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C3652

Sigma-Aldrich

5α-Cholest-7-en-3β-ol

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C27H46O
Número de CAS:
80-99-9
Peso molecular:
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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Colesterol United States Pharmacopeia (USP) Reference Standard

USP

1131960

Colesterol

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
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
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
Y H Han et al.
Biological & pharmaceutical bulletin, 23(10), 1247-1249 (2000-10-21)
From the butanol fraction of the starfish Asterina pectinifera Müler et Troschel (Asteriidae), we have isolated a new component, 5alpha-cholest-7-en-3beta-ol. Its antigenotoxic and antimutagenic activities were examined by the SOS chromotest with Escherichia coli PQ37 and by Ames test with
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
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