474-73-7 Usage
Uses
Used in Pharmaceutical Industry:
24(S)-HydroxycholeSTEROL is used as a therapeutic agent for modulating cholesterol homeostasis and activating LXRα and LXRβ nuclear receptors, which can help in the treatment of various cholesterol-related disorders.
Used in Neurological Research:
24(S)-HydroxycholeSTEROL is used as a research tool for studying the role of cholesterol processing in neurological repair during Alzheimer's disease and other neuropathological conditions.
Used as a Biomarker in Medical Analysis:
(3β,24S)-Cholest-5-ene-3,24-diol, also known as 24(S)-HydroxycholeSTEROL, is used as a biomarker in the analysis of diseases, particularly those related to cholesterol metabolism and neurological conditions.
Biochem/physiol Actions
24(S)-hydroxycholesterol (24HC) elevated levels are reported in liver inflammation and fibrosis. It is a N-methyl-D-aspartate receptor (NMDAR) modulator. The levels of 24HC are potential indicators of brain development as well as pathology including Alzheimer′s disease (AD) and multiple sclerosis. Polymorphism in the cholesterol 24-hydroxylase (CYP46A1) gene leads to elevated 24HC levels and toxicity. 24HC is a mediator of apoptosis and necroptosis. Elevated levels of 24HC are reported in liver inflammation and fibrosis.
References
1) Lujohann et al. (1996), Cholesterol homeostasis in human brain: evidence for an age-dependent flux of 24S-hydroxycholesterol from the brain into circulation; Proc. Natl. Acad. Sci. USA, 93 9799
2) Chawla et al. (2001), Nuclear receptors and lipid physiology:opening the X-files; Science, 294 1866
3) Kolsch et al. (1999), The neurotoxic effect of 24-hydroxycholesterol on SH-SY5Y human neuroblastoma cells; Brain Res., 818 171
4) Yamanaka et al. (2011), 24(S)-hydroxycholesterol induces neuronal cell death through necroptosis, a form of programmed necrosis; J. Biol. Chem., 286 24666
5) Wang et al. (2010), A second class of nuclear receptors for oxysterols: regulation of RORalpha and RORgamma activity by 24(S)-hydroxycholesteraol (cerebrosterol); Biochim. Biophys. Acta, 1801 917
6) Leoni and Caccia (2013), Potential diagnostic applications of side chain oxysterols analysis in plasma and cerebrospinal fluid; Biochem. Pharmacol., 86 26
7) Urano et al. (2013), Suppression of amyloid-β production by 24S-hydroxycholesterol via inhibition of intracellular amyloid precursor protein trafficking; FASEB J.,?27?4305
Check Digit Verification of cas no
The CAS Registry Mumber 474-73-7 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, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 474-73:
(5*4)+(4*7)+(3*4)+(2*7)+(1*3)=77
77 % 10 = 7
So 474-73-7 is a valid CAS Registry Number.
InChI:InChI=1/C27H46O2/c1-17(2)25(29)11-6-18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20+,21+,22-,23+,24+,25+,26+,27-/m1/s1
474-73-7Relevant academic research and scientific papers
Synthesis of 24-functionalized oxysterols
Khripach,Zhabinskii,Konstantinova,Khripach,Antonchick
, p. 257 - 261 (2007/10/03)
The syntheses of (24S)-24,25-epoxycholesterol, (24S)-hydroxycholesterol, and 24-ketocholesterol are described. The compounds belong to oxysterols, which can be considered to be the modulators of cholesterol metabolism. The asymmetric hydroxylation of desmosterol acetate according to Sharpless was used as the key reaction in the stereoselective introduction of functionality in position 24.
