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C9523

Sodium cholesteryl sulfate

Synonym(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

Empirical Formula (Hill Notation):
C27H45NaO4S
CAS Number:
2864-50-8
Molecular Weight:
488.70
NACRES:
NA.77
PubChem Substance ID:
24893166
eCl@ss:
39023139
UNSPSC Code:
41141804
MDL number:
MFCD00079091
Beilstein/REAXYS Number:
3899884
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biological source

synthetic

Quality Level

200

description

anionic

assay

≥98% (TLC)

form

powder

shipped in

ambient

storage temp.

−20°C

SMILES string

[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

InChI key

LMPVQXVJTZWENW-KPNWGBFJSA-M

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.

Biochem/physiol Actions

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.

Preparation Note

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
SLCL1023
SLCD6791
SLBX9797
SLBW1537
SLBS7209

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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
View All Related Papers

Global Trade Item Number

SKUGTIN
C9523-250MG04061833076217
C9523-100MG04061833076200
C9523-25MG04061833076224