Lanosterol | CAS#79-63-0 | triterpene

MedKoo Cat#: 598335 | Name: Lanosterol

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Description:

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

Lanosterol is a triterpene that derives from the chair-boat-chair-boat folding of 2,3-oxidosqualene. It is metabolized to CHOLESTEROL and CUCURBITACINS. Lanosterol is a naturally-occurring sterol and biosynthetic precursor of several animal, fungal, and protozoan steroids, including cholesterol and ergosterol. Defects in the processing of lanosterol contribute to a wide variety of disorders, including the formation of cataracts. Similarly, certain fungicides act by blocking lanosterol processing by fungi.

Chemical Structure

Lanosterol

CAS#79-63-0

Theoretical Analysis

MedKoo Cat#: 598335

Name: Lanosterol

CAS#: 79-63-0

Chemical Formula: C30H50O

Exact Mass: 426.3862

Molecular Weight: 426.73

Elemental Analysis: C, 84.44; H, 11.81; O, 3.75

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 600.00	2 Weeks
10mg	USD 1,050.00	2 Weeks

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Related CAS #

No Data

Synonym

Lanosterol; NSC 60677; NSC-60677; NSC60677;

IUPAC/Chemical Name

(3S,5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-17-((R)-6-methylhept-5-en-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

CAHGCLMLTWQZNJ-BQNIITSRSA-N

InChi Code

InChI=1S/C30H50O/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/h10,21-22,25-26,31H,9,11-19H2,1-8H3/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)CC/C=C(C)\C)C)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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Lanosterol is an intermediate of cholesterol synthesis and use of lanosterol induces ubiquitination and degradation of a rate-controlling enzyme of cholesterol synthesis, i.e., HMG CoA reductase.

In vitro activity:

Treatment of lanosterol diminishes aberrant proteotoxic aggregation and mitigates their cytotoxicity via induced expression of co-chaperone CHIP and elevated autophagy. The addition of lanosterol not only reduces aggregation of mutant bonafide misfolded proteins but also effectively prevents accumulation of various mutant disease-prone proteotoxic proteins. Finally, this study observed that lanosterol mitigates cytotoxicity in cells, mediated by different stress-inducing agents. Reference: Mol Neurobiol. 2018 Feb;55(2):1169-1182. https://pubmed.ncbi.nlm.nih.gov/28102469/

In vivo activity:

SCNT (somatic cell nuclear transfer) blastocysts derived from 50-μM lanosterol-treated pig oocytes had significantly higher POU5F1, FGFR2, and Bcl-2 transcript levels than control SCNT-derived blastocysts. In conclusion, supplementation with 50 μM of lanosterol during IVM improves preimplantation development of SCNT embryos by elevating lipid content of oocytes, increasing GSH levels, decreasing reactive oxygen species levels, and regulating genes related to the cholesterol biosynthetic pathway in cumulus cells, to lipid metabolism and apoptosis in oocytes, and their developmental potential and apoptosis in blastocysts. Reference: Theriogenology. 2016 Mar 1;85(4):575-84. https://pubmed.ncbi.nlm.nih.gov/26494176/

	Solvent	mg/mL	mM
Solubility
	DMF	3.0	7.03
	Ethanol	5.1	12.01

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 426.73 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.

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

Formulation protocol:

1. Hu LD, Wang J, Chen XJ, Yan YB. Lanosterol modulates proteostasis via dissolving cytosolic sequestosomes/aggresome-like induced structures. Biochim Biophys Acta Mol Cell Res. 2020 Feb;1867(2):118617. doi: 10.1016/j.bbamcr.2019.118617. Epub 2019 Nov 27. PMID: 31785334. 2. Upadhyay A, Amanullah A, Mishra R, Kumar A, Mishra A. Lanosterol Suppresses the Aggregation and Cytotoxicity of Misfolded Proteins Linked with Neurodegenerative Diseases. Mol Neurobiol. 2018 Feb;55(2):1169-1182. doi: 10.1007/s12035-016-0377-2. Epub 2017 Jan 19. PMID: 28102469. 3. Lee S, Jin JX, Khoirinaya C, Kim GA, Lee BC. Lanosterol influences cytoplasmic maturation of pig oocytes in vitro and improves preimplantation development of cloned embryos. Theriogenology. 2016 Mar 1;85(4):575-84. doi: 10.1016/j.theriogenology.2015.09.041. Epub 2015 Sep 26. PMID: 26494176. 4. Lim L, Jackson-Lewis V, Wong LC, Shui GH, Goh AX, Kesavapany S, Jenner AM, Fivaz M, Przedborski S, Wenk MR. Lanosterol induces mitochondrial uncoupling and protects dopaminergic neurons from cell death in a model for Parkinson's disease. Cell Death Differ. 2012 Mar;19(3):416-27. doi: 10.1038/cdd.2011.105. Epub 2011 Aug 5. PMID: 21818119; PMCID: PMC3278725.

In vitro protocol:

In vivo protocol:

1. Lee S, Jin JX, Khoirinaya C, Kim GA, Lee BC. Lanosterol influences cytoplasmic maturation of pig oocytes in vitro and improves preimplantation development of cloned embryos. Theriogenology. 2016 Mar 1;85(4):575-84. doi: 10.1016/j.theriogenology.2015.09.041. Epub 2015 Sep 26. PMID: 26494176. 2. Lim L, Jackson-Lewis V, Wong LC, Shui GH, Goh AX, Kesavapany S, Jenner AM, Fivaz M, Przedborski S, Wenk MR. Lanosterol induces mitochondrial uncoupling and protects dopaminergic neurons from cell death in a model for Parkinson's disease. Cell Death Differ. 2012 Mar;19(3):416-27. doi: 10.1038/cdd.2011.105. Epub 2011 Aug 5. PMID: 21818119; PMCID: PMC3278725.

1: Zhao L, Chen XJ, Zhu J, Xi YB, Yang X, Hu LD, Ouyang H, Patel SH, Jin X, Lin D, Wu F, Flagg K, Cai H, Li G, Cao G, Lin Y, Chen D, Wen C, Chung C, Wang Y, Qiu A, Yeh E, Wang W, Hu X, Grob S, Abagyan R, Su Z, Tjondro HC, Zhao XJ, Luo H, Hou R, Jefferson J, Perry P, Gao W, Kozak I, Granet D, Li Y, Sun X, Wang J, Zhang L, Liu Y, Yan YB, Zhang K. Lanosterol reverses protein aggregation in cataracts. Nature. 2015 Jul 30;523(7562):607-11. doi: 10.1038/nature14650. Epub 2015 Jul 22. Erratum in: Nature. 2015 Oct 22;526(7574):595. PubMed PMID: 26200341. 2: Chen N, Wang S, Smentek L, Hess BA Jr, Wu R. Biosynthetic Mechanism of Lanosterol: Cyclization. Angew Chem Int Ed Engl. 2015 Jul 20;54(30):8693-6. doi: 10.1002/anie.201501986. Epub 2015 Jun 9. PubMed PMID: 26069216. 3: Lee S, Jin JX, Khoirinaya C, Kim GA, Lee BC. Lanosterol influences cytoplasmic maturation of pig oocytes in vitro and improves preimplantation development of cloned embryos. Theriogenology. 2016 Mar 1;85(4):575-84. doi: 10.1016/j.theriogenology.2015.09.041. Epub 2015 Sep 26. PubMed PMID: 26494176. 4: Kaluzhsiy LA, Gnedenko OV, Gilep AA, Strushkevich NV, Shkel TV, Chernovetsky MA, Ivanov AS, Lisitsa AV, Usanov AS, Stonik VA, Archakov AI. [The screening of the inhibitors of the human cytochrome P450(51) (CYP51A1): the plant and animal structural lanosterol's analogs]. Biomed Khim. 2014 Sep-Oct;60(5):528-37. Russian. PubMed PMID: 25386880. 5: 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. 6: Venkatesh R, Gurav P, Tibrewal S. Comment to: Effect of lanosterol on human nuclei. Indian J Ophthalmol. 2016 Jun;64(6):475. doi: 10.4103/0301-4738.187689. PubMed PMID: 27488164; PubMed Central PMCID: PMC4991188. 7: Hoshino T, Chiba A, Abe N. Lanosterol biosynthesis: the critical role of the methyl-29 group of 2,3-oxidosqualene for the correct folding of this substrate and for the construction of the five-membered D ring. Chemistry. 2012 Oct 8;18(41):13108-16. doi: 10.1002/chem.201201779. Epub 2012 Aug 30. PubMed PMID: 22933236. 8: Wu TK, Chang YC, Liu YT, Chang CH, Wen HY, Li WH, Shie WS. Mutation of isoleucine 705 of the oxidosqualene-lanosterol cyclase from Saccharomyces cerevisiae affects lanosterol's C/D-ring cyclization and 17α/β-exocyclic side chain stereochemistry. Org Biomol Chem. 2011 Feb 21;9(4):1092-7. doi: 10.1039/c0ob00582g. Epub 2010 Dec 15. PubMed PMID: 21157613. 9: Ignatenko VA, Han Y, Tochtrop GP. Direct access to 6/5/7/5- and 6/7/5/5-fused tetracyclic triterpenoids via divergent transannular aldol reaction of lanosterol-derived diketone. J Org Chem. 2013 Dec 6;78(23):12229-35. doi: 10.1021/jo402005b. Epub 2013 Nov 12. PubMed PMID: 24161022; PubMed Central PMCID: PMC3903653. 10: Ačimovič J, Goyal S, Košir R, Goličnik M, Perše M, Belič A, Urlep Ž, Guengerich FP, Rozman D. Cytochrome P450 metabolism of the post-lanosterol intermediates explains enigmas of cholesterol synthesis. Sci Rep. 2016 Jun 23;6:28462. doi: 10.1038/srep28462. PubMed PMID: 27334049; PubMed Central PMCID: PMC4917857. 11: Aoyama Y, Yoshida Y, Sato R. Yeast cytochrome P-450 catalyzing lanosterol 14 alpha-demethylation. II. Lanosterol metabolism by purified P-450(14)DM and by intact microsomes. J Biol Chem. 1984 Feb 10;259(3):1661-6. PubMed PMID: 6420412. 12: 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. 13: Cho SY, Kim JH, Paik YK. Cholesterol biosynthesis from lanosterol: differential inhibition of sterol delta 8-isomerase and other lanosterol-converting enzymes by tamoxifen. Mol Cells. 1998 Apr 30;8(2):233-9. PubMed PMID: 9638657. 14: Hejtmancik JF. Ophthalmology: Cataracts dissolved. Nature. 2015 Jul 30;523(7562):540-1. doi: 10.1038/nature14629. Epub 2015 Jul 22. PubMed PMID: 26200338. 15: Quinlan RA. DRUG DISCOVERY. A new dawn for cataracts. Science. 2015 Nov 6;350(6261):636-7. doi: 10.1126/science.aad6303. PubMed PMID: 26542559. 16: Tuck SF, Patel H, Safi E, Robinson CH. Lanosterol 14 alpha-demethylase (P45014DM): effects of P45014DM inhibitors on sterol biosynthesis downstream of lanosterol. J Lipid Res. 1991 Jun;32(6):893-902. PubMed PMID: 1940622. 17: Aoyama Y, Yoshida Y, Sonoda Y, Sato Y. Deformylation of 32-oxo-24,25-dihydrolanosterol by the purified cytochrome P-45014DM (lanosterol 14 alpha-demethylase) from yeast evidence confirming the intermediate step of lanosterol 14 alpha-demethylation. J Biol Chem. 1989 Nov 5;264(31):18502-5. PubMed PMID: 2509459. 18: Gundersen BB. Clearing cataracts without surgery. Lab Anim (NY). 2015 Oct;44(10):367. doi: 10.1038/laban.870. PubMed PMID: 26398599. 19: Aoyama Y, Yoshida Y, Sonoda Y, Sato Y. The 3-hydroxy group of lanosterol is essential for orienting the substrate site of cytochrome P-450(14DM) (lanosterol 14 alpha- demethylase). Biochim Biophys Acta. 1989 Nov 28;1006(2):209-13. PubMed PMID: 2688742. 20: Ohyama K, Suzuki M, Kikuchi J, Saito K, Muranaka T. Dual biosynthetic pathways to phytosterol via cycloartenol and lanosterol in Arabidopsis. Proc Natl Acad Sci U S A. 2009 Jan 20;106(3):725-30. doi: 10.1073/pnas.0807675106. Epub 2009 Jan 12. PubMed PMID: 19139393; PubMed Central PMCID: PMC2621255.