| Identification | More | [Name]
beta-Sitosterol | [CAS]
83-46-5 | [Synonyms]
22,23-DIHYDROSTIGMASTEROL
22,23-DIHYDROSTIMASTEROL
24-ALPHA-ETHYLCHOLESTEROL
24BETA-ETHYLCHOLESTEROL
(3)-BETA-SITOSTEROL(2)
5-CHOLESTEN-24-BETA-ETHYL-3-BETA-OL
5-STIGMASTEN-3BETA-OL
ALPHA-DIHYDROFUCOSTEROL
ALPHA-PHYTOSTEROL
A-PHYTOSTEROL
BETA-SITOSTEROL
B-SITOSTEROL
CINCHOL
PHYTOSTEROL
SITOSTEARIN
SITOSTEROL
SITOSTEROL, B-
SITOSTEROLS
(3.beta.)-Stigmast-5-en-3-ol
(3-beta)-stigmast-5-en-3-o | [EINECS(EC#)]
201-480-6 | [Molecular Formula]
C29H50O | [MDL Number]
MFCD00003631 | [Molecular Weight]
414.71 | [MOL File]
83-46-5.mol |
| Chemical Properties | Back Directory | [Appearance]
White powder | [Melting point ]
136-140 °C(lit.)
| [alpha ]
-28 º (c=2, CHCl3) | [Boiling point ]
473.52°C (rough estimate) | [density ]
0.9540 (rough estimate) | [refractive index ]
1.5000 (estimate) | [storage temp. ]
−20°C
| [solubility ]
chloroform: 20 mg/mL, clear, colorless
| [form ]
White solid | [pka]
15.03±0.70(Predicted) | [color ]
White to Off-White | [Water Solubility ]
INSOLUBLE | [Detection Methods]
NMR,HPLC | [Merck ]
8556 | [BRN ]
1916165 | [InChIKey]
KZJWDPNRJALLNS-VJSFXXLFSA-N | [LogP]
10.482 (est) | [CAS DataBase Reference]
83-46-5(CAS DataBase Reference) | [NIST Chemistry Reference]
«beta»-Sitosterol(83-46-5) | [EPA Substance Registry System]
83-46-5(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R38:Irritating to the skin.
R40:Limited evidence of a carcinogenic effect.
R48/20/22:Harmful: danger of serious damage to health by prolonged exposure through inhalation and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [RIDADR ]
UN 1888 6.1/PG 3 | [WGK Germany ]
3
| [RTECS ]
WJ2600000
| [F ]
10 | [HS Code ]
29061300 |
| Hazard Information | Back Directory | [Description]
24α-ethyl Cholesterol is a naturally occurring plant sterol with antioxidant, anticancer, anti-inflammatory, angiogenic, chemopreventive, and immunomodulatory activities. It inhibits the absorption of dietary and endogenously-produced cholesterol from the small intestine, reducing blood cholesterol concentrations.1 Because of its nutraceutical benefits, 24α-ethyl cholesterol has been used as a food additive intended to lower LDL cholesterol.1,2 24α-ethyl Cholesterol (0.1 - 100 μM) can dose-dependently induce adipogenesis and lipolysis in rat primary preadipocytes as well as stimulate glucose uptake in differentiated adipocytes.2 | [Chemical Properties]
White powder | [Uses]
A common sterol in plants. Isolated from wheat germ oil, corn oil. Antilipemic. Used in the treatment of prostatic adenoma. | [Uses]
antiinflammatory, immunomodulator | [Definition]
A steroid with long
aliphatic side chains (8–10 carbons) and at
least one hydroxyl group. They are lipidsoluble and often occur in membranes. Examples are cholesterol and ergosterol. | [Definition]
ChEBI: A phytosterols that is stigmast-5-ene substituted by a beta-hydroxy group at position 3. | [Definition]
sterol: Any of a group of steroidbasedalcohols having a hydrocarbonside-chain of 8–10 carbon atoms.Sterols exist either as free sterols oras esters of fatty acids. Animal sterols(zoosterols) include cholesterol andlanosterol. The major plant sterol(phytosterol) is beta-sitosterol, whilefungal sterols (mycosterols) includeergosterol. | [General Description]
Sitosterol, also called as β-sitosterol, is synthesized through the mevalonate and deoxy xylulose pathways. Synthetically, it is synthesized from stigmasterol by Δ22–23 alkene group hydrogenation. Structurally sitosterol differ from cholesterol with ethyl (sitosterol) group in C24 position of side chain(65). Sitosterol is a lipid component of membranes. It corresponds to a molecular mass of 414.71 g/mol). | [Biochem/physiol Actions]
Sitosterol promotes the antioxidant levels and is used as an effective anti-inflammatory, antiapoptotic and anticancer agent in medicinal preparations. It acts as a neutralizing agent for the venom from viper and cobra. Sitosterol acts on protein kinase C (PKC) and in the sphingomyelin cycle to mediate tumor progression inhibition. | [Purification Methods]
Crystallise -sitosterol from EtOH, MeOH, Me2CO, Me2CO/EtOH or Me2CO/MeOH. It has also been purified by zone melting. The acetate crystallises from MeOH or EtOH as plates with m 127128o and [] D 20 -41o (c 2, CHCl3). The benzoate crystallises from EtOH as needles with m 146-147o and [] D 20 –13.8o (c 2, CHCl3). [Fujimoto & Jacobson J Org Chem 29 3377, 3381 1964, Shoppee J Chem Soc 10431948, Heilbron et al. J Chem Soc 344, 347 1941, Beilstein 6 III 2696.] |
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