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C3652

Sigma-Aldrich

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
MDL number:
MFCD00056176
UNSPSC Code:
12352211
PubChem Substance ID:
24892635
NACRES:
NA.77

Assay

≥98% (TLC)

Quality Level

200

form

powder

shipped in

ambient

storage temp.

−20°C

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

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

InChI key

IZVFFXVYBHFIHY-IRRCOBOTSA-N

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 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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);
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
Matthew G K Benesch et al.
Biochemistry, 50(46), 9982-9997 (2011-09-29)
We performed differential scanning calorimetry (DSC) and Fourier transform infrared (FTIR) spectroscopic measurements to study the effects of lathosterol (Lath) on the thermotropic phase behavior and organization of dipalmitoylphosphatidylcholine (DPPC) bilayer membranes and compared our results with those previously reported
Artyom Kopp
Current biology : CB, 22(23), R1004-R1006 (2012-12-12)
Host-plant specialization plays a key role in insect evolution, but little is known about its molecular basis. A new paper shows that a cactus-feeding fly became restricted to its host by changes in an enzyme that converts dietary sterols into
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