Procyanidin B6
Basic information
- CAS
12798-58-2- 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-ZBRHZRBFSA-N- Molecular formula
- C30H26O12
- Average molar mass
- 578.5 g/mol
- Monoisotopic mass
- 578.14242626
Overview
Procyanidin B6 is a proanthocyanidin consisting of two molecules of (+)-catechin joined by a bond between positions 4 and 6' in alpha-configuration. Procyanidin B6 is isolated from leaves and fruit of cowberry Vaccinium vitis-idaea and other plants. It can also be found in grape seeds and in beer. It has a role as a metabolite. It is a proanthocyanidin, a biflavonoid and a hydroxyflavan. It is functionally related to a (+)-catechin.
Names & identifiers
- Preferred name
- Procyanidin B6
- IUPAC
- (2R,3S)-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)-CATECHIN
- Molecular formula
- C30H26O12
- Molecular weight
- 578.52
Names & synonyms
Procyanidin B612798-58-2Procyanidin dimer B6Catechin(4a->6)catechincatechin-(4alpha->6)-catechinCHEBI:75619C-(4,6)-C(2r,2'r,3s,3's,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:176137Procyanidol B6SZ77QV8UB3(2R,3S)-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
Show more names
(4→6)-Procyanidin B6(2R,2'R,3S,3'S,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[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'S,4R)-(2R)-2α-(3,4-Dihydroxyphenyl)-4α-[(2R)-2α-(3,4-dihydroxyphenyl)-3β,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-6-yl]-3,4-dihydro-2H-1-benzopyran-3β,5,7-triol(2R,3S)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-6-[[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-3,5,7-trihydroxy-2H-1-benzopyran]-4α-yl]-2H-1-benzopyran-3,5,7-triol
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
- 77 QV8UB3 · SZ77QV8UB3
Chemistry & industry
Additional notes
DefinitionChEBI: Procyanidin B6 is a proanthocyanidin consisting of two molecules of (+)-catechin joined by a bond between positions 4 and 6' in alpha-configuration. Procyanidin B6 is isolated from leaves and fruit of cowberry Vaccinium vitis-idaea and other plants. It can also be found in grape seeds and in beer. It has a role as a metabolite. It is a hydroxyflavan, a proanthocyanidin and a biflavonoid. It is functionally related to a (+)-catechin.
Related reactions
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Compound notes
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