1.0 2016-09-30 22:49:13 UTC 2020-05-11 20:48:55 UTC BMDB0001964 BMDB01964 Caffeic acid 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. 3,4-Dihydroxy-trans-cinnamate 3,4-Dihydroxycinnamic acid trans-Caffeate 3,4-Dihydroxy-trans-cinnamic acid 3,4-Dihydroxycinnamate Caffeate Caffeic acid, monosodium salt Caffeic acid, (e)-isomer Sodium caffeate (2E)-(3,4-Dihydroxyphenyl)-2-propenoic acid (2E)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid (e)-3,4-Dihydroxycinnamic acid (e)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid (e)-3-(3,4-Dihydroxyphenyl)acrylic acid (e)-Caffeic acid 3,4-Dihydroxybenzeneacrylic acid 3-(3,4-Dihydroxyphenyl)-2-propenoic acid 3-(3,4-Dihydroxyphenyl)propenoic acid 4-(2'-Carboxyvinyl)-1,2-dihydroxybenzene 4-(2-Carboxyethenyl)-1,2-dihydroxybenzene 4-(2’-carboxyvinyl)-1,2-dihydroxybenzene DHCA trans-3,4-Dihydroxycinnamic acid Caffeic acid 3',4'-Dihydroxycinnamic acid (2E)-3-(3,4-Dihydroxyphenyl)prop-2-enoic acid; C9H8O4 180.1574 180.042258744 (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid caffeic acid 501-16-6 OC(=O)\C=C\C1=CC(O)=C(O)C=C1 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+ QAIPRVGONGVQAS-DUXPYHPUSA-N 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. Organic compounds Phenylpropanoids and polyketides Cinnamic acids and derivatives Hydroxycinnamic acids and derivatives Hydroxycinnamic acids 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Carbonyl compounds Carboxylic acids Catechols Cinnamic acids Coumaric acids and derivatives Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Styrenes 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Aromatic homomonocyclic compound Benzenoid Carbonyl group Carboxylic acid Carboxylic acid derivative Catechol Cinnamic acid Coumaric acid or derivatives Hydrocarbon derivative Hydroxycinnamic acid Monocarboxylic acid or derivatives Monocyclic benzene moiety Organic oxide Organic oxygen compound Organooxygen compound Phenol Styrene Aromatic homomonocyclic compounds Caffeate derivatives caffeic acid Solid melting_point 225 °C logp 1.15 SANGSTER (1993) logp 1.67 ALOGPS logs -2.05 ALOGPS logp 1.53 ChemAxon pka_strongest_acidic 3.64 ChemAxon pka_strongest_basic -6.3 ChemAxon iupac (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid ChemAxon average_mass 180.1574 ChemAxon mono_mass 180.042258744 ChemAxon smiles OC(=O)\C=C\C1=CC(O)=C(O)C=C1 ChemAxon formula C9H8O4 ChemAxon inchi 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+ ChemAxon inchikey QAIPRVGONGVQAS-DUXPYHPUSA-N ChemAxon polar_surface_area 77.76 ChemAxon refractivity 47.02 ChemAxon polarizability 17.34 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::MsIr 1489 Specdb::MsIr 1490 Specdb::MsIr 1491 Specdb::CMs 1823 Specdb::CMs 2354 Specdb::CMs 27718 Specdb::CMs 28715 Specdb::CMs 30492 Specdb::CMs 31466 Specdb::CMs 31913 Specdb::CMs 38615 Specdb::CMs 159451 Specdb::MsMs 107598 Specdb::MsMs 107599 Specdb::MsMs 107600 Specdb::MsMs 174609 Specdb::MsMs 174610 Specdb::MsMs 174611 Specdb::MsMs 374048 Specdb::MsMs 2226766 Specdb::MsMs 2226854 Specdb::MsMs 2227851 Specdb::MsMs 2227941 Specdb::MsMs 2229148 Specdb::MsMs 2229199 Specdb::MsMs 2230277 Specdb::MsMs 2231628 Specdb::MsMs 2232548 Specdb::MsMs 2233997 Specdb::MsMs 2234953 Specdb::MsMs 2236241 Specdb::MsMs 2237122 Specdb::MsMs 2238416 Specdb::MsMs 2239189 Specdb::MsMs 2240394 Specdb::MsMs 2241290 Specdb::MsMs 2242452 Specdb::NmrOneD 297155 Specdb::NmrOneD 297156 Specdb::NmrOneD 297157 Specdb::NmrOneD 297158 Specdb::NmrOneD 297159 Specdb::NmrOneD 297160 Specdb::NmrOneD 297161 Specdb::NmrOneD 297162 Specdb::NmrOneD 297163 Specdb::NmrOneD 297164 Specdb::NmrOneD 297165 Specdb::NmrOneD 297166 Specdb::NmrOneD 297167 Specdb::NmrOneD 297168 Specdb::NmrOneD 297169 Specdb::NmrOneD 297170 Specdb::NmrOneD 297171 Specdb::NmrOneD 297172 Specdb::NmrOneD 297173 Specdb::NmrOneD 297174 Epidermis Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Milk Commercial milk, by CIL LC-MS Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. 28306241 Platelet Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Prostate Tissue Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Urine Samples collected from 16 multiparous Holstein cows Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28. 25599412 C01481 600426 FDB002559 DB01880 689043 16433 CPD-676 C00000615 Caffeic_acid Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. 28306241