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Beta-Sitosterol

CAT: 0931-T2966-05Size: 100 mgDry Ice: NoHazardous: No
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CAT#:0931-T2966-05Size:100 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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CAS Number
83-46-5
Target
Apoptosis, Lipase, Endogenous Metabolite
Related Pathways
Apoptosis, Metabolism
Purity
0.9995
Bioactivity
Beta-Sitosterol (SKF 14463) has recently been shown to induce G2/M arrest, endoreduplication, and apoptosis through the Bcl-2 and PI3K/Akt signaling pathways. Beta-Sitosterol (SKF 14463), a main dietary phytosterol found in plants, may have the potential for prevention and therapy for human cancer. Although the exact mechanism of action of Beta-Sitosterol (SKF 14463) is unknown, it may be related to cholesterol metabolism or anti-inflammatory effects (via interference with prostaglandin metabolism) . Beta-Sitosterol (SKF 14463) induces apoptosis and activates key caspases in MDA-MB-231 human breast cancer cells.
Smiles
C[C@@]12[C@]([C@]3([C@@]([C@]4(C)C(=CC3)C[C@@H](O)CC4)(CC1)[H])[H])(CC[C@@]2([C@@H](CC[C@H](C(C)C)CC)C)[H])[H]
Molecular Formula
C29H50O
Molecular Weight
414.71
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

(-)-beta-Sitosterol

Sitosterol is a member of the class of phytosterols that is stigmast-5-ene substituted by a beta-hydroxy group at position 3. It has a role as an antioxidant, an anticholesteremic drug, a sterol methyltransferase inhibitor, a mouse metabolite and a plant metabolite. It is a stigmastane sterol, a 3beta-hydroxy-Delta(5)-steroid, a C29-steroid, a member of phytosterols and a 3beta-sterol. It derives from a hydride of a stigmastane.

CAS Number83-46-5
PubChem CID222284
IUPAC Name(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Molecular FormulaC29H50O
Molecular Weight414.7
XLogP9.3
Topological Polar Surface Area20.2
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count6
Heavy Atom Count30
Formal Charge0
Complexity634
SMILES
CC[C@H](CC[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)C(C)C
InChI
InChI=1S/C29H50O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1
InChIKey
KZJWDPNRJALLNS-VJSFXXLFSA-N
Chemical Structure
2D Structure
2D structure of (-)-beta-Sitosterol
CAS: 83-46-5
CID: 222284
Formula: C29H50O
MW: 414.7
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight414.7
XLogP39.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count6
Exact Mass414.386166214
Monoisotopic Mass414.386166214
Topological Polar Surface Area20.2 Ų
Heavy Atom Count30
Formal Charge0
Complexity634
Isotope Atom Count0
Defined Atom Stereocenter Count9
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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