83-46-5 Usage
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
Different sources of media describe the Uses of 83-46-5 differently. You can refer to the following data:
1. A common sterol in plants. Isolated from wheat germ oil, corn oil. Antilipemic. Used in the treatment of prostatic adenoma.
2. antiinflammatory, immunomodulator
3. 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
Different sources of media describe the Definition of 83-46-5 differently. You can refer to the following data:
1. 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.
2. 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.
3. 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.]
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.
Chemical Constituents of Astragalus falcatus
Alaniya,Sutiashvili,Kavtaradze, N. Sh.,Skhirtladze
, p. 1202 - 1203 (2017/11/27)
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