Basic information
- CAS
15291-77-7- Standard SMILES
CC1C(=O)OC2C(O)C34C5CC(C(C)(C)C)C36C(OC(=O)C6O)OC4(C(=O)O5)C12O- InChIKey
SQOJOAFXDQDRGF-UHFFFAOYSA-N- Molecular formula
- C20H24O10
- Average molar mass
- 424.4 g/mol
- Monoisotopic mass
- 424.13694696
Overview
Ginkgolide B has been reported in Ginkgo and Ginkgo biloba with data available.
Names & identifiers
- Preferred name
- Npc169089
- IUPAC
- 8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.01,11.03,7.07,11.013,17]nonadecane-5,15,18-trione
- English name
- Ginkgolide B
- Molecular formula
- C20H24O10
- Molecular weight
- 424.4
Names & synonyms
RefChem:1092769Npc169089Gingko lactoneGinkgolideBSR-01000597598bn52021Ginklide BGink;lide BCHEMBL266625ginkgolide B from ginkgo leavesorb1305072orb3140886
Show more names
BN 52021BGinkgolidGINKGOLIDE BGINKGOLIDE B(SH)7-DEOXYGINKGOLIDE CGINKOLIDE BBN 52021Ginkgolide B (BN-52021)Ginkgolide B (Standard)Ginkgolide B, 10 mM in DMSOGinkgolideA,1-hydroxy-, (1β)-
SCHEMBL142799031-Hydroxy-(1beta)-Ginkgolide ASQOJOAFXDQDRGF-UHFFFAOYSA-NMSK10397NSC110257PDSP1_000734PDSP2_000724AKOS015895882
Database identifiers
- CAS
15291-77-7- PubChem CID
- 65243
- ChEMBL
CHEMBL266625
Properties
Computed structural properties
- XLogP
- -0.4
- Topological polar surface area
- 149 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 1
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 925
Experimental & physicochemical properties
LogP0.59
Melting Point280 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 280 °C · 280°C (dec.)
- alpha
- 24 · D24 -52.6° (c = 1 in ethanol)
- Boiling point
- 762.4 · 762.4±60.0 °C(Predicted)
- Density
- 1 · 1+-.0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Sealed in dry,Store in freezer, under -20°C
- solubility
- Soluble in DMSO (up to 40 mg/ml) or in Ethanol (up to 10 mg/ml).
- form
- Solid
- pka
- 1 · pKa1 7.14; pKa2 8.60; pKa3 11.89(at 25℃)
- color
- White
- Water Solubility
- Soluble in DMSO. Slightly soluble in water and ethanol
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 10-21
- wgk
- 3
- hs_code
- 29322090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 24/25
- Hazard statements
- H319-H315-H335
- Precautionary statements
- P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Applications
DescriptionGinkgolide B is an important active ingredient derived from the leaf extract of Ginkgo biloba (Ginkgo biloba leaf extract, GBLPE), a member of the Ginkgoaceae family. It belongs to the class of terpenoid ketones and is a diterpene trilactone containing six five-membered rings in its molecular structure. The molecule comprises a spiro[4.4]nonane skeleton and a tetrahydrofuran ring, and is readily soluble in solvents such as ethyl acetate, methanol, ethanol, and dimethyl sulfoxide.
HistoryThe leaf of Ginkgo biloba is sweet, bitter, astringent, and mild. With activating blood circulation to remove blood stasis, dredging collaterals, relieving pain, and asthma, it is applied for treating blood stasis, chest pain, stroke, lung deficiency cough, and hyperlipidemia.As early as in the 1930s, scientists began to study ginkgo and harvest a variety of ginkgolide . Ginkgolide B was isolated and its structure illustrated by Wan Shan etal. in 1967. Subsequently, it was synthesized by Corey etal. in 1988. The preparation of effective components of Ginkgo biloba has been listed at home and abroad with development.The Ginkgo biloba extract consisting of ticlopidine is widely used in overseas market for the treatment of cerebral infarction. Intravenous injection of ginkgolide B is applied for the treatment of inflammation, but the project has been in the state, and there is no progress in it for many years. In addition, whether other extract of Ginkgo biloba can be used for the treatment of stable angina, cognitive impairment is still in preclinical research status.
UsesFamily of bioactive terpenes treating cardiovascular and cerebrovascular diseases. Specific platelet activating factor (PAF) antagonists
UsesGinkgolide B is used as a potent PAF-R antagonist. Ginkgolide B speeds up PAF hydrolysis by promoting PAF-AH I α2 homodimer activity. Additionally, this compound has been reported to inhibit neutrophil degranulation in vitro. Inhibits superoxide production in vitro and inhibits bronchoconstriction and is neuroprotective following oral administration in vivo.
Upstream & downstream products
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…