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Bilobalide

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Bilobalide Basic information

Product Name:
Bilobalide
Synonyms:
  • BILOBALID
  • 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-, (3aS,5aR,8R,8aS,9R,10aS)-
  • (5AR- (3AS*,5AΑ,8B,8AS*,9A,10AΑ))- 9-(1,1-DIMETHYLETHYL)- 10,10A-DIHYDRO- 8,9-DIHYDROXY- 4H,5AH,9H-FURO[2,3-B]FURO[3',2':2,3]CYCLOPENTA[1,2-C]FURAN- 2,4,7(3H,8H)-TRIONE
  • (-)-Bilobalide, 98%, from Ginkgo biloba L.
  • Bilobalide 33570-04-6
  • (-)-BILOBALIDE
  • BILOBALIDE
  • 5,3'-DIHYDROXY-3,6,7,4'-TETRAMETHOXYFLAVONE
CAS:
33570-04-6
MF:
C15H18O8
MW:
326.3
EINECS:
608-892-9
Product Categories:
  • Inhibitors
  • chemical reagent
  • pharmaceutical intermediate
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract
  • Heterocycles
  • Biochemicals Found in Plants
  • Isoprenoid/terpenoid
  • Nutrition Research
Mol File:
33570-04-6.mol
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Bilobalide Chemical Properties

Melting point:
>300°
alpha 
57820 -64.3° (c = 2 in acetone)
Boiling point:
651.7±55.0 °C(Predicted)
Density 
1.56±0.1 g/cm3(Predicted)
storage temp. 
−20°C
solubility 
Acetone (Slightly), Methanol (Slightly)
pka
11.74±0.40(Predicted)
color 
White to Off-White
Merck 
14,1220
Stability:
Hygroscopic
LogP
-0.450 (est)
CAS DataBase Reference
33570-04-6(CAS DataBase Reference)
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Safety Information

Safety Statements 
24/25
WGK Germany 
3
RTECS 
LV1665000
10
HS Code 
29322090
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Bilobalide Usage And Synthesis

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

Reference Standard in the analysis of herbal medicinal products

Uses

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.

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