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Merck

136115

Sigma-Aldrich

Thiocholesterin

Synonym(e):

5-Cholesten-3β-thiol, Cholesteryl-mercaptan

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About This Item

Empirische Formel (Hill-System):
C27H46S
CAS-Nummer:
Molekulargewicht:
402.72
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
12352002
PubChem Substanz-ID:
NACRES:
NA.22

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Form

powder

Optische Aktivität

[α]20/D −23°, c = 1 in chloroform

mp (Schmelzpunkt)

97-99 °C (lit.)

Lagertemp.

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

InChIKey

QGVQZRDQPDLHHV-DPAQBDIFSA-N

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Allgemeine Beschreibung

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

Anwendung

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]

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

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
B Oberhauser et al.
Nucleic acids research, 20(3), 533-538 (1992-02-11)
Cholesterol was linked to 2'-O-methyl-oligoribonucleotides (2'-OMe-RNA) via a disulfide bond by reacting the 3'-(pyridyldithio)-modified 2'-OMe-RNA with thiocholesterol in dichloromethane-methanol solution. This ligation reaction was made possible by a novel strategy in which the highly charged oligonucleotide was rendered soluble in
Elisabetta Ranucci et al.
Biomacromolecules, 9(10), 2693-2704 (2008-09-11)
Poly(amidoamine) (PAA) networks that are obtained by the use of cystamine as a cross-linking agent in the reaction with 2,2'-dithiodipyridine turn into linear PAAs with dithiopyridyl side groups that easily undergo an exchange reaction with thiocholesterol. The resultant products represent

Fragen

  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 Antwort
    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.

      Hilfreich?

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