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188174

Sigma-Aldrich

(+)-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:
601-57-0
Molecular Weight:
384.64
Beilstein:
2224119
EC Number:
210-005-1
MDL number:
MFCD00003663
UNSPSC Code:
12352115
PubChem Substance ID:
24851303
NACRES:
NA.22

Quality Level

100

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 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

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Certificates of Analysis (COA)

Lot/Batch Number
STBK8231
STBH6865
STBF4322V
STBC4769V
10120TH

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B Zipser et al.
Comparative biochemistry and physiology. Part C, Pharmacology, toxicology & endocrinology, 120(2), 269-282 (1998-11-25)
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Daniel L Motola et al.
Cell, 124(6), 1209-1223 (2006-03-15)
In response to environmental and dietary cues, the C. elegans orphan nuclear receptor, DAF-12, regulates dauer diapause, reproductive development, fat metabolism, and life span. Despite strong evidence for hormonal control, the identification of the DAF-12 ligand has remained elusive. In
G Tibolla et al.
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Atherosclerosis is associated with Alzheimer's disease (AD) in humans, but the nature of this link is still elusive. Aim of this study was to investigate aortic atherosclerosis development in a mouse model with central nervous system (CNS) restricted beta-amyloid precursor
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
Jonathan B Johnston et al.
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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
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