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MedKoo Cat#: 146363 | Name: Mintalactone

Description:

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

Mintalactone is a naturally occurring monoterpene lactone found in some mint species, such as Mentha aquatica and Mentha citrata. It functions primarily as a bioactive compound with potential insect-repellent and pheromone-like properties. While not widely used in commercial applications, it has attracted interest for its role in plant defense and potential use in natural pest control.

Chemical Structure

Mintalactone
Mintalactone
CAS#38049-04-6

Theoretical Analysis

MedKoo Cat#: 146363

Name: Mintalactone

CAS#: 38049-04-6

Chemical Formula: C17H24ClNO4

Exact Mass: 341.1394

Molecular Weight: 341.83

Elemental Analysis: C, 59.73; H, 7.08; Cl, 10.37; N, 4.10; O, 18.72

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
Mintalactone;
IUPAC/Chemical Name
(6R,7aR)-3,6-dimethyl-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one
InChi Key
VUVQBYIJRDUVHT-HZGVNTEJSA-N
InChi Code
1S/C10H14O2/c1-6-3-4-8-7(2)10(11)12-9(8)5-6/h6,9H,3-5H2,1-2H3/t6-,9-/m1/s1
SMILES Code
C[C@@H]1CCC2=C(C)C(=O)O[C@@H]2C1
Appearance
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 341.83 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: Thakkar Y, Moustakas H, Api AM, Smith B, Williams G, Greim H, Eisenbrand G, Dekant W. Assessment of the genotoxic potential of mintlactone. Food Chem Toxicol. 2022 Jan;159:112659. doi: 10.1016/j.fct.2021.112659. Epub 2021 Nov 19. PMID: 34801651. 2: Bates RW, Sridhar S. A synthesis of (-)-mintlactone. J Org Chem. 2008 Oct 17;73(20):8104-5. doi: 10.1021/jo801433f. Epub 2008 Sep 24. PMID: 18811204. 3: Nguyen TH, Dein M, Munafo JP Jr. Characterization of Odorants in Clustered Mountain Mint Pycnanthemum muticum. J Agric Food Chem. 2024 Oct 30;72(43):23947-23956. doi: 10.1021/acs.jafc.4c07582. Epub 2024 Oct 17. PMID: 39417598. 4: Gao P, Xu PF, Zhai H. Expeditious construction of (+)-mintlactone via intramolecular hetero-Pauson-Khand reaction. J Org Chem. 2009 Mar 20;74(6):2592-3. doi: 10.1021/jo900045k. PMID: 19228032. 5: Picard M, de Revel G, Marchand S. First identification of three p-menthane lactones and their potential precursor, menthofuran, in red wines. Food Chem. 2017 Feb 15;217:294-302. doi: 10.1016/j.foodchem.2016.08.070. Epub 2016 Aug 23. PMID: 27664637. 6: Ferraz HM, Grazini MV, Ribeiro CM, Brocksom U, Brocksom TJ. A short route to (-)-mintlactone by thallium(III)-mediated cyclization of (-)-isopulegol. J Org Chem. 2000 Apr 21;65(8):2606-7. doi: 10.1021/jo991802j. PMID: 10789485. 7: Nelson SD, McClanahan RH, Thomassen D, Gordon WP, Knebel N. Investigations of mechanisms of reactive metabolite formation from (R)-(+)-pulegone. Xenobiotica. 1992 Sep-Oct;22(9-10):1157-64. doi: 10.3109/00498259209051869. PMID: 1441606. 8: Zhuang Z, Sheng T, Qiao JX, Yeung KS, Yu JQ. Versatile Copper-Catalyzed γ-C(sp3)-H Lactonization of Aliphatic Acids. J Am Chem Soc. 2024 Jun 26;146(25):17311-17317. doi: 10.1021/jacs.4c04043. Epub 2024 Jun 12. PMID: 38867480. 9: Khojasteh-Bakht SC, Nelson SD, Atkins WM. Glutathione S-transferase catalyzes the isomerization of (R)-2-hydroxymenthofuran to mintlactones. Arch Biochem Biophys. 1999 Oct 1;370(1):59-65. doi: 10.1006/abbi.1999.1361. PMID: 10496977. 10: Khojasteh-Bakht SC, Chen W, Koenigs LL, Peter RM, Nelson SD. Metabolism of (R)-(+)-pulegone and (R)-(+)-menthofuran by human liver cytochrome P-450s: evidence for formation of a furan epoxide. Drug Metab Dispos. 1999 May;27(5):574-80. PMID: 10220485. 11: Poli JP, Guinoiseau E, de Rocca Serra D, Sutour S, Paoli M, Tomi F, Quilichini Y, Berti L, Lorenzi V. Anti-Quorum Sensing Activity of 12 Essential Oils on chromobacterium violaceum and Specific Action of cis- cis-p-Menthenolide from Corsican Mentha suaveolens ssp. Insularis. Molecules. 2018 Aug 23;23(9):2125. doi: 10.3390/molecules23092125. PMID: 30142938; PMCID: PMC6225197. 12: Chen LJ, Lebetkin EH, Burka LT. Metabolism of (R)-(+)-menthofuran in Fischer-344 rats: identification of sulfonic acid metabolites. Drug Metab Dispos. 2003 Oct;31(10):1208-13. doi: 10.1124/dmd.31.10.1208. PMID: 12975329. 13: Patel RM, Puranik VG, Argade NP. Regio- and stereoselective selenium dioxide allylic oxidation of (E)-dialkyl alkylidenesuccinates to (Z)-allylic alcohols: synthesis of natural and unnatural butenolides. Org Biomol Chem. 2011 Sep 21;9(18):6312-22. doi: 10.1039/c1ob05709j. Epub 2011 Jul 26. PMID: 21792406. 14: Thomassen D, Knebel N, Slattery JT, McClanahan RH, Nelson SD. Reactive intermediates in the oxidation of menthofuran by cytochromes P-450. Chem Res Toxicol. 1992 Jan-Feb;5(1):123-30. doi: 10.1021/tx00025a021. PMID: 1581528. 15: Lisanti MT, Laboyrie J, Marchand-Marion S, de Revel G, Moio L, Riquier L, Franc C. Minty aroma compounds in red wine: Development of a novel automated HS- SPME-arrow and gas chromatography-tandem mass spectrometry quantification method. Food Chem. 2021 Nov 1;361:130029. doi: 10.1016/j.foodchem.2021.130029. Epub 2021 May 9. PMID: 34077885. 16: Ferguson LJ, Lebetkin EH, Lih FB, Tomer KB, Parkinson HD, Borghoff SJ, Burka LT. 14C-labeled pulegone and metabolites binding to alpha2u-globulin in kidneys of male F-344 rats. J Toxicol Environ Health A. 2007 Sep;70(17):1416-23. doi: 10.1080/15287390701382720. PMID: 17687727. 17: Sutour S, Tomi F, Bradesi P, Casanova J. Chemical composition of the essential oil from Corsican Mentha aquatica--combined analysis by GC(RI), GC-MS and 13C NMR spectroscopy. Nat Prod Commun. 2011 Oct;6(10):1479-82. PMID: 22164788. 18: Khojasteh SC, Oishi S, Nelson SD. Metabolism and toxicity of menthofuran in rat liver slices and in rats. Chem Res Toxicol. 2010 Nov 15;23(11):1824-32. doi: 10.1021/tx100268g. Epub 2010 Oct 14. PMID: 20945912; PMCID: PMC2981629. 19: Tsubuki M, Takahashi K, Honda T. Practical ruthenium-catalyzed cyclocarbonylation of allenyl alcohols in 2,4,6-collidine leading to alpha,beta- unsaturated lactones: concise stereoselective synthesis of (+)-isomintlactone. J Org Chem. 2009 Feb 6;74(3):1422-5. doi: 10.1021/jo8025127. PMID: 19093838. 20: Dams I, Bialoniska A, Ciunik Z, Wawrzenczyk C. Lactones. 21. Synthesis and odoriferous properties of lactones with the p-menthane system. J Agric Food Chem. 2004 Mar 24;52(6):1630-4. doi: 10.1021/jf035272a. PMID: 15030222.

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