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Sigma-Aldrich

Thiocholesterol

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Synonym(s):
5-Cholestene-3β-thiol, Cholesteryl mercaptan
Empirical Formula (Hill Notation):
C27H46S
CAS Number:
1249-81-6
Molecular Weight:
402.72
EC Number:
215-003-4
MDL number:
MFCD00003647
UNSPSC Code:
12352002
PubChem Substance ID:
24848256
NACRES:
NA.22

form

powder

optical activity

[α]20/D −23°, c = 1 in chloroform

mp

97-99 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](S)CC[C@]4(C)[C@H]3CC[C@]12C

InChI

1S/C27H46S/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1

InChI key

QGVQZRDQPDLHHV-DPAQBDIFSA-N

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General description

Thiocholesterol is a lipid similar to cholesterol except that the hydroxyl group is replaced with thiol group.

Application

Thiocholesterol is used in biological cross-linking and membrane studies.
It can also be used as a chain transfer agent (CTA) for the radical polymerization of HPMA monolactate and HPMA dilactate monomers to form copolymers. [HPMA=N-(2-hydroxypropyl)methacrylamide]

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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Kun Cheng et al.
The Journal of pharmacology and experimental therapeutics, 317(2), 797-805 (2006-02-03)
A triplex-forming oligonucleotide (TFO) specific for type alpha1(I) collagen promoter is a promising candidate for treating liver fibrosis. Earlier, we determined the pharmacokinetics and biodistribution of TFO after systemic administration into normal and fibrotic rats. In this study, we conjugated
M Tanaka et al.
Lipids, 30(4), 321-325 (1995-04-01)
The effect of thiocholesterol (SH-Chol) on the copper-induced in vitro oxidation of low-density lipoprotein (LDL; 1.019 < d < 1.063) was investigated. Among the antioxidants tested, including cysteine, glutathione, 2-mercaptoethanol, dithiothreitol, probucol, thiopalmitic acid, and SH-Chol, SH-Chol was the most
Zhaohua Huang et al.
Molecular therapy : the journal of the American Society of Gene Therapy, 11(3), 409-417 (2005-02-25)
A series of thiocholesterol-based cationic lipids (TCL) has been designed and synthesized by the attachment of thiocholesterol to a cationic amine via a disulfide bond. TCL can be incorporated into liposomes and used to package DNA into a lipoplex, thereby
Avinash Bajaj et al.
Journal of medicinal chemistry, 51(8), 2533-2540 (2008-04-02)
A structure-activity investigation was undertaken to see the effect of the nature of the spacer on the gene transfection efficacies of thiocholesterol-derived cationic gemini lipids possessing disulfide linkage between the cationic headgroup and the thiocholesterol moiety. Three gemini cationic lipids
G Zhou et al.
Biochimica et biophysica acta, 1258(2), 101-106 (1995-09-14)
Lecithin:cholesterol acyltransferase (LCAT) is a plasma enzyme which catalyses cholesteryl ester formation from lecithin and cholesterol present in the surface of plasma lipoproteins. Sterol fatty acid acceptors have previously been shown to require the presence of a trans conformation of
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