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MedKoo Cat#: 574903 | Name: Testololactone
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Description:

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

Testololactone is the derivative of Testolactone -- an antineoplastic derivative of progesterone used to treat advanced stage breast cancer.

Chemical Structure

Testololactone
CAS#4416-57-3

Theoretical Analysis

MedKoo Cat#: 574903

Name: Testololactone

CAS#: 4416-57-3

Chemical Formula: C19H26O3

Exact Mass: 302.1882

Molecular Weight: 302.41

Elemental Analysis: C, 75.46; H, 8.67; O, 15.87

Price and Availability

Size Price Availability Quantity
1mg USD 500.00 2 Weeks
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Related CAS #
No Data
Synonym
NSC 12173; Testololactone
IUPAC/Chemical Name
(4aS,4bR,10aR,10bS,12aS)-3,4,4a,5,6,9,10,10a,10b,11,12,12a-Dodecahydro-10a,12a-dimethyl-2H-phenanthro[2,1-b]pyran-2,8(4bH)-dione
InChi Key
CNIXJDVUMXTEKX-DZBHQSCQSA-N
InChi Code
InChI=1S/C19H26O3/c1-18-9-7-13(20)11-12(18)3-4-14-15(18)8-10-19(2)16(14)5-6-17(21)22-19/h11,14-16H,3-10H2,1-2H3/t14-,15+,16+,18+,19+/m1/s1
SMILES Code
O=C1CC[C@]2([H])[C@@](CC[C@]3([H])[C@@]4(C)CCC(C=C4CC[C@]32[H])=O)(C)O1
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 302.41 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: Abdel-Kareem MM, Zohri AA, Rasmey AM, Hawary H. Enhancing the biotransformation of progesterone to the anticancer compound testololactone by Penicillium chrysogenum Ras3009: kinetic modelling and efficiency maximization. BMC Biotechnol. 2024 Oct 4;24(1):73. doi: 10.1186/s12896-024-00896-9. PMID: 39367307; PMCID: PMC11451084. 2: Melo de Queiroz T, Valdes TA, Leitão A, Porto ALM. Bio-oxidation of progesterone by Penicillium oxalicum CBMAI 1185 and evaluation of the cytotoxic activity. Steroids. 2024 May;205:109392. doi: 10.1016/j.steroids.2024.109392. Epub 2024 Mar 5. PMID: 38452910. 3: Lobastova TG, Khomutov SM, Shutov AA, Donova MV. Microbiological synthesis of stereoisomeric 7(α/β)-hydroxytestololactones and 7(α/β)-hydroxytestolactones. Appl Microbiol Biotechnol. 2019 Jun;103(12):4967-4976. doi: 10.1007/s00253-019-09828-6. Epub 2019 Apr 26. PMID: 31028438. 4: Javid M, Nickavar B, Vahidi H, Faramarzi MA. Baeyer-Villiger oxidation of progesterone by Aspergillus sojae PTCC 5196. Steroids. 2018 Dec;140:52-57. doi: 10.1016/j.steroids.2018.07.008. Epub 2018 Jul 26. PMID: 30055193. 5: Mascotti ML, Palazzolo MA, Bisogno FR, Kurina-Sanz M. Biotransformation of dehydro-epi-androsterone by Aspergillus parasiticus: Metabolic evidences of BVMO activity. Steroids. 2016 May;109:44-9. doi: 10.1016/j.steroids.2016.03.018. Epub 2016 Mar 26. PMID: 27025973. 6: Hunter AC, Patel S, Dedi C, Dodd HT, Bryce RA. Metabolic fate of 3α,5-cycloandrostanes in the endogenous lactonization pathway of Aspergillus tamarii KITA. Phytochemistry. 2015 Nov;119:19-25. doi: 10.1016/j.phytochem.2015.09.003. Epub 2015 Sep 11. PMID: 26372080. 7: Lone SH, Bhat KA. Phytosterols as precursors for the synthesis of aromatase inhibitors: Hemisynthesis of testololactone and testolactone. Steroids. 2015 Apr;96:164-8. doi: 10.1016/j.steroids.2015.02.011. Epub 2015 Feb 17. PMID: 25697056. 8: Świzdor A. Baeyer-Villiger oxidation of some C(19) steroids by Penicillium lanosocoeruleum. Molecules. 2013 Nov 7;18(11):13812-22. doi: 10.3390/molecules181113812. PMID: 24213656; PMCID: PMC6270215. 9: Zhang L, Wang H, Yang Y, Liu H, Zhang Q, Xiang Q, Ge R, Su Z, Huang Y. NGF induces adult stem Leydig cells to proliferate and differentiate during Leydig cell regeneration. Biochem Biophys Res Commun. 2013 Jun 28;436(2):300-5. doi: 10.1016/j.bbrc.2013.05.098. Epub 2013 Jun 4. PMID: 23743199. 10: Hunter AC, Collins C, Dodd HT, Dedi C, Koussoroplis SJ. Transformation of a series of saturated isomeric steroidal diols by Aspergillus tamarii KITA reveals a precise stereochemical requirement for entrance into the lactonization pathway. J Steroid Biochem Mol Biol. 2010 Nov;122(5):352-8. doi: 10.1016/j.jsbmb.2010.08.010. Epub 2010 Sep 9. PMID: 20832471. 11: Huang LH, Li J, Xu G, Zhang XH, Wang YG, Yin YL, Liu HM. Biotransformation of dehydroepiandrosterone (DHEA) with Penicillium griseopurpureum Smith and Penicillium glabrum (Wehmer) Westling. Steroids. 2010 Dec 12;75(13-14):1039-46. doi: 10.1016/j.steroids.2010.06.008. Epub 2010 Jun 26. PMID: 20600202. 12: Christy Hunter A, Khuenl-Brady H, Barrett P, Dodd HT, Dedi C. Transformation of some 3alpha-substituted steroids by Aspergillus tamarii KITA reveals stereochemical restriction of steroid binding orientation in the minor hydroxylation pathway. J Steroid Biochem Mol Biol. 2010 Feb 15;118(3):171-6. doi: 10.1016/j.jsbmb.2009.12.003. Epub 2009 Dec 21. PMID: 20026270. 13: Kołek T, Szpineter A, Swizdor A. Studies on Baeyer-Villiger oxidation of steroids: DHEA and pregnenolone D-lactonization pathways in Penicillium camemberti AM83. Steroids. 2009 Oct;74(10-11):859-62. doi: 10.1016/j.steroids.2009.05.007. Epub 2009 May 28. PMID: 19481558. 14: Hunter AC, Coyle E, Morse F, Dedi C, Dodd HT, Koussoroplis SJ. Transformation of 5-ene steroids by the fungus Aspergillus tamarii KITA: mixed molecular fate in lactonization and hydroxylation pathways with identification of a putative 3beta-hydroxy-steroid dehydrogenase/Delta5-Delta4 isomerase pathway. Biochim Biophys Acta. 2009 Feb;1791(2):110-7. doi: 10.1016/j.bbalip.2008.12.005. Epub 2008 Dec 24. PMID: 19136076. 15: Kołek T, Szpineter A, Swizdor A. Baeyer-Villiger oxidation of DHEA, pregnenolone, and androstenedione by Penicillium lilacinum AM111. Steroids. 2008 Dec 22;73(14):1441-5. doi: 10.1016/j.steroids.2008.07.008. Epub 2008 Aug 5. PMID: 18755205. 16: Hunter AC, Bergin-Simpson H. Distinct metabolic handling of 3beta- hydroxy-17a-oxa-D-homo-5alpha-androstan-17-one by the filamentous fungus Aspergillus tamarii KITA: Evidence in support of steroid/hydroxylase binding hypothesis. Biochim Biophys Acta. 2007 Sep;1771(9):1254-61. doi: 10.1016/j.bbalip.2007.07.001. Epub 2007 Jul 13. PMID: 17692565. 17: Hunter AC, Elsom J, Ross L, Barrett R. Ring-B functionalized androst-4-en-3-ones and ring-C substituted pregn-4-en-3-ones undergo differential transformation in Aspergillus tamarii KITA: ring-A transformation with all C-6 substituted steroids and ring-D transformation with C-11 substituents. Biochim Biophys Acta. 2006 Mar;1761(3):360-6. doi: 10.1016/j.bbalip.2006.02.011. Epub 2006 Mar 15. PMID: 16574481. 18: Hunter AC, Kennedy S, Clabby SJ, Elsom J. Fate of novel Quasi reverse steroidal substrates by Aspergillus tamarii KITA: bypass of lactonisation and an exclusive role for the minor hydroxylation pathway. Biochim Biophys Acta. 2005 May 15;1734(2):190-7. doi: 10.1016/j.bbalip.2005.02.009. Epub 2005 Mar 9. PMID: 15904875. 19: Voĭshvillo NE, Andriushina VA, Savinova TS, Stytsenko TS. Transformatsiia androstendiona i androstadiendiona bakteriiami degradiruiushchimi steriny [Conversion of androstenedione and androstadienedione by sterol-degrading bacteria]. Prikl Biokhim Mikrobiol. 2004 Sep-Oct;40(5):536-43. Russian. PMID: 15553785. 20: Hunter AC, Carragher NE. Flexibility of the endogenous progesterone lactonisation pathway in Aspergillus tamarii KITA: transformation of a series of cortical steroid analogues. J Steroid Biochem Mol Biol. 2003 Dec;87(4-5):301-8. doi: 10.1016/j.jsbmb.2003.10.001. PMID: 14698211.