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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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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.
Atherosclerosis, 210(1), 78-87 (2009-12-01)
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
Liang-Bin Xiong et al.
Microbial cell factories, 19(1), 80-80 (2020-04-02)
The bioconversion of phytosterols into high value-added steroidal intermediates, including the 9α-hydroxy-4-androstene-3,17-dione (9-OHAD) and 22-hydroxy-23,24-bisnorchol-4-ene-3-one (4-HBC), is the cornerstone in steroid pharmaceutical industry. However, the low transportation efficiency of hydrophobic substrates into mycobacterial cells severely limits the transformation. In this
Yin-Ru Chiang et al.
Applied and environmental microbiology, 74(1), 107-113 (2007-11-13)
The anoxic metabolism of cholesterol was studied in the denitrifying bacterium Sterolibacterium denitrificans, which was grown with cholesterol and nitrate. Cholest-4-en-3-one was identified before as the product of cholesterol dehydrogenase/isomerase, the first enzyme of the pathway. The postulated second enzyme
Satoshi Yamaguchi et al.
Scientific reports, 7, 41007-41007 (2017-01-25)
A chemically-activatable alkynyl steroid analogue probe has been synthesized for visualizing the lipid raft membrane domains by Raman microscopy. The Raman probe, in which ring A of its steroid backbone is replaced with an alkynyl group, was designed to enable
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