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Compound Summary

General Compound Information

procyanidin B1

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Description

Procyanidin B1 is a proanthocyanidin consisting of (-)-epicatechin and (+)-catechin units joined by a bond between positions 4 and 8" respectively in a beta-configuration.. Procyanidin B1 can be found in Cinnamomum verum (Ceylon cinnamon, in the rind, bark or cortex), in Uncaria guianensis (cat"s claw, in the root), and in Vitis vinifera (common grape vine, in the leaf) or in peach. It has a role as a metabolite, an EC 3.4.21.5 (thrombin) inhibitor and an anti-inflammatory agent. It is a hydroxyflavan, a proanthocyanidin, a biflavonoid and a polyphenol. It derives from a (-)-epicatechin and a (+)-catechin.

Synonyms

Procyanidin B1; 20315-25-7; Proanthocyanidin B1; Endotelon; Procyanidin dimer B1;

CHEBI:75633;Epicatechin-(4beta->8)-ent-epicatechin;EC-(4b,8)-C;0566J48E7X;(2R,3S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol;(4,8-Bi-2H-1-benzopyran)-3,3',5,5',7,7'-hexol, 2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-;2,2'-Bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-(4,8-Bi-2H-1-benzopyran)-3,3',5,5',7,7'-hexol;Procyanidin B;Procyanidin D;Procyanidol D;[4,8'-Bi-2H-1-benzopyran]-3,3',5,5',7,7'-hexol, 2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-, (2R,2'R,3R,3'S,4R)-;ProcyanidinB1;Procyanidin-B1;UNII-0566J48E7X;procyanidin-B-2;(4,8'-BI-2H-1-BENZOPYRAN)-3,3',5,5',7,7'-HEXOL, 2,2'-BIS(3,4-DIHYDROXYPHENYL)-3,3',4,4'-TETRAHYDRO-, (2R,2'R,3R,3'S,4R)-;MFCD01861512;PROCYANIDOL B1;Epicatechin(4b->8)catechin;(+)-PROCYANIDIN B1;SCHEMBL676745;Epicatechin(4beta->8)catechin;CHEMBL504937;PROCYANIDIN B1, (+)-;cis,trans''-4,8''-Bi-(3,3',4',5,7-Pentahydroxyflavane);DTXSID401030238;HY-N0795;Procyanidin B1, analytical standard;BDBM50553252;LMPK12030001;ZINC26490620;AKOS030530133;CS-5955;AC-34943;AS-78072;4,8-Bi-(3,3',4',5,7-Pentahydroxyflavane);Q-100247;Q7247551;(-)-EPICATECHIN-(4.BETA.-8)-(+)-CATECHIN;PROCYANIDIN B1 (CONSTITUENT OF MARITIME PINE) [DSC];(2R,2'R,3R,3'S,4R)-2,2'-Bis(3,4-dihydroxyphenyl)-[4,8'-bichroman]-3,3',5,5',7,7'-hexaol;(2R,2'R,3R,3'S,4R)-2,2'-Bis(3,4-dihydroxyphenyl)-[4,8'-bichromane]-3,3',5,5',7,7'-hexaol;(2R,2'R,3R,3'S,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;(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chroman-8-yl]chromane-3,5,7-triol;(4,8'-BI-2H-1-BENZOPYRAN)-3,3',5,5',7,7'-HEXOL, 2,2'-BIS(3,4-DIHYDROXYPHENYL)-3,3',4,4'-TETRAHYDRO-, (2R-(2.ALPHA.,3.ALPHA.,4.BETA.(2'R,3'S)))-;

FlavorDB ID

489

PUBCHEM ID

11250133

Molecular Weight

578.5

Molecular Formula

C30H26O12

Openeye Can Smiles

C1C(C(OC2=C1C(=CC(=C2C3C(C(OC4=CC(=CC(=C34)O)O)C5=CC(=C(C=C5)O)O)O)O)O)C6=CC(=C(C=C6)O)O)O

IUPAC Inchikey

XFZJEEAOWLFHDH-UKWJTHFESA-N

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Compound Classification

Classification (Parent Nodes)

ClassyFire Ontology

Compound Quality

CATEGORY	QUALITY	THRESHOLD	OCCURENCE	REFERENCE
taste	astringent	2.400e+2 µmol/L	red wine	details
taste	bitter	4.000e+2 µmol/L	red wine	details
taste	astringent	2.400e+2 µmol/L	apple apple juice	details
taste	bitter	4.000e+2 µmol/L	apple apple juice	details

Compound Toxicity

Toxicity and Food Additive Safety of this compound is not available!

Receptors

Receptor	REFERENCE	EC50 [µM]	Effective Concentration [µM]
TAS2R5	details	119.34	67.00
TAS2R7	details	123.95	67.00

Consensus Spectra

Spectrum Type	Spectrum View	Description	Polarity
Experimental LCMS	view	LCMS_Negative	negative