Lanostenol
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MedKoo CAT#: 598372

CAS#: 79-62-9

Description: Lanostenol is a derivative of Lanosterol. It is also one of cytochrome P 450 lanosterol 14α-demethylase , which is shown to have an important role in regulating meiosis and reproduction.


Price and Availability

Size Price Shipping out time Quantity
100mg USD 330 2 Weeks
1g USD 1490 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-09-27. Prices are subject to change without notice.

Lanostenol purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 598372
Name: Lanostenol
CAS#: 79-62-9
Chemical Formula: C30H52O
Exact Mass: 428.4018
Molecular Weight: 428.74
Elemental Analysis: C, 84.04; H, 12.23; O, 3.73


Synonym: Lanostenol; Dihydrolanosterin; Dihydrolanosterol;

IUPAC/Chemical Name: (3S,5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

InChi Key: MBZYKEVPFYHDOH-BQNIITSRSA-N

InChi Code: InChI=1S/C30H52O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h20-22,25-26,31H,9-19H2,1-8H3/t21-,22-,25+,26+,28-,29-,30+/m1/s1

SMILES Code: CC1(C)[C@@H](O)CC[C@]2(C)C3=C([C@@]4(CC[C@@H]([C@]4(CC3)C)[C@H](C)CCCC(C)C)C)CC[C@@]12[H]


Technical Data

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


References

1: Bailen M, Khamlichi MD, Benharref A, Martinez-Diaz RA, Gonzalez-Coloma A. New Bioactive Semisynthetic Derivatives of 31-Norlanostenol and Obtusifoliol from Euphorbia officinarum. Nat Prod Commun. 2016 Jun;11(6):733-8. PubMed PMID: 27534104.

2: Itoh T, Jeong TM, Hirano Y, Tamura T, Matsumoto T. Occurrence of lanosterol and lanostenol in seeds of red pepper (Capsicum annuum). Steroids. 1977 May;29(5):569-77. PubMed PMID: 898228.

3: Jeong TM, Itoh T, Tamura T, Matsumoto T. Analysis of methylsterol fractions from twenty vegetable oils. Lipids. 1975 Oct;10(10):634-40. PubMed PMID: 1186450.

4: Hornby GM, Boyd GS. A carboxylic acid intermediate of lanostenol demethylation. Biochem Biophys Res Commun. 1970 Sep 30;40(6):1452-4. PubMed PMID: 4326582.

5: Jennings GK, Modi A, Elenewski JE, Ritchie CM, Nguyen T, Ellis KC, Hackett JC. Spin equilibrium and O₂-binding kinetics of Mycobacterium tuberculosis CYP51 with mutations in the histidine-threonine dyad. J Inorg Biochem. 2014 Jul;136:81-91. doi: 10.1016/j.jinorgbio.2014.03.017. Epub 2014 Apr 12. PubMed PMID: 24793591; PubMed Central PMCID: PMC4085784.

6: Keber R, Acimovic J, Majdic G, Motaln H, Rozman D, Horvat S. Male germ cell-specific knockout of cholesterogenic cytochrome P450 lanosterol 14α-demethylase (Cyp51). J Lipid Res. 2013 Jun;54(6):1653-61. doi: 10.1194/jlr.M035717. Epub 2013 Mar 18. PubMed PMID: 23509403; PubMed Central PMCID: PMC3646466.

7: Beck JP. Can oxysterols have some interest in the treatment of tumors? Prog Clin Biol Res. 1990;348:71-93. Review. PubMed PMID: 2201035.

8: Jeong TM, Ito T, Tamura T, Matsumoto T. Sterols from a species of Pichia, a n-alkane-utilizing yeast. Steroids. 1975 Jun;25(6):741-51. PubMed PMID: 1154452.

9: Dillon J, Mehlman B, Ponticorvo L, Spector A. The state of neutral lipids in normal and cataractous human lenses. Exp Eye Res. 1983 Jul;37(1):91-8. PubMed PMID: 6873207.

10: Keber R, Motaln H, Wagner KD, Debeljak N, Rassoulzadegan M, Ačimovič J, Rozman D, Horvat S. Mouse knockout of the cholesterogenic cytochrome P450 lanosterol 14alpha-demethylase (Cyp51) resembles Antley-Bixler syndrome. J Biol Chem. 2011 Aug 19;286(33):29086-97. doi: 10.1074/jbc.M111.253245. Epub 2011 Jun 25. PubMed PMID: 21705796; PubMed Central PMCID: PMC3190716.

11: Sonoda Y, Obi N, Onoda M, Sakakibara Y, Sato Y. Effects of 32-oxygenated lanosterol derivatives on 3-hydroxy-3-methylglutaryl coenzyme A reductase activity and cholesterol biosynthesis from 24,25-dihydrolanosterol. Chem Pharm Bull (Tokyo). 1992 Oct;40(10):2796-9. Erratum in: Chem Pharm Bull (Tokyo) 1993 Jun;41(6):1206. PubMed PMID: 1464112.

12: Kavtaradze LK, Manley-Harris M, Nicholson BK. A low-toxicity method for the separation of lanosterol and dihydrolanosterol from commercial mixtures. Steroids. 2004 Sep;69(10):697-700. PubMed PMID: 15465116.

13: Warrilow AG, Melo N, Martel CM, Parker JE, Nes WD, Kelly SL, Kelly DE. Expression, purification, and characterization of Aspergillus fumigatus sterol 14-alpha demethylase (CYP51) isoenzymes A and B. Antimicrob Agents Chemother. 2010 Oct;54(10):4225-34. doi: 10.1128/AAC.00316-10. Epub 2010 Jul 26. PubMed PMID: 20660663; PubMed Central PMCID: PMC2944604.

14: Zhu J, Mounzih K, Chehab EF, Mitro N, Saez E, Chehab FF. Effects of FoxO4 overexpression on cholesterol biosynthesis, triacylglycerol accumulation, and glucose uptake. J Lipid Res. 2010 Jun;51(6):1312-24. doi: 10.1194/jlr.M001586. Epub 2009 Dec 25. PubMed PMID: 20037138; PubMed Central PMCID: PMC3035494.

15: Liu XT, Winkler AL, Schwan WR, Volk TJ, Rott MA, Monte A. Antibacterial compounds from mushrooms I: a lanostane-type triterpene and prenylphenol derivatives from Jahnoporus hirtus and Albatrellus flettii and their activities against Bacillus cereus and Enterococcus faecalis. Planta Med. 2010 Feb;76(2):182-5. doi: 10.1055/s-0029-1186001. Epub 2009 Jul 30. PubMed PMID: 19644795.

16: Nicolaides N, Santos EC, Smith RE, Jester JV. Meibomian gland dysfunction. III. Meibomian gland lipids. Invest Ophthalmol Vis Sci. 1989 May;30(5):946-51. PubMed PMID: 2498228.

17: Patouraux D, Lacave C, Promé JC. Detection and quantification of lanosterol and dihydrolanosterol esters by measurements of metastable decompositions. Application to their direct analysis in wool wax. Biomed Mass Spectrom. 1981 Mar;8(3):118-21. PubMed PMID: 6894557.

18: Aoyama Y, Yoshida Y. Different substrate specificities of lanosterol 14a-demethylase (P-45014DM) of Saccharomyces cerevisiae and rat liver for 24-methylene-24,25-dihydrolanosterol and 24,25-dihydrolanosterol. Biochem Biophys Res Commun. 1991 Aug 15;178(3):1064-71. PubMed PMID: 1872829.

19: Nes WD, Norton RA, Parish EJ, Meenan A, Popják G. Concerning the role of 24,25-dihydrolanosterol and lanostanol in sterol biosynthesis by cultured cells. Steroids. 1989 Mar-May;53(3-5):461-75. PubMed PMID: 2799854.

20: Sonoda Y, Endo M, Ishida K, Sato Y, Fukusen N, Fukuhara M. Purification of a human cytochrome P-450 isozyme catalyzing lanosterol 14 alpha-demethylation. Biochim Biophys Acta. 1993 Sep 29;1170(1):92-7. PubMed PMID: 8399332.