Procyanidin B4

Base Information

• Chemical Name: Procyanidin B4
• CAS No.: 29106-51-2
• Molecular Formula: C30H26 O12
• Molecular Weight: 578.529
• UNII: 2OP8987K2X
• DSSTox Substance ID: DTXSID50183357
• Nikkaji Number: J56.255F
• Wikipedia: Procyanidin_B4
• Wikidata: Q7247555
• Metabolomics Workbench ID: 22117
• ChEMBL ID: CHEMBL447373
• Mol file: 29106-51-2.mol

Synonyms:Procyanidin B4;29106-51-2;Procyanidol B4;(-)-procyanidin B4;Catechin-(4alpha->8)-epicatechin;Procyanidin B4, (-)-;(2R,2'R,3S,3'R,4S)-2,2'-Bis(3,4-dihydroxyphenyl)-[4,8'-bichroman]-3,3',5,5',7,7'-hexaol;UNII-2OP8987K2X;CHEBI:27589;2OP8987K2X;(2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol;(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-(2alpha,3beta,4alpha(2'R*,3'R*)))-;C30-H26-O12;SCHEMBL718738;CHEMBL447373;DTXSID50183357;LMPK12030004;ZB1882;Catechin-(4.alpha.-->8)epicatechin;MS-30397;HY-107208;CATECHIN-(4.ALPHA.->8)-EPICATECHIN;CS-0027644;Q7247555;(+)-CATECHIN-(4.ALPHA.->8)-(-)-EPICATECHIN;(2R,2'R,3S,3'R,4S)-2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-2H,2'H-4,8'-bichromene-3,3',5,5',7,7'-hexol;(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chroman-8-yl]chromane-3,5,7-triol;(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'R,4S)-;(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.ALPHA.,3.BETA.,4.ALPHA.(2'R*,3'R*)))-

Chemical Property of Procyanidin B4

Chemical Property:

• Melting Point: 178-180 °C (decomp)
• Boiling Point: 955.3°Cat760mmHg
• PKA: 9.29±0.60(Predicted)
• Flash Point: 531.6°C
• PSA: 220.76000
• Density: 1.705g/cm³
• LogP: 2.99500
• 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:

Analysis control,HPLC≥98% ^*data from raw suppliers

Procyanidin B4 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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 B4 is a bioactive flavonoid and a proanthocyanidin grape seed extract that reduces inflammation and oxidative stress and restores tight junction barrier function in caco-2 colon cells.

Technology Process of Procyanidin B4

There total 21 articles about Procyanidin B4 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-4α,8-(3',4',5,7-tetra-O-benzylepicatechin) (923565-05-3) → procyanidin B4 (29106-51-2)

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: 66.0%

[4,8']-2,3-trans-3,4-trans:2',3'-cis-octa-O-benzyl-(+)-catechin-(-)-epicatechin (195145-79-0) → procyanidin B4 (29106-51-2)

Guidance literature:

With hydrogen; palladium dihydroxide; In tetrahydrofuran; methanol; water; at 20 ℃; for 12h;

DOI:10.3987/com-03-s37

Reference yield: 35.0%

4-benzylthioether of catechin (698998-85-5) + (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol (490-46-0) → procyanidin B4 (29106-51-2)

Guidance literature:

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

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

upstream raw materials:

procyanidin B₄ 3'-O-gallate

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

phenylmethanethiol

catechin-(4α->8)-epicatechin-(4β->S)-benzylthioether

Downstream raw materials:

procyanidin octamethyl ether

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

catechin

(-)-catechin

Refernces

• 1、 -. "COMPOSITION FOR PROMOTING EXPRESSION OF AQUAPORIN 3, AND USE THEREOF". Paragraph 0239; 0243. . Retrieved 2020/09/22.
• 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.