Basic information
- CAS
29106-51-2- Standard 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- InChIKey
XFZJEEAOWLFHDH-VUGKQVTMSA-N- Molecular formula
- C30H26O12
- Average molar mass
- 578.5 g/mol
- Monoisotopic mass
- 578.14242626
Overview
Procyanidin B4 is a proanthocyanidin obtained by the condensation of ()-epicatechin and (+)-catechin units. It has a role as an antioxidant, an antineoplastic agent and an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor. It is a proanthocyanidin and a hydroxyflavan. It is functionally related to a (+)-catechin and a (-)-epicatechin.
Names & identifiers
- Preferred name
- Procyanidin B4
- IUPAC
- (2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-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->8)-EPICATECHIN
- Molecular formula
- C30H26O12
- Molecular weight
- 578.52
Names & synonyms
Procyanidin B429106-51-2Catechin-(4alpha->8)-epicatechinProcyanidin B4, (-)-2OP8987K2X(2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triolCHEBI:27589DTXSID50183357(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-(2alpha,3beta,4alpha(2'R*,3'R*)))-(2R,3R)-2-(3,4-dihydroxyphenyl)-8-((2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl)-3,4-dihydro-2H-chromene-3,5,7-triolRefChem:176136DTXCID60105848
Show more names
PROCYANIDIN B-48)-EPICATECHINPROCYANIDINDIMERB4CATECHIN-(4ALPHA-gtProanthocyanidin B4Procyanidin Impurity 4(+)-Catechin-(4α-8)-(-)-epicatechinCATECHIN-(4ALPHA->8)-EPICATECHIN USP/EP/BP
Procyanidol B4(-)-procyanidin B4(2R,2'R,3S,3'R,4S)-2,2'-Bis(3,4-dihydroxyphenyl)-[4,8'-bichroman]-3,3',5,5',7,7'-hexaolUNII-2OP8987K2XC30H26O12SCHEMBL718738CHEMBL447373orb1684936
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
Experimental & physicochemical properties
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Proanthocyanidins [PK1203]
Physicochemical properties
- Melting point
- 178 · 178-180 °C (decomp)
- Boiling point
- 955.3 · 955.3±65.0 °C(Predicted)
- Density
- 1.705 · 1.705±0.06 g/cm3(Predicted)
- storage temp.
- 4 °C, · 4°C, away from moisture and light
- solubility
- Acetone: soluble; Chloroform: soluble; Dichloromethane: soluble; DMSO: soluble; Ethyl Acetate: soluble
- form
- A solid
- pka
- 9.29 · 9.29±0.60(Predicted)
- color
- White to off-white
- FDA UNII
- 2 OP8987K2X · 2OP8987K2X
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H315-H319
- Precautionary statements
- P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
Chemistry & industry
Pharmacology
Cellular LocationsMembrane
Applications
UsesProcyanidin B4 is a bioactive flavonoid and a proanthocyanidin grape seed extract that reduces inflammation and oxidative stress and restores tight junction barrier function in caco-2 colon cells.
Suppliers75 total
南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
銘瑞集團有限公司17318633522 · [email protected]
成都曼思特生物科技有限公司18010516991 · [email protected]
济南百隆化学有限公司[email protected] · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
南京普怡生物科技有限公司13814510036 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
上海纯优生物科技有限公司15921393123 18302135232 · [email protected]
成都埃法生物科技有限公司028-028-85142057 19983342022 · [email protected]
Related reactions
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Compound notes
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