1.0 2010-04-08 22:05:27 UTC 2025-11-18 22:38:51 UTC FDB002628 3,5-Di-O-caffeoylquinic acid Isolated from coffee and maté, globe artichoke (Cynara scolymus) and caucasian whortleberry (Vaccinium arctostaphylos). 3,5-Di-O-caffeoylquinic acid is found in many foods, some of which are potato, green vegetables, coffee and coffee products, and carrot. (1S,3R,4S,5R)-1,3,4,5-Tetrahydroxy-1-carboxycyclohexane3,5-di-3-(3,4-dihydroxyphenyl)propenoate (1S,3R,4S,5R)-1,3,4,5-Tetrahydroxy-1-carboxycyclohexane3,5-di-3-(3,4-dihydroxyphenyl)propenoic acid 3,5-Bis-(3,4-dihydroxycinnamoyl)quinic acid 3,5-DCQA 3,5-Dicaffeoylquinate 3,5-Dicaffeoylquinic acid Isochlorogenate a Isochlorogenic acid a Quinate 3,5-di-O-caffeate Quinic acid 3,5-di-O-caffeate Quinic acid 3,5-di-O-caffeic acid C25H24O12 516.4509 516.126776232 (1S,3R,4S,5R)-3,5-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid (1S,3R,4S,5R)-3,5-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid 2450-53-5 O[C@H]1[C@H](OC(=O)\C=C\C2=CC=C(O)C(O)=C2)C[C@@](O)(C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1)C(=O)O InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(30)36-19-11-25(35,24(33)34)12-20(23(19)32)37-22(31)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-29,32,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23-,25+/m1/s1 KRZBCHWVBQOTNZ-PSEXTPKNSA-N belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, and 5, as well as a carboxylic acid at position 1. Quinic acids and derivatives Organic compounds Organic oxygen compounds Organooxygen compounds Alcohols and polyols Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alpha hydroxy acids and derivatives Carbonyl compounds Carboxylic acids Catechols Cinnamic acid esters Coumaric acids and derivatives Cyclohexanols Enoate esters Fatty acid esters Hydrocarbon derivatives Organic oxides Styrenes Tertiary alcohols Tricarboxylic acids and derivatives 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Alpha,beta-unsaturated carboxylic ester Alpha-hydroxy acid Aromatic homomonocyclic compound Benzenoid Carbonyl group Carboxylic acid Carboxylic acid derivative Carboxylic acid ester Catechol Cinnamic acid ester Cinnamic acid or derivatives Coumaric acid or derivatives Cyclohexanol Enoate ester Fatty acid ester Fatty acyl Hydrocarbon derivative Hydroxy acid Hydroxycinnamic acid or derivatives Monocyclic benzene moiety Organic oxide Phenol Quinic acid Secondary alcohol Styrene Tertiary alcohol Tricarboxylic acid or derivatives carboxylic ester cyclitol carboxylic acid logp 2.05 ALOGPS logs -3.61 ALOGPS solubility 1.25e-01 g/l ALOGPS melting_point Mp 170-172° dec. logp 2.16 ChemAxon pka_strongest_acidic 3.28 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac (1S,3R,4S,5R)-3,5-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid ChemAxon average_mass 516.4509 ChemAxon mono_mass 516.126776232 ChemAxon smiles O[C@H]1[C@H](OC(=O)\C=C\C2=CC=C(O)C(O)=C2)C[C@@](O)(C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1)C(=O)O ChemAxon formula C25H24O12 ChemAxon inchi InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(30)36-19-11-25(35,24(33)34)12-20(23(19)32)37-22(31)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-29,32,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23-,25+/m1/s1 ChemAxon inchikey KRZBCHWVBQOTNZ-PSEXTPKNSA-N ChemAxon polar_surface_area 211.28 ChemAxon refractivity 126.76 ChemAxon polarizability 49.46 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 10 ChemAxon donor_count 7 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 9810 Specdb::CMs 41243 Specdb::MsMs 51081 Specdb::MsMs 51082 Specdb::MsMs 51083 Specdb::MsMs 171519 Specdb::MsMs 171520 Specdb::MsMs 171521 Specdb::MsMs 374124 Specdb::MsMs 374125 Specdb::MsMs 2226369 Specdb::MsMs 2228358 Specdb::MsMs 2228700 Specdb::MsMs 2230726 Specdb::MsMs 2231178 Specdb::MsMs 2233037 Specdb::MsMs 2401643 Specdb::MsMs 2401644 Specdb::MsMs 2401645 Specdb::MsMs 2533758 Specdb::MsMs 2533759 Specdb::MsMs 2533760 HMDB30706 521393 #<Reference:0x000055ce32063c58> Arabica coffee Type 1 specific Coffea arabica 13443 3.515889 6.345666915 1.549999952 mg/100 g Carrot Type 1 specific Daucus carota ssp. sativus 79200 2.096667 2.096666654 2.096666654 mg/100 g Coffee Type 1 generic Coffea 13442 3.947833 6.345666915 1.549999952 mg/100 g Coffee and coffee products Unknown generic Eggplant Type 1 specific Solanum melongena 4111 Fruits Unknown generic Green vegetables Unknown generic Lettuce Type 1 specific Lactuca sativa 4236 Potato Type 1 specific Solanum tuberosum 4113 Quince Type 1 specific Cydonia oblonga 36610 0.510625 0.581250008 0.439999998 mg/100 g Robusta coffee Type 1 specific Coffea canephora 49390 4.105222 6.345666915 1.549999952 mg/100 g Anti peroxidant 519 Anti radicular 572 Anti-hemolytic 319 Drug that acts on blood and blood-forming organs and those that affect the hemostatic system. Anti-oxidant 502 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. Xanthine oxidase inhibitor 1431 An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).