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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:
1249-81-6
Molekulargewicht:
402.72
EG-Nummer:
215-003-4
MDL-Nummer:
MFCD00003647
UNSPSC-Code:
12352002
PubChem Substanz-ID:
24848256
NACRES:
NA.22

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.

Anwendung

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]

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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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
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