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Merck
CN

136115

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
NACRES:
NA.22
PubChem Substance ID:
24848256
UNSPSC Code:
12352002
EC Number:
215-003-4
MDL number:
MFCD00003647

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InChI key

QGVQZRDQPDLHHV-DPAQBDIFSA-N

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

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

form

powder

optical activity

[α]20/D −23°, c = 1 in chloroform

mp

97-99 °C (lit.)

storage temp.

2-8°C

Quality Level

200

Related Categories

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

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
0000472339
0000472339
0000263033
0000243850
0000263033

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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
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)
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
E A Dawidowicz et al.
Biochimica et biophysica acta, 644(2), 373-375 (1981-06-22)
Cholesterol is a major component of biological membranes, yet there is very little information concerning its distribution across the membrane. Recent experiments in our laboratory, using cholesterol oxidase, have demonstrated that cholesterol can undergo a rapid transbilayer movement in lecithin-cholesterol
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