1.0 2010-04-08 22:08:17 UTC 2019-11-26 03:03:19 UTC FDB008857 3-(3,4-Dihydroxyphenyl)propanoic acid 3,4-Dihydroxyhydrocinnamic acid (or Dihydrocaffeic acid, DHCA) is a metabolite product of the hydrogenation of caffeoylquinic acids, occurring in normal human biofluids, with potent antioxidant properties. DHCA has been detected in human plasma following coffee ingestion (PMID 15607645), and is increased with some dietary sources, such as after ingestion of phenolic constituents of artichoke leaf extract. (PMID 15693705) Polyphenol-rich foods such as vegetables and fruits have been shown to significantly improve platelet function in ex vivo studies in humans. (PMID 16038718) Its antioxidant activity has been tested to reduce ferric iron in the ferric reducing antioxidant power (FRAP) assay, and it has been suggested that its catechol structure convey the antioxidant effect in plasma and in erythrocytes. (PMID 11768243) [HMDB]. 3-(3,4-Dihydroxyphenyl)propanoic acid is found in red beetroot, common beet, and olive. 3-(3,4-Dihydroxyphenyl)propanoate 3-(3,4-Dihydroxyphenyl)propanoic acid 3-(3,4-Dihydroxyphenyl)propionate 3-(3,4-Dihydroxyphenyl)propionic acid 3,4-Dihydroxy-(6ci,7ci,8ci)hydrocinnamate 3,4-Dihydroxy-(6ci,7ci,8ci)hydrocinnamic acid 3,4-Dihydroxy-b-phenylpropionate 3,4-Dihydroxy-b-phenylpropionic acid 3,4-Dihydroxy-beta-phenylpropionate 3,4-Dihydroxy-beta-phenylpropionic acid 3,4-Dihydroxybenzenepropanoate 3,4-Dihydroxybenzenepropanoic acid 3,4-Dihydroxybenzenepropanoic acid, 9CI 3,4-Dihydroxybenzenepropionate 3,4-Dihydroxybenzenepropionic acid 3,4-Dihydroxydihydrocinnamate 3,4-Dihydroxydihydrocinnamic acid 3,4-Dihydroxyhydrocinnamate 3,4-Dihydroxyhydrocinnamic acid 3,4-Dihydroxyhydrocinnamic acid, 8CI 3,4-Dihydroxyphenylpropionate 3,4-Dihydroxyphenylpropionic acid Dihydrocaffeate Dihydrocaffeic acid Hydrocaffeate Hydrocaffeic acid C9H10O4 182.1733 182.057908808 3-(3,4-dihydroxyphenyl)propanoic acid dihydrocaffeic acid 1078-61-1 OC(=O)CCC1=CC=C(O)C(O)=C1 InChI=1S/C9H10O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1,3,5,10-11H,2,4H2,(H,12,13) DZAUWHJDUNRCTF-UHFFFAOYSA-N belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. Phenylpropanoic acids Organic compounds Phenylpropanoids and polyketides Phenylpropanoic acids Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Benzene and substituted derivatives Carbonyl compounds Carboxylic acids Catechols Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 3-phenylpropanoic-acid Aromatic homomonocyclic compound Benzenoid Carbonyl group Carboxylic acid Carboxylic acid derivative Catechol Hydrocarbon derivative Monocarboxylic acid or derivatives Monocyclic benzene moiety Organic oxide Organic oxygen compound Organooxygen compound Phenol catechols monocarboxylic acid Solid logp 1.04 ALOGPS logs -1.84 ALOGPS solubility 2.62e+00 g/l ALOGPS logp 1.45 ChemAxon pka_strongest_acidic 3.84 ChemAxon pka_strongest_basic -6.3 ChemAxon iupac 3-(3,4-dihydroxyphenyl)propanoic acid ChemAxon average_mass 182.1733 ChemAxon mono_mass 182.057908808 ChemAxon smiles OC(=O)CCC1=CC=C(O)C(O)=C1 ChemAxon formula C9H10O4 ChemAxon inchi InChI=1S/C9H10O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1,3,5,10-11H,2,4H2,(H,12,13) ChemAxon inchikey DZAUWHJDUNRCTF-UHFFFAOYSA-N ChemAxon polar_surface_area 77.76 ChemAxon refractivity 45.93 ChemAxon polarizability 17.85 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::NmrTwoD 1307 Specdb::MsIr 502 Specdb::MsIr 503 Specdb::MsIr 504 Specdb::CMs 1675 Specdb::CMs 5557 Specdb::CMs 31142 Specdb::CMs 37522 Specdb::CMs 148240 Specdb::CMs 1061356 Specdb::CMs 1061358 Specdb::CMs 1061359 Specdb::CMs 1061361 Specdb::CMs 1061363 Specdb::CMs 1061365 Specdb::CMs 1061367 Specdb::CMs 1061368 Specdb::CMs 1061370 Specdb::CMs 1061372 Specdb::CMs 1061374 Specdb::CMs 1061376 Specdb::CMs 1061378 Specdb::NmrOneD 1363 Specdb::NmrOneD 143830 Specdb::NmrOneD 143831 Specdb::NmrOneD 143832 Specdb::NmrOneD 143833 Specdb::NmrOneD 143834 Specdb::NmrOneD 143835 Specdb::NmrOneD 143836 Specdb::NmrOneD 143837 Specdb::NmrOneD 143838 Specdb::NmrOneD 143839 Specdb::NmrOneD 143840 Specdb::NmrOneD 143841 Specdb::NmrOneD 143842 Specdb::NmrOneD 143843 Specdb::NmrOneD 143844 Specdb::NmrOneD 143845 Specdb::NmrOneD 143846 Specdb::NmrOneD 143847 Specdb::NmrOneD 143848 Specdb::NmrOneD 143849 Specdb::MsMs 626 Specdb::MsMs 627 Specdb::MsMs 628 Specdb::MsMs 4052 Specdb::MsMs 4053 Specdb::MsMs 4054 Specdb::MsMs 4055 Specdb::MsMs 4056 Specdb::MsMs 12215 Specdb::MsMs 12216 Specdb::MsMs 12217 Specdb::MsMs 18887 Specdb::MsMs 18888 Specdb::MsMs 18889 Specdb::MsMs 437534 Specdb::MsMs 437535 Specdb::MsMs 437536 Specdb::MsMs 437537 Specdb::MsMs 437538 Specdb::MsMs 2374443 Specdb::MsMs 2374444 Specdb::MsMs 2374445 Specdb::MsMs 2560461 Specdb::MsMs 2560462 Specdb::MsMs 2560463 HMDB00423 #<Reference:0x000055ac403d0508> #<Reference:0x000055ac403d0288> #<Reference:0x000055ac403cbfa8> #<Reference:0x000055ac403cbdf0> #<Reference:0x000055ac403cbc38> Apple cider Type 2 specific Arabica coffee Type 1 specific Coffea arabica 13443 Broccoli Type 1 specific Brassica oleracea var. italica 36774 Coffee Type 1 generic Coffea 13442 Common beet Type 1 specific Beta vulgaris 161934 Common wheat Type 1 specific Triticum aestivum 4565 Corn Type 1 specific Zea mays 4577 Grape Type 1 specific Vitis 3603 Lemon Type 1 specific Citrus limon 2708 Lettuce Type 1 specific Lactuca sativa 4236 Lime Type 1 specific Citrus aurantiifolia 159033 Olive Type 1 specific Olea europaea 4146 3.75 6.0 1.5 mg/100 g Red beetroot Type 1 specific Beta vulgaris var. rubra Robusta coffee Type 1 specific Coffea canephora 49390 Spinach Type 1 specific Spinacia oleracea 3562 Wheat bread Type 2 specific antioxidant 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.