474-62-4 Usage
Description
24α-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 Properties
White Solid
Uses
Different sources of media describe the Uses of 474-62-4 differently. You can refer to the following data:
1. A phytosterol, which may inhibit the intestinal absorption of cholesterol.
2. Campesterol 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 Description
Campesterol 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 Actions
Campesterol 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 Methods
Campesterol 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.]
Check Digit Verification of cas no
The CAS Registry Mumber 474-62-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,7 and 4 respectively; the second part has 2 digits, 6 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 474-62:
(5*4)+(4*7)+(3*4)+(2*6)+(1*2)=74
74 % 10 = 4
So 474-62-4 is a valid CAS Registry Number.
InChI:InChI=1/C28H48O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h9,18-20,22-26,29H,7-8,10-17H2,1-6H3/t19?,20-,22+,23+,24-,25+,26+,27+,28-/m1/s1
474-62-4Relevant articles and documents
New glycosides of the campesterol derivative from the rhizomes of Tacca chantrieri
Yokosuka, Akihito,Mimaki, Yoshihiro,Sakuma, Chiseko,Sashida, Yutaka
, p. 257 - 265 (2005)
Seven new glycosides of the campesterol derivative (24R,25S)-ergost-5-ene- 3β,26-diol (1-7) were isolated from the rhizomes of Tacca chantrieri (Taccaceae). Their structures were determined by extensive spectroscopic analysis, including 2D NMR data, and a few chemical transformations.
Mechanism of the second methylation in sitosterol side-chain biosynthesis in higher plants: Metabolic fate of 28-hydrogens of 24- methylenecholesterol in Morus alba cell cultures
Okuzumi, Tatsuya,Kaji, Yuko,Hamada, Hiroki,Fujimoto, Yoshinori
, p. 3623 - 3626 (2000)
Biosynthesis of the side-chain of sitosterol in higher plants involves two methylation steps by attack of S-adenosylmethionine. The stereochemical features of the second methylation, namely, of the conversion from 24- methylenecholesterol to isofucosterol in higher plants has been investigated. Feeding studies of synthesized [28E-2H]- and [28Z-2H]-24- methylenecholesterols to cultured cells of Morus alba followed by 2H NMR analysis of the resulting isofucosterol established that the second methylation proceeded in such a manner that addition of the methyl group and proton loss occur on opposite faces of the original Δ(24(28))-double bond. (C) 2000 Elsevier Science Ltd.
PROCESS FOR RECOVERING STEROLS FROM A CRUDE SOURCE CONTAINING STEROL ESTERS
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Page/Page column 3, (2008/12/06)
A process of obtaining sterols suitable for human consumption from a crude wood pulping source containing sterol esters is disclosed. The sterols are obtained at high yield and purity. In particular, a process of obtaining sterols at high yield and purity from tall oil pitch (TOP) is disclosed. The sterols obtained can be esterified to sterol esters for use in dietary supplements and as additives for food and beverage products.
