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Merck

188174

(+)-4-Cholesten-3-one

98%

Synonym(s):

3-Keto-4-cholestene, 3-Oxo-4-cholestene, 4-Cholesten-3-one

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About This Item

Empirical Formula (Hill Notation):
C27H44O
CAS Number:
Molecular Weight:
384.64
UNSPSC Code:
12352115
NACRES:
NA.22
PubChem Substance ID:
EC Number:
210-005-1
Beilstein/REAXYS Number:
2224119
MDL number:
Assay:
98%
Form:
solid
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assay

98%

form

solid

optical activity

[α]23/D +91.0°, c = 2 in chloroform

mp

79-81 °C (lit.)

functional group

ketone

SMILES string

[H][C@@]12[C@]([C@](CC3)(C)C(CC2)=CC3=O)([H])CC[C@@]4(C)[C@@]1([H])CC[C@]4([H])[C@]([H])(C)CCCC(C)C

InChI

1S/C27H44O/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/h17-19,22-25H,6-16H2,1-5H3/t19-,22+,23-,24+,25+,26+,27-/m1/s1

InChI key

NYOXRYYXRWJDKP-GYKMGIIDSA-N

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Jonathan B Johnston et al.
The Journal of biological chemistry, 285(47), 36352-36360 (2010-09-17)
One challenge to the development of new antitubercular drugs is the existence of multiple virulent strains that differ genetically. We and others have recently demonstrated that CYP125A1 is a steroid C(26)-monooxygenase that plays a key role in cholesterol catabolism in
J A Weststrate et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 37(11), 1063-1071 (1999-11-24)
A study was conducted in 12 healthy males and 12 females (mean age 36 years) to assess the impact of a margarine enriched with phytosterol esters on faecal concentrations of bile acids and sterols. During the run-in period, volunteers consumed
Jenna K Capyk et al.
The Journal of biological chemistry, 284(51), 35534-35542 (2009-10-23)
Cyp125 (Rv3545c), a cytochrome P450, is encoded as part of the cholesterol degradation gene cluster conserved among members of the Mycobacterium tuberculosis complex. This enzyme has been implicated in mycobacterial pathogenesis, and a homologue initiates cholesterol catabolism in the soil
Hugues Ouellet et al.
Molecular microbiology, 77(3), 730-742 (2010-06-16)
The infectivity and persistence of Mycobacterium tuberculosis requires the utilization of host cell cholesterol. We have examined the specific role of cytochrome P450 CYP125A1 in the cholesterol degradation pathway using genetic, biochemical and high-resolution mass spectrometric approaches. The analysis of
A M Wolfreys et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 40(4), 461-470 (2002-03-15)
Phytosterol esters are phytosterols derived from vegetable oils following esterification to fatty acids. When phytosterols are added to foods, they inhibit the absorption of dietary and endogenous cholesterol and thereby reduce blood cholesterol concentrations. As part of a comprehensive programme

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