| Identification | Back Directory | [Name]
PROCYANIDIN B3 | [CAS]
23567-23-9 | [Synonyms]
PROCYANIDIN B3
Procyanidol B3
PROCYANIDIN B3 USP/EP/BP
procyanidin B3 from barley
CATECHIN-(4ALPHA->8)-CATECHIN
CATECHIN-(4ALPHA->8)-CATECHIN B3
[4,8''-Biflavan]-3,3',3'',3''',4',4''',5,5'',7,7''-decol stereoisomer
(2R,2'R,3S,3'S,4S)-2,2'-Bis(3,4-dihydroxyphenyl)-4,8'-bichroman-3,3',5,5',7,7'-hexol
(2R,2'R,3S,3'S,4S)-2,2'-Bis(3,4-dihydroxyphenyl)-[4,8'-bichroman]-3,3',5,5',7,7'-hexaol
3,3',4,4'-Tetrahydro-2α,2'α-bis(3,4-dihydroxyphenyl)-4α,8'-bi[2H-1-benzopyran]-3β,3'β,5,5',7,7'-hexol
(2R,2'R,3S,3'S,4S)-2,2'-Bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-[4,8'-bi-2H-1-benzopyran]-3,3',5,5',7,7'-hexol
(2R,2'R,3S,3'S,4α)-3,3',4,4'-Tetrahydro-2α,2'α-bis(3,4-dihydroxyphenyl)-4,8'-bi[2H-1-benzopyran]-3,3',5,5',7,7'-hexol
[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,3S,3'S,4S)- | [Molecular Formula]
C30H26O12 | [MDL Number]
MFCD00166354 | [MOL File]
23567-23-9.mol | [Molecular Weight]
578.523 |
| Chemical Properties | Back Directory | [Melting point ]
218-219℃ | [Boiling point ]
955.3±65.0 °C(Predicted) | [density ]
1.705 | [storage temp. ]
?20°C | [solubility ]
Soluble in acetone and acetonitrile | [form ]
powder | [pka]
9.29±0.60(Predicted) | [color ]
White | [InChIKey]
XFZJEEAOWLFHDH-AVFWISQGSA-N | [SMILES]
[C@H]1(C2=CC=C(O)C(O)=C2)OC2=CC(O)=CC(O)=C2[C@@H](C2=C3O[C@H](C4=CC=C(O)C(O)=C4)[C@@H](O)CC3=C(O)C=C2O)[C@@H]1O | [CAS DataBase Reference]
23567-23-9 |
| Hazard Information | Back Directory | [Uses]
Procyanidin B3 is a natural product that acts as a specific HAT inhibitor. Procyanidin B3 is a polyphenol flavonoid dimer of (+)-catechin with diverse biological properties. Procyanidin B3 is a dimeric flavanol and an antifungal phenol extracted from Woodfordia uniflora. | [Definition]
ChEBI: A proanthocyanidin consisting of two molecules of (+)-catechin joined by a bond between positions 4 and 8' in alpha-configuration. It can be found in red wine, in barley, in beer, in peach or in Jatropha macrantha, the Huanarp
Macho. | [in vivo]
Procyanidin B3 (100 mg/kg, p.o., 5 days a week for 4 weeks) prevents articular cartilage degeneration and heterotopic cartilage formation in a surgically-induced osteoarthritis mice model[2].
Procyanidin B3 (30 mg/kg, p.o., once daily for 4 weeks) delays the development of intervertebral disc degeneration (IVDD) in a Lipopolysaccharides (HY-D1056)-induced IVDD Sprague-Dawley rats model[2]. | Animal Model: | Lipopolysaccharides (HY-D1056)-induced IVDD (intervertebral disc degeneration) Sprague-Dawley rats model | | Dosage: | 30 mg/kg | | Administration: | Oral gavage (p.o.),once daily for 4 weeks | | Result: | Prevented the loss of gelatin NP cells and structural damage of annulus fibrosus in IVDD rat model. |
| Animal Model: | Surgically-induced osteoarthritis mice model[2] | | Dosage: | 100 mg/kg | | Administration: | Oral gavage (p.o.), once daily, 5 days a week for 4 weeks | | Result: | Prevented aberrant articular cartilage degeneration and heterotopic cartilage formation through suppression of the nitric oxide synthase (iNOS). |
| [IC 50]
CBP/p300; TLR4 | [storage]
Store at -20°C |
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