Ginkgolide B supplier | CasNO.15291-77-7

Name
Ginkgolide B
EINECS 604-876-0
CAS No. 15291-77-7
Article Data5
CAS DataBase
Density 1.645 g/cm³
Solubility Soluble in DMSO. Slightly soluble in water and ethanol
Melting Point 280 °C (dec.)
Formula C₂₀H₂₄O₁₀
Boiling Point 762.416 °C at 760 mmHg
Molecular Weight 424.405
Flash Point 274.337 °C
Transport Information
Appearance white crystal powder
Safety 24/25
Risk Codes
Molecular Structure
Hazard Symbols
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)-;
PSA 148.82000
LogP -1.36950

Synthetic route

: 170288-58-1
α-benzylginkgolide B

: 15291-77-7
ginkgolide B

Conditions

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

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 2h;	73%

: 145473-36-5
C28H32O11

: 15291-77-7
ginkgolide B

Conditions

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

Conditions	Yield
With tetrabutylammonium borohydride

: 15291-76-6
1,3,7,10-Tetrahydroxyginkgolid

: 15291-77-7
ginkgolide B

Conditions

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

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

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

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

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

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

: 130523-05-6
1-O-(tert-Butyldiphenylsilyl)-7-O-(phenyloxythiocarbonyl)ginkgolid C

: 15291-77-7
ginkgolide B

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / tributyltin hydride, AIBN / toluene / 3 h / Heating 2: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h View Scheme

: 104-83-6
1-Chloro-4-(chloromethyl)benzene

: 15291-77-7
ginkgolide B

: 10-O-p-chlorobenzylginkgolide B

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile for 0.5h; Alkylation; Heating;	98.3%

: 15291-77-7
ginkgolide B

: 58479-61-1
tert-butylchlorodiphenylsilane

: 130523-06-7
1-(tert-butyldiphenylsilyloxy)-3,10-dihydroxyginkgolid

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide for 48h; Ambient temperature;	98%

: 15291-77-7
ginkgolide B

: 352-11-4
1-chloromethyl-4-fluorobenzene

: 10-O-p-fluorobenzylginkgolide B

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile for 0.5h; Alkylation; Heating;	96.7%

: 4584-46-7
(2-chloroethyl)dimethylamine hydrochloride

: 15291-77-7
ginkgolide B

: 914251-20-0
10-O-(2-dimethylaminoethyl)ginkgolide B

Conditions

Conditions	Yield
With calcium carbonate; potassium iodide In water; acetonitrile at 85℃; Reagent/catalyst; Temperature; Flow reactor;	94.1%
With calcium carbonate; potassium iodide In water; acetonitrile at 85℃; for 0.05h; Reagent/catalyst; Temperature; Concentration; Flow reactor;	94.1%

: 100-14-1
4-nitrobenzyl chloride

: 15291-77-7
ginkgolide B

: 10-O-p-nitrobenzylginkgolide B

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile for 0.5h; Alkylation; Heating;	92.3%

: 15291-77-7
ginkgolide B

: 2632-13-5
2-Bromo-4'-methoxyacetophenone

: 10-O-p-methoxyphenacylginkgolide B

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile for 0.5h; Alkylation; Heating;	90.1%

: 541-41-3
chloroformic acid ethyl ester

: 15291-77-7
ginkgolide B

: 10-O-ethoxycarbonylginkgolide B

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile for 0.5h; Acylation; Heating;	89.4%

: 15291-77-7
ginkgolide B

: 532-27-4
1-chloroacetophenone

: 10-O-phenacylginkgolide B

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile for 0.5h; Alkylation; Heating;	89.2%

: 18355-05-0
1-hydroxybenzotriazolyl acetate

: 15291-77-7
ginkgolide B

A: C20H24O10(CH2CO)

B: C20H24O10(CH2CO)

Conditions

Conditions	Yield
With pyridine; dmap In N,N-dimethyl-formamide	A 88% B 9%

...Expand

: 15291-77-7
ginkgolide B

: 106-95-6
allyl bromide

: 289490-32-0
10-O-allylginkgolide B

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile for 0.5h; Alkylation; Heating;	87.8%

: 4535-90-4
N-methyl-2-chloroethylamine hydrochloride

: 15291-77-7
ginkgolide B

: 914251-23-3
10-O-methylaminoethyl ginkgolide B

Conditions

Conditions	Yield
With calcium carbonate; potassium iodide In water; acetonitrile at 85℃; Flow reactor;	83.5%

: 870-24-6
2-chloroethanamine hydrochloride

: 15291-77-7
ginkgolide B

: 10-O-aminoethyl ginkgolide B

Conditions

Conditions	Yield
With calcium carbonate; potassium iodide In water; acetonitrile at 85℃; Flow reactor;	79.4%

: 15291-77-7
ginkgolide B

: 105-36-2
ethyl bromoacetate

A: 10-O-ethyloxycarbonylmethylginkgolide B

B: 1-O-ethyloxycarbonylmethylginkgolide B

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile for 0.5h; Alkylation; Heating;	A 78.3% B 12.1%

...Expand

: 15291-77-7
ginkgolide B

: 107-07-3
2-chloro-ethanol

: 10-O-hydroxyethyl ginkgolide B

Conditions

Conditions	Yield
With calcium carbonate; potassium iodide In water; acetonitrile at 85℃; Flow reactor;	76.3%
With calcium carbonate; potassium iodide In water; acetonitrile at 85℃; for 0.05h; Flow reactor;	76.3%

: 42879-03-8
4-bromobut-2-enenitrile

: 15291-77-7
ginkgolide B

: 10-O-(3-cyanoallyl)ginkgolide B

Conditions

Conditions	Yield
With triethylamine; potassium iodide In chloroform Reflux;	75%

: 15291-77-7
ginkgolide B

: 104-81-4
4-Methylbenzyl bromide

: 170288-73-0
10-O-p-methylbenzylginkgolide B

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile at 75℃; for 0.75h;	72.9%

: 16004-15-2
1-bromomethyl-4-iodobenzene

: 15291-77-7
ginkgolide B

: 170289-24-4
10-O-p-iodobenzylginkgolide B

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile at 70℃; for 0.666667h;	72.4%

: 15291-77-7
ginkgolide B

: 19481-82-4
2-bromopropionitrile

: 10-O-(1-cyanoethyl)ginkgolide B

Conditions

Conditions	Yield
With triethylamine; potassium iodide In chloroform Reflux;	71%

: 100-44-7
benzyl chloride

: 15291-77-7
ginkgolide B

: 170288-58-1
α-benzylginkgolide B

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile for 0.5h; Alkylation; Heating;	65.3%

: 15291-77-7
ginkgolide B

: 106-96-7
propargyl bromide

: 10-O-propargylated ginkgolide B

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 24h; Reflux; Inert atmosphere;	65%
With potassium carbonate; potassium iodide In acetonitrile at 100℃; for 2.5h;

: 15291-77-7
ginkgolide B

: 589-15-1
1-bromomethyl-4-bromobenzene

: 170289-51-7
10-O-p-bromobenzylginkgolide B

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile at 70℃; for 0.833333h;	64.5%

: 50-00-0
formaldehyd

: 15291-77-7
ginkgolide B

: 1,10-O,O-methyleneginkgolide B

Conditions

Conditions	Yield
With sulfuric acid; acetic acid In tetrahydrofuran for 8h; Condensation; Heating;	61.8%

: 99-34-3
3,5-dinitrobenzoic acid

: 15291-77-7
ginkgolide B

: C27H26N2O15

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 6h;	61.25%

: 15291-77-7
ginkgolide B

: 74-88-4
methyl iodide

A: 1-O-methylginkgolide B

B: 10-O-methylginkgolide B

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile for 0.5h; Alkylation; Heating;	A 26.7% B 60.1%

...Expand

: 5292-43-3
bromoacetic acid tert-butyl ester

: 15291-77-7
ginkgolide B

: 10-O-(tert-butoxyformylmethyl)ginkgolide B

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In tetrahydrofuran for 2h; Reflux;	58%

: 15291-77-7
ginkgolide B

: 84424-42-0
methyl 2-(2-iodoethoxy)acetate

: 10-O-(methoxyformylmethoxyethyl)ginkgolide B

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In tetrahydrofuran for 2h; Reflux;	58%

: methyl bromoethoxyethoxyacetate

: 15291-77-7
ginkgolide B

: 10-O-(methoxyformylmethoxyethoxyethyl)ginkgolide B

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In tetrahydrofuran for 2h; Reflux;	56%

: 15291-77-7
ginkgolide B

: 100-09-4
4-methoxybenzoic acid

A: C28H30O12

B: C28H30O12

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 6h;	A 8.4% B 55.57%

...Expand

Ginkgolide B 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

Product Name

Ginkgolide B

Synthetic route

Ginkgolide B Specification

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