Pulegone Explained

Pulegone is a naturally occurring organic compound obtained from the essential oils of a variety of plants such as Nepeta cataria (catnip), Mentha piperita, and pennyroyal.[1] [2] It is classified as a monoterpenoid, which means that it is an oxidized derivative of a terpene, a large class of naturally occuring C10 hydrocarbons.

Pulegone is a colorless oil with a pleasant odor similar to pennyroyal, peppermint, and camphor. It is used in flavoring agents, in perfumery, and in aromatherapy.

Isolation and some uses

Pulegone comprises 75% of the oil pressed from pennyroyal, which is cultivated for that purpose. Hydrogenation of pulegone gives menthone. Pulegone is also a precursor to menthofuran, another flavorant.[3]

Toxicology

It was reported that the chemical is toxic to rats if a large quantity is consumed.[4] [5]

Pulegone is also an insecticide − the most powerful of three insecticides naturally occurring in many mint species.[6]

As of October 2018, the FDA withdrew authorization for the use of pulegone as a synthetic flavoring substance for use in food, but that naturally-occurring pulegone can continue to be used.

Sources

See also

Notes and References

  1. Grundschober, F. . 1979 . Literature review of pulegone . Perfum. Flavorist . 4 . 15–17.
  2. Sullivan, J.B., Rumack, B.H., Thomas, H., Peterson, R.G. & Brysch, P. . 1979 . Pennyroyal oil poisoning and hepatotoxicity . J. Am. Med. Assoc. . 242 . 2873–2874 . 10.1001/jama.1979.03300260043027 . 26. 513258 .
  3. Book: 10.1002/0471238961.2005181602120504.a01.pub2. Terpenoids . Kirk-Othmer Encyclopedia of Chemical Technology . 2006 . Sell . Charles S. . 0471238961 .
  4. Thorup. I.. Short term toxicity study in rats dosed with pulegone and menthol. Toxicology Letters. 19. 3. 207–210. 1983. 10.1016/0378-4274(83)90120-0. 6658833. Würtzen. G. Carstensen. J. Olsen. P. etal.
  5. Asekun. O.T.. Effects of drying methods on the quality and quantity of the essential oil of Mentha longifolia L. subsp. Capensis. Food Chemistry. 101. 3. 995–998. 2006. 10.1016/j.foodchem.2006.02.052. Grierson. D. Afolayan. A. etal.
  6. Franzios. G. Mirotsou M. Hatziapostolou E. Kral J. Scouras ZG. Mavragani-Tsipidou P. Insecticidal and genotoxic activities of mint essential oils. Journal of Agricultural and Food Chemistry. 16 July 1997. 2690–2694. 10.1021/jf960685f. https://archive.today/20121223054744/http://ukpmc.ac.uk/abstract/AGR/IND21242689/reload=0;jsessionid=IzuDur4k1KjWolRsRlm2.0. dead. 23 December 2012. 19 October 2012. 45. 7.
  7. Božović M, Pirolli A, Ragno R . Mentha suaveolens Ehrh. (Lamiaceae) Essential Oil and Its Main Constituent Piperitenone Oxide: Biological Activities and Chemistry . . 20 . 5 . 8605–33 . May 2015 . 25985361 . 6272761 . 10.3390/molecules20058605 . free .
  8. Gordon. W. Perry. Valerie Howland. Hepatotoxicity and pulmonary toxicity of pennyroyal oil and its constituent terpenes in the mouse. Toxicology and Applied Pharmacology. 65. 3. 413–424. 1982. 10.1016/0041-008X(82)90387-8. 7157374. etal.
  9. Farley. Derek R.. Valerie Howland. The natural variation of the pulegone content in various oils of peppermint. Journal of the Science of Food and Agriculture. 31. 11. 1143–1151. 2006. 10.1002/jsfa.2740311104.

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