Date published: 2025-11-20

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Thiocholesterol (CAS 1249-81-6)

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Alternate Names:
5-Cholestene-3β-thiol; Cholesteryl mercaptan
Application:
Thiocholesterol is a compound used in biological cross-linking and membrane studies
CAS Number:
1249-81-6
Molecular Weight:
402.72
Molecular Formula:
C27H46S
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Thiocholesterol is a compound used in biological cross-linking and membrane studies. It is a key component of many biological processes, including the synthesis of hormones, cholesterol transport, and the regulation of gene expression. It is known that thiocholesterol binds to membrane-bound proteins, such as G-proteins, and modulates their activity. Additionally, it may act to interact with cholesterol-binding proteins, such as low-density lipoprotein receptors, and has been implicated in the regulation of cholesterol metabolism.


Thiocholesterol (CAS 1249-81-6) References

  1. Differential interaction of the two cholesterol-dependent, membrane-damaging toxins, streptolysin O and Vibrio cholerae cytolysin, with enantiomeric cholesterol.  |  Zitzer, A., et al. 2003. FEBS Lett. 553: 229-31. PMID: 14572629
  2. New approach to writing and simultaneous reading of micropatterns: combining surface plasmon resonance imaging with scanning electrochemical microscopy (SECM).  |  Szunerits, S., et al. 2004. Langmuir. 20: 9236-41. PMID: 15461512
  3. Thiocholesterol-based lipids for ordered assembly of bioresponsive gene carriers.  |  Huang, Z., et al. 2005. Mol Ther. 11: 409-17. PMID: 15727937
  4. Temperature-sensitive poly(N-(2-hydroxypropyl)methacrylamide mono/dilactate)-coated liposomes for triggered contents release.  |  Paasonen, L., et al. 2007. Bioconjug Chem. 18: 2131-6. PMID: 17963354
  5. Cholesterol modification of (Bio)polymers using UV-Vis traceable chemistry in aqueous solutions.  |  Rasmussen, KF., et al. 2014. Macromol Biosci. 14: 33-44. PMID: 24106046
  6. A calorimetric and spectroscopic comparison of the effects of cholesterol and its sulfur-containing analogs thiocholesterol and cholesterol sulfate on the thermotropic phase behavior and organization of dipalmitoylphosphatidylcholine bilayer membranes.  |  Benesch, MG., et al. 2016. Biochim Biophys Acta. 1858: 168-80. PMID: 26585353
  7. Regulation of Cholesterol Sulfotransferase SULT2B1b by Hepatocyte Nuclear Factor 4α Constitutes a Negative Feedback Control of Hepatic Gluconeogenesis.  |  Bi, Y., et al. 2018. Mol Cell Biol. 38: PMID: 29378829
  8. Substrate-led cholesterol extraction from supported lipid membranes.  |  Miller, EJ., et al. 2018. Nanoscale. 10: 16332-16342. PMID: 30132496
  9. Studies on phosphatidylcholine vesicles with thiocholesterol and a thiocholesterol-linked spin label incorporated in the vesicle wall.  |  Huang, C., et al. 1970. Biochemistry. 9: 3422-6. PMID: 4330857
  10. L-Proline transport in Saccharomyces cerevisiae.  |  Horák, J. and Ríhová, L. 1982. Biochim Biophys Acta. 691: 144-50. PMID: 6753931
  11. Interaction of cholesterol and cholesterol analogs with egg phosphatidylcholine in a lipid solvent.  |  Oppenheimer, NJ. and Cordes, EH. 1981. J Biol Chem. 256: 6714-20. PMID: 7195401
  12. The rapid transbilayer movement of thiocholesterol in small unilamellar phospholipid vesicles.  |  Dawidowicz, EA. and Backer, JM. 1981. Biochim Biophys Acta. 644: 373-5. PMID: 7260079
  13. Mercapto steroids in protection against mercury and lead poisoning.  |  Blickenstaff, RT., et al. 1980. J Pharm Sci. 69: 556-8. PMID: 7381742
  14. Human plasma lecithin:cholesterol acyltransferase. On the substrate efficiency of cholest-5-ene-3 beta-thiol as a fatty acyl acceptor.  |  Zhou, G. and Dolphin, PJ. 1995. Biochim Biophys Acta. 1258: 101-6. PMID: 7548172
  15. Antioxidant activity of thiocholesterol on copper-induced oxidation of low-density lipoprotein.  |  Tanaka, M. and Nakagawa, M. 1995. Lipids. 30: 321-5. PMID: 7609599

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Thiocholesterol, 1 g

sc-213033
1 g
$582.00