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Proanthocyanidin B2

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Name

Proanthocyanidin B2

EINECS N/A
CAS No. 29106-49-8 Density 1.706 g/cm3
PSA 220.76000 LogP 2.99500
Solubility N/A Melting Point 197-198 °C
Formula C30H26O12 Boiling Point 955.319 °C at 760 mmHg
Molecular Weight 578.529 Flash Point 531.558 °C
Transport Information N/A Appearance N/A
Safety 22-24/25 Risk Codes N/A
Molecular Structure Molecular Structure of 29106-49-8 (PROCYANIDIN B2) Hazard Symbols N/A
Synonyms

[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-[2a,3a,4b(2'R*,3'R*)]]-;[4,8''-Biflavan]-3,3',3'',3''',4',4''',5,5'',7,7''-decol,stereoisomer (8CI);(+)-Procyanidin B2;(-)-Epicatechin-(4b,8)-(+)-epicatechin;(-)-Epicatechin-(4b-8)-(-)-epicatechin;Proanthocyanidin B2;Procyanidol B2;

Article Data 26

Proanthocyanidin B2 Synthetic route

442626-19-9

3',4',5,7-tetra-O-benzyl-8-bromoepicatechin-4β,8-(3',4',5,7-tetra-O-benzylepicatechin)

29106-49-8

procyanidin B2

Conditions
ConditionsYield
With hydrogen; sodium hydrogencarbonate; triethylamine; palladium dihydroxide In methanol; water; ethyl acetate at 20℃; for 18h;99%
223387-28-8

5,7,3',4'-tetra-O-benzyl-(-)-epicatechin-(4β,8)-[5,7,3',4'-tetra-O-benzyl-(-)-epicatechin]

29106-49-8

procyanidin B2

Conditions
ConditionsYield
With hydrogen; palladium dihydroxide In tetrahydrofuran; methanol; water at 20℃; for 12h;86%
With palladium hydroxide on carbon; hydrogen In water; ethyl acetate at 20℃; under 760.051 Torr; for 18h;85%
With 20 % Pd(OH)2/C; hydrogen In water; ethyl acetate at 20℃; for 18h;85%
37064-35-0

4β-benzylthioepicatechin

490-46-0

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

29106-49-8

procyanidin B2

Conditions
ConditionsYield
silver tetrafluoroborate In tetrahydrofuran at 0℃; for 1h; Condensation;37%
79907-44-1, 123051-12-7, 134054-57-2

procyanidin B2-3,3'-di-O-gallate

29106-49-8

procyanidin B2

Conditions
ConditionsYield
With tannase In water at 37℃; for 1h;
79907-44-1, 123051-12-7, 134054-57-2

procyanidin B2-3,3'-di-O-gallate

A

29106-49-8

procyanidin B2

B

149-91-7

3,4,5-trihydroxybenzoic acid

Conditions
ConditionsYield
With tannase at 37℃; for 1h; 0.05 M acetate buffer (pH 5.0);
96182-33-1

kandelin B-1

A

29106-49-8

procyanidin B2

B

(2R,3R,4R,10R)-4-[(2R,3S,4S)-4-Benzylsulfanyl-2-(3,4-dihydroxy-phenyl)-3,5,7-trihydroxy-chroman-8-yl]-2,10-bis-(3,4-dihydroxy-phenyl)-3,5-dihydroxy-3,4,9,10-tetrahydro-2H-pyrano[2,3-f]chromen-8-one

Conditions
ConditionsYield
With acetic acid; phenylmethanethiol In ethanol for 8h; Heating;
86631-38-1

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

100-53-8

phenylmethanethiol

A

29106-49-8

procyanidin B2

B

37064-35-0

4β-benzylthioepicatechin

C

68200-27-1

(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

D

37064-30-5

procyanidin C1

E

103215-52-7

procyanidin C-1 4''-benzylthioether

F

490-46-0

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

Conditions
ConditionsYield
acetic acid In ethanol for 6h; Product distribution; Heating; other reaction time;
86631-39-2

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

100-53-8

phenylmethanethiol

A

29106-49-8

procyanidin B2

B

37064-35-0

4β-benzylthioepicatechin

C

68200-27-1

(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

D

37064-30-5

procyanidin C1

E

490-46-0

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

Conditions
ConditionsYield
acetic acid In ethanol for 6h; Product distribution; Heating; other reaction time;
88847-05-6

epicatechin (4β,8)5-hexamer

100-53-8

phenylmethanethiol

A

29106-49-8

procyanidin B2

B

37064-35-0

4β-benzylthioepicatechin

C

68200-27-1

(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

D

37064-30-5

procyanidin C1

E

86631-39-2

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

F

490-46-0

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

Conditions
ConditionsYield
acetic acid In ethanol for 5h; Product distribution; Heating; other reaction time;

epicatechin-(4β-6)-epicatechin-(4β-8)-epecatechin

100-53-8

phenylmethanethiol

A

29106-49-8

procyanidin B2

B

78591-32-9, 82863-23-8

procyanidin B-5 4'-benzykthioether

Conditions
ConditionsYield
In ethanol; acetic acid for 8h; Heating; degradation;

Proanthocyanidin B2 Specification

The Procyanidin B2, with the CAS registry number 29106-49-8, is also known as (2R-(2alpha,3alpha,4beta(2'R*,3'R*)))-2,2'-Bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-(4,8'-Bi-2H-1-benzopyran)-3,3',5,5',7,7'-hexol. It belongs to the product category of Catechins & Tannins. This chemical's molecular formula is C30H26O12 and molecular weight is 578.52024. Its IUPAC name is called (2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol. Procyanidin B2 is a B type proanthocyanidin ((-)-Epicatechin-(4β→8)-(-)-epicatechin) which can be found in Cinchona pubescens, in Cinnamomum verum, in Crataegus monogyna, in Uncaria guianensis, in Vitis vinifera, in Litchi chinensis, in the apple, and in Ecdysanthera utilis. When you are using this chemical, please be cautious about it. You should not breathe its dust and avoid contacting it with skin and eyes.

Physical properties of Procyanidin B2: (1) ACD/LogP: 0.30; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): 0.3; (4)ACD/LogD (pH 7.4): 0.3; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 34.77; (8)ACD/KOC (pH 7.4): 34.33; (9)#H bond acceptors: 12; (10)#H bond donors: 10; (11)#Freely Rotating Bonds: 13; (12)Index of Refraction: 1.803; (13)Molar Refractivity: 145.37 cm3; (14)Molar Volume: 339.1 cm3; (15)Surface Tension: 103.8 dyne/cm; (16)Density: 1.705 g/cm3; (17)Flash Point: 531.6 °C; (18)Enthalpy of Vaporization: 145.7 kJ/mol; (19)Boiling Point: 955.3 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: Oc1ccc(cc1O)[C@H]6Oc2cc(O)cc(O)c2[C@H](c5c(O)cc(O)c4c5O[C@H](c3ccc(O)c(O)c3)[C@H](O)C4)[C@H]6O
(2)InChI: InChI=1/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26-,27-,28-,29-/m1/s1
(3)InChIKey: XFZJEEAOWLFHDH-NFJBMHMQBY

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