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136115

Sigma-Aldrich

Thiocholesterol

Synonym(s):

5-Cholestene-3β-thiol, Cholesteryl mercaptan

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About This Item

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]

Storage Class

11 - Combustible Solids

wgk_germany

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
0000263033
0000243850
0000162904
0000177439
BGBC2962V

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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
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
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
IRCS Med. Sci., 13, 68-68 (1985)
Temperature-sensitive poly (N-(2-hydroxypropyl) methacrylamide mono/dilactate)-coated liposomes for triggered contents release
Paasonen L, et al
Bioconjugate Chemistry, 18(6), 2131-2136 (2007)
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