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C75004

Sigma-Aldrich

5-Cholesten-3-one

Synonym(s):

3-Keto-5-cholestene

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About This Item

Empirical Formula (Hill Notation):
C27H44O
CAS Number:
601-54-7
Molecular Weight:
384.64
EC Number:
210-004-6
MDL number:
MFCD00009940
UNSPSC Code:
12352115
PubChem Substance ID:
24892964
NACRES:
NA.22

form

powder

mp

125-127 °C (lit.)

SMILES string

CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C

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/h9,18-19,22-25H,6-8,10-17H2,1-5H3/t19-,22+,23-,24+,25+,26+,27-/m1/s1

InChI key

GGCLNOIGPMGLDB-GYKMGIIDSA-N

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)

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I J Kass et al.
Biochemistry, 37(51), 17990-18000 (1999-01-28)
Cholesterol oxidase catalyzes the oxidation and isomerization of cholesterol to cholest-4-en-3-one via cholest-5-en-3-one. It has been proposed that His447 acts as the general base catalyst for oxidation, and that the resulting imidazolium ion formed acts as an electrophile for isomerization.
I J Kass et al.
Bioorganic & medicinal chemistry letters, 8(19), 2663-2668 (1999-01-05)
Cholesterol oxidase stereospecifically isomerizes cholest-5-en-3-one to cholest-4-en-3-one. When the base catalyst for isomerization, Glu361, is mutated to Asp, the rate of deprotonation of cholest-5-en-3-one is not affected, but protonation of the dienolic intermediate becomes rate-limiting. This may be a consequence
J P Slotte et al.
Biochimica et biophysica acta, 1145(2), 243-249 (1993-02-09)
In this study we have examined the cholesterol oxidase (Streptomyces cinnamomeus) catalyzed conversion of either 5-cholesten-3 beta-ol or 5-cholesten-3-one into 4-cholesten-3-one in pure sterol or mixed phospholipid-containing monolayers at the air/buffer interface. The mean molecular area requirement of 5-cholesten-3-one in
Hui-Min Qin et al.
Protein expression and purification, 139, 1-7 (2017-07-18)
Cholesterol oxidases, which catalyze the degradation of cholesterol to cholest-4-en-3-one, are widely used in the pharmaceutical and food processing industries. The cholesterol oxidase from Pimelobacter simplex (PsChO3) was transformed into E. coli BL21(DE3), but it was expressed mainly as inclusion bodies
Khondker Rufaka Hossain et al.
Biochimica et biophysica acta. General subjects, 1863(8), 1243-1253 (2019-05-11)
Sterols have been reported to modulate conformation and hence the function of several membrane proteins. One such group is the Chloride Intracellular Ion Channel (CLIC) family of proteins. The CLIC protein family consists of six evolutionarily conserved protein members in
View All Related Papers

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