Diosgenone | CAS# 2137-22-6 | malaria

MedKoo Cat#: 413779 | Name: Diosgenone

Description:

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

Diosgenone is isolated from Solanum nudum and has been proposed as a new therapeutic alternative for the treatment of malaria.

Chemical Structure

Diosgenone

CAS#2137-22-6

Theoretical Analysis

MedKoo Cat#: 413779

Name: Diosgenone

CAS#: 2137-22-6

Chemical Formula: C27H38O3

Exact Mass: 410.2821

Molecular Weight: 410.59

Elemental Analysis: C, 78.98; H, 9.33; O, 11.69

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

Diosgenone

IUPAC/Chemical Name

(5'R,6aR,6bS,8aS,8bR,9S,10R,11aS,12aS,12bS)-5',6a,8a,9-tetramethyl-1,3',4',5',6a,6b,6',7,8,8a,8b,9,11a,12,12a,12b-hexadecahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4(2H)-one

InChi Key

QEGQIJLALWETNE-CLGLNXEMSA-N

InChi Code

InChI=1S/C27H38O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h8,10,13,16-17,20-24H,5-7,9,11-12,14-15H2,1-4H3/t16-,17+,20-,21+,22+,23+,24+,25+,26+,27-/m1/s1

SMILES Code

C[C@@H]1CC[C@]2(O[C@H]3C[C@H]4[C@@H]5CCC6=CC(C=C[C@@]6([C@H]5CC[C@@]4([C@H]3[C@@H]2C)C)C)=O)OC1

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 410.59 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

1: Pabón A, Escobar G, Vargas E, Cruz V, Notario R, Blair S, Echeverri F. Diosgenone synthesis, anti-malarial activity and QSAR of analogues of this natural product. Molecules. 2013 Mar 14;18(3):3356-78. doi: 10.3390/molecules18033356. PMID: 23493102; PMCID: PMC6270258. 2: Li L, Zhao Y, Lang B, Xie Y, Shaowu Meng M, He Y, Yang L, Liu A. Microbial transformation of diosgenin to diosgenone by Wickerhamomyces anomalus JQ-1 obtained from Naxi traditional Jiu Qu. Bioorg Chem. 2020 Jan;95:103508. doi: 10.1016/j.bioorg.2019.103508. Epub 2019 Dec 15. PMID: 31927315. 3: Wang W, Wang FQ, Wei DZ. Characterization of P450 FcpC, the enzyme responsible for bioconversion of diosgenone to isonuatigenone in Streptomyces virginiae IBL-14. Appl Environ Microbiol. 2009 Jun;75(12):4202-5. doi: 10.1128/AEM.02606-08. Epub 2009 Apr 17. PMID: 19376895; PMCID: PMC2698366. 4: Segura C, Cuesta-Astroz Y, Nunes-Batista C, Zalis M, von Krüger WM, Mascarello Bisch P. Partial characterization of Plasmodium falciparum trophozoite proteome under treatment with quinine, mefloquine and the natural antiplasmodial diosgenone. Biomedica. 2014 Apr-Jun;34(2):237-49. doi: 10.1590/S0120-41572014000200010. PMID: 24967929. 5: Hernández Linares MG, Guerrero-Luna G, Bernès S, Flores-Alamo M, Fernández- Herrera MA. Diosgenone: a second P2(1) polymorph. Acta Crystallogr Sect E Struct Rep Online. 2012 Aug 1;68(Pt 8):o2358. doi: 10.1107/S160053681202908X. Epub 2012 Jul 7. PMID: 22904824; PMCID: PMC3414291. 6: Wang FQ, Li B, Wang W, Zhang CG, Wei DZ. Biotransformation of diosgenin to nuatigenin-type steroid by a newly isolated strain, Streptomyces virginiae IBL-14. Appl Microbiol Biotechnol. 2007 Dec;77(4):771-7. doi: 10.1007/s00253-007-1216-1. Epub 2007 Oct 23. PMID: 17955193. 7: Wang W, Wang W, Ge H, Li G, Shen P, Xu S, Yu B, Zhang J. Biocatalytic allylic hydroxylation of unsaturated triterpenes and steroids by Bacillus megaterium CGMCC 1.1741. Bioorg Chem. 2020 Jun;99:103826. doi: 10.1016/j.bioorg.2020.103826. Epub 2020 Apr 6. PMID: 32315895. 8: López ML, Blair S, Sáez J, Segura C. Effect of Solanum nudum steroids on uninfected and Plasmodium falciparum-infected erythrocytes. Mem Inst Oswaldo Cruz. 2009 Aug;104(5):683-8. doi: 10.1590/s0074-02762009000500003. PMID: 19820825. 9: Wojtkiewicz AM, Wójcik P, Procner M, Flejszar M, Oszajca M, Hochołowski M, Tataruch M, Mrugała B, Janeczko T, Szaleniec M. The efficient Δ1-dehydrogenation of a wide spectrum of 3-ketosteroids in a broad pH range by 3-ketosteroid dehydrogenase from Sterolibacterium denitrificans. J Steroid Biochem Mol Biol. 2020 Sep;202:105731. doi: 10.1016/j.jsbmb.2020.105731. Epub 2020 Aug 7. PMID: 32777354. 10: Alvarez G, Pabón A, Carmona J, Blair S. Evaluation of clastogenic potential of the antimalarial plant Solanum nudum. Phytother Res. 2004 Oct;18(10):845-8. doi: 10.1002/ptr.1534. PMID: 15551372.