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700016P

Avanti

cholesterol sulfate

Avanti Research™ - A Croda Brand

Synonym(s):

cholesterol sulfonate; cholesteryl sulfate; sodium cholesteryl sulfate; cholesteryl sulphate

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About This Item

Empirical Formula (Hill Notation):
C27H45NaO4S
CAS Number:
2864-50-8
Molecular Weight:
488.70
MDL number:
MFCD00079091
UNSPSC Code:
12352211
NACRES:
NA.25
eCl@ss:
39023139
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Product Name

cholesterol sulfate, Avanti Research™ - A Croda Brand

description

cholesterol 3-sulfate (sodium salt)

assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 1 g (700016P-1g), pkg of 1 × 25 mg (700016P-25mg), pkg of 1 × 500 mg (700016P-500mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand

shipped in

dry ice

storage temp.

−20°C

SMILES string

[Na+].[S](=O)(=O)([O-])O[C@H]1CC[C@@]2([C@@H]3[C@H]([C@H]4[C@@]([C@H](CC4)[C@@H](CCCC(C)C)C)(CC3)C)CC=C2C1)C

InChI

1S/C27H46O4S.Na/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(31-32(28,29)30)13-15-26(20,4)25(22)14-16-27(23,24)5;/h9,18-19,21-25H,6-8,10-17H2,1-5H3,(H,28,29,30);/q;+1/p-1/t19-,21+,22+,23-,24+,25+,26+,27-;/m1./s1

InChI key

LMPVQXVJTZWENW-KPNWGBFJSA-M

General description

Cholesterol sulfate is synthesized by the sulfoconjugation of cholesterol in the presence of enzyme cholesterol sulfotransferase. It is present in brain, lungs, hair and skin tissues as well as cells including erythrocytes, platelets and spermatozoa.

Application

Cholesterol sulfate has been used in micelle preparation and in surface plasmon resonance (SPR) studies.

Biochem/physiol Actions

Cholesterol sulfate is associated with atherosclerotic lesions and serves as a substrate for platelet adhesion. It stabilizes the spermatozoa membranes and erythrocytes. Cholesterol sulfate is involved in the keratinocyte differentiation and its levels are elevated in recessive X-linked ichthyosis. It serves as a ligand for retinoic acid-related orphan receptor α (RORα). Cholesterol sulfate regulates glucose metabolism and is a potential target for metabolic disorders. It is also a potential marker for human uterine cervical carcinoma tissue and prostate carcinoma.

Packaging

20 mL Clear Glass Screw Cap Vial (700016P-1g)
20 mL Clear Glass Screw Cap Vial (700016P-500mg)
5 mL Amber Glass Screw Cap Vial (700016P-25mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Patrizia Lopalco et al.
Frontiers in physiology, 10, 1344-1344 (2019-11-19)
The reduction of sperm motility and count, or oligoasthenozoospermia, is one of the major causes of reduced fertility or infertility in men. Lipid composition of spermatozoa is important in determining their functional characteristics, in particular on motility, acrosomal exocytosis or
Livia S Eberlin et al.
Analytical chemistry, 82(9), 3430-3434 (2010-04-09)
Development of methods for rapid distinction between cancerous and non-neoplastic tissues is an important goal in disease diagnosis. To this end, desorption electrospray ionization mass spectrometry (DESI-MS) imaging was applied to analyze the lipid profiles of thin tissue sections of
Rebecca A Shapiro et al.
Journal of the American Chemical Society, 132(33), 11406-11407 (2010-08-06)
Doping DMPC/DHPC bicelles with cholesterol sulfate broadens the temperature range over which stable alignment occurs, forming an aligned phase at lower temperatures even with high lipid concentrations. Cholesterol sulfate appears to combine the advantages of cholesterol with those of charged

Global Trade Item Number

SKUGTIN
700016P-25MG04061835383269
700016P-1G04061835383252
700016P-500MG04061835383276