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700054P

Avanti

5α,6β-dihydroxycholestanol

Cholestane-3β,5α,6β-triol, powder

Sinónimos:
3β,5α,6β-trihydroxycholestane
Empirical Formula (Hill Notation):
C27H48O3
Número de CAS:
Peso molecular:
420.67
NACRES:
NA.25

assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 25 mg (700054P-25mg)
pkg of 1 × 5 mg (700054P-5mg)

shipped in

dry ice

storage temp.

−20°C

InChI

1S/C27H48O3/c1-17(2)7-6-8-18(3)21-9-10-22-20-15-24(29)27(30)16-19(28)11-14-26(27,5)23(20)12-13-25(21,22)4/h17-24,28-30H,6-16H2,1-5H3/t18-,19+,20+,21-,22+,23+,24-,25-,26-,27+/m1/s1

InChI key

YMMFNKXZULYSOQ-RUXQDQFYSA-N

General description

5α,6β-dihydroxycholestanol is a structural derivative of cholesterol. It is produced by the low-density lipoprotein oxidation (LDL) and is a cholesterol autooxidation product. 5α,6β-dihydroxycholestanol is an abundant oxysterol.

Application

5α,6β-dihydroxycholestanol has been used as a cholesterol oxidation product in reversed phase chromatography (RP-HPLC) and mass spectroscopy analysis. It may be used as an internal standard in tandem mass spectrometry (MS/MS analysis) of plasma samples.

Biochem/physiol Actions

5α,6β-dihydroxycholestanol (5α,6α-diOH-Chol) or cholestan-3β,5α,6β-triol (C-triol) levels are elevated along with 7-ketocholesterol in Niemann-Pick type C (NP-C) disease and is a key biomarkers for detection. It exhibits neuroprotective functionality during central nervous system (CNS) ischemia.

Packaging

5 mL Amber Glass Screw Cap Vial (700054P-25mg)
5 mL Amber Glass Screw Cap Vial (700054P-5mg)

hcodes

Hazard Classifications

Aquatic Chronic 4

Storage Class Code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Certificado de Análisis

Certificado de origen

Sara Boenzi et al.
Journal of lipid research, 57(3), 361-367 (2016-01-07)
Oxysterols are intermediates of cholesterol metabolism and are generated from cholesterol via either enzymatic or nonenzymatic pathways under oxidative stress conditions. Cholestan-3β,5α,6β-triol (C-triol) and 7-ketocholesterol (7-KC) have been proposed as new biomarkers for the diagnosis of Niemann-Pick type C (NP-C)...
Haiyan Hu et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 34(34), 11426-11438 (2014-08-22)
Overstimulation of NMDA-type glutamate receptors is believed to be responsible for neuronal death of the CNS in various disorders, including cerebral and spinal cord ischemia. However, the intrinsic and physiological mechanisms of modulation of these receptors are essentially unknown. Here...
Ren Sheng et al.
Nature communications, 5, 4393-4393 (2014-07-16)
Wnt proteins control diverse biological processes through β-catenin-dependent canonical signalling and β-catenin-independent non-canonical signalling. The mechanisms by which these signalling pathways are differentially triggered and controlled are not fully understood. Dishevelled (Dvl) is a scaffold protein that serves as the...
M Voorink-Moret et al.
Molecular genetics and metabolism, 123(2), 76-84 (2018-01-02)
In patients suspected of a lipid storage disorder (sphingolipidoses, lipidoses), confirmation of the diagnosis relies predominantly on the measurement of specific enzymatic activities and genetic studies. New UPLC-MS/MS methods have been developed to measure lysosphingolipids and oxysterols, which, combined with...
Changguang Wang et al.
International journal of pharmaceutics, 569, 118576-118576 (2019-07-31)
Cholesterol is one of the major structural constituents in a liposomal bilayer. Cholesterol is susceptible to various reactions in the presence of oxygen, heat, light, certain metals, and radicals during manufacturing or storage, which may cause to generate cholesterol oxidation...

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