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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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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
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
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

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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