33570-04-6

Basic information

• Product Name: Bilobalide
• Synonyms: BILOBALID;(-)-BILOBALIDE;BILOBALIDE;5,3'-DIHYDROXY-3,6,7,4'-TETRAMETHOXYFLAVONE;4H,5AH,9H-FURO[2,3-B]FURO[3',2':2,3]CYCLOPENTA[1,2-C]FURAN-2,4,7(3H,8H)-TRIONE,9-(1,1-DIMETHYLETHYL)-10,10A-DIHYDRO-8,9-DIHYDROXY-, [5AR-(3AS*,5A,8,8AS*,9,10A)]-;3',5-DIHYDROXY-3,4',6,7-TETRAMETHOXY FLAVONE;VITEXICARPIM;(-)-bilobalidefromginkgoleaves
• CAS NO: 33570-04-6
• Molecular Formula: C₁₅H₁₈O₈
• Molecular Weight: 326.3
• Product Categories: Heterocycles;Biochemicals Found in Plants;Isoprenoid/terpenoid;Nutrition Research;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors
• Mol File: 33570-04-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: >300°
• Boiling Point: 651.737 °C at 760 mmHg
• Flash Point: 247.487 °C
• Appearance: /
• Density: 1.56 g/cm³
• Vapor Pressure: 9.57E-20mmHg at 25°C
• Refractive Index: 1.605
• Storage Temp.: −20°C
• Solubility: Acetone (Slightly), Methanol (Slightly)
• PKA: 11.74±0.40(Predicted)
• Stability: Hygroscopic
• Merck: 14,1220
• CAS DataBase Reference: Bilobalide(CAS DataBase Reference)
• NIST Chemistry Reference: Bilobalide(33570-04-6)
• EPA Substance Registry System: Bilobalide(33570-04-6)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: LV1665000
• F: 10
• Hazardous Substances Data: 33570-04-6(Hazardous Substances Data)

Usage

Description

Bilobalide is a sesquiterpene lactone which is found in extracts of G. biloba. It has been shown to protect against cerebral edema, decrease cortical infarct volume, and reduce cerebral ischemic damage. Bilobalide, at 10 μM, reduces the release of glycine and glutamate from hippocampal slices under ischemic conditions. It also activates the rat constitutive androstane receptor at 100 μM and increases the levels and activities of several cytochrome P450 isoforms in rat liver microsomes.

Uses

Different sources of media describe the Uses of 33570-04-6 differently. You can refer to the following data:
1. Reference Standard in the analysis of herbal medicinal products
2. Bilobalide provides protection against learning and memory impairment by reducing free radical injury and inhibiting neuronal apoptosis in the brain cortex and hippocampal CA1 region in induced vascular dementia rats.

Definition

ChEBI: A terpenoid trilactone found in extracts of Ginkgo biloba.

General Description

Produced and qualified by HWI pharma services GmbH.Exact content by quantitative NMR can be found on the certificate.

Enzyme inhibitor

This plant natural product (FW = 326.30 g/mol; CAS 33570-04-6) from the gingko tree (Ginkgo biloba) is a terpene trilactone that exhibits anticonvulsant properties. Bilobalide has multiple mechanisms of action (e.g., acting as a GABAA receptor antagonist (/1), preserving mitochondrial ATP synthesis, inhibiting staurosporine-induced apoptotic damage, suppressing hypoxia-induced membrane deterioration in the brain, and increasing the expression the mitochondrial DNA-encoded COX III subunit of cytochrome c oxidase and the ND1 subunit of NADH dehydrogenase). Bilobalide was later synthesized in E. J. Corey’s laboratory in the late 1980s.

InChI:InChI=1/C15H18O8/c1-12(2,3)14(20)4-6-13(5-7(16)21-6)10(19)23-11-15(13,14)8(17)9(18)22-11/h6,8,11,17,20H,4-5H2,1-3H3/t6-,8?,11+,13-,14+,15?/m0/s1

Upstream product

• 110569-44-3 10,12-Di-O-acetyl-iso-bilobalid 
• 110569-43-2 10-O-Acetyl-12-O-(p-brombenzoyl)-iso-bilobalid 
• 141509-72-0 (3aR,5aR,8aS,9S,10aR)-9-tert-Butyl-9-hydroxy-2-methoxy-2,3,10,10a-tetrahydro-9H-furo[2,3-b]furo[3',2':2,3]cyclopenta[1,2-c]furan-4-one 
• 111436-74-9 (3aR,5aR,8aR,10aR)-9-tert-Butyl-2,7-dimethoxy-2,3,7,8-tetrahydro-10aH-furo[2,3-b]furo[3',2':2,3]cyclopenta[1,2-c]furan-4-one 
• 111436-75-0 (3aS,5aS,8aS,10aS)-9-tert-Butyl-7-hydroxy-2-methoxy-2,3,7,8-tetrahydro-10aH-furo[2,3-b]furo[3',2':2,3]cyclopenta[1,2-c]furan-4-one 
• 111436-76-1 (3aS,5aR,8aS,10aS)-9-tert-Butyl-7-chloro-2-methoxy-2,3,7,8-tetrahydro-10aH-furo[2,3-b]furo[3',2':2,3]cyclopenta[1,2-c]furan-4-one 
• 111436-77-2 (3aS,5aS,8aS,10aS)-9-tert-Butyl-2-methoxy-2,3-dihydro-10aH-furo[2,3-b]furo[3',2':2,3]cyclopenta[1,2-c]furan-4-one 
• 111436-73-8 (3aR,5aS,8aR,10aR)-9-tert-Butyl-2,7-dimethoxy-2,3,7,8-tetrahydro-10aH-furo[2,3-b]furo[3',2':2,3]cyclopenta[1,2-c]furan-4-ol 
• 111436-68-1 (1R,3aR,7aR)-3-tert-Butyl-1-hydroxy-4,7-dihydro-1H-indene-3a,7a-dicarboxylic acid dimethyl ester 
• 111436-71-6 (3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-3a,4-diyl)dimethanol 
• 111436-67-0 (3aR,7aR)-3-tert-Butyl-1-oxo-4,7-dihydro-1H-indene-3a,7a-dicarboxylic acid dimethyl ester 
• 111436-86-3 phenyl 3-tert-butylpropiolate 
• 917-92-0 3,3-Dimethylbut-1-yne 
• 33570-05-7 (+/-)-bilobalide 6-acetate 

Downstream Products

• 110569-47-6 7,8-Anhydrobilobalid 
• 33570-05-7 10-O-Acetylbilobalid 
• 110569-39-6 10-O-Pivaloylbilobalid 
• 110569-40-9 10-O-Acetyl-8-O-(p-bromobenzoyl)bilobalid 
• 110569-44-3 10,12-Di-O-acetyl-iso-bilobalid 
• 110569-46-5 10,12-Di-O-(p-brombenzoyl)-iso-bilobalid 
• 110569-42-1 8,10-Di-O-(p-brombenzoyl)bilobalid 
• 33570-07-9 10-Acetyl-7,8-anhydrobilobalid 
• 33570-06-8 8,10-Di-O-acetylbilobalid 
• 110569-48-7 12-O-Pivaloyl-iso-bilobalid 
• 110569-41-0 8,10-Di-O-pivaloylbilobalid 
• 110569-45-4 10,12-Di-O-Pivaloyl-iso-bilobalid 

Relevant articles and documents

Concise asymmetric synthesis of (?)-bilobalide

The Ginkgo biloba metabolite bilobalide is widely ingested by humans but its effect on the mammalian central nervous system is not fully understood1–4. Antagonism of γ-aminobutyric acid A receptors (GABAARs) by bilobalide has been linked to the rescue of cognitive deficits in mouse models of Down syndrome5. A lack of convulsant activity coupled with neuroprotective effects have led some to postulate an alternative, unidentified target4; however, steric congestion and the instability of bilobalide1,2,6 have prevented pull-down of biological targets other than the GABAΑRs. A concise and flexible synthesis of bilobalide would facilitate the development of probes for the identification of potential new targets, analogues with differential selectivity between insect and human GABAΑRs, and stabilized analogues with an enhanced serum half-life7. Here we exploit the unusual reactivity of bilobalide to enable a late-stage deep oxidation that symmetrizes the molecular core and enables oxidation states to be embedded in the starting materials. The same overall strategy may be applicable to G. biloba congeners, including the ginkgolides—some of which are glycine-receptor-selective antagonists8. A chemical synthesis of bilobalide should facilitate the investigation of its biological effects and its therapeutic potential.

Separation Of Ginkgolides And Bilobalide From G. Biloba

The subject invention provides a method for separating a terpene trilactone from Ginkgo biloba plant material or from an extract of Ginkgo biloba comprising a mixture of terpene trilactones, the process comprising the steps of: a) subjecting the Ginkgo biloba plant material or the extract to column chromatography with an appropriate solvent system to produce at least a first fraction containing the terpene trilactone bilobalide, a second fraction eluted after the first fraction containing the terpene trilactones GA and GB, and a third fraction eluted after the second fraction containing at least a preponderance of the terpene trilactones GC and GJ; and b) alkylating the terpene trilactone GB of the second fraction so as to produce a first mixture including terpene trilactone GA and alkylated terpene trilactone GB; or alkylating the terpene trilactone GC of the third fraction so as produce a second mixture including terpene trilactone GJ and alkylated terpene trilactone GC, so as to thereby isolate a terpene trilactone.

Chemistry of Ginkgolides, III. - Bilobalide/iso-Bilobalide - Structure Determination by X-ray Analysis

Bilobalide (1a) shows remarkable biological effects and uncommon chemical properties.Its striking characteristic is the tendency to isomerize under mild acylation conditions to yield the diacyl derivatives 2e-g of the spiro compound 2a.The structures of biobalide (1a) and 10,12-di-O-pivaloyl-iso-bilobalide (2f) are determined by X-ray analysis.