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700095P

Avanti

sitosterol

Avanti Polar Lipids

Synonym(s):

stigmast-5-en-3β-ol; β-sitosterin

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About This Item

Empirical Formula (Hill Notation):
C29H50O
CAS Number:
83-46-5
Molecular Weight:
414.71
UNSPSC Code:
12352211
NACRES:
NA.25

description

22,23-dihydrostigmasterol

Assay

>99% (contains ~2% of the 24 alpha isomer, TLC)

form

powder

packaging

pkg of 1 × 25 mg (700095P-25mg)
pkg of 1 × 5 mg (700095P-5mg)

manufacturer/tradename

Avanti Polar Lipids

shipped in

dry ice

storage temp.

−20°C

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

InChI key

KZJWDPNRJALLNS-VJSFXXLFSA-N

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).
ß-sitosterol is a phytosterol (plant sterol) found in a wide variety of plants, including pecans, saw palmetto, avocados, pumpkin seed, rice bran, wheat germ, and soybeans. Chemically resembling cholesterol, phytosterols inhibit the absorption of cholesterol. Phytosterols have also been shown to have anticancer properties

Application

Sitosterol has been used as a sterol compound to test its interaction with human Mincle protein. It has also been used as a component of erythrocyte lipid model membrane for biophysical studies.

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.

Packaging

5 mL Amber Glass Screw Cap Vial (700095P-25mg)
5 mL Amber Glass Screw Cap Vial (700095P-5mg)

also commonly purchased with this product

Product No.
Description
Pricing

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Stigmasterol ~95%

Sigma-Aldrich

S2424

Stigmasterol

β-Sitosterol United States Pharmacopeia (USP) Reference Standard

USP

1612947

β-Sitosterol

Campesterol ~65%

Sigma-Aldrich

C5157

Campesterol

β-Sitosterol certified reference material, 100 μg/mL in chloroform

Supelco

47133

β-Sitosterol

cholestanol Avanti Polar Lipids

Avanti

700064P

cholestanol

Lupeol analytical standard

Supelco

18692

Lupeol

Brassicasterol from semisynthetic

Sigma-Aldrich

B4936

Brassicasterol

Maria Luz Fernandez et al.
Cardiovascular drug reviews, 23(1), 57-70 (2005-05-04)
Elevated levels of plasma LDL cholesterol (LDL-C) represent a major risk factor for cardiovascular disease. Treatments aimed at reducing levels of circulating LDL are regarded, therefore, as cardioprotective. The cholesterol lowering properties of plant sterols have been known for some
Atif B Awad et al.
Molecular nutrition & food research, 52(4), 419-426 (2008-03-14)
The objective of this study was to investigate the effects of the dietary phytosterol beta-sitosterol (SIT) and the antiestrogen drug tamoxifen (TAM) on cell growth and ceramide (CER) metabolism in MCF-7 and MDA-MB-231 human breast cancer cells. The MCF-7 and
The story of beta-sitosterol-a review
Saeidnia S, et al.
European Journal of Medicinal Plants, 590-609 (2014)
Keisuke Matsuoka et al.
Chemistry and physics of lipids, 154(2), 87-93 (2008-06-12)
We investigated the difference between the molecular structures of plant sterols and stanols that affect the solubilization of cholesterol in bile salt micelles (in vitro study). First, the aqueous solubility of beta-sitosterol, beta-sitostanol, and campesterol was determined by considering the
A B Awad et al.
The Journal of nutrition, 130(9), 2127-2130 (2000-08-26)
Phytosterols (PS) or plant sterols are structurally similar to cholesterol. The most common PS are beta-sitosterol, campesterol and stigmasterol. Epidemiologic and experimental studies suggest that dietary PS may offer protection from the most common cancers in Western societies, such as
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