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MedKoo Cat#: 463126 | Name: 24(S),25-Epoxycholesterol

Description:

WARNING: This product is for research use only, not for human or veterinary use.

24(S),25-Epoxycholesterol is an oxysterol agonist of the liver X receptor.

Chemical Structure

24(S),25-Epoxycholesterol
24(S),25-Epoxycholesterol
CAS#77058-74-3

Theoretical Analysis

MedKoo Cat#: 463126

Name: 24(S),25-Epoxycholesterol

CAS#: 77058-74-3

Chemical Formula: C27H44O2

Exact Mass: 400.3341

Molecular Weight: 400.65

Elemental Analysis: C, 80.94; H, 11.07; O, 7.99

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
24(S),25-Epoxycholesterol; 24(S),25 Epoxycholesterol;
IUPAC/Chemical Name
(3S,8S,9S,10R,13R,14S,17R)-17-((R)-4-((S)-3,3-dimethyloxiran-2-yl)butan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
InChi Key
OSENKJZWYQXHBN-XVYZBDJZSA-N
InChi Code
InChI=1S/C27H44O2/c1-17(6-11-24-25(2,3)29-24)21-9-10-22-20-8-7-18-16-19(28)12-14-26(18,4)23(20)13-15-27(21,22)5/h7,17,19-24,28H,6,8-16H2,1-5H3/t17-,19+,20+,21-,22+,23+,24+,26+,27-/m1/s1
SMILES Code
C[C@]12C(C[C@@H](O)CC2)=CC[C@@H]3[C@@H]1CC[C@@]4(C)[C@H]3CC[C@@H]4[C@H](C)CC[C@@H]5OC5(C)C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 400.65 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
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Cryo-EM structure of oxysterol-bound human Smoothened coupled to a heterotrimeric Gi. Nature. 2019 Jul;571(7764):279-283. doi: 10.1038/s41586-019-1286-0. Epub 2019 Jun 5. PMID: 31168089; PMCID: PMC6777001. 5: Saida-Tamiya K, Tamiya M, Sekiya G, Isobe K, Kitazawa T, Isaka N, Matsukawa A, Kawahara K, Komuro A, Ishiguro M. Structural requirements of cholenamide derivatives as the LXR ligands. Bioorg Med Chem Lett. 2019 Jun 1;29(11):1330-1335. doi: 10.1016/j.bmcl.2019.03.051. Epub 2019 Mar 30. PMID: 30952591. 6: Phillips RE, Yang Y, Smith RC, Thompson BM, Yamasaki T, Soto-Feliciano YM, Funato K, Liang Y, Garcia-Bermudez J, Wang X, Garcia BA, Yamasaki K, McDonald JG, Birsoy K, Tabar V, Allis CD. Target identification reveals lanosterol synthase as a vulnerability in glioma. Proc Natl Acad Sci U S A. 2019 Apr 16;116(16):7957-7962. doi: 10.1073/pnas.1820989116. Epub 2019 Mar 28. PMID: 30923116; PMCID: PMC6475387. 7: Theofilopoulos S, Abreu de Oliveira WA, Yang S, Yutuc E, Saeed A, Abdel- Khalik J, Ullgren A, Cedazo-Minguez A, Björkhem I, Wang Y, Griffiths WJ, Arenas E. 24(S),25-Epoxycholesterol and cholesterol 24S-hydroxylase (CYP46A1) overexpression promote midbrain dopaminergic neurogenesis in vivo. J Biol Chem. 2019 Mar 15;294(11):4169-4176. doi: 10.1074/jbc.RA118.005639. Epub 2019 Jan 17. PMID: 30655290; PMCID: PMC6422085. 8: Guo F, Hong W, Yang M, Xu D, Bai Q, Li X, Chen Z. Upregulation of 24(R/S),25-epoxycholesterol and 27-hydroxycholesterol suppresses the proliferation and migration of gastric cancer cells. Biochem Biophys Res Commun. 2018 Oct 12;504(4):892-898. doi: 10.1016/j.bbrc.2018.09.058. Epub 2018 Sep 14. PMID: 30224060. 9: McCrae C, Dzgoev A, Ståhlman M, Horndahl J, Svärd R, Große A, Großkopf T, Skujat MA, Williams N, Schubert S, Echeverri C, Jackson C, Guedán A, Solari R, Vaarala O, Kraan M, Rådinger M. Lanosterol Synthase Regulates Human Rhinovirus Replication in Human Bronchial Epithelial Cells. Am J Respir Cell Mol Biol. 2018 Dec;59(6):713-722. doi: 10.1165/rcmb.2017-0438OC. PMID: 30084659. 10: Lu DL, Sookthai D, Le Cornet C, Katzke VA, Johnson TS, Kaaks R, Fortner RT. Reproducibility of serum oxysterols and lanosterol among postmenopausal women: Results from EPIC-Heidelberg. Clin Biochem. 2018 Feb;52:117-122. doi: 10.1016/j.clinbiochem.2017.11.001. Epub 2017 Nov 22. PMID: 29108727. 11: Endo-Umeda K, Aoyama A, Shimizu M, Ishikawa M, Hashimoto Y, Yamada S, Makishima M. 1α-Hydroxy derivatives of 7-dehydrocholesterol are selective liver X receptor modulators. J Steroid Biochem Mol Biol. 2017 Sep;172:136-148. doi: 10.1016/j.jsbmb.2017.07.014. Epub 2017 Jul 20. PMID: 28736297. 12: Hong YF, Kim H, Kim HS, Park WJ, Kim JY, Chung DK. Lactobacillus acidophilus K301 Inhibits Atherogenesis via Induction of 24 (S), 25-Epoxycholesterol- Mediated ABCA1 and ABCG1 Production and Cholesterol Efflux in Macrophages. PLoS One. 2016 Apr 27;11(4):e0154302. doi: 10.1371/journal.pone.0154302. PMID: 27120199; PMCID: PMC4847857. 13: Wang Z, Yang X, Chen L, Zhi X, Lu H, Ning Y, Yeong J, Chen S, Yin L, Wang X, Li X. Upregulation of hydroxysteroid sulfotransferase 2B1b promotes hepatic oval cell proliferation by modulating oxysterol-induced LXR activation in a mouse model of liver injury. Arch Toxicol. 2017 Jan;91(1):271-287. doi: 10.1007/s00204-016-1693-z. Epub 2016 Apr 6. PMID: 27052460. 14: Stäubert C, Krakowsky R, Bhuiyan H, Witek B, Lindahl A, Broom O, Nordström A. Increased lanosterol turnover: a metabolic burden for daunorubicin-resistant leukemia cells. Med Oncol. 2016 Jan;33(1):6. doi: 10.1007/s12032-015-0717-5. Epub 2015 Dec 23. PMID: 26698156; PMCID: PMC4689760. 15: Wang Y, Karu K, Meljon A, Turton J, Yau JL, Seckl JR, Wang Y, Griffiths WJ. 24S,25-Epoxycholesterol in mouse and rat brain. Biochem Biophys Res Commun. 2014 Jun 27;449(2):229-34. doi: 10.1016/j.bbrc.2014.05.012. Epub 2014 May 14. PMID: 24832732; PMCID: PMC4053837. 16: Bentinger M, Kania M, Danikiewicz W, Kaczorowska E, Wojcik J, Brismar K, Dallner G, Chojnacki T, Swiezewska E, Tekle M. Effects of various squalene epoxides on coenzyme Q and cholesterol synthesis. Biochim Biophys Acta. 2014 Jul;1841(7):977-86. doi: 10.1016/j.bbalip.2014.03.007. Epub 2014 Apr 16. PMID: 24747199. 17: Meljon A, Wang Y, Griffiths WJ. Oxysterols in the brain of the cholesterol 24-hydroxylase knockout mouse. Biochem Biophys Res Commun. 2014 Apr 11;446(3):768-74. doi: 10.1016/j.bbrc.2014.01.153. Epub 2014 Jan 31. PMID: 24491562; PMCID: PMC4000437. 18: Mazein A, Watterson S, Hsieh WY, Griffiths WJ, Ghazal P. A comprehensive machine-readable view of the mammalian cholesterol biosynthesis pathway. Biochem Pharmacol. 2013 Jul 1;86(1):56-66. doi: 10.1016/j.bcp.2013.03.021. Epub 2013 Apr 10. PMID: 23583456; PMCID: PMC3912678. 19: Javitt NB. Alzheimer's disease: neuroprogesterone, epoxycholesterol, and ABC transporters as determinants of neurodesmosterol tissue levels and its role in amyloid protein processing. J Alzheimers Dis. 2013;35(3):441-50. doi: 10.3233/JAD-130044. PMID: 23455994. 20: Theofilopoulos S, Wang Y, Kitambi SS, Sacchetti P, Sousa KM, Bodin K, Kirk J, Saltó C, Gustafsson M, Toledo EM, Karu K, Gustafsson JÅ, Steffensen KR, Ernfors P, Sjövall J, Griffiths WJ, Arenas E. Brain endogenous liver X receptor ligands selectively promote midbrain neurogenesis. Nat Chem Biol. 2013 Feb;9(2):126-33. doi: 10.1038/nchembio.1156. Epub 2012 Dec 23. PMID: 23292650.

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