1.0 2010-04-08 22:05:03 UTC 2025-11-18 22:32:19 UTC FDB001634 Epigallocatechin 3-caffeate Epigallocatechin 3-caffeate is a member of the class of compounds known as epigallocatechins. Epigallocatechins are compounds containing epigallocatechin or a derivative. Epigallocatechin is a flavan-3-ol containing a benzopyran-3,5,7-triol linked to a 3,4,5-hydroxyphenyl moiety. Thus, epigallocatechin 3-caffeate is considered to be a flavonoid lipid molecule. Epigallocatechin 3-caffeate is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Epigallocatechin 3-caffeate can be found in tea, which makes epigallocatechin 3-caffeate a potential biomarker for the consumption of this food product. (-)-Epigallocatechin 3-caffeate Epigallocatechin 3-caffeate Epigallocatechin 3-O-caffeate C24H20O10 468.4096 468.10564686 (2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate epigallocatechin 3-O-caffeate 122412-14-0 OC1=CC2=C(C[C@@H](OC(=O)\C=C\C3=CC(O)=C(O)C=C3)[C@H](O2)C2=CC(O)=C(O)C(O)=C2)C(O)=C1 InChI=1S/C24H20O10/c25-13-8-16(27)14-10-21(33-22(31)4-2-11-1-3-15(26)17(28)5-11)24(34-20(14)9-13)12-6-18(29)23(32)19(30)7-12/h1-9,21,24-30,32H,10H2/b4-2+/t21-,24-/m1/s1 BNLVODKLELGOBT-WEDYXYFPSA-N belongs to the class of organic compounds known as epigallocatechins. Epigallocatechins are compounds containing epigallocatechin or a derivative. Epigallocatechin is a flavan-3-ol containing a benzopyran-3,5,7-triol linked to a 3,4,5-hydroxyphenyl moiety. Epigallocatechins Organic compounds Phenylpropanoids and polyketides Flavonoids Flavans Aromatic heteropolycyclic compounds 1-benzopyrans 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 3'-hydroxyflavonoids 4'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids Alkyl aryl ethers Carbonyl compounds Catechols Cinnamic acid esters Coumaric acids and derivatives Enoate esters Fatty acid esters Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Oxacyclic compounds Polyols Pyrogallols and derivatives Styrenes 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 3'-hydroxyflavonoid 4'-hydroxyflavonoid 5-hydroxyflavonoid 7-hydroxyflavonoid Alkyl aryl ether Alpha,beta-unsaturated carboxylic ester Aromatic heteropolycyclic compound Benzenetriol Benzenoid Benzopyran Carbonyl group Carboxylic acid derivative Carboxylic acid ester Catechol Chromane Cinnamic acid ester Cinnamic acid or derivatives Coumaric acid or derivatives Enoate ester Epigallocatechin Ether Fatty acid ester Fatty acyl Hydrocarbon derivative Hydroxycinnamic acid or derivatives Hydroxyflavonoid Monocarboxylic acid or derivatives Monocyclic benzene moiety Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol Polyol Pyrogallol derivative Styrene Flavans, Flavanols and Leucoanthocyanidins logp 2.90 ALOGPS logs -4.47 ALOGPS solubility 1.57e-02 g/l ALOGPS logp 3.92 ChemAxon pka_strongest_acidic 8.53 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac (2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate ChemAxon average_mass 468.4096 ChemAxon mono_mass 468.10564686 ChemAxon smiles OC1=CC2=C(C[C@@H](OC(=O)\C=C\C3=CC(O)=C(O)C=C3)[C@H](O2)C2=CC(O)=C(O)C(O)=C2)C(O)=C1 ChemAxon formula C24H20O10 ChemAxon inchi InChI=1S/C24H20O10/c25-13-8-16(27)14-10-21(33-22(31)4-2-11-1-3-15(26)17(28)5-11)24(34-20(14)9-13)12-6-18(29)23(32)19(30)7-12/h1-9,21,24-30,32H,10H2/b4-2+/t21-,24-/m1/s1 ChemAxon inchikey BNLVODKLELGOBT-WEDYXYFPSA-N ChemAxon polar_surface_area 177.14 ChemAxon refractivity 119.51 ChemAxon polarizability 45.71 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 9 ChemAxon donor_count 7 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 59883 Specdb::MsMs 59884 Specdb::MsMs 59885 Specdb::MsMs 116103 Specdb::MsMs 116104 Specdb::MsMs 116105 Specdb::MsMs 3597899 Specdb::MsMs 3597900 Specdb::MsMs 3597901 Specdb::MsMs 3597902 Specdb::MsMs 3597903 Specdb::MsMs 3597904 Black tea Type 1 0.2 0.2 0.2 mg/100 g Green tea Type 1 0.2 0.2 0.2 mg/100 g Herbal tea Type 1 0.2 0.2 0.2 mg/100 g Red tea Type 1 0.2 0.2 0.2 mg/100 g Tea Type 1 specific Camellia sinensis 4442 0.2 0.2 0.2 mg/100 g