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Merck
CN

C3652

5α-Cholest-7-en-3β-ol

Synonym(s):

3β-Hydroxy-5α,7-cholestene, Lathosterol

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About This Item

Empirical Formula (Hill Notation):
C27H46O
CAS Number:
80-99-9
Molecular Weight:
386.65
NACRES:
NA.77
PubChem Substance ID:
24892635
UNSPSC Code:
12352211
MDL number:
MFCD00056176

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InChI

1S/C27H46O/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/h10,18-21,23-25,28H,6-9,11-17H2,1-5H3/t19-,20+,21?,23?,24?,25?,26?,27?/m1/s1

SMILES string

CC(CCC[C@@H](C)[C@@](CC[C@]1(C2=CC[C@@]3([H])C[C@@](O)(CC[C@]43C)[H])[H])([C@]1(CC[C@@]24[H])C)[H])C

InChI key

IZVFFXVYBHFIHY-IRRCOBOTSA-N

assay

≥98% (TLC)

form

powder

shipped in

ambient

storage temp.

−20°C

Quality Level

200

Related Categories

Application

5α-Cholest-7-en-3β-ol was used as a substrate in enzymatic assay for plasma cholesterol. It was used to supplement diet of Daphnia galeata to study the effect on life-history traits.

Biochem/physiol Actions

5α-Cholest-7-en-3β-ol (Lathosterol) is an intermediate in cholesterol biosynthesis pathway. Lathosterol in serum is carried on lipoproteins and is indicative of the rate of cholesterol synthesis. It acts as a marker of synthesis of cholesterol and is not affected by dietary consumption of cholesterol.

Preparation Note

5α-Cholest-7-en-3β-ol yields clear, colorless solution in chloroform at 10 mg/ml.

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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Certificates of Analysis (COA)

Lot/Batch Number
0000480158
0000480158
0000458104
0000458104
0000453602

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A Besga et al.
Neuroscience letters, 510(2), 121-126 (2012-01-28)
Investigate possible associations of white matter hyperintensities (WMHs) with the metabolism of cholesterol and insulin in two subgroups of patients with memory complaints and different CSF Aβ42 and CSF tau levels. 59 patients from the memory clinic at Karolinska Hospital
G S Tint et al.
Journal of lipid research, 15(3), 256-262 (1974-05-01)
The metabolism of Delta(7)-cholestenol, cholesterol, and cholestanol was examined in a patient with cerebrotendinous xanthomatosis after intravenous pulse-labeling with a mixture of dl-[2-(14)C]mevalonate and stereospecific 3S,4S,3R,4R-[4-(3)H]mevalonate. Silver nitrate and reversed-phase thin-layer chromatography were used to purify the sterols isolated from
Dominik Martin-Creuzburg et al.
Journal of chemical ecology, 30(3), 483-500 (2004-05-14)
In crustaceans, cholesterol is an essential nutrient, which they must directly obtain from their food or by bioconversion from other dietary sterols. Eukaryotic phytoplankton contain a great variety of sterols that differ from cholesterol in having additional substituents or different
A Rahier
Biochemistry, 40(1), 256-267 (2001-01-05)
Deuterium-labeled 5alpha-cholest-7-en-3beta-ol (1) bearing one or two deuteriums at the C-5alpha and (or) C-6alpha positions was synthesized in high isotopic and chiral purity. These compounds were used as substrates with the microsomal wild-type Zea mays and recombinant Arabidopsis thaliana Delta(7)-sterol-C5(6)-desaturases
W C Duane
Journal of lipid research, 36(2), 343-348 (1995-02-01)
We measured serum lathosterol levels and whole body cholesterol synthesis by sterol balance in 12 human subjects on a metabolic ward in four randomly allocated, 6-7 week periods: 1) lovastatin (40 mg b.i.d.) + low cholesterol diet (mean 246 mg/day);
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