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C9523

Sigma-Aldrich

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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$765.00

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25 MG
$135.00
250 MG
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About This Item

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

$135.00

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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

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1 of 4

This Item
700016P71959204447
Sodium cholesteryl sulfate

C9523

Sodium cholesteryl sulfate

cholesterol sulfate Avanti Research™ - A Croda Brand 700016P

700016P

cholesterol sulfate

Sodium sulfate BioUltra, anhydrous, ≥99.0% (T)

71959

Sodium sulfate

Sodium sulfate ≥99.99% trace metals basis

204447

Sodium sulfate

assay

≥98% (TLC)

assay

>99% (TLC)

assay

≥99.0% (T)

assay

≥99.99% trace metals basis

storage temp.

−20°C

storage temp.

−20°C

storage temp.

-

storage temp.

-

biological source

synthetic

biological source

-

biological source

-

biological source

-

description

anionic

description

cholesterol 3-sulfate (sodium salt)

description

-

description

-

Quality Level

200

Quality Level

-

Quality Level

100

Quality Level

200

Application

Sodium cholesteryl sulfate was used as the source of cholesterol in the preparation of Edgar′s growth medium used for embryology experiments.[1] It was used as a standard for the separation of human stratum corneum lipids by thin layer chromatography.[2]

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.[3]

Preparation Note

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves
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    Certificates of Analysis (COA)

    Lot/Batch Number
    SLCL1023
    SLCD6791
    SLBX9797
    SLBW1537
    SLBS7209

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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
    View All Related Papers

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