Procyanidin B2

Base Information

• Chemical Name: Procyanidin B2
• CAS No.: 29106-49-8
• Molecular Formula: C30H26O12
• Molecular Weight: 578.529
• UNII: L88HKE854X
• DSSTox Substance ID: DTXSID701028797
• Nikkaji Number: J56.253J
• Wikipedia: Procyanidin_B2
• Wikidata: Q7247552
• Metabolomics Workbench ID: 22115
• ChEMBL ID: CHEMBL38714
• Mol file: 29106-49-8.mol

Synonyms:procyanidin B2

Chemical Property of Procyanidin B2

Chemical Property:

• Melting Point: 197-198 °C
• Boiling Point: 955.319 °C at 760 mmHg
• PKA: 9.29±0.60(Predicted)
• Flash Point: 531.558 °C
• PSA: 220.76000
• Density: 1.706 g/cm³
• LogP: 2.99500
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
• 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:

95%-98% ^*data from raw suppliers

Procyanidin B2 ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

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 B2 is a selective protein kinase C inhibitor and was also found to promote hair epithelial cell growth and stimulate anagen induction. Procyanidin B2 extracted from apples have also shown anti-inflammatory activities. Procyanidin B2 is a selective protein kinase C inhibitor and was also found to promote hair epithelial cell growth and stimulate anagen induction. Procyanidin B2 extracted from apples have also shown anti-inflammatory activities.

Technology Process of Procyanidin B2

There total 33 articles about Procyanidin B2 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: 99.0%

3',4',5,7-tetra-O-benzyl-8-bromoepicatechin-4β,8-(3',4',5,7-tetra-O-benzylepicatechin) (442626-19-9) → procyanidin B2 (29106-49-8)

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: 37.0%

4β-benzylthioepicatechin (37064-35-0) + (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol (490-46-0) → procyanidin B2 (29106-49-8)

Guidance literature:

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

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

Reference yield:

epicatechin-(4β->8)-epicatechin-(4β->8)-epicatechin-(4β->8)-epicatechin-(4β->8)-epicatechin (86631-39-2) + phenylmethanethiol (100-53-8) → procyanidin B2 (29106-49-8) + 4β-benzylthioepicatechin (37064-35-0) + (2R,3R,4R)-2,3-cis-3,4-trans-3,5,7,3',4'-pentahydroxy-4-<(2R,3S,4S)-2,3-cis-3,4-trans-3,5,7,3',4'-pentahydroxy-4-benzylthioflavan-8-yl>flavan (68200-27-1) + procyanidin C1 (37064-30-5) + (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol (490-46-0)

Guidance literature:

acetic acid; In ethanol; for 6h; Product distribution; Heating; other reaction time;

DOI:10.1248/cpb.34.633

upstream raw materials:

procyanidin B₂-3,3'-di-O-gallate

kandelin B-1

(-)-epicatechin-<4β->8>-(-)-epicatechin-<4β->8>-(-)-epicatechin-<4β->8>-(-)-epicatechin

phenylmethanethiol

Downstream raw materials:

5,7,3',4'-tetra-O-methylepicatechin-4β,8-(5,7,3',4'-tetra-O-methylepicatechin)

4β-benzylthioepicatechin

(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol

(-)-epicatechin benzylthioether

Refernces

• 1、 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.
• 2、 Mohri, Yoshihiro,Sagehashi, Masayoshi,Yamada, Taiji,Hattori, Yasunao,Morimura, Keiji,Hamauzu, Yasunori,Kamo, Tsunashi,Hirota, Mitsuru,Makabe, Hidefumi. "An efficient synthesis of procyanidins using equimolar condensation of catechin and/or epicatechin catalyzed by ytterbium triflate". experimental part. p. 549 - 563. Retrieved 2009/12/07.