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Pulegone

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Pulegone
Names
IUPAC name (R)-5-Methyl-2-(1-methylethylidine)cyclohexanone
Other names 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
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.767 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3/t8-/m1/s1Key: NZGWDASTMWDZIW-MRVPVSSYSA-N
  • Key: NZGWDASTMWDZIW-MRVPVSSYBS
SMILES
  • O=C1/C(=C(/C)C)CC(C)C1
Properties
Chemical formula C10H16O
Molar mass 152.23 g/mol
Appearance Colorless oil
Density 0.9346 g/cm
Boiling point 224 °C (435 °F; 497 K)
Solubility in water Insoluble
Solubility in Ethanol
Ether
Chloroform 		Miscible
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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 monoterpene.

Pulegone is a clear colorless oily liquid and has a pleasant odor similar to pennyroyal, peppermint and camphor. It is used in flavoring agents, in perfumery, and in aromatherapy.

Toxicology

It was reported that the chemical is toxic to rats if a large quantity is consumed. Asekun et al. found that the chemical content of Mentha longifolia L was decreased by the treatments at high temperatures, suggesting that the herb should be oven dried or thoroughly cooked before consumption.

Plants that contain the chemical

Notes and references

  1. Merck Index, 11th Edition, 7955.
  2. Grundschober, F. (1979) Literature review of pulegone. Perfum. Flavorist, 4, 15–17.
  3. 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.
  4. Thorup, I.; Würtzen, G; Carstensen, J; Olsen, P; et al. (1983). "Short term toxicity study in rats dosed with pulegone and menthol". Toxicology Letters. 19 (3): 207–210. doi:10.1016/0378-4274(83)90120-0. PMID 6658833. {{cite journal}}: |access-date= requires |url= (help); Cite has empty unknown parameter: |coauthors= (help); Explicit use of et al. in: |first= (help)
  5. ^ Asekun, O.T.; Grierson, D; Afolayan, A; et al. (2006). "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. doi:10.1016/j.foodchem.2006.02.052. {{cite journal}}: |access-date= requires |url= (help); Cite has empty unknown parameter: |coauthors= (help); Explicit use of et al. in: |first= (help)
  6. Gordon, W. Perry; et al. (1982). "Hepatotoxicity and pulmonary toxicity of pennyroyal oil and its constituent terpenes in the mouse". Toxicology and Applied Pharmacology. 65 (3): 413–424. doi:10.1016/0041-008X(82)90387-8. PMID 7157374. {{cite journal}}: |access-date= requires |url= (help); Explicit use of et al. in: |first= (help); Unknown parameter |coauthors= ignored (|author= suggested) (help)
  7. Farley, Derek R. (2006). "The natural variation of the pulegone content in various oils of peppermint". Journal of the Science of Food and Agriculture. 31 (11): 1143–1151. doi:10.1002/jsfa.2740311104. {{cite journal}}: |access-date= requires |url= (help); Unknown parameter |coauthors= ignored (|author= suggested) (help)

See also

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