Procyanidin B3

Base Information

• Chemical Name: Procyanidin B3
• CAS No.: 23567-23-9
• Molecular Formula: C30H26O12
• Molecular Weight: 578.529
• European Community (EC) Number: 621-754-2
• UNII: 2TC1A0KEAQ
• DSSTox Substance ID: DTXSID60178193
• Nikkaji Number: J56.254H
• Wikipedia: Procyanidin_B3
• Wikidata: Q7247553
• Metabolomics Workbench ID: 22116
• ChEMBL ID: CHEMBL501490
• Mol file: 23567-23-9.mol

Synonyms:procyanidin B-3;procyanidin B3

Chemical Property of Procyanidin B3

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 218-219℃
• Refractive Index: 1.803
• Boiling Point: 955.3 °C at 760 mmHg
• PKA: 9.29±0.60(Predicted)
• Flash Point: 531.6 °C
• PSA: 220.76000
• Density: 1.705 g/cm³
• LogP: 2.99500
• Storage Temp.: ?20°C
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 3
• Exact Mass: 578.14242626
• Heavy Atom Count: 42
• Complexity: 925

Purity/Quality:

99%, ^*data from raw suppliers

Procyanidin B3 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC2=C1C(=CC(=C2C3C(C(OC4=CC(=CC(=C34)O)O)C5=CC(=C(C=C5)O)O)O)O)O)C6=CC(=C(C=C6)O)O)O
• Isomeric SMILES: C1[C@@H]([C@H](OC2=C1C(=CC(=C2[C@H]3[C@@H]([C@H](OC4=CC(=CC(=C34)O)O)C5=CC(=C(C=C5)O)O)O)O)O)C6=CC(=C(C=C6)O)O)O
• 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.

Technology Process of Procyanidin B3

There total 30 articles about Procyanidin B3 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-bromocatechin-(4α8)-3’,4’,5,7-tetra-O-benzylcatechin (923565-04-2) → procyanidin B3 (23567-23-9)

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: 91.0%

5,7,3',4'-tetra-O-benzyl-4α-(5,7,3',4'-tetra-O-benzylcatechin)catechin (137550-06-2) → procyanidin B3 (23567-23-9)

Guidance literature:

With hydrogen; palladium dihydroxide; In tetrahydrofuran; methanol; water; at 20 ℃; for 3h;

DOI:10.1016/j.tetlet.2008.02.173

Reference yield: 76.0%

8-bromo-3,5,7,3',4'-penta-O-benzyl-catechin-(4α->8)-3,5,7,3',4'-penta-O-benzyl-catechin (777063-26-0) → procyanidin B3 (23567-23-9)

Guidance literature:

With 20 % Pd(OH)2/C; hydrogen; triethylamine; In methanol; ethyl acetate; at 20 ℃; for 20h;

DOI:10.1016/j.tet.2011.10.039

upstream raw materials:

(+)-leucocyanidin

catechin

taxifolin

epicatechin-(4β<*>8)-catechin-(4α<*>8)-catechin

Downstream raw materials:

5,7,3',4',5'',7'',3''',4'''-octa-O-methylprocyanidin B-3

(2R,3S)-(+)-catechin 3',4',5,7-tetramethyl ether

catechin-(4α <*> 8)-catechin-(4α <*> 8)-catechin (C2)

(+)-catechin tetramethyl ether acetate

Refernces

• 1、 Goncalves, Rui,Mateus, Nuno,De Freitas, Victor. "Influence of carbohydrates on the interaction of procyanidin B3 with trypsin". . p. 11794 - 11802. Retrieved 2011.
• 2、 -. "COMPOSITION FOR PROMOTING EXPRESSION OF AQUAPORIN 3, AND USE THEREOF". Paragraph 0239; 0242. . Retrieved 2020/09/22.
• 3、 Dennis, Eric G.,Jeffery, David W.,Johnston, Martin R.,Perkins, Michael V.,Smith, Paul A.. "Procyanidin oligomers. A new method for 4→8 interflavan bond formation using C8-boronic acids and iterative oligomer synthesis through a boron-protection strategy". experimental part. p. 340 - 348. Retrieved 2012/01/06.