CAMPESTEROL

CAMPESTEROL
  • CAS No.:474-62-4
Other grades of this product :
CAMPESTEROL Basic information
Product Name:CAMPESTEROL
Synonyms:(24R)-5-Ergosten-3beta-ol;(24R)-Methylcholest-5-en-3beta-ol;24alpha-Methylcholesterol;Campesterin;DELTA5-24-Isoergosten-3beta-ol;Ergost-5-en-3beta-ol, (24R)-;Ergost-5-en-3-ol;Ergost-5-en-3-ol, (3beta,24R)-
CAS:474-62-4
MF:C28H48O
MW:400.69
EINECS:207-484-4
Product Categories:chemical reagent;pharmaceutical intermediate;Intermediates & Fine Chemicals;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Isotope Labelled Compounds;Pharmaceuticals;Steroids
Mol File:474-62-4.mol
CAMPESTEROL Chemical Properties
Melting point 156-160 °C
alpha D23 -33° (22.5 mg in 5 ml chloroform)
Boiling point 463.29°C (rough estimate)
density 0.98±0.1 g/cm3 (20 ºC 760 Torr)
refractive index 1.5100 (estimate)
storage temp. -20°C
solubility Chloroform (Sparingly), Methanol (Slightly, Sonicated)
pka15.03±0.70(Predicted)
form crystalline
color white
Merck 13,1736
BRN 3216975
InChIKeySGNBVLSWZMBQTH-ZRUUVFCLSA-N
Safety Information
Hazard Codes Xn,T
Risk Statements 20/21/22-36/37/38-48/20/22-40-38-22
Safety Statements 26-36-45-36/37/39-23
RIDADR UN 1888 6.1/PG 3
WGK Germany 3
HS Code 29061990
MSDS Information
ProviderLanguage
SigmaAldrich English
CAMPESTEROL Usage And Synthesis
Description24α-methyl Cholesterol is a phytosterol found in vegetables, fruits, nuts, and seeds that competitively inhibits the absorption of intestinal cholesterol and decreases the transcription of genes important for cholesterol metabolism. The cholesterol lowering effects of phytosterols, such as 24α-methyl cholesterol, have been reported to be beneficial for lowering the incidence of atherosclerotic plaques. 24α-methyl Cholesterol can also act as an agonist at liver X receptors (LXR) and, through activation of LXR signaling, has been shown to suppress the proliferation of prostate and breast cancer cells.
Chemical PropertiesWhite Solid
UsesA phytosterol, which may inhibit the intestinal absorption of cholesterol.
UsesCampesterol may be used as a plant sterol to test its effect on the transcriptional activation of liver X receptor α (LXRA) in breast cancer cells. It may also be used as a sterol standard for calibration curve generation in liquid chromatography multiple reaction monitoring (LC-MRM) analysis.
General DescriptionCampesterol is a plant sterol, which is an analog of cholesterol and a brassinosteroid (BR) precursor. The enzyme diminute/dwarf1 mediates the synthesis of campesterol from 24-methylenecholesterol. Campesterol possesses methyl group at C-24 position of the side chain in the cholesterol structure.
Biochem/physiol ActionsCampesterol is a phytosterol, primarily found in nuts, fruits, legumes and seeds. Though an analogue of cholesterol, it is poorly absorbed in humans and competitively inhibits the absorption of cholesterol. Campesterol decreases the transcription of genes involved in cholesterol metabolism in hepatocytes and enterocytes and has positive impact in treatment of cardiovascular disease.
Purification MethodsCampesterol is recrystallised twice from hexane and once from Me2CO. The benzoyl derivative has m 158-160o [] D 23 -8.6o (CHCl3), and the acetyl derivative has m 137138o (EtOH) and [] D 23 -35.1o (c 2.9, CHCl3) [Fernholz & MacPhillamy J Am Chem Soc 6 3 1155 1941]. [Beilstein 6 III 2680.]
CAMPESTEROL Preparation Products And Raw materials
Preparation ProductsErgostan-3-ol, (3.beta.,5.alpha.,24R)-

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