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15291-77-7

Basic Information
CAS No.: 15291-77-7
Name: Ginkgolide B
Article Data: 5
Cas Database
Molecular Structure:
Molecular Structure of 15291-77-7 (Ginkgolide B)
Formula: C20H24O10
Molecular Weight: 424.405
Synonyms: GinkgolideA, 1-hydroxy-, (1b)- (8CI);5H-Dicyclopenta[b,c]furan-3,5a(6H)-diacetic acid, 6-tert-butyl-3a-carboxyhexahydro-a5a,1,2,3,5,8-hexahydroxy-a3-methyl-, tri-g-lactone (8CI);9H-1,7a-(Epoxymethano)-1H,6aH-cyclopenta[c]furo[2,3-b]furo[3',2':3,4]cyclopenta[1,2-d]furan-5,9,12(4H)-trione,3-(1,1-dimethylethyl)hexahydro-4,7b,11-trihydroxy-8-methyl-, [1R-(1a,3b,3aS*,4b,6aa,7aa,7ba,8a,10aa,11b,11aR*)]-;BN 52051;9H-1,7a-(Epoxymethano)-1H,6aH-cyclopenta[c]furo[2,3-b]furo[3',2':3,4]cyclopenta[1,2-d]furan-5,9,12(4H)-trione,3-(1,1-dimethylethyl)hexahydro-4,7b,11-trihydroxy-8-methyl-, (1R,3S,3aS,4R,6aR,7aR,7bR,8S,10aS,11R,11aR)-;
EINECS: 604-876-0
Density: 1.645 g/cm3
Melting Point: 280 °C (dec.)
Boiling Point: 762.416 °C at 760 mmHg
Flash Point: 274.337 °C
Solubility: Soluble in DMSO. Slightly soluble in water and ethanol
Appearance: white crystal powder
Hazard Symbols: N/A
Risk Codes: N/A
Safety: 24/25
Transport Information: N/A
PSA: 148.82000
LogP: -1.36950
Synthetic route
170288-58-1

α-benzylginkgolide B

15291-77-7

ginkgolide B

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol under 2888 Torr; for 24h;97%
130523-06-7

1-O-(tert-Butyldiphenylsilyl)ginkgolid B

15291-77-7

ginkgolide B

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 2h;73%
145473-36-5

C28H32O11

15291-77-7

ginkgolide B

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol at 23℃; under 760 Torr; for 5h; Yield given;
173102-79-9

7-trifluoromethanesulfonyloxy ginkgolide B

15291-77-7

ginkgolide B

Conditions
ConditionsYield
With tetrabutylammonium borohydride
15291-76-6

1,3,7,10-Tetrahydroxyginkgolid

15291-77-7

ginkgolide B

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine
2: nBu4NBH4
View Scheme
15291-77-7

ginkgolide B

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: diisopropylethylamine / acetonitrile / 5 h / 0 °C
2: 63 percent / 4-N,N-dimethylaminopyridine / acetonitrile / 12 h / 5 °C
3: tri-n-butyltin hydride, bisazoisobutyronitrile / benzene / 12 h / Heating
4: H2 / Pd-C / methanol / 5 h / 23 °C / 760 Torr
View Scheme
145497-37-6

C28H32O12

15291-77-7

ginkgolide B

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 63 percent / 4-N,N-dimethylaminopyridine / acetonitrile / 12 h / 5 °C
2: tri-n-butyltin hydride, bisazoisobutyronitrile / benzene / 12 h / Heating
3: H2 / Pd-C / methanol / 5 h / 23 °C / 760 Torr
View Scheme
145497-38-7

C35H31F5O13S

15291-77-7

ginkgolide B

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tri-n-butyltin hydride, bisazoisobutyronitrile / benzene / 12 h / Heating
2: H2 / Pd-C / methanol / 5 h / 23 °C / 760 Torr
View Scheme
15291-76-6

Ginkgolide C

15291-77-7

ginkgolide B

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 95 percent / imidazole / dimethylformamide / 48 h
2: 66 percent / DMAP / acetonitrile / 24 h
3: 93 percent / tributyltin hydride, AIBN / toluene / 3 h / Heating
4: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h
View Scheme
130523-04-5

1-O-(tert-Butyldiphenylsilyl)ginkgolid C

15291-77-7

ginkgolide B

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 66 percent / DMAP / acetonitrile / 24 h
2: 93 percent / tributyltin hydride, AIBN / toluene / 3 h / Heating
3: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h
View Scheme
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Specification

The Ginkgolide B, with the CAS registry number 15291-77-7, is also known as 9H-1,7a-(Epoxymethano)-1H,6aH-cyclopenta[c]furo[2,3-b]furo[3',2':3,4]cyclopenta[1,2-d]furan-5,9,12(4H)-trione,3-(1,1-dimethylethyl)hexahydro-4,7b,11-trihydroxy-8-methyl-, (1R,3S,3aS,4R,6aR,7aR,7bR,8S,10aS,11R,11aR)-. It belongs to the product categories of Saponins; Intermediates & Fine Chemicals; Pharmaceuticals; PAF receptor. This chemical's molecular formula is C20H24O10 and molecular weight is 424.40. Its classification codes are: (1)Cardiovascular Agents; (2)Fibrin Modulating Agents; (3)Fibrinolytic agents; (4)Hematologic Agents. It is a PAF-receptor antagonist. It may be effective as preventive treatment in reducing migraine attack frequency.

Physical properties of Ginkgolide B are: (1)ACD/LogP: 2.07; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 2.07; (4)ACD/LogD (pH 7.4): 2.07; (5)ACD/BCF (pH 5.5): 22.036; (6)ACD/BCF (pH 7.4): 22.03; (7)ACD/KOC (pH 5.5): 318.44; (8)ACD/KOC (pH 7.4): 318.362; (9)#H bond acceptors: 10; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 148.82 Å2; (13)Index of Refraction: 1.651; (14)Molar Refractivity: 94.203 cm3; (15)Molar Volume: 258.046 cm3; (16)Polarizability: 37.345×10-24cm3; (17)Surface Tension: 79 dyne/cm; (18)Density: 1.645 g/cm3; (19)Flash Point: 274.337 °C; (20)Enthalpy of Vaporization: 126.648 kJ/mol; (21)Boiling Point: 762.416 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Preparation: this chemical can be prepared by 1-O-(tert-Butyldiphenylsilyl)ginkgolid B. This reaction will need reagent tetrabutylammonium fluoride and solvent tetrahydrofuran with the reaction time of 2 hours. The yield is about 73%.

Ginkgolide B can be prepared by 1-O-(tert-Butyldiphenylsilyl)ginkgolid B

Uses of Ginkgolide B: it can be used to produce 1-(tert-butyldiphenylsilyloxy)-3,10-dihydroxyginkgolid at the ambient temperature. It will need reagent imidazole and solvent dimethylformamide with the reaction time of 48 hours. The yield is about 98%.

Ginkgolide B can be used to produce 1-(tert-butyldiphenylsilyloxy)-3,10-dihydroxyginkgolid at the ambient temperature

You can still convert the following datas into molecular structure:
(1)SMILES: C[C@H]1[C@@]2([C@]34O[C@@H]5OC(=O)[C@@H]([C@]56C3([C@@H](C[C@H]6[C@](C)(C)C)OC4=O)[C@H](C2OC1=O)O)O)O
(2)Std. InChI: InChI=1S/C20H24O10/c1-6-12(23)28-11-9(21)18-8-5-7(16(2,3)4)17(18)10(22)13(24)29-15(17)30-20(18,14(25)27-8)19(6,11)26/h6-11,15,21-22,26H,5H2,1-4H3/t6-,7+,8-,9+,10+,11?,15+,17+,18?,19-,20-/m1/s1
(3)Std. InChIKey: SQOJOAFXDQDRGF-REVVDZANSA-N