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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:
Molecular Weight:
402.72
EC Number:
MDL number:
UNSPSC Code:
12352002
PubChem Substance ID:
NACRES:
NA.22

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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.[1]

Application

Thiocholesterol is used in biological cross-linking[2] and membrane[3] 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][4]

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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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
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)
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

Questions

  1. For Thiocholesterol, what should I use to configure the solution since it looks like it should be hard to dissolve in water. Do you know how soluble it is in alcohol.

    1 answer
    1. A traditional solubility test is not performed on the material, but it is tested for optical activity and this is done as a 1% concentration in chloroform so, it would definitely be soluble in chloroform. It may also be slightly soluble in dichloromethane and methanol.

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