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MedKoo Cat#: 462134 | Name: Carbolactone
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Description:

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

Carbolactone is a fungal metabolite originally isolated from Sporormiella australis that has fungicidal and herbicidal activities.

Chemical Structure

Carbolactone
Carbolactone
CAS#155443-55-3

Theoretical Analysis

MedKoo Cat#: 462134

Name: Carbolactone

CAS#: 155443-55-3

Chemical Formula: C24H36O3

Exact Mass: 372.2664

Molecular Weight: 372.55

Elemental Analysis: C, 77.38; H, 9.74; O, 12.88

Price and Availability

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1mg USD 750.00 Back order
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Related CAS #
No Data
Synonym
Carbolactone
IUPAC/Chemical Name
(2aR,2a1R,3S,5aR,6bS,9S,10aR,12bS)-9-hydroxy-2a1,3,6b,10,10-pentamethyl-1,2,2a,2a1,3,5a,6,6b,7,8,9,10,10a,11,12,12b-hexadecahydro-4H-cyclopenta[de]naphtho[2,1-g]chromen-4-one
InChi Key
ICBKTZVCTSCWTL-WYCYEJLCSA-N
InChi Code
InChI=1S/C24H36O3/c1-13-15-7-8-16-14-6-9-18-22(2,3)19(25)10-11-23(18,4)17(14)12-20(24(15,16)5)27-21(13)26/h13,15-16,18-20,25H,6-12H2,1-5H3/t13-,15+,16-,18-,19-,20+,23+,24+/m0/s1
SMILES Code
C[C@@](C1=O)([H])[C@@]2([H])CC[C@@]3([H])C(CC[C@@]4([H])C(C)([C@](O)([H])CC[C@]54C)C)=C5C[C@](O1)([H])[C@]23C
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 372.55 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: Ou-Yang DW, Gao JP, Li QS, Guo JP. (1S*,2R*,4aS*,6aS*,6bR*,10S*,12aR*,14aS*)-10-Hydr-oxy-1,2,6a,6b,9,9,12a-hepta- methyl-perhydro-picene-4a,14a-carbolactone. Acta Crystallogr Sect E Struct Rep Online. 2009 Mar 14;65(Pt 4):o753. doi: 10.1107/S1600536809008253. PMID: 21582484; PMCID: PMC2969035. 2: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Spironolactone. 2022 Jul 18. PMID: 30000160. 3: Kang U, Wang D, Bokesch HR, Gustafson KR. Four New Pregnane-10,2-carbolactones from an Epipolasis sp. Marine Sponge. Chem Pharm Bull (Tokyo). 2021;69(1):48-51. doi: 10.1248/cpb.c20-00128. PMID: 33390521; PMCID: PMC9341129. 4: Baydoun E, Atia-Tul-Wahab, Iqbal S, Smith C, Choudhary MI. Biotransformation of drospirenone, a contraceptive drug, with Cunninghamella elegans. Steroids. 2017 Oct;126:30-34. doi: 10.1016/j.steroids.2017.07.010. Epub 2017 Jul 30. PMID: 28768150. 5: Jastrzebska I, Niemirowicz K, Brzozowska WI, Bucki R. The synthesis and antifungal activity of (20S)-3β-acetoxy-5α-pregnane-20,16β-carbolactone against fluconazole - Resistant Candida cells. Steroids. 2017 Feb;118:55-60. doi: 10.1016/j.steroids.2016.12.009. Epub 2016 Dec 18. PMID: 27998758. 6: Sam K, Labrie F, Poirier D. N-Butyl-N-methyl-11-(3'-hydroxy-21', 17'-carbolactone-19'-nor-17'alpha-pregna-1',3', 5'(10')-trien-7'alpha- yl)-undecanamide: an inhibitor of type 2 17beta-hydroxysteroid dehydrogenase that does not have oestrogenic or androgenic activity. Eur J Med Chem. 2000 Feb;35(2):217-25. doi: 10.1016/s0223-5234(00)00124-0. PMID: 10758283. 7: Jastrzebska I. Synthesis and application of steroidal 22,16β-carbolactones: A review. J Steroid Biochem Mol Biol. 2020 May;199:105592. doi: 10.1016/j.jsbmb.2020.105592. Epub 2020 Jan 14. PMID: 31953168. 8: Jastrzebska I, Morzycki JW. Some observations on solasodine reactivity. Steroids. 2017 Nov;127:13-17. doi: 10.1016/j.steroids.2017.08.015. Epub 2017 Sep 5. PMID: 28887171. 9: Li G, Zhang Y. Stereoselective synthesis of the two major metabolites of spironolactone, 3alpha- and 3beta-hydroxy-7alpha-methylthio-17alpha- pregn-4-ene-21,17-carbolactone. Steroids. 2007 Jun;72(6-7):569-72. doi: 10.1016/j.steroids.2007.03.011. Epub 2007 Mar 30. PMID: 17493649. 10: Bain BM, Phillipps GH, Procopiou PA, Steeples IP, Upton RJ. Rearrangement of a 16alpha,17alpha-Epoxy-16beta-methylandrostane-17beta-carbothioic Acid to a 17beta-Mercapto-16beta-methylandrostane-17alpha,16alpha-carbolactone. J Org Chem. 1998 Oct 16;63(21):7421-7424. doi: 10.1021/jo9812375. PMID: 11672393. 11: Aburto-Luna V, Meza-León RL, Bernès S. (R)-3,4,5-Tride- oxy-5,6-didehydro-1,2-O-(2,2,2-trichloro-ethyl-idene)-α-d-gluco-furan- ose-6,3-carbolactone: a new derivative of α-chloralose. Acta Crystallogr Sect E Struct Rep Online. 2008 Aug 20;64(Pt 9):o1784. doi: 10.1107/S1600536808026196. PMID: 21201764; PMCID: PMC2960566. 12: Dai J, Yoshida WY, Kelly M, Williams P. Pregnane-10,2-carbolactones from a Hawaiian Marine Sponge in the Genus Myrmekioderma. J Nat Prod. 2016 May 27;79(5):1464-7. doi: 10.1021/acs.jnatprod.6b00042. Epub 2016 Apr 22. PMID: 27104967; PMCID: PMC4917361. 13: Rao KV, Sreeramulu K, Gunasekar D, Ramesh D. Two new sesquiterpene lactones from Ceiba pentandra. J Nat Prod. 1993 Dec;56(12):2041-5. doi: 10.1021/np50102a003. PMID: 8133294. 14: Fillion H, Porte M, Bartoli MH, Bouaziz Z, Berlion M, Villard J. Synthesis of Mannich bases of 5-hydroxynapthalene-1,8-carbolactone as potential antifungal or antitumor agents. Chem Pharm Bull (Tokyo). 1991 Feb;39(2):493-5. doi: 10.1248/cpb.39.493. PMID: 2054874. 15: Parrish SM, Neupane RP, Harper MK, Head J, Williams PG. Myrmenaphthol A, Isolated from a Hawaiian Sponge of the Genus Myrmekioderma. J Nat Prod. 2019 Sep 27;82(9):2668-2671. doi: 10.1021/acs.jnatprod.9b00665. Epub 2019 Aug 28. PMID: 31461285; PMCID: PMC6919962. 16: Yang Q, Ye WD, Yuan JY, Nie JJ, Xu DJ. Eplerenone ethanol solvate. Acta Crystallogr Sect E Struct Rep Online. 2008 Apr 10;64(Pt 5):o829. doi: 10.1107/S1600536808009240. PMID: 21202318; PMCID: PMC2961083. 17: Dams I, Białońska A, Cmoch P, Krupa M, Pietraszek A, Ostaszewska A, Chodyński M. Synthesis and Physicochemical Characterization of the Process- Related Impurities of Eplerenone, an Antihypertensive Drug. Molecules. 2017 Aug 15;22(8):1354. doi: 10.3390/molecules22081354. PMID: 28809817; PMCID: PMC6152353. 18: Vijaya Bhaskar Reddy M, Kesava Reddy M, Gunasekar D, Marthanda Murthy M, Caux C, Bodo B. A new sesquiterpene lactone from Bombax malabaricum. Chem Pharm Bull (Tokyo). 2003 Apr;51(4):458-9. doi: 10.1248/cpb.51.458. PMID: 12673007. 19: Riondel J, Boitard M, Bouaziz Z, Fillion H. In vivo antitumor activity of 5-hydroxy-6-[N,N-bis(2-chloroethyl)aminomethyl]naphthalene-1,8- carbolactone. Pharmazie. 1992 Jan;47(1):67-8. PMID: 1608991. 20: Colombo D, Bombieri G, Lenna R, Marchini N, Modica E, Scala A. Structure elucidation of new compounds from acidic treatment of the progestins gestodene and drospirenone. Steroids. 2006 Aug;71(8):745-50. doi: 10.1016/j.steroids.2006.05.002. PMID: 16769098.