Pulegone

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title: "Pulegone" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["ketones", "flavors", "cooling-flavors", "perfume-ingredients", "monoterpenes", "iarc-group-2b-carcinogens"] topic_path: "general/ketones" source: "https://en.wikipedia.org/wiki/Pulegone" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Reference = | ImageFile = Pulegon.svg | ImageSize = 150px | PIN = (5R)-5-Methyl-2-(propan-2-ylidene)cyclohexan-1-one | OtherNames = p-Menth-4(8)-en-3-one; δ-4(8)-p-Menthen-3-one; (R)-2-Isopropylidene-5-methylcyclohexanone; (R)-p-Menth-4(8)-en-3-one; (R)-(+)-Pulegone |Section1={{Chembox Identifiers | Abbreviations = | ChemSpiderID_Ref = | ChemSpiderID = 390923 | InChI = 1/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3/t8-/m1/s1 | InChIKey = NZGWDASTMWDZIW-MRVPVSSYBS | StdInChI_Ref = | StdInChI = 1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3/t8-/m1/s1 | StdInChIKey_Ref = | StdInChIKey = NZGWDASTMWDZIW-MRVPVSSYSA-N | CASNo_Ref = | CASNo = 89-82-7 | EINECS = | PubChem = 442495 | UNII_Ref = | UNII = 4LF2673R3G | SMILES = O=C1/C(=C(/C)C)CCC@@HC1 | RTECS = | MeSHName = | ChEBI_Ref = | ChEBI = 35596 | KEGG_Ref = | KEGG = |Section2={{Chembox Properties | C=10 | H=16 | O=1 | Appearance = Colorless oil | Density = 0.9346 g/cm3 | MeltingPt = | MeltingPt_notes = | BoilingPtC = 224 | BoilingPt_notes = | Solubility = Insoluble | SolubleOther = Miscible | Solvent = organic solvent | pKa = | pKb = |Section7={{Chembox Hazards | ExternalSDS = MSDS | MainHazards = | NFPA-H = | NFPA-F = | NFPA-R = | NFPA-S = | HPhrases = | PPhrases = | GHS_ref = | FlashPt = | AutoignitionPt = | ExploLimits = | PEL =

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 | last1 = Thorup | first1 = I. | title = Short term toxicity study in rats dosed with pulegone and menthol | journal = Toxicology Letters | volume = 19 | issue = 3 | pages = 207–210 | year = 1983 | doi = 10.1016/0378-4274(83)90120-0 | pmid = 6658833 | last2 = Würtzen | first2 = G | last3 = Carstensen | first3 = J | last4 = Olsen | first4 = P|display-authors=etal}}{{cite journal | last1 = Asekun | first1 = O.T. | title = Effects of drying methods on the quality and quantity of the essential oil of Mentha longifolia L. subsp. Capensis | journal = Food Chemistry | volume = 101 | issue = 3 | pages = 995–998 | year = 2006 | doi = 10.1016/j.foodchem.2006.02.052 | last2 = Grierson | first2 = D | last3 = Afolayan | first3 = A|display-authors=etal}}

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 | last = Gordon | first = W. Perry | author2=Valerie Howland | title = Hepatotoxicity and pulmonary toxicity of pennyroyal oil and its constituent terpenes in the mouse | journal = Toxicology and Applied Pharmacology | volume = 65 | issue = 3 | pages = 413–424 | year = 1982 | doi = 10.1016/0041-008X(82)90387-8 | pmid = 7157374|display-authors=etal
  • Peppermint{{cite journal | last = Farley | first = Derek R. | author2=Valerie Howland | title = The natural variation of the pulegone content in various oils of peppermint | journal = Journal of the Science of Food and Agriculture | volume = 31 | issue = 11 | pages = 1143–1151 | year = 2006 | doi = 10.1002/jsfa.2740311104
  • 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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