Procyanidin B1

Base Information

• Chemical Name: Procyanidin B1
• CAS No.: 20315-25-7
• Molecular Formula: C30H26O12
• Molecular Weight: 578.529
• Hs Code.: 29329990
• Mol file: 20315-25-7.mol

Synonyms:Procyanidin B1;

Chemical Property of Procyanidin B1

Chemical Property:

• Appearance/Colour: Red-Brown Powder
• Melting Point: 231～232℃
• Boiling Point: 955.3 °C at 760 mmHg
• PKA: 9.29±0.60(Predicted)
• Flash Point: 531.6 °C
• PSA: 220.76000
• Density: 1.705g/cm³
• LogP: 2.99500
• Storage Temp.: 2-8°C
• Solubility.: Acetone (Slightly), Ethanol (Slightly), Methanol (Slightly), Water (Slightly)

Purity/Quality:

98% ^*data from raw suppliers

Procyanidin B1 ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Procyanidin B1

There total 29 articles about Procyanidin B1 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

3’,4’,5,7-tetra-O-benzyl-8-bromoepicatechin-(4β8)-3’,4’,5,7-tetra-O-benzylepicatechin (923565-06-4) → procyanidin B1 (20315-25-7)

Guidance literature:

With hydrogen; sodium hydrogencarbonate; triethylamine; palladium dihydroxide; In methanol; water; ethyl acetate; at 20 ℃; for 18h;

DOI:10.1002/ejoc.200600668

Reference yield: 98.0%

5,7,3',4'-tetra-O-benzyl-(-)-epicatechin-(4β,8β)-[5,7,3',4'-tetra-O-benzyl-(+)-catechin] (664351-43-3) → procyanidin B1 (20315-25-7)

Guidance literature:

With 10 wt% Pd(OH)2 on carbon; hydrogen; In water; ethyl acetate; at 25 ℃; for 4h; under 775.743 Torr; Reagent/catalyst; Solvent; Pressure; Inert atmosphere;

DOI:10.1021/op700031n

Reference yield: 38.0%

4β-benzylthioepicatechin (37064-35-0) + catechin (154-23-4) → procyanidin B1 (20315-25-7)

Guidance literature:

silver tetrafluoroborate; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1016/S0040-4020(98)00454-2

upstream raw materials:

3-O-galloyl-epicatechin-(4β->8)-catechin

C₆₀H₄₈O₂₄

4'α-benzylthioprocyanidin B-1

phenylmethanethiol

Downstream raw materials:

4β-benzylthioepicatechin

4α-Benzylthioepicatechin

catechin

procyanidin A1

Refernces

• 1、 Mohri, Yoshihiro,Sagehashi, Masayoshi,Yamada, Taiji,Hattori, Yasunao,Morimura, Keiji,Kamo, Tsunashi,Hirota, Mitsuru,Makabe, Hidefumi. "An efficient synthesis of procyanidins. Rare earth metal Lewis acid catalyzed equimolar condensation of catechin and epicatechin". . p. 5891 - 5894. Retrieved 2007.
• 2、 Fabre, Sandy,Gueroux, Marie,Nunes, Emeline,Szlosek-Pinaud, Magali,Pianet, Isabelle,Fouquet, Eric. "From the gold-catalysed benzylation of arenes to the regio- and stereoselective synthesis of procyanidins dimers". . p. 3045 - 3051. Retrieved 2015/05/04.
• 3、 Esatbeyoglu, Tuba,Winterhalter, Peter. "Preparation of dimeric procyanidins B1, B2, B5, and B7 from a polymeric procyanidin fraction of black chokeberry (Aronia melanocarpa)". experimental part. p. 5147 - 5153. Retrieved 2011/07/29.