1.0 2016-09-30 22:50:14 UTC 2020-05-11 20:02:33 UTC BMDB0002035 BMDB02035 4-Hydroxycinnamic acid trans-4-Coumaric acid, also known as 4-hydroxycinnamic acid or trans-p-hydroxycinnamate, 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. trans-4-Coumaric acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. trans-4-Coumaric acid exists in all living species, ranging from bacteria to humans. (2E)-3-(4-Hydroxyphenyl)acrylic acid (e)-3-(4-Hydroxyphenyl)-2-propenoic acid (e)-p-Coumaric acid (e)-p-Hydroxycinnamic acid 4'-HYDROXYCINNAMIC ACID Naringeninic acid p-Coumaric acid trans-p-Coumaric acid trans-p-Coumarinic acid trans-p-Hydroxycinnamate trans-p-Hydroxycinnamic acid trans-4-Hydroxycinnamate 4-Hydroxycinnamate (2E)-3-(4-Hydroxyphenyl)acrylate (e)-3-(4-Hydroxyphenyl)-2-propenoate (e)-p-Coumarate (e)-p-Hydroxycinnamate 4'-HYDROXYCINNAMate Naringeninate p-Coumarate trans-p-Coumarate trans-p-Coumarinate 4-Coumaric acid, (e)-isomer 4-Coumaric acid, (Z)-isomer 4-Coumaric acid, disodium salt p-Coumaryl alcohol p-Hydroxycinnamic acid Para-coumaric acid trans-3-(4'-Hydroxyphenyl)-2-propenoic acid trans-HPPA 3-(4-Hydroxyphenyl)-2-propenoate 3-(4-Hydroxyphenyl)-2-propenoic acid 3-(4-Hydroxyphenyl)acrylate 3-(4-Hydroxyphenyl)acrylic acid 4-Coumarate 4-Hydroxy cinnamate 4-Hydroxy cinnamic acid 4-Hydroxyphenylpropenoate 4-Hydroxyphenylpropenoic acid b-[4-Hydroxyphenyl]acrylate b-[4-Hydroxyphenyl]acrylic acid beta-[4-Hydroxyphenyl]acrylate beta-[4-Hydroxyphenyl]acrylic acid cis-P-Coumarate Hydroxycinnamate Hydroxycinnamic acid P-Cumarate P-Cumaric acid P-Hydroxycinnamate P-Hydroxyphenylacrylate P-Hydroxyphenylacrylic acid Para coumarate Para coumaric acid Para-coumarate 4-Hydroxycinnamic acid trans-4-Coumarate (2E)-3-(4-Hydroxyphenyl)-2-propenoic acid (2E)-3-(4-Hydroxyphenyl)prop-2-enoic acid (E)-3-(4-Hydroxyphenyl)acrylic acid (E)-4-Hydroxycinnamic acid 4’-Hydroxycinnamic acid p-Cumaric acid p-Hydroxy-trans-cinnamic acid p-Hydroxyphenylacrylic acid p-trans-Coumaric acid trans-3-(4-Hydroxyphenyl)-2-propenoic acid trans-4-Coumaric acid β-[4-Hydroxyphenyl]acrylic acid C9H8O3 164.158 164.047344122 (2E)-3-(4-hydroxyphenyl)prop-2-enoic acid coumaric acid 7400-08-0 OC(=O)\C=C\C1=CC=C(O)C=C1 InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+ NGSWKAQJJWESNS-ZZXKWVIFSA-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 Carbonyl compounds Carboxylic acids Cinnamic acids Coumaric acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Styrenes 1-hydroxy-2-unsubstituted benzenoid Aromatic homomonocyclic compound Benzenoid Carbonyl group Carboxylic acid Carboxylic acid derivative Cinnamic acid Coumaric 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 4-coumaric acid Paracoumaryl alcohol derivatives Solid melting_point 211.5 °C logp 1.79 SANGSTER (1994) logp 1.74 ALOGPS logs -2.21 ALOGPS logp 1.83 ChemAxon pka_strongest_acidic 4 ChemAxon pka_strongest_basic -6 ChemAxon iupac (2E)-3-(4-hydroxyphenyl)prop-2-enoic acid ChemAxon average_mass 164.158 ChemAxon mono_mass 164.047344122 ChemAxon smiles OC(=O)\C=C\C1=CC=C(O)C=C1 ChemAxon formula C9H8O3 ChemAxon inchi InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+ ChemAxon inchikey NGSWKAQJJWESNS-ZZXKWVIFSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 45.04 ChemAxon polarizability 16.43 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 3 ChemAxon donor_count 2 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 1553 Specdb::MsIr 1554 Specdb::MsIr 1555 Specdb::EiMs 1872 Specdb::CMs 887 Specdb::CMs 1682 Specdb::CMs 3278 Specdb::CMs 28714 Specdb::CMs 29925 Specdb::CMs 30665 Specdb::CMs 31384 Specdb::CMs 32086 Specdb::CMs 38236 Specdb::CMs 163406 Specdb::NmrOneD 4900 Specdb::NmrOneD 4901 Specdb::NmrOneD 328032 Specdb::NmrOneD 328033 Specdb::NmrOneD 328034 Specdb::NmrOneD 328035 Specdb::NmrOneD 328036 Specdb::NmrOneD 328037 Specdb::NmrOneD 328038 Specdb::NmrOneD 328039 Specdb::NmrOneD 328040 Specdb::NmrOneD 328041 Specdb::NmrOneD 328042 Specdb::NmrOneD 328043 Specdb::NmrOneD 328044 Specdb::NmrOneD 328045 Specdb::NmrOneD 328046 Specdb::NmrOneD 328047 Specdb::NmrOneD 328048 Specdb::NmrOneD 328049 Specdb::NmrOneD 328050 Specdb::NmrOneD 328051 Specdb::MsMs 6485 Specdb::MsMs 6486 Specdb::MsMs 6487 Specdb::MsMs 6488 Specdb::MsMs 6489 Specdb::MsMs 6490 Specdb::MsMs 6492 Specdb::MsMs 6493 Specdb::MsMs 6494 Specdb::MsMs 6495 Specdb::MsMs 179817 Specdb::MsMs 179818 Specdb::MsMs 179819 Specdb::MsMs 182151 Specdb::MsMs 182152 Specdb::MsMs 182153 Specdb::MsMs 374051 Specdb::MsMs 374069 Specdb::MsMs 437395 Specdb::MsMs 437396 Specdb::MsMs 437397 Specdb::MsMs 437398 Specdb::MsMs 437399 Specdb::MsMs 439156 Specdb::MsMs 439266 Fibroblasts 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 GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54. 14168161 Milk Milk from Friesuan Holstein cows (n=1035) Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. 23438684 FDB002593 C00811 DB04066 553148 637542 500 C00000152 32374 COUMARATE 36077 P-Coumaric_acid 6450 Ben-Bassat, Arie; Sariaslani, Fateme Sima; Huang, Lisa L.; Patnaik, Ranjan; Lowe, David J. Fermentative preparation of para-hydroxycinnamic acid and cinnamic acid at alkaline ph. U.S. Pat. Appl. Publ. (2005), 23 pp. GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54. 14168161