Procyanidin B8
Basic information
- CAS
12798-60-6- Standard SMILES
Oc1cc(O)c2c(c1)O[C@H](c1ccc(O)c(O)c1)[C@@H](O)[C@@H]2c1c(O)cc2c(c1O)C[C@@H](O)[C@@H](c1ccc(O)c(O)c1)O2- InChIKey
GMISZFQPFDAPGI-JJYFIROESA-N- Molecular formula
- C30H26O12
- Average molar mass
- 578.5 g/mol
- Monoisotopic mass
- 578.14242626
Overview
Procyanidin B8 is a proanthocyanidin that is (+)-catechin and ()-epicatechin units joined by a bond between positions 4 and 6' respectively in an alpha-configuration. Procyanidin B8 is found in acorn and is present in fruit and leaves of blackberry (Rubus fruticosus), raspberry (Rubus idaeus) and cowberry (Vaccinium vitis idaea). It can be also found in grape seeds and in beer. It has a role as a metabolite. It is a polyphenol, a proanthocyanidin, a biflavonoid and a hydroxyflavan. It is functionally related to a (+)-catechin and a (-)-epicatechin.
Names & identifiers
- Preferred name
- Procyanidin B8
- IUPAC
- (2R,3R)-2-(3,4-dihydroxyphenyl)-6-[(2R,3S,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
- English name
- CATECHIN-(4ALPHA->6)-EPICATECHIN
- Molecular formula
- C30H26O12
- Molecular weight
- 578.52
Names & synonyms
Procyanidin B812798-60-6CHEBI:75618catechin-(4alpha->6)-epicatechin(2r,2'r,3s,3'r,4r)-2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-2h,2'h-4,6'-bichromene-3,3',5,5',7,7'-hexolRefChem:176138Catechin(4a->6) epicatechinProcyanidol B8KW4926C35LUNII-KW4926C35L(2R,3R)-2-(3,4-dihydroxyphenyl)-6-[(2R,3S,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(+)-Catechin-(4alpha-6)-(-)-epicatechin
Show more names
(2R,2'R,3S,3'R,4α)-3,3',4,4'-Tetrahydro-2α,2'α-bis(3,4-dihydroxyphenyl)-4,6'-bi[2H-1-benzopyran]-3,3',5,5',7,7'-hexol
(2R,2'R,3S,3'R,4R)-2,2'-Bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro(4,6'-bi-2H-1-benzopyran)-3,3',5,5',7,7'-hexol(4,6'-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,3S,3'R,4R)-(2R,2'R,3S,3'R,4R)-2,2'-Bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro[4,6'-bi-2H-1-benzopyran]-3,3',5,5',7,7'-hexol[4,6'-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,3S,3'R,4R)-CHEMBL451115SCHEMBL28938040DTXSID701028816Catechin-(4.alpha.-->6)epicatechin
Database identifiers
- CAS
12798-60-6- PubChem CID
- 474541
- DTXSID
DTXSID701028816- ChEMBL
CHEMBL451115- ChEBI
CHEBI:75618- UNII
- KW4926C35L
- Nikkaji
- J413.375G
Properties
Computed structural properties
- XLogP
- 2.4
- Topological polar surface area
- 221 Ų
- Hydrogen bond donors
- 10
- Hydrogen bond acceptors
- 12
- Rotatable bonds
- 3
- Heavy atoms
- 42
- Formal charge
- 0
- Complexity
- 925
Physicochemical properties
- Boiling point
- 1009.6 · 1009.6±65.0 °C(Predicted)
- Density
- 1.705 · 1.705±0.06 g/cm3(Predicted)
- pka
- 9.29 · 9.29±0.60(Predicted)
- FDA UNII
- 4926 C35L · KW4926C35L
Chemistry & industry
Additional notes
DefinitionChEBI: Procyanidin B8 is a proanthocyanidin that is (+)-catechin and (-)-epicatechin units joined by a bond between positions 4 and 6' respectively in an alpha-configuration. Procyanidin B8 is found in acorn and is present in fruit and leaves of blackberry (Rubus fruticosus), raspberry (Rubus idaeus) and cowberry (Vaccinium vitis idaea). It can be also found in grape seeds and in beer. It has a role as a metabolite. It is a hydroxyflavan, a proanthocyanidin, a biflavonoid and a polyphenol. It is functionally related to a (-)-epicatechin and a (+)-catechin.
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