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188174

(+)-4-Cholesten-3-one

Name: (+)-4-Cholesten-3-one
Brand: ALDRICH

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

UNSPSC Code:

12352115

NACRES:

NA.22

PubChem Substance ID:

24851303

EC Number:

210-005-1

Beilstein/REAXYS Number:

2224119

MDL number:

MFCD00003663

Assay:

98%

Form:

solid

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Properties

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

Description

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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Cholesterol and its derivatives, are the principal steroids isolated from the leech species Hirudo medicinalis.

B Zipser et al.

Comparative biochemistry and physiology. Part C, Pharmacology, toxicology & endocrinology, 120(2), 269-282 (1998-11-25)

Steroids were isolated from the blood-sucking leech species Hirudo medicinalis and their structure was studied with one- and two-dimensional NMR spectroscopy (DQF-COSY and HMQC), GC-MS and ESI-MS spectrometry. Fractionating leech lipid using silicic acid chromatography led to the isolation of

Mycobacterial cytochrome p450 125 (cyp125) catalyzes the terminal hydroxylation of c27 steroids.

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

Safety evaluation of phytosterol esters. Part 7. Assessment of mutagenic activity of phytosterols, phytosterol esters and the cholesterol derivative, 4-cholesten-3-one.

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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Global Trade Item Number

SKU	GTIN
188174-10G	04061838346766
188174-1G	04061838758750