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C9523

Sigma-Aldrich

Sodium cholesteryl sulfate

Synonyme(s) :

5-Cholesten-3β-ol sulfate sodium salt, Cholesterol 3-sulfate sodium salt, Cholesteryl sodium sulfate, Cholesteryl sulfate sodium salt

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About This Item

Formule empirique (notation de Hill):
C27H45NaO4S
Numéro CAS:
2864-50-8
Poids moléculaire :
488.70
Numéro Beilstein :
3899884
Numéro MDL:
MFCD00079091
Code UNSPSC :
41141804
eCl@ss :
39023139
ID de substance PubChem :
24893166
Nomenclature NACRES :
NA.77

Source biologique

synthetic

Description

anionic

Pureté

≥98% (TLC)

Forme

powder

Conditions d'expédition

ambient

Température de stockage

−20°C

Chaîne SMILES 

[H][C@@]([C@H](C)CCCC(C)C)([C@@]1(C)CC[C@@]23[H])CC[C@]1([C@](CC=C4C[C@H](CC[C@]34C)OS([O-])(=O)=O)2[H])[H].[Na+]

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

Clé InChI

LMPVQXVJTZWENW-KPNWGBFJSA-M

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Catégories apparentées

Application

Sodium cholesteryl sulfate was used as the source of cholesterol in the preparation of Edgar′s growth medium used for embryology experiments. It was used as a standard for the separation of human stratum corneum lipids by thin layer chromatography.

Actions biochimiques/physiologiques

Cholesteryl sulfate is a natural constituent of human spermatozoa and has major role in the maturation of sperms. It could also be involved in the capacitation of sperms and enables ovum penetration. Low concentrations of cholesteryl sulfate inhibits acrosin, the proteinase present in sperm acrosome that facilitates ovum penetration.

Notes préparatoires

Sodium cholesteryl sulfate yields clear, colorless solution in chloroform-methanol (1:1) mixture at 10 mg/ml.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Consulter la Bibliothèque de documents

Lois G Edgar et al.
Methods in cell biology, 107, 151-175 (2012-01-10)
The direct manipulation of embryonic cells is an important tool for addressing key questions in cell and developmental biology. C. elegans is relatively unique among genetic model systems in being amenable to manipulation of embryonic cells. Embryonic cell manipulation has
N Y Schürer et al.
Experimental dermatology, 4(1), 46-51 (1995-02-01)
There is a need in many studies on the epidermal permeability barrier for practical and reliable separation of all major fractions of human stratum corneum lipids. Various methods have been described including thin layer chromatography, high performance thin layer chromatography
J Langlais et al.
Proceedings of the National Academy of Sciences of the United States of America, 78(12), 7266-7270 (1981-12-01)
Cholesteryl sulfate is a normal constituent of human spermatozoa. The in vitro uptake of tritiated cholesteryl sulfate resulted in the labeling of all spermatozoa as demonstrated by light-microscope radioautography. The binding of the sterol sulfate was localized mainly in the
Carlos Silvestre-Roig et al.
Nature, 569(7755), 236-240 (2019-05-03)
The perpetuation of inflammation is an important pathophysiological contributor to the global medical burden. Chronic inflammation is promoted by non-programmed cell death1,2; however, how inflammation is instigated, its cellular and molecular mediators, and its therapeutic value are poorly defined. Here
Thida Phoeung et al.
Langmuir : the ACS journal of surfaces and colloids, 25(10), 5778-5784 (2009-03-04)
In recent studies, it has been shown that mixtures of palmitic acid (PA), and cholesterol or cholesterol sulfate (Schol), in a PA/sterol molar ratio of 30/70 lead to the formation of liquid-ordered (lo) lamellar phases. The extrusion of these systems
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