1.0 2010-04-08 22:12:24 UTC 2020-02-24 19:11:05 UTC FDB016397 Helichrysoside (6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4h-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate is a member of the class of compounds known as flavonoid 3-o-p-coumaroyl glycosides. Flavonoid 3-o-p-coumaroyl glycosides are flavonoid 3-O-glycosides where the carbohydrate moiety is esterified with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring (6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4h-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4h-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate can be found in european chestnut and saffron, which makes (6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4h-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate a potential biomarker for the consumption of these food products. Helichrysoside C30H26O14 610.519 610.13225554 (6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate (6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate 56343-26-1 [H]\C(=C(\[H])C1=CC=C(O)C=C1)C(=O)OCC1OC(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC(O)=C(O)C=C2)C(O)C(O)C1O InChI=1S/C30H26O14/c31-15-5-1-13(2-6-15)3-8-22(36)41-12-21-24(37)26(39)27(40)30(43-21)44-29-25(38)23-19(35)10-16(32)11-20(23)42-28(29)14-4-7-17(33)18(34)9-14/h1-11,21,24,26-27,30-35,37,39-40H,12H2/b8-3+ NBAZENYUDPJQIH-FPYGCLRLSA-N belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Alpha amino acids Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic acyclic compounds Amino acids Amino fatty acids Branched fatty acids Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Medium-chain fatty acids Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Unsaturated fatty acids Aliphatic acyclic compound Alpha-amino acid Amine Amino acid Amino fatty acid Branched fatty acid Carbonyl group Carboxylic acid Fatty acid Fatty acyl Hydrocarbon derivative Medium-chain fatty acid Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Unsaturated fatty acid logp 2.82 ALOGPS logs -3.45 ALOGPS solubility 2.18e-01 g/l ALOGPS melting_point Mp 181-184° logp 2.59 ChemAxon pka_strongest_acidic 6.37 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac (6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate ChemAxon average_mass 610.519 ChemAxon mono_mass 610.13225554 ChemAxon smiles [H]\C(=C(\[H])C1=CC=C(O)C=C1)C(=O)OCC1OC(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC(O)=C(O)C=C2)C(O)C(O)C1O ChemAxon formula C30H26O14 ChemAxon inchi InChI=1S/C30H26O14/c31-15-5-1-13(2-6-15)3-8-22(36)41-12-21-24(37)26(39)27(40)30(43-21)44-29-25(38)23-19(35)10-16(32)11-20(23)42-28(29)14-4-7-17(33)18(34)9-14/h1-11,21,24,26-27,30-35,37,39-40H,12H2/b8-3+ ChemAxon inchikey NBAZENYUDPJQIH-FPYGCLRLSA-N ChemAxon polar_surface_area 232.9 ChemAxon refractivity 150.82 ChemAxon polarizability 58.29 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 13 ChemAxon donor_count 8 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 55971 Specdb::MsMs 55972 Specdb::MsMs 55973 Specdb::MsMs 111261 Specdb::MsMs 111262 Specdb::MsMs 111263 Specdb::MsMs 2381951 Specdb::MsMs 2381952 Specdb::MsMs 2381953 Specdb::MsMs 2581248 Specdb::MsMs 2581249 Specdb::MsMs 2581250 Specdb::CMs 51831 Specdb::CMs 71911 Specdb::CMs 511553 Specdb::CMs 511554 Specdb::CMs 511555 Specdb::CMs 511556 Specdb::CMs 511557 Specdb::CMs 511558 Specdb::CMs 511559 Specdb::CMs 511560 Specdb::CMs 511561 Specdb::CMs 511562 Specdb::CMs 511563 Specdb::CMs 511564 Specdb::CMs 511565 Specdb::CMs 511566 Specdb::CMs 511567 Specdb::CMs 511568 Specdb::CMs 511569 Specdb::CMs 511570 Specdb::CMs 511571 Specdb::CMs 511572 Specdb::CMs 511573 Specdb::CMs 511574 Specdb::CMs 511575 European chestnut Type 1 specific Castanea sativa 21020 Saffron Type 1 specific Crocus sativus 82528