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CHEBI:65664 - 6'-coumaroyl-1'-O-[2-(3,4-dihydroxyphenyl)ethyl]-β-D-glucopyranoside

ChEBI IDCHEBI:65664
ChEBI Name6'-coumaroyl-1'-O-[2-(3,4-dihydroxyphenyl)ethyl]-β-D-glucopyranoside
Stars
ASCII Name6'-coumaroyl-1'-O-[2-(3,4-dihydroxyphenyl)ethyl]-beta-D-glucopyranoside
DefinitionA cinnamate ester obtained by the formal condensation of trans-4-coumaric acid with 2-(3,4-dihydroxyphenyl)ethyl β-D-glucopyranoside. It is a phenolic glycoside derivative obtained from the aerial parts of Globularia alypum and exhibits antioxidant activity.
Last Modified17 December 2012
DownloadsMolfile
FormulaC23H26O10
Net Charge0
Average Mass462.451
Monoisotopic Mass462.15260
SMILESO=C(/C=C/c1ccc(O)cc1)OC[C@H]1O[C@@H](OCCc2ccc(O)c(O)c2)[C@H](O)[C@@H](O)[C@@H]1O
InChIInChI=1S/C23H26O10/c24-15-5-1-13(2-6-15)4-8-19(27)32-12-18-20(28)21(29)22(30)23(33-18)31-10-9-14-3-7-16(25)17(26)11-14/h1-8,11,18,20-26,28-30H,9-10,12H2/b8-4+/t18-,20-,21+,22-,23-/m1/s1
InChIKeyDNMNWOHCZHSQAI-FZYQUXMESA-N
Species of MetaboliteComponentSourceComments
Globularia alypum (IPNI:813050-1) aerial part (BTO:0001658) PubMed (16124783)
Roles Classification
Chemical Role:
antioxidant  A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Role:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
6'-coumaroyl-1'-O-[2-(3,4-dihydroxyphenyl)ethyl]-β-D-glucopyranoside (CHEBI:65664) has functional parent trans-4-coumaric acid (CHEBI:32374)
6'-coumaroyl-1'-O-[2-(3,4-dihydroxyphenyl)ethyl]-β-D-glucopyranoside (CHEBI:65664) has role antioxidant (CHEBI:22586)
6'-coumaroyl-1'-O-[2-(3,4-dihydroxyphenyl)ethyl]-β-D-glucopyranoside (CHEBI:65664) has role metabolite (CHEBI:25212)
6'-coumaroyl-1'-O-[2-(3,4-dihydroxyphenyl)ethyl]-β-D-glucopyranoside (CHEBI:65664) is a catechols (CHEBI:33566)
6'-coumaroyl-1'-O-[2-(3,4-dihydroxyphenyl)ethyl]-β-D-glucopyranoside (CHEBI:65664) is a cinnamate ester (CHEBI:36087)
6'-coumaroyl-1'-O-[2-(3,4-dihydroxyphenyl)ethyl]-β-D-glucopyranoside (CHEBI:65664) is a polyphenol (CHEBI:26195)
6'-coumaroyl-1'-O-[2-(3,4-dihydroxyphenyl)ethyl]-β-D-glucopyranoside (CHEBI:65664) is a β-D-glucoside (CHEBI:22798)
IUPAC Name 
2-(3,4-dihydroxyphenyl)ethyl 6-O-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-β-D-glucopyranoside
Registry NumbersSources
Reaxys:15769700Reaxys
Citations