1.0 2010-04-08 22:05:25 UTC 2025-11-18 22:38:19 UTC FDB002559 trans-Caffeic acid 3,4-Dihydroxy-trans-cinnamate, also known as trans-Caffeate, is a polyphenol present in normal human urine positively correlated to coffee consumption and influenced by the dietary intake of diverse types of food (PMID:16870009). trans-Caffeic acid is found in many foods, some of which are flaxseed, cereal and cereal products, common grape, fruits, and common sage. It is also found in wine and coffee in free and conjugated forms. (2E)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid (2E)-3-(3,4-dihydroxyphenyl)acrylic acid (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid (E)-3-(3,4-dihydroxyphenyl)-2-propenoic acid 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, (E)- 3,4-Dihydroxy-trans-cinnamate 3,4-Dihydroxy-trans-cinnamic acid trans-Caffeate trans-Caffeic 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. Hydroxycinnamic acids Organic compounds Phenylpropanoids and polyketides Cinnamic acids and derivatives Hydroxycinnamic acids and derivatives Aromatic homomonocyclic compounds 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 Caffeate derivatives caffeic acid Solid logp 1.67 ALOGPS logs -2.05 ALOGPS solubility 1.61e+00 g/l ALOGPS melting_point Mp 223-225° dec. 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 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::MsIr 1489 Specdb::MsIr 1490 Specdb::MsIr 1491 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 HMDB03501 16433 DHC #<Reference:0x000055ce2dd466a0> Alcoholic beverages Unknown generic Alfalfa Type 1 specific Medicago sativa 3879 Arabica coffee Type 1 specific Coffea arabica 13443 Breakfast cereal Type 2 specific Cereals and cereal products Unknown generic Chickpea Type 1 specific Cicer arietinum 3827 Coffee and coffee products Unknown generic Common bean Type 1 specific Phaseolus vulgaris 3885 Common grape Type 1 specific Vitis vinifera 29760 Common pea Type 1 specific Pisum sativum 3888 Common sage Type 1 specific Salvia officinalis 38868 Dandelion Type 1 specific Taraxacum officinale 50225 Flaxseed Type 1 specific Linum usitatissimum 4006 Fruits Unknown generic Grape wine Type 2 specific 0.0 0.0 0.0 mg/100 g Green bean Type 1 specific Phaseolus vulgaris 3885 Opium poppy Type 1 specific Papaver somniferum 3469 Peanut Type 1 specific Arachis hypogaea 3818 Robusta coffee Type 1 specific Coffea canephora 49390 Roman camomile Type 1 specific Chamaemelum nobile 99037 Soy bean Type 1 specific Glycine max 3847 Sweet cherry Type 1 specific Prunus avium 42229 Yellow wax bean Type 1 specific Phaseolus vulgaris 3885