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Merck

C8003

Sigma-Aldrich

5-α-Cholestane

≥97.0% (HPLC)

Sinónimos:

NSC 224419

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About This Item

Fórmula empírica (notación de Hill):
C27H48
Número de CAS:
Peso molecular:
372.67
Beilstein/REAXYS Number:
2051806
EC Number:
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥97.0% (HPLC)

form

powder

mp

80-82 °C (lit.)

SMILES string

CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CCCC[C@]4(C)[C@H]3CC[C@]12C

InChI

1S/C27H48/c1-19(2)9-8-10-20(3)23-14-15-24-22-13-12-21-11-6-7-17-26(21,4)25(22)16-18-27(23,24)5/h19-25H,6-18H2,1-5H3/t20-,21-,22+,23-,24+,25+,26+,27-/m1/s1

InChI key

XIIAYQZJNBULGD-XWLABEFZSA-N

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Application

5-α-Cholestane has been used:
  • as an internal standard in gas phase chromatography (GC) and high-performance liquid chromatography (HPLC) to quantify cholesterol in meat products for a comparison study
  • to quantify the active compounds in the oils using a gas chromatograph coupled to a mass spectrometer
  • as a reference standard in GC analyses to quantify sterol content in the unsaponifiables obtained from oat lipids and different sterol standards like fucosterol, sitosterol, campesterol, and stigmasterol

Biochem/physiol Actions

5α-Cholestane is a sterol produced endogenously from cholesterol and has been isolated from human feces. It is derived from cholesterol by the action of intestinal microorganisms. Derivatives of 5α-cholestane in plants are called brassinosteroids that selectively activate the PPI3K/Akt pathway.

Preparation Note

5α-Cholestane yields clear to slightly hazy, colorless to faint yellow solution in chloroform at 50 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)

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Los clientes también vieron

Abdulaziz A Alaqil et al.
Animals : an open access journal from MDPI, 10(9) (2020-09-10)
This study examines the effect of dietary supplementation with Lactobacillus acidophilus (LA) on the cholesterol levels, immune response, and productive performance of laying hens. A total of 216, 40-week-old, commercial Hy-Line brown chicken layers were randomly assigned into four treatment
Comparative Analysis and Validation Methodologies of GC and HPLC for Analysis of Cholesterol in Meat Products
Stroher GL et al
American Journal of Analytical Chemistry, 3, 306-311 (2012)
Paweł Górnaś et al.
Journal of agricultural and food chemistry, 64(4), 898-905 (2016-01-06)
The profile of bioactive compounds (carotenoids, tocopherols, tocotrienols, phytosterols, and squalene) in oils recovered from the kernels of 28 plum varieties of hexaploid species Prunus domestica L. and diploid plums Prunus cerasifera Ehrh. and their crossbreeds were studied. Oil yields
Stefanie M Hixson et al.
PloS one, 11(3), e0152264-e0152264 (2016-03-25)
Nutritional enhancement of crops using genetic engineering can potentially affect herbivorous pests. Recently, oilseed crops have been genetically engineered to produce the long-chain omega-3 polyunsaturated fatty acids, eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) at levels similar to that found
Debora Esposito et al.
Journal of medicinal chemistry, 54(12), 4057-4066 (2011-04-16)
Brassinosteroids are plant-derived polyhydroxylated derivatives of 5α-cholestane, structurally similar to cholesterol-derived animal steroid hormones and insect ecdysteroids. In this study, we synthesized a set of brassinosteroid analogues of a natural brassinosteroid (22S,23S)-homobrassinolide (HB, 1), including (22S,23S)-homocastasterone (2), (22S,23S)-3α-fluoro-homobrasinolide (3), (22S,23S)-3α-fluoro-homocastasterone

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