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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.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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