procyanidin B2 (CHEBI:75632)

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CHEBI:75632 - procyanidin B2

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ChEBI ID	CHEBI:75632
ChEBI Name	procyanidin B2
Stars
Definition	A proanthocyanidin consisting of two molecules of (−)-epicatechin joined by a bond between positions 4 and 8' in a β-configuration. Procyanidin B2 can be found in Cinchona pubescens (Chinchona, in the rind, bark and cortex), in Cinnamomum verum (Ceylon cinnamon, in the rind, bark and cortex), in Crataegus monogyna (Common hawthorn, in the flower and blossom), in Uncaria guianensis (Cat's claw, in the root), in Vitis vinifera (Common grape vine, in the leaf), in Litchi chinensis (litchi, in the pericarp), in the apple, in Ecdysanthera utilis and in red wine.
Last Modified	28 July 2014
Submitter	mwilliams
Downloads	Molfile

Formula	C30H26O12
Net Charge	0
Average Mass	578.526
Monoisotopic Mass	578.14243
SMILES	Oc1cc(O)c2c(c1)O[C@H](c1ccc(O)c(O)c1)[C@H](O)[C@H]2c1c(O)cc(O)c2c1O[C@H](c1ccc(O)c(O)c1)[C@H](O)C2
InChI	InChI=1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26-,27-,28-,29-/m1/s1
InChIKey	XFZJEEAOWLFHDH-NFJBMHMQSA-N

Wikipedia

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.
Application:	astringent A compound that causes the contraction of body tissues, typically used to reduce bleeding from minor abrasions.

ChEBI Ontology

Outgoing Relation(s)
	procyanidin B2 (CHEBI:75632) has functional parent (−)-epicatechin (CHEBI:90)
	procyanidin B2 (CHEBI:75632) has role antioxidant (CHEBI:22586)
	procyanidin B2 (CHEBI:75632) has role metabolite (CHEBI:25212)
	procyanidin B2 (CHEBI:75632) is a biflavonoid (CHEBI:50128)
	procyanidin B2 (CHEBI:75632) is a hydroxyflavan (CHEBI:72010)
	procyanidin B2 (CHEBI:75632) is a polyphenol (CHEBI:26195)
	procyanidin B2 (CHEBI:75632) is a proanthocyanidin (CHEBI:26267)
Incoming Relation(s)
	procyanidin B2 3-O-gallate (CHEBI:75652) has functional parent procyanidin B2 (CHEBI:75632)
	procyanidin B2 3'-O-gallate (CHEBI:75647) has functional parent procyanidin B2 (CHEBI:75632)

IUPAC Name
(2R,2'R,3R,3'R,4R)-2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-2H,2'H-4,8'-bichromene-3,3',5,5',7,7'-hexol

Synonyms	Source
Procyanidol B2	KEGG COMPOUND
Epicathechin-(4β→8)-epicathechin	HMDB
Proanthocyanidin B2	HMDB
EC-(4b,8)-EC	HMDB

Manual Xrefs	Databases
LMPK12030002	LIPID MAPS
C17639	KEGG COMPOUND
HMDB0033973	HMDB
Procyanidin_B2	Wikipedia

Registry Numbers	Sources
Reaxys:1279736	Reaxys
CAS:29106-49-8	ChemIDplus
CAS:29106-49-8	KEGG COMPOUND

Citations