Name: PROCYANIDIN B2
SKU: 29106-49-8

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Basic Information

Molecular Structure:
CAS No.:	29106-49-8
Name:	PROCYANIDIN B2
Article Data:	26

Formula:	C₃₀H₂₆O₁₂
Molecular Weight:	578.529
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;
Density:	1.706 g/cm³
Melting Point:	197-198 °C
Boiling Point:	955.319 °C at 760 mmHg
Flash Point:	531.558 °C
Safety:	22-24/25
PSA:	220.76000
LogP:	2.99500

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
acetic acid In ethanol for 6h; Product distribution; Heating; other reaction time;

...Expand

: 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

Conditions	Yield
acetic acid In ethanol for 6h; Product distribution; Heating; other reaction time;

...Expand

: 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

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

...Expand

: 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

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

...Expand

Raw Materials

154-23-4

Downstream Products

154-23-4

490-46-0

Total:107 Page 1 of 3 1 2 3 Next>>

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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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Specification