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Bilobalide

CAT: 0804-HY-N0076-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N0076-01Size:5 mg
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Description
Bilobalide, a sesquiterpene trilactone constituent of Ginkgo biloba, inhibits the NMDA-induced efflux of choline with an IC50 value of 2.3 μM. Bilobalide prevents apoptosis through activation of the PI3K/Akt pathway in SH-SY5Y cells. Exerts protective and trophic effects on neurons[1][2].
CAS Number
33570-04-6
Product Name Alternative
(-) -Bilobalide
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Apoptosis; Autophagy; Endogenous Metabolite
Type
Natural Products
Related Pathways
Apoptosis; Autophagy; Metabolic Enzyme/Protease
Applications
Neuroscience-Neurodegeneration
Field of Research
Neurological Disease
Assay Protocol
https://www.medchemexpress.com/Bilobalide.html
Purity
99.92
Solubility
DMSO : ≥ 100 mg/mL
Smiles
O=C(O1)C[C@@]2([C@]1([H])C[C@]3(C(C)(C)C)O)[C@@]34[C@](OC([C@@H]4O)=O)([H])OC2=O
Molecular Formula
C15H18O8
Molecular Weight
326.30
Precautions
H302, H315, H319, H335
References & Citations
[1]O Weichel, et al. Bilobalide, a constituent of Ginkgo biloba, inhibits NMDA-induced phospholipase A2 activation and phospholipid breakdown in rat hippocampus. Naunyn Schmiedebergs Arch Pharmacol. 1999 Dec;360 (6) :609-15.|[2]Chun Shi, et al. Bilobalide prevents apoptosis through activation of the PI3K/Akt pathway in SH-SY5Y cells. Apoptosis. 2010 Jun;15 (6) :715-27.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Bilobalide

Bilobalide is a terpenoid trilactone found in extracts of Ginkgo biloba.

CAS Number33570-04-6
PubChem CID73581
IUPAC Name(1S,4R,7R,8S,9R,11S)-9-tert-butyl-7,9-dihydroxy-3,5,12-trioxatetracyclo[6.6.0.01,11.04,8]tetradecane-2,6,13-trione
Molecular FormulaC15H18O8
Molecular Weight326.30
XLogP-0.3
Topological Polar Surface Area119
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count8
Rotatable Bond Count1
Heavy Atom Count23
Formal Charge0
Complexity650
SMILES
CC(C)(C)[C@@]1(C[C@H]2[C@@]3([C@]14[C@H](C(=O)O[C@H]4OC3=O)O)CC(=O)O2)O
InChI
InChI=1S/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
InChIKey
MOLPUWBMSBJXER-YDGSQGCISA-N
Chemical Structure
2D Structure
2D structure of Bilobalide
CAS: 33570-04-6
CID: 73581
Formula: C15H18O8
MW: 326.30
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight326.30
XLogP3-0.3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count8
Rotatable Bond Count1
Exact Mass326.10016753
Monoisotopic Mass326.10016753
Topological Polar Surface Area119 Ų
Heavy Atom Count23
Formal Charge0
Complexity650
Isotope Atom Count0
Defined Atom Stereocenter Count6
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
326714Bilobalide
AR-B01627-01(-) -Bilobalide
300016Bilobalide A

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