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| CAS No.: | 15291-77-7 |
|---|---|
| Name: | Ginkgolide B |
| Molecular Structure: | |
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| 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 |
| Safety: | 24/25 |
| PSA: | 148.82000 |
| LogP: | -1.36950 |
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- 170288-58-1
α-benzylginkgolide B
- 15291-77-7
ginkgolide B
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With tetrabutyl ammonium fluoride In tetrahydrofuran for 2h; | 73% |
- 145473-36-5
C28H32O11
- 15291-77-7
ginkgolide B
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With tetrabutylammonium borohydride |
- 15291-76-6
1,3,7,10-Tetrahydroxyginkgolid
- 15291-77-7
ginkgolide B
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: pyridine 2: nBu4NBH4 View Scheme |
- 15291-76-6, 119322-55-3
gingkolide C
- 15291-77-7
ginkgolide B
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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%.
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%.
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