20315-25-7

Basic information

• Product Name: PROCYANIDIN B1
• Synonyms: PROCYANIDIN B1;CIS,TRANS''-4,8''-BI-(3,3',4',5,7-PENTAHYDROXYFLAVANE);EPICATECHIN(4B-8)CATECHIN;EPICATECHIN(4BETA->8)CATECHIN;PROCYANIDIN B1(RG);PROCYANIDINDIMERB1;(2R,2'R,3R,3'S,4R)-2,2'-Bis(3,4-dihydroxyphenyl)-4,8'-bichroman-3,3',5,5',7,7'-hexol;(2R,2'R,3R,3'S,4β)-3,3',4,4'-Tetrahydro-2α,2'α-bis(3,4-dihydroxyphenyl)-4,8'-bi[2H-1-benzopyran]-3,3',5,5',7,7'-hexol
• CAS NO: 20315-25-7
• Molecular Formula: C₃₀H₂₆O₁₂
• Molecular Weight: 578.52
• Product Categories: Catechins & Tannins;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 20315-25-7.mol
• Article Data: 22

Chemical Properties

• Melting Point: 231～232℃
• Boiling Point: 955.3 °C at 760 mmHg
• Flash Point: 531.6 °C
• Appearance: Red-Brown Powder
• Density: 1.705g/cm³
• Storage Temp.: 2-8°C
• Solubility: Acetone (Slightly), Ethanol (Slightly), Methanol (Slightly), Water (Slightly)
• PKA: 9.29±0.60(Predicted)
• CAS DataBase Reference: PROCYANIDIN B1(CAS DataBase Reference)
• NIST Chemistry Reference: PROCYANIDIN B1(20315-25-7)
• EPA Substance Registry System: PROCYANIDIN B1(20315-25-7)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 20315-25-7(Hazardous Substances Data)

Usage

Description

Procyanidin B1 is a polyphenol flavonoid existing as a dimer of (+)-catechin and (?)-epicatechin. It is a B type proanthocyanidin found in Ceylon cinnamon and is known to exhibit anti-inflammatory effects. Procyanidin B1 has the unique ability to inhibit hepatitis C virus RNA replication, a function that its constituent monomers, (+)-catechin and (?)-epicatechin, do not possess. Procyanidin B1 also plays a role in preventing the phosphorylation of ERK1/2 and the production of reactive oxygen species (ROS) in THP-1 cells. Furthermore, it has been shown to decrease levels of TNF-α, phosphorylated p38 MAPK, and NF-κB following lipopolysaccharide (LPS) administration.

Uses

Used in Pharmaceutical Applications:
Procyanidin B1 is used as an anti-inflammatory agent for its ability to inhibit the production of reactive oxygen species (ROS) and decrease levels of TNF-α, phosphorylated p38 MAPK, and NF-κB. This makes it a promising candidate for the development of treatments targeting inflammation-related conditions.
Used in Antiviral Applications:
Procyanidin B1 is used as an antiviral agent for its unique ability to inhibit hepatitis C virus RNA replication. This characteristic distinguishes it from its constituent monomers, (+)-catechin and (?)-epicatechin, which do not exhibit this effect even at higher concentrations.
Used in Nutraceutical Applications:
Given its presence in Ceylon cinnamon and its anti-inflammatory and antiviral properties, Procyanidin B1 can be used as a key ingredient in the development of nutraceutical products aimed at promoting overall health and well-being.

Upstream product

• 114715-46-7 C₆₀H₄₈O₂₄ 
• 100-53-8 phenylmethanethiol 
• 22970-70-3 (2R,3R,4S)-2,3-cis-3,4-trans-3',4',5,7-tetramethoxyflavan-3,4-diol 
• 154-23-4 catechin 
• 86849-67-4 (2R,3S,4S)-2,3-cis-3,4-trans-3,3',4',5,7-pentahydroxy-4-phenylthioflavan 
• 99297-45-7 4'β-benzylthioprocyanidin B-1 
• 23459-99-6 arecatannin A-1 
• 664351-42-2 [4,8]-2,3-cis-3,4-trans:2,3-trans-octa-O-benzyl-(-)-3-O-acetyl-(-)-epicatechin-(+)-catechin 
• 223387-42-6 3’,4’,5,7-tetra-O-benzyl-4β-(2-hydroxyethyloxy)-8-bromoepicatechin 
• 88191-48-4 5,7,3',4'-tetrahydroxyflavan-3-ol hydrate 
• 61540-96-3 C₁₅H₁₃O₆⁽¹⁺⁾ 
• 87727-69-3 epicatechin-(4β<*>8)-catechin-(4α<*>8)-catechin 
• 490-46-0 (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol 
• 20728-73-8 5,7,3',4'-tetra-O-benzyl-(+)-catechin 

Downstream Products

• 37064-35-0 4β-benzylthioepicatechin 
• 128837-34-3 4α-Benzylthioepicatechin 
• 154-23-4 catechin 
• 103883-03-0 procyanidin A1 
• 13306-05-3 cyanidin 
• 35323-91-2 (+)-epicatechin 
• 51079-25-5 (2R,3S)-(+)-catechin 3',4',5,7-tetramethyl ether 
• 51196-02-2 5,7,3',4'-tetra-O-methylepicatechin 
• 58065-35-3 (+)-catechin tetramethyl ether acetate 
• 21179-20-4 epicatechin-(4β->8)-catechin decaacetate 
• 490-46-0 (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol 
• 213007-61-5 (-)-epicatechin benzylthioether 

Relevant articles and documents

Synthesis of procyanidin B1, B2, and B4 and their anti-inflammatory activity: The effect of 4-alkoxy group of catechin and/or epicatechin electrophiles for condensation

Abstract: Procyanidin B1, B2, and B3 were synthesized based on a Yb(OTf)3 catalyzed equimolar condensation using methoxy and/or 4-(2-ethoxyethoxy) drivatives as electrophiles. The anti-inflammatory effect of synthetic procyanidin B1, B2, and B4 on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation of mouse ears was examined. Procyanidin B1, B2, B 4 suppressed TPA-induced inflammation of mouse ears by 48%, 34%, and 29%, respectively, at a dose of 200 μg. Their activities are stronger than those of indomethacin and glycyrrhetinic acid, the normally used antiinflammatory agent.

An efficient synthesis of procyanidins using equimolar condensation of catechin and/or epicatechin catalyzed by ytterbium triflate

Stereoselective synthesis of catechin and epicatechin dimers under intermolecular condensation of equimolar amount of catechin derivatives catalyzed by Yb(OTf)3. The coupled products were successfully converted to procyanidins B1, B2, B3, and B4, respectively. Procyanidins B1, B2, B3, and B4 could be used as standard compounds for identifying the polyphenols in natural source.