beta-Sitosterol Property

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. 

2-8°C

solubility 

chloroform: 20 mg/mL, clear, colorless

form 

White solid

pka

15.03±0.70(Predicted)

color 

White to Off-White

optical activity

-3725 (c 2, CHCl3)

Water Solubility 

INSOLUBLE

Merck 

14,8556

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

.beta.-Sitosterol (83-46-5)

Safety

Hazard Codes 

Xn,Xi

Risk Statements 

22-38-40-48/20/22-36/37/38-67-36/38-20-63

Safety Statements 

22-24/25-36-26-36/37

RIDADR 

UN 1888 6.1/PG 3

WGK Germany 

3

RTECS 

WJ2600000

F 

10

HS Code 

29061990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H331Toxic if inhaled

H336May cause drowsiness or dizziness

H351Suspected of causing cancer

H372Causes damage to organs through prolonged or repeated exposure

H412Harmful to aquatic life with long lasting effects

Precautionary statements

P201Obtain special instructions before use.

P273Avoid release to the environment.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P308+P313IF exposed or concerned: Get medical advice/attention.

beta-Sitosterol Chemical Properties,Usage,Production

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. Because of its nutraceutical benefits, 24α-ethyl cholesterol has been used as a food additive intended to lower LDL cholesterol. 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.

Chemical Properties

White powder

Uses

antiinflammatory, immunomodulator

Uses

A common sterol in plants. Isolated from wheat germ oil, corn oil. Antilipemic. Used in the treatment of prostatic adenoma.This compound is a contaminant of emerging concern (CECs)

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

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.

Definition

ChEBI: A phytosterols that is stigmast-5-ene substituted by a beta-hydroxy group at position 3.

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.]