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MilliporeSigma

136115

Sigma-Aldrich

Thiocholesterol

Sinónimos:

5-Cholestene-3β-thiol, Cholesteryl mercaptan

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1 G
$570.38

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1 G
$570.38

About This Item

Fórmula empírica (notación de Hill):
C27H46S
Número de CAS:
Peso molecular:
402.72
Número CE:
Número MDL:
Código UNSPSC:
12352002
ID de la sustancia en PubChem:
NACRES:
NA.22

$570.38

Precio de catálogo$612.00Ahorre 7 %
Web-Only Promotion

Disponible para envío el14 de abril de 2025Detalles


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Formulario

powder

actividad óptica

[α]20/D −23°, c = 1 in chloroform

mp

97-99 °C (lit.)

temp. de almacenamiento

2-8°C

cadena SMILES

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

Clave InChI

QGVQZRDQPDLHHV-DPAQBDIFSA-N

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Descripción general

Thiocholesterol is a lipid similar to cholesterol except that the hydroxyl group is replaced with thiol group.[1]

Aplicación

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]

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)


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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
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
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
IRCS Med. Sci., 13, 68-68 (1985)
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

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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