| Identification | More | [Name]
Bilobalide | [CAS]
33570-04-6 | [Synonyms]
3',5-DIHYDROXY-3,4',6,7-TETRAMETHOXY FLAVONE
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)]-
5,3'-DIHYDROXY-3,6,7,4'-TETRAMETHOXYFLAVONE
BILOBALID
(-)-BILOBALIDE
BILOBALIDE
CASTICIN
VITEXICARPIM
VITEXICARPIN
(-)-bilobalidefromginkgoleaves
BILOBALIDE: 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)]-,
(-)-bilobalide from ginkgo biloba leaves
BILOBALIDE(AHP)
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*,5aα,8β,8aS*,9α,10aα)]- | [EINECS(EC#)]
608-892-9 | [Molecular Formula]
C19H18O8 | [MDL Number]
MFCD00210481 | [Molecular Weight]
374.34 | [MOL File]
33570-04-6.mol |
| Chemical Properties | Back Directory | [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) | [form ]
neat | [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) |
| Hazard Information | Back Directory | [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.1 Bilobalide, at 10 μM, reduces the release of glycine and glutamate from hippocampal slices under ischemic conditions.2,3 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.4,5 | [Uses]
Reference Standard in the analysis of herbal medicinal products | [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. | [storage]
Store at -20°C |
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