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C9523

Sigma-Aldrich

Sodium cholesteryl sulfate

Sinônimo(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

Fórmula empírica (Notação de Hill):
C27H45NaO4S
Número CAS:
Peso molecular:
488.70
Beilstein:
3899884
Número MDL:
Código UNSPSC:
41141804
eCl@ss:
39023139
ID de substância PubChem:
NACRES:
NA.77

fonte biológica

synthetic

descrição

anionic

Ensaio

≥98% (TLC)

forma

powder

Condições de expedição

ambient

temperatura de armazenamento

−20°C

cadeia de caracteres 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

chave InChI

LMPVQXVJTZWENW-KPNWGBFJSA-M

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Aplicação

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.

Ações bioquímicas/fisiológicas

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 de preparo

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

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)


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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
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
Lois G Edgar et al.
Methods in cell biology, 107, 151-175 (2012-01-10)
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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

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