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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
M Merten et al.
Circulation, 103(16), 2032-2034 (2001-04-25)
Cholesterol 3-sulfate is present on a variety of cells and in human LDL, and it has been found in atherosclerotic lesions of human aorta. Its precise biological role has not yet been described. In this study, we investigated the interaction
Charles A Strott et al.
Journal of lipid research, 44(7), 1268-1278 (2003-05-06)
Cholesterol sulfate is quantitatively the most important known sterol sulfate in human plasma, where it is present in a concentration that overlaps that of the other abundant circulating steroid sulfate, dehydroepiandrosterone (DHEA) sulfate. Although these sulfolipids have similar production and
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Global Trade Item Number

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