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Pulegone

δ-4(8)-p-Menthen-3-one; (R)-2-Isopropylidene-5-methylcyclohexanone; (R)-p-Menth-4(8)-en-3-one; (R)-(+)-Pulegone | NFPA-H = | NFPA-F = | NFPA-R = | NFPA-S =

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. It is classified as a monoterpenoid, which means that it is an oxidized derivative of a terpene, a large class of naturally occurring 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.

Biochemistry

The enzyme (+)-pulegone reductase from peppermint catalyses a reduction reaction which gives a mixture of (–)-menthone and (+)-isomenthone:

It uses nicotinamide adenine dinucleotide phosphate (NADPH) as its cofactor.

Toxicology

It was reported that the chemical is toxic to rats if a large quantity is consumed.{{cite journal

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

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

  • Creeping charlie
  • Mentha longifolia
  • Mentha suaveolens
  • Pennyroyal{{cite journal
  • Peppermint{{cite journal
    • Schizonepeta tenuifolia*
  • Bursera graveolens

References

References

  1. ''Merck Index'', 11th Edition, '''7955'''.
  2. [[Universiti Malaysia Pahang]]. (April 2018). "Safety data sheet".
  3. Grundschober, F.. (1979). "Literature review of pulegone". Perfum. Flavorist.
  4. Sullivan, J.B., Rumack, B.H., Thomas, H., Peterson, R.G. & Brysch, P.. (1979). "Pennyroyal oil poisoning and hepatotoxicity". J. Am. Med. Assoc..
  5. (2006). "Kirk-Othmer Encyclopedia of Chemical Technology".
  6. (October 2003). "Monoterpene double-bond reductases of the (−)-menthol biosynthetic pathway: isolation and characterization of cDNAs encoding (−)-isopiperitenone reductase and (+)-pulegone reductase of peppermint". Archives of Biochemistry and Biophysics.
  7. Franzios, G. (16 July 1997). "Insecticidal and genotoxic activities of mint essential oils". Journal of Agricultural and Food Chemistry.
  8. {{Federal Register. 83. 50490
  9. (May 2015). "Mentha suaveolens Ehrh. (Lamiaceae) Essential Oil and Its Main Constituent Piperitenone Oxide: Biological Activities and Chemistry". [[Molecules (Basel, Switzerland)]].
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ketones flavors cooling-flavors perfume-ingredients monoterpenes iarc-group-2b-carcinogens
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