Caffeic acid is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 3,4-Dihydroxycinnamic acid | ChEBI | | Caffeate | ChEBI | | Caffeic acid | ChEBI | | 3,4-Dihydroxycinnamate | Generator | | cis-Caffeate | Generator | | 3,4-Dihydroxybenzeneacrylate | HMDB | | 3,4-Dihydroxybenzeneacrylic acid | HMDB | | Caffeic acid pure | HMDB | | Caffeicacid | HMDB | | (2Z)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid | HMDB | | (Z)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid | HMDB | | (Z)-Caffeic acid | HMDB | | 3-(3,4-Dihydroxyphenyl)-2-propenoic acid | HMDB | | 3-(3,4-Dihydroxyphenyl)propenoic acid | HMDB | | 4-(2'-Carboxyvinyl)-1,2-dihydroxybenzene | HMDB | | 4-(2-Carboxyethenyl)-1,2-dihydroxybenzene | HMDB | | 4-(2’-carboxyvinyl)-1,2-dihydroxybenzene | HMDB | | DHCA | HMDB | | Isocaffeic acid | HMDB | | cis-3,4-Dihydroxycinnamic acid | HMDB | | cis-Caffeic acid | HMDB |
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| Chemical Formula | C9H8O4 |
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| Average Molecular Weight | 180.1574 |
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| Monoisotopic Molecular Weight | 180.042258744 |
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| IUPAC Name | (2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid |
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| Traditional Name | caffeicacid |
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| CAS Registry Number | 501-16-6 |
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| SMILES | OC(=O)\C=C/C1=CC(O)=C(O)C=C1 |
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| InChI Identifier | InChI=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- |
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| InChI Key | QAIPRVGONGVQAS-RQOWECAXSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. |
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| Kingdom | Organic compounds |
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| Super Class | Phenylpropanoids and polyketides |
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| Class | Cinnamic acids and derivatives |
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| Sub Class | Hydroxycinnamic acids and derivatives |
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| Direct Parent | Hydroxycinnamic acids |
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| Alternative Parents | |
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| Substituents | - Cinnamic acid
- Coumaric acid or derivatives
- Hydroxycinnamic acid
- Catechol
- Styrene
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Monocyclic benzene moiety
- Benzenoid
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic oxide
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aromatic homomonocyclic compound
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| Molecular Framework | Aromatic homomonocyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Status | Expected but not Quantified |
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| Origin | Not Available |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | Not Available |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | 1.35 | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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