Procyanidin B1 Chemical Properties

Melting point:

231～232℃

Boiling point:

955.3±65.0 °C(Predicted)

Density 

1.705±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

solubility 

Acetone (Slightly), Ethanol (Slightly), Methanol (Slightly), Water (Slightly)

pka

9.29±0.60(Predicted)

form 

Solid

color 

Pale Brown

InChIKey

XFZJEEAOWLFHDH-UKWJTHFESA-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

LogP

0.300 (est)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

F 

10-23

HS Code 

29329990

MSDS

• Language:English Provider:SigmaAldrich

Procyanidin B1 Usage And Synthesis

Description

Procyanidin B1 is a polyphenol flavonoid existing as a dimer of (+)-catechin and (−)-epicatechin . It inhibits hepatitis C virus RNA replication (EC₅₀ = 72 μM), while (+)-catechin and (−)-epicatechin do not, up to concentrations of 200 μM. Procyanidin B1 (10 μg/ml) prevents phosphorylation of ERK1/2 and the production of reactive oxygen species (ROS) in THP-1 cells. It decreases TNF-α, phosphorylated p38 MAPK, and NF-κB levels following LPS administration.

Chemical Properties

Pale yellow powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from grape seeds.

Uses

Procyanidins B1 is a B type proanthocyanidins found in ceylon cinnamon and is known to exhibit anti-inflammatory effects.

Definition

ChEBI: 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 is functionally related to a (-)-epicatechin and a (+)-catechin.

References

[1] SHENWEI LI. Procyanidin B1 purified from Cinnamomi cortex suppresses hepatitis C virus replication.[J]. Antiviral Chemistry and Chemotherapy, 2010, 20 6: 239-248. DOI: 10.3851/imp1597
[2] X TERRA. Procyanidin dimer B1 and trimer C1 impair inflammatory response signalling in human monocytes.[J]. Free Radical Research, 2011, 45 5: 611-619. DOI: 10.3109/10715762.2011.564165
[3] JING XING. Anti-inflammatory effect of procyanidin B1 on LPS-treated THP1 cells via interaction with the TLR4-MD-2 heterodimer and p38 MAPK and NF-κB signaling.[J]. Molecular and Cellular Biochemistry, 2015, 407 1-2: 89-95. DOI: 10.1007/s11010-015-2457-4

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