79907-44-1 (原花青素B-23'-O-没食子酸酯,Procyanidin B2 3,3'-di-O-gallate (>80%))

快速询单

结构式：

原花青素B-23'-O-没食子酸酯MOL文件

CAS号：

79907-44-1

中文名称：

原花青素B-23'-O-没食子酸酯

英文名称：

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

分子式：

C₄₄H₃₄O₂₀

分子量：

882.728774547577

原花青素B-23'-O-没食子酸酯(79907-44-1)名称与标识符

名称

中文别名：

[(2R,3R,4R)-2-(3,4-二羟基苯基)-4-[(2R,3R)-2-(3,4-二羟基苯基)-5,7-二羟基-3-(3,4,5-三羟基苯甲酰基)氧基-色满-8-基]-5,7-二羟基-色满-3-基]3,4,5-三羟基苯甲酸酯;原花青素B-23'-O-没食子酸酯;原花青素B2-3,3'-二-O-没食子酸酯;

英文别名：

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;

标识符

InChIKey：

KTLUHRSHFRODPS-RIQPQZJCSA-N

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

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

原花青素B-23'-O-没食子酸酯(79907-44-1)物化性质

实验特性

LogP : 4.95800
PSA : 354.28000
颜色与性状 : Brown powder

计算特性

精确分子量 : 882.16400
氢键供体数量 : 14
氢键受体数量 : 20
可旋转化学键数量 : 9
同位素质量 : 882.16434347g/mol
重原子数量 : 64
复杂度 : 1580
同位素原子数量 : 0
确定原子立构中心数量 : 5
不确定原子立构中心数量 : 0
确定化学键立构中心数量 : 0
不确定化学键立构中心数量 : 0
共价键单元数量 : 1
疏水参数计算参考值（XlogP） : 4.7
拓扑分子极性表面积 : 354Å²

原花青素B-23'-O-没食子酸酯(79907-44-1)推荐厂家更多厂家(11)

公司名称	手机号/电话	联系人	QQ	询单
云南西力生物技术股份有限公司	18788556290 +86-871-65217109	郑经理	1477035482	询单
上海吉至生化科技有限公司	18117592386 021-57481218	吉至试剂	3007522982	询单
江苏永健医药科技有限公司	17701422016	韩经理	3587493084	询单
上海瀚思化工有限公司	18939883912 021-34536277	顾经理	3003949364	询单
上海维亦特生物科技有限公司	15317051735	赵静	2033721411	询单
深圳市瑞吉特生物科技有限公司	15813841136 0755-89459231	钦先生	1029374309	询单
上海源叶生物科技有限公司	15026964105 15026964105	汤思磊	2881489226	询单
四川维克奇生物科技有限公司	13348961525	杨洋	2851167780	询单
上海阿拉丁生化科技股份有限公司	13167063860 13167063860	阿拉丁	3004013043	询单
上海诗丹德标准技术服务有限公司	17621252073	卢忠花	3002368231	询单

原花青素B-23'-O-没食子酸酯(79907-44-1)合成路线

合成路线：1 步

223387-33-5

_100%

79907-44-1

反应条件：

1.1 Reagents: Hydrogen Catalysts: Palladium dihydroxide Solvents: Methanol , Tetrahydrofuran , Water ; 5 h, rt

参考文献：

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

合成路线：1 步

223387-33-5

_99%

79907-44-1

反应条件：

1.1 Reagents: Hydrogen Catalysts: Palladium dihydroxide Solvents: Methanol , Tetrahydrofuran , Water ; 5 h, rt

参考文献：

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

合成路线：2 步

1449769-15-6

256236-30-3

79907-44-1

反应条件：

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

参考文献：

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

合成路线：2 步

223387-28-8

1486-48-2

79907-44-1

反应条件：

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

参考文献：

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

合成路线：2 步

223387-28-8

1486-48-2

79907-44-1

反应条件：

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

参考文献：

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

合成路线：2 步

851775-46-7

256236-30-3

79907-44-1

反应条件：

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

参考文献：

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

合成路线：2 步

2820450-54-0

79907-44-1

反应条件：

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

参考文献：

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

合成路线：3 步

664351-39-7

1486-48-2

79907-44-1

反应条件：

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

参考文献：

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

合成路线：3 步

87292-49-7

1486-48-2

79907-44-1

反应条件：

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

参考文献：

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

合成路线：3 步

256236-25-6

87292-49-7

79907-44-1

反应条件：

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

参考文献：

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

合成路线：3 步

256236-25-6

87292-49-7

79907-44-1

反应条件：

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

参考文献：

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

合成路线：3 步

851775-46-7

79907-44-1

反应条件：

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

参考文献：

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