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C2882

Sigma-Aldrich

5β-Cholestan-3α-ol

≥95%

Synonym(s):

Epicoprostanol

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About This Item

Empirical Formula (Hill Notation):
C27H48O
CAS Number:
516-92-7
Molecular Weight:
388.67
MDL number:
MFCD00064143
UNSPSC Code:
12352211
PubChem Substance ID:
24892540
NACRES:
NA.28

Quality Level

200

Assay

≥95%

form

powder

shipped in

ambient

storage temp.

room temp

SMILES string

CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

InChI

1S/C27H48O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-25,28H,6-17H2,1-5H3/t19-,20-,21-,22+,23-,24+,25+,26+,27-/m1/s1

InChI key

QYIXCDOBOSTCEI-KKFSNPNRSA-N

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Application

5β-Cholestan-3α-ol was used as internal standard for analysis of sterols in plasma by GC and HPLC.

Biochem/physiol Actions

5β-Cholestan-3α-ol is a sterol produced endogenously from cholesterol and has been isolated from feces of human and rats. It is derived from cholesterol by the action of intestinal microorganisms.

Preparation Note

5β-Cholestan-3α-ol yields clear, colorless to faint yellow solution in chloroform at 50 mg/ml.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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M Souidi et al.
Life sciences, 64(17), 1585-1593 (1999-06-03)
Our purpose was to examine the in vitro modulation of liver mitochondrial sterol 27-hydroxylase (S27OHase) and microsomal cholesterol 7alpha-hydroxylase (CH7alphaOHase) activities by certain drugs, sterols, oxysterols and bile acids, and to compare the influence of sex, age, diet and cholestyramine
Anna N Bukiya et al.
The Journal of general physiology, 137(1), 93-110 (2010-12-15)
The activity (Po) of large-conductance voltage/Ca(2+)-gated K(+) (BK) channels is blunted by cholesterol levels within the range found in natural membranes. We probed BK channel-forming α (cbv1) subunits in phospholipid bilayers with cholesterol and related monohydroxysterols and performed computational dynamics
D Blache et al.
Journal of chromatography. B, Biomedical sciences and applications, 702(1-2), 103-110 (1998-02-04)
Resveratrol is a trihydroxystilbene present in certain red wines. It may play a role in the inhibition of lipoprotein oxidation and platelet activity. We have developed the first method to measure resveratrol in animal and human samples and to study
Quantitative analysis of sterols in serum by high-performance liquid chromatography: application to the biochemical diagnosis of cerebrotendinous xanthomatosis
Kasama T et al
Journal of Chromatography A, 400, 241-246 (1987)
Vikaskumar G Shah et al.
Water research, 41(16), 3691-3700 (2007-07-07)
Faecal samples from humans, herbivores, carnivores and birds as well as samples from septic tanks and effluents from a sewage treatment plant (STP) were extracted and analyzed by gas chromatography-mass spectrometry for faecal sterols including coprostanol, epicoprostanol, cholestanol, cholesterol, stigmasterol
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