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C9523

Sigma-Aldrich

Sodium cholesteryl sulfate

Sinonimo/i:

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

Formula empirica (notazione di Hill):
C27H45NaO4S
Numero CAS:
2864-50-8
Peso molecolare:
488.70
Beilstein:
3899884
Numero MDL:
MFCD00079091
Codice UNSPSC:
41141804
eCl@ss:
39023139
ID PubChem:
24893166
NACRES:
NA.77

Origine biologica

synthetic

Descrizione

anionic

Saggio

≥98% (TLC)

Forma fisica

powder

Condizioni di spedizione

ambient

Temperatura di conservazione

−20°C

Stringa SMILE

[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
LMPVQXVJTZWENW-KPNWGBFJSA-M

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Applicazioni

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.

Azioni biochim/fisiol

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.

Nota sulla preparazione

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

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

Certificati d'analisi (COA)

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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
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
Minako Koizumi et al.
Human reproduction (Oxford, England), 25(1), 192-197 (2009-11-10)
Matrix metalloproteinases (MMPs) and the plasminogen activator (PA)/plasmin system are two major groups of proteases involved in the matrix degradation required for embryo implantation. We previously showed that the content of cholesterol sulfate (CS) in rabbit endometrium increases characteristically during
Gelen Rodríguez et al.
Physical chemistry chemical physics : PCCP, 14(42), 14523-14533 (2012-09-27)
Bicellar systems are a fascinating category of versatile lipid assemblies that comprise bilayered disk-shaped nanoaggregates formed in water by long and short alkyl chain phospholipids. Bicelles bridge the gap between micelles and lipid vesicles by combining the attractive properties of
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