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C8128

Sigma-Aldrich

5α-Cholestan-3-one

crystalline

Synonym(s):

3-Keto-5α-cholestane

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About This Item

Empirical Formula (Hill Notation):
C27H46O
CAS Number:
566-88-1
Molecular Weight:
386.65
MDL number:
MFCD00065901
UNSPSC Code:
12352200
PubChem Substance ID:
24893027
NACRES:
NA.77

form

crystalline

Quality Level

200

mp

128-130 °C (lit.)

SMILES string

[H][C@@]12CC[C@@]3([H])[C@]4([H])CC[C@H]([C@H](C)CCCC(C)C)[C@@]4(C)CC[C@]3([H])[C@@]1(C)CCC(=O)C2

InChI

1S/C27H46O/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/h18-20,22-25H,6-17H2,1-5H3/t19-,20+,22+,23-,24+,25+,26+,27-/m1/s1

InChI key

PESKGJQREUXSRR-UXIWKSIVSA-N

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Storage Class

11 - Combustible Solids

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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Cholestanol United States Pharmacopeia (USP) Reference Standard

USP

1131858

Cholestanol

5α-Cholestane-2,2,4,4-d4 98 atom % D, 97% (CP)

Sigma-Aldrich

747505

5α-Cholestane-2,2,4,4-d4

5-α-Cholestane certified reference material, 10 mg/mL in chloroform

Supelco

47124

5-α-Cholestane

W F Lau et al.
Experientia, 51(7), 731-737 (1995-07-14)
The effects of cholesterol and cholesterol-derived oxysterols (cholestanone, cholestenone, coprostanone and epicoprostanol) on adipocyte ghost membrane fluidity were studied using a fluorescence depolarization method. The fluorescence anisotropy of the treated membranes was determined using 1,6-diphenyl-1,3,5-hexatriene (DPH) and 1-(4-trimethylammoniumphenyl)-6-phenyl-1,3,5-hexatriene (TMA-DPH). Cholestanone
Dina S El-Kady et al.
Applied biochemistry and biotechnology, 188(3), 635-662 (2019-01-08)
Modification of steroid molecules by introducing heterocyclic ring into the core structure of steroids has been utilized as an attractive approach for either cancer prognosis or diagnosis. Several new cholestanoheterocyclic steroids were synthesized, and analytical and spectral data proved the
W F Lau et al.
Biochemistry and molecular biology international, 35(6), 1349-1358 (1995-05-01)
Cholesterol-derived oxysterols such as cholestanol, cholestanone and coprostanone were able to potentiate epinephrine-induced lipolysis in intact rat adipocytes but not cholesterol. The relative potency of the oxysterols followed the sequence: cholestanone > or = coprostanone > cholestanol. Cholestanone was selected
G E Mott et al.
Journal of lipid research, 21(4), 480-484 (1980-05-01)
After oral administration of a mixture of [1,2(n)-3H]cholesterol and [4-14C]cholesterol to a baboon, fecal coprostanone had a 46% lower 3H/14C ratio than the dose administered. Loss of 3H by enolization of the 3-ketone could account for the decrease in 3H/14C.
G V Vahouny et al.
The Journal of nutrition, 117(12), 2009-2015 (1987-12-01)
Young adult rats were fed ad libitum for 4 wk on defined diets containing either no fiber, 10% levels of insoluble fiber sources [cellulose, wheat bran, alfalfa, mixed fibers (Fibyrax)], 5% levels of soluble fiber sources [pectin, guar gum, psyllium
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