83-46-5 Usage
Description
Beta-Sitosterol, also known as β-sitosterol, is a common plant sterol with a molecular mass of 414.71 g/mol. It is synthesized through the mevalonate and deoxy xylulose pathways and can be isolated from wheat germ oil and corn oil. Structurally, it differs from cholesterol with an ethyl group in the C24 position of the side chain. Beta-sitosterol is a lipid component of membranes and has a white powder form. It possesses antioxidant, anticancer, anti-inflammatory, angiogenic, chemopreventive, and immunomodulatory activities.
Uses
Used in Pharmaceutical Industry:
Beta-Sitosterol is used as an antilipemic agent for reducing blood cholesterol concentrations by inhibiting the absorption of dietary and endogenously-produced cholesterol from the small intestine.
Used in Prostatic Adenoma Treatment:
Beta-Sitosterol is used in the treatment of prostatic adenoma, a benign enlargement of the prostate gland.
Used in Anti-Inflammatory Applications:
Beta-Sitosterol is used as an anti-inflammatory agent, helping to reduce inflammation and associated symptoms.
Used as an Immunomodulator:
Beta-Sitosterol is used as an immunomodulator, which can help regulate the immune system and potentially treat autoimmune disorders.
Used in Food Industry:
Due to its nutraceutical benefits, beta-sitosterol has been used as a food additive intended to lower LDL cholesterol levels.
Used in Cosmetics Industry:
As a contaminant of emerging concern (CECs), beta-sitosterol may be found in cosmetic products, although its presence and effects are still under investigation.
Used in Research:
Beta-sitosterol can be used in research for its potential applications in various fields, such as its role in inducing adipogenesis and lipolysis in rat primary preadipocytes, as well as stimulating glucose uptake in differentiated adipocytes.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 83-46-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 3 respectively; the second part has 2 digits, 4 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 83-46:
(4*8)+(3*3)+(2*4)+(1*6)=55
55 % 10 = 5
So 83-46-5 is a valid CAS Registry Number.
InChI:InChI=1/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+/m0/s1
83-46-5Relevant articles and documents
SPECTROSCOPIC STUDIES ON A WITHANOLIDE FROM WITHANIA COAGULANS
Ramaiah, Parimi Atchuta,Lavie, David,Budhiraja, Ramji D.,Sudhir, Sharan,Garg, Kailash N.
, p. 143 - 150 (1984)
The structure of a new withanolide was elucidated as 3β,14α,20αF,27-tetrahydroxy-1-oxo-20R,22R-witha-5,24-dienolide using chemical and spectroscopic methods.The structure was corroborated by comparative studies with known closely related withanolides.Sitosterol-β-D-glucoside was identified through chemical and spectroscopic means.Key Word Index - Withania coagulans; Solanaceae; whitanolides; steroidal lactones; trichloroacetylcarbamate esters; sitosterol glucoside.
Biosynthesis of Sitosterol in Tissue Cultures of Rabdosia japonica Hara and Ergosterol in Yeast from Acetate
Seo, Shujiro,Sankawa, Ushio,Seto, Haruo,Uomori, Atsuko,Yoshimura, Yohko,et al.
, p. 1139 - 1141 (1986)
The fate of the hydrogen atoms originating from acetate was investigated in the biosynthesis of sitosterol (5) in cultured cells of Rabdosia japonica Hara and ergosterol (6) in yeast and the 1,2-hydride shifts, 20-H from C-17 and 17-H from C-13, were verified.
Sitosterol 3-O-α-riburonofuranoside from Bauhinia candicans
M. Iribarren, Adolfo,B. Pomilio, Alicia
, p. 360 - 361 (1985)
From the aerial parts of Bauhinia candicans a novel steroidal glycoside was isolated and identified as sitosterol 3-O-α-D-riburonofuranoside.
Chemical constituents of the aerial parts of Algerian Galium brunneum: Isolation of new hydroperoxy sterol glucosyl derivatives
Bertella, Anis,Bitam, Fatma,Carbone, Marianna,Ciavatta, Maria Letizia,Gavagnin, Margherita,Smadi, Abla
, p. 39 - 45 (2020/05/25)
The liposoluble extract of Galium brunneum aerial parts from North-eastern Algeria was chemically investigated. The EtOAc soluble portion contained a series of glycosyl cucurbitacins and sterols including three new glucosyl hydroperoxy sterols 1–3 among other phenolic components whereas the BuOH soluble fraction was dominated by glycosyl derivatives of flavonoids, iridoids and lignans, according to the chemistry reported in the literature for the genus Galium. The structure of new oxidized sterols 1–3 was determined by spectroscopic methods as well as by comparison with related known metabolites. Selected main compounds from both extracts, which revealed moderate antibacterial activities, were tested for their growth inhibitory properties against Gram-positive and Gram-negative bacteria. This is the first report of cucurbitacins in plants of genus Galium.
Nurotoxic sterol glycosides
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Page/Page column 47; 48; 49, (2017/03/14)
The invention relates to compositions for use in animal models of neurodegenerative disease and methods therefor. More particularly, the invention relates to the use of neurotoxic sterol glycosides or neurotoxic glycolipids, or combinations thereof, in animal models of neurodegenerative disease. Neurotoxicity-modulating chromenols can also be used in these animal models in combination with the neurotoxic sterol glycosides or neurotoxic glycolipids, or combinations thereof.