Cas no 79907-44-1 (Procyanidin B2 3,3'-di-O-gallate (>80%))

Procyanidin B2 3,3'-di-O-gallate (>80%) structure
79907-44-1 structure
Product Name:Procyanidin B2 3,3'-di-O-gallate (>80%)
CAS No:79907-44-1
MF:C44H34O20
MW:882.728774547577
CID:573296
PubChem ID:124016
Update Time:2024-10-27

Procyanidin B2 3,3'-di-O-gallate (>80%) Chemical and Physical Properties

Names and Identifiers

    • Benzoic acid,3,4,5-trihydroxy-,(2R,2'R,3R,3'R,4R)-2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-5,5',7,7'-tetrahydroxy[4,8'-bi-2H-1-benzopyran]-3,3'-diylester
    • [(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyl)oxy-chroman-8-yl]-5,7-dihydroxy-chroman-3-yl] 3,4,5-trihydroxybenzoate
    • B2-3,3'-di-O-gallate
    • Procyanidin B2 3,3'-di-O-gallate
    • PROCYANIDIN B-2,3'-O-GALLATE,
    • Procyanidin B-2 3
    • Benzoic acid, 3,4,5-trihydroxy-, 2,2′-bis(3,4-dihydroxyphenyl)-3,3′,4,4′-tetrahydro-5,5′,7,7′-tetrahydroxy[4,8′-bi-2H-1-benzopyran]-3,3′-diyl ester, [2R-[2α,3α,4β(2′R*,3′R*)]]- (ZCI)
    • (-)-Epicatechin-3-O-galloyl-(4β,8)-(-)-epicatechin-3-O-gallate
    • (2R,3R)-3-O-Galloylepicatechin-4β,8-[(2R,3R)-3-O-galloylepicatechin]
    • 3,3′-Digalloylprocyanidin B2
    • [3-O-Galloyl]-(-)-epicatechin-(4β,8)-(+)-epicatechin-3-O-gallate
    • Proanthocyanidin B2 3,3′-O-gallate
    • Procyanidin B2 3,3′-di-O-gallate
    • 3-O-Galloylepicatechin-(4beta->8)-epicatechin-3-O-gallate
    • AKOS040762700
    • Benzoic acid, 3,4,5-trihydroxy-, 2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-5,5',7,7'-tetrahydroxy(4,8'-bi-2H-1-benzopyran)-3,3'-diyl ester, (2R-(2alpha,3alpha,4beta(2'R*,3'R*)))-
    • CHEMBL39504
    • 79907-44-1
    • 212066-01-8
    • CS-0203848
    • Procyanidin B2 3,3'-di-O-gallate (>80%)
    • 2,2'-Bis(3,4-dihydroxyphenyl)-5,5',7,7'-tetrahydroxy-3,3',4,4'-tetrahydro-2H,2'H-[4,8'-bi-1-benzopyran]-3,3'-diyl bis(3,4,5-trihydroxybenzoate)
    • Benzoic acid, 3,4,5-trihydroxy-, (2R,2'R,3R,3'R,4R)-2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-5,5',7,7'-tetrahydroxy[4,8'-bi-2H-1-benzopyran]-3,3'-diyl ester
    • [(2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyl)oxy-3,4-dihydro-2H-chromen-4-yl]-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
    • Procyanidin B2-3,3'-di-O-gallate
    • Proanthocyanidin B2 3,3'-O-gallate
    • BDBM50423642
    • CHEBI:172846
    • (2R,3R)-3-O-Galloylepicatechin-4.beta.,8-[(2R,3R)-3-O-galloylepicatechin]
    • Benzoic acid, 3,4,5-trihydroxy-, 2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-5,5',7,7'-tetrahydroxy[4,8'-bi-2H-1-benzopyran]-3,3'-diyl ester, [2R-[2.alpha.,3.alpha.,4.beta.(2'R*,3'R*)]]-
    • 3,3'-Digalloylprocyanidin B2
    • [(2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyl)oxy-chroman-4-yl]-5,7-dihydroxy-chroman-3-yl] 3,4,5-trihydroxybenzoate
    • HY-N9790
    • (2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(3,4,5-trihydroxyphenyl)carbonyloxy]-3,4-dihydro-2H-1-benzopyran-4-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
    • DTXSID101000836
    • (2R,2'R,3R,3'R,4R)-2,2'-Bis(3,4-dihydroxyphenyl)-5,5',7,7'-tetrahydroxy-[4,8'-bichromane]-3,3'-diyl bis(3,4,5-trihydroxybenzoate)
    • 3,3a(2)-Digalloylprocyanidin B2
    • G89056
    • DB-225168
    • Inchi： 1S/C44H34O20/c45-19-11-26(51)34-32(12-19)61-40(16-2-4-22(47)25(50)6-16)42(64-44(60)18-9-30(55)38(58)31(56)10-18)36(34)35-27(52)14-23(48)20-13-33(62-43(59)17-7-28(53)37(57)29(54)8-17)39(63-41(20)35)15-1-3-21(46)24(49)5-15/h1-12,14,33,36,39-40,42,45-58H,13H2/t33-,36-,39-,40-,42-/m1/s1
    • InChI Key： KTLUHRSHFRODPS-RIQPQZJCSA-N
    • SMILES： O([C@H]1[C@@H](C2C=CC(O)=C(O)C=2)OC2C=C(C=C(C=2[C@@H]1C1C(O)=CC(O)=C2C[C@H]([C@@H](C3C=CC(O)=C(O)C=3)OC=12)OC(C1C=C(O)C(O)=C(O)C=1)=O)O)O)C(C1C=C(O)C(O)=C(O)C=1)=O

Computed Properties

  • Exact Mass: 882.16400
  • Monoisotopic Mass: 882.16434347g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 14
  • Hydrogen Bond Acceptor Count: 20
  • Heavy Atom Count: 64
  • Rotatable Bond Count: 9
  • Complexity: 1580
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 5
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 4.7
  • Topological Polar Surface Area: 354?2

Experimental Properties

  • Color/Form: Brown powder
  • PSA: 354.28000
  • LogP: 4.95800

Procyanidin B2 3,3'-di-O-gallate (>80%) Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
SHANG HAI JI ZHI SHENG HUA Technology Co., Ltd.
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Benzoic acid,3,4,5-trihydroxy-,(2R,2'R,3R,3'R,4R)-2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-5,5',7,7'-tetrahydroxy[4,8'-bi-2H-1-benzopyran]-3,3'-diylester
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Procyanidin B2 3,3'-di-O-gallate (>80%) Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Hydrogen Catalysts: Palladium dihydroxide Solvents: Methanol ,  Tetrahydrofuran ,  Water ;  5 h, rt
Reference
Syntheses of procyanidin B2 and B3 gallate derivatives using equimolar condensation mediated by Yb(OTf)3 and their antitumor activities
Suda, Manato; et al, Bioorganic & Medicinal Chemistry Letters, 2013, 23(17), 4935-4939

Production Method 2

Reaction Conditions
1.1 Reagents: Hydrogen Catalysts: Palladium dihydroxide Solvents: Methanol ,  Tetrahydrofuran ,  Water ;  5 h, rt
Reference
Concise Synthesis of Procyanidin B2 3,3''-Digallate Using Yb(OTf)3-Mediated Self-Condensation
Tanaka, Yuuri; et al, Synlett, 2022, 33(11), 1071-1074

Production Method 3

Reaction Conditions
1.1 Catalysts: Trimethylsilyl triflate Solvents: Dichloromethane ;  -10 °C; 5 min, -10 °C
1.2 Reagents: Sodium bicarbonate Solvents: Water
2.1 Reagents: Hydrogen Catalysts: Palladium dihydroxide Solvents: Methanol ,  Tetrahydrofuran ,  Water ;  6 h, rt
Reference
Systematic synthesis of galloyl-substituted procyanidin B1 and B2, and their ability of DPPH radical scavenging activity and inhibitory activity of DNA polymerases
Saito, Akiko; et al, Bioorganic & Medicinal Chemistry, 2005, 13(8), 2759-2771

Production Method 4

Reaction Conditions
1.1 Reagents: Boron trifluoride etherate ,  Triethylsilane Solvents: Dichloromethane ;  1.5 h, -40 °C
1.2 Reagents: Sodium bicarbonate Solvents: Water
2.1 Reagents: Hydrogen Catalysts: Palladium dihydroxide Solvents: Methanol ,  Tetrahydrofuran ,  Water ;  5 h, rt
Reference
Concise Synthesis of Procyanidin B2 3,3''-Digallate Using Yb(OTf)3-Mediated Self-Condensation
Tanaka, Yuuri; et al, Synlett, 2022, 33(11), 1071-1074

Production Method 5

Reaction Conditions
1.1 Reagents: Titanium tetrachloride Solvents: Dichloromethane ,  Tetrahydrofuran
2.1 Reagents: Oxalyl chloride Catalysts: Dimethylformamide Solvents: Dichloromethane
2.2 Reagents: Zinc Solvents: Pyridine
3.1 Reagents: Hydrogen Catalysts: Carbon ,  Palladium dihydroxide Solvents: Methanol ,  Tetrahydrofuran ,  Water
Reference
Studies in Polyphenol Chemistry and Bioactivity. 1. Preparation of Building Blocks from (+)-Catechin. Procyanidin Formation. Synthesis of the Cancer Cell Growth Inhibitor, 3-O-Galloyl-(2R,3R)-epicatechin-4β,8-[3-O-galloyl-(2R,3R)-epicatechin]
Tueckmantel, Werner; et al, Journal of the American Chemical Society, 1999, 121(51), 12073-12081

Production Method 6

Reaction Conditions
1.1 Reagents: Ytterbium triflate Solvents: Dichloromethane ;  24 h, rt
1.2 Reagents: Water
2.1 Reagents: Hydrogen Catalysts: Palladium dihydroxide Solvents: Methanol ,  Tetrahydrofuran ,  Water ;  5 h, rt
Reference
Syntheses of procyanidin B2 and B3 gallate derivatives using equimolar condensation mediated by Yb(OTf)3 and their antitumor activities
Suda, Manato; et al, Bioorganic & Medicinal Chemistry Letters, 2013, 23(17), 4935-4939

Production Method 7

Reaction Conditions
1.1 Reagents: 4-(Dimethylamino)pyridine ,  1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride
2.1 Reagents: Hydrogen Catalysts: Palladium dihydroxide Solvents: Methanol ,  Tetrahydrofuran ,  Water ;  5 h, rt
Reference
Syntheses of procyanidin B2 and B3 gallate derivatives using equimolar condensation mediated by Yb(OTf)3 and their antitumor activities
Suda, Manato; et al, Bioorganic & Medicinal Chemistry Letters, 2013, 23(17), 4935-4939

Production Method 8

Reaction Conditions
1.1 Reagents: Oxalyl chloride Catalysts: Dimethylformamide Solvents: Dichloromethane ;  2.5 h, rt
1.2 Reagents: Pyridine Solvents: Pyridine ;  rt
1.3 Reagents: Water ;  4 h, rt
2.1 Reagents: Hydrogen Catalysts: Palladium dihydroxide Solvents: Ethyl acetate ,  Water ;  4 h, 15 psi, rt
Reference
Scale-Up Syntheses of Two Naturally Occurring Procyanidins: (-)-Epicatechin-(4β,8)-(+)-catechin and (-)-Epicatechin-3-O-galloyl-(4β,8)-(-)-epicatechin-3-O-gallate
Sharma, Pradeep K.; et al, Organic Process Research & Development, 2007, 11(3), 422-430

Production Method 9

Reaction Conditions
1.1 Reagents: Dicyclohexylcarbodiimide Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ;  48 h, rt
1.2 Reagents: Water ;  rt
2.1 Catalysts: Trimethylsilyl triflate Solvents: Dichloromethane ;  -10 °C; 5 min, -10 °C
2.2 Reagents: Sodium bicarbonate Solvents: Water
3.1 Reagents: Hydrogen Catalysts: Palladium dihydroxide Solvents: Methanol ,  Tetrahydrofuran ,  Water ;  6 h, rt
Reference
Systematic synthesis of galloyl-substituted procyanidin B1 and B2, and their ability of DPPH radical scavenging activity and inhibitory activity of DNA polymerases
Saito, Akiko; et al, Bioorganic & Medicinal Chemistry, 2005, 13(8), 2759-2771

Production Method 10

Reaction Conditions
1.1 Reagents: Dicyclohexylcarbodiimide Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ;  12 h, rt
1.2 Reagents: Water ;  rt
2.1 Catalysts: Trimethylsilyl triflate Solvents: Dichloromethane ;  -10 °C; 5 min, -10 °C
2.2 Reagents: Sodium bicarbonate Solvents: Water
3.1 Reagents: Hydrogen Catalysts: Palladium dihydroxide Solvents: Methanol ,  Tetrahydrofuran ,  Water ;  6 h, rt
Reference
Systematic synthesis of galloyl-substituted procyanidin B1 and B2, and their ability of DPPH radical scavenging activity and inhibitory activity of DNA polymerases
Saito, Akiko; et al, Bioorganic & Medicinal Chemistry, 2005, 13(8), 2759-2771

Production Method 11

Reaction Conditions
1.1 Solvents: Dichloromethane ;  2.5 h, < 5 °C; 1 h, < 5 °C
2.1 Reagents: Oxalyl chloride Catalysts: Dimethylformamide Solvents: Dichloromethane ;  2.5 h, rt
2.2 Reagents: Pyridine Solvents: Pyridine ;  rt
2.3 Reagents: Water ;  4 h, rt
3.1 Reagents: Hydrogen Catalysts: Palladium dihydroxide Solvents: Ethyl acetate ,  Water ;  4 h, 15 psi, rt
Reference
Scale-Up Syntheses of Two Naturally Occurring Procyanidins: (-)-Epicatechin-(4β,8)-(+)-catechin and (-)-Epicatechin-3-O-galloyl-(4β,8)-(-)-epicatechin-3-O-gallate
Sharma, Pradeep K.; et al, Organic Process Research & Development, 2007, 11(3), 422-430

Production Method 12

Reaction Conditions
1.1 Catalysts: Ytterbium triflate Solvents: Dichloromethane ;  18 h, rt
1.2 Solvents: Water ;  rt
2.1 Reagents: Boron trifluoride etherate ,  Triethylsilane Solvents: Dichloromethane ;  1.5 h, -40 °C
2.2 Reagents: Sodium bicarbonate Solvents: Water
3.1 Reagents: Hydrogen Catalysts: Palladium dihydroxide Solvents: Methanol ,  Tetrahydrofuran ,  Water ;  5 h, rt
Reference
Concise Synthesis of Procyanidin B2 3,3''-Digallate Using Yb(OTf)3-Mediated Self-Condensation
Tanaka, Yuuri; et al, Synlett, 2022, 33(11), 1071-1074

Procyanidin B2 3,3'-di-O-gallate (>80%) Raw materials

Procyanidin B2 3,3'-di-O-gallate (>80%) Preparation Products

Procyanidin B2 3,3'-di-O-gallate (>80%) Related Literature

Related Categories

79907-44-1 (Procyanidin B2 3,3'-di-O-gallate (>80%)) Related Products

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