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MedKoo Cat#: 598346 | Name: Holostanol

Description:

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

Holostanol is a toxin from holothurians.

Chemical Structure

Holostanol
Holostanol
CAS#34437-55-3

Theoretical Analysis

MedKoo Cat#: 598346

Name: Holostanol

CAS#: 34437-55-3

Chemical Formula: C30H51O4

Exact Mass: 475.3787

Molecular Weight: 475.73

Elemental Analysis: C, 75.74; H, 10.81; O, 13.45

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
Holostanol;
IUPAC/Chemical Name
(3S,5R,8R,9S,10R,13S,17S)-3-hydroxy-17-((S)-2-hydroxy-6-methylheptan-2-yl)-4,4,10,14-tetramethylhexadecahydro-14l5-14,13-(epoxymethano)cyclopenta[a]phenanthren-19-one
InChi Key
RXLVILSGNTXZOM-DFXLEQEESA-N
InChi Code
InChI=1S/C30H51O4/c1-19(2)9-8-15-28(6,33)23-14-18-30(7)21-10-11-22-26(3,4)24(31)13-16-27(22,5)20(21)12-17-29(23,30)25(32)34-30/h19-24,31,33H,8-18H2,1-7H3/t20-,21+,22-,23+,24-,27+,28-,29+/m0/s1
SMILES Code
CC1(C)[C@@H](O)CC[C@]2(C)[C@@]3([H])CC[C@]4(C(O5)=O)[C@@H]([C@@](C)(O)CCCC(C)C)CCC45(C)[C@]3([H])CC[C@@]12[H]
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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 475.73 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
1: Moraes EA, Matos WC, Graham JK, Ferrari WD Jr. Cholestanol-loaded-cyclodextrin improves the quality of stallion spermatozoa after cryopreservation. Anim Reprod Sci. 2015 Jul;158:19-24. doi: 10.1016/j.anireprosci.2015.04.004. Epub 2015 Apr 21. PubMed PMID: 26005214. 2: Mutanen A, Nissinen MJ, Lohi J, Heikkilä P, Gylling H, Pakarinen MP. Serum plant sterols, cholestanol, and cholesterol precursors associate with histological liver injury in pediatric onset intestinal failure. Am J Clin Nutr. 2014 Oct;100(4):1085-94. doi: 10.3945/ajcn.114.088781. Epub 2014 Aug 6. PubMed PMID: 25099547. 3: Chen Y, Si YA, Ni W, Yan H, Qin XJ, Chen CX, Liu HY. Ypsiyunnosides A-E, Five New Cholestanol Glycosides from Ypsilandra yunnanensis. Nat Prod Bioprospect. 2016 Jun;6(3):173-82. doi: 10.1007/s13659-016-0098-2. Epub 2016 Apr 20. PubMed PMID: 27095014; PubMed Central PMCID: PMC5385661. 4: Hojo K, Hakamata H, Takahashi A, Hosokawa YY, Kusu F. Determination of serum cholestanol by semi-micro high-performance liquid chromatography with electrochemical detection. Biomed Chromatogr. 2010 Jun;24(6):600-5. doi: 10.1002/bmc.1332. PubMed PMID: 19795364. 5: Skrede S, Björkhem I, Buchmann MS, Hopen G, Fausa O. A novel pathway for biosynthesis of cholestanol with 7 alpha-hydroxylated C27-steroids as intermediates, and its importance for the accumulation of cholestanol in cerebrotendinous xanthomatosis. J Clin Invest. 1985 Feb;75(2):448-55. PubMed PMID: 3919058; PubMed Central PMCID: PMC423517. 6: Valayil JM, Kuriakose GC, Jayabaskaran C. Isolation, Purification and Characterization of a Novel Steroidal Saponin Cholestanol Glucoside from Lasiodiplodia theobromae that Induces Apoptosis in A549 Cells. Anticancer Agents Med Chem. 2016;16(7):865-74. PubMed PMID: 26338072. 7: Bhattacharyya AK, Lin DS, Connor WE. Cholestanol metabolism in patients with cerebrotendinous xanthomatosis: absorption, turnover, and tissue deposition. J Lipid Res. 2007 Jan;48(1):185-92. Epub 2006 Oct 1. PubMed PMID: 17012751. 8: Panzenboeck U, Andersson U, Hansson M, Sattler W, Meaney S, Björkhem I. On the mechanism of cerebral accumulation of cholestanol in patients with cerebrotendinous xanthomatosis. J Lipid Res. 2007 May;48(5):1167-74. Epub 2007 Feb 26. PubMed PMID: 17325385. 9: Moraes EA, Graham JK, Torres CA, Meyers M, Spizziri B. Delivering cholesterol or cholestanol to bull sperm membranes improves cryosurvival. Anim Reprod Sci. 2010 Apr;118(2-4):148-54. doi: 10.1016/j.anireprosci.2009.08.002. Epub 2009 Aug 15. PubMed PMID: 19733986. 10: Inoue K, Kubota S, Seyama Y. Cholestanol induces apoptosis of cerebellar neuronal cells. Biochem Biophys Res Commun. 1999 Mar 5;256(1):198-203. PubMed PMID: 10066446. 11: Gylling H, Vuoristo M, Färkkilä M, Miettinen TA. The metabolism of cholestanol in primary biliary cirrhosis. J Hepatol. 1996 Apr;24(4):444-51. PubMed PMID: 8738731. 12: Salen G, Grundy SM. The metabolism of cholestanol, cholesterol, and bile acids in cerebrotendinous xanthomatosis. J Clin Invest. 1973 Nov;52(11):2822-35. PubMed PMID: 4355999; PubMed Central PMCID: PMC302550. 13: Skrede S, Björkhem I, Buchmann MS, Midtvedt T. Biosynthesis of cholestanol from bile acid intermediates in the rabbit and the rat. J Biol Chem. 1985 Jan 10;260(1):77-81. PubMed PMID: 3917436. 14: Kim KS, Kano K, Kasama T, Ishii Y, Yamashita H, Seyama Y. Effects of cholestanol feeding on corneal dystrophy in mice. Biochim Biophys Acta. 1991 Oct 1;1085(3):343-9. PubMed PMID: 1911869. 15: Seyama Y. Cholestanol metabolism, molecular pathology, and nutritional implications. J Med Food. 2003 Fall;6(3):217-24. Review. PubMed PMID: 14585188. 16: SMITH PF. Fate of ergosterol and cholestanol in pleuro-pneumonia-like organisms. J Bacteriol. 1962 Sep;84:534-8. PubMed PMID: 13989541; PubMed Central PMCID: PMC277910. 17: von Bahr S, Movin T, Papadogiannakis N, Pikuleva I, Rönnow P, Diczfalusy U, Björkhem I. Mechanism of accumulation of cholesterol and cholestanol in tendons and the role of sterol 27-hydroxylase (CYP27A1). Arterioscler Thromb Vasc Biol. 2002 Jul 1;22(7):1129-35. PubMed PMID: 12117727. 18: Nakajima N, Fujioka S, Tanaka T, Takatsuto S, Yoshida S. Biosynthesis of cholestanol in higher plants. Phytochemistry. 2002 Jun;60(3):275-9. PubMed PMID: 12031446. 19: Salen G, Batta AK, Tint GS, Shefer S, Ness GC. Inverse relationship between plasma cholestanol concentrations and bile acid synthesis in sitosterolemia. J Lipid Res. 1994 Oct;35(10):1878-87. PubMed PMID: 7852865. 20: Chupin SP, Tiuriumin IaL, Krikshtopaĭtis MI, Nikiforov SB, Salenko VL, Kun OV, Vialkov AI, Dmitriev AE, Gritskikh GL. [Role of cholestanol in the pathogenesis of cholesterol cholelithiasis]. Ross Med Zh. 1992;(1):11-3. Russian. PubMed PMID: 1611258.