Open main menu

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.[3][4] It is classified as a monoterpene.

Pulegone[1]
Pulegone Structural Formulae.png
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
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.767
UNII
Properties
C10H16O
Molar mass 152.237 g·mol−1
Appearance Colorless oil
Density 0.9346 g/cm3
Boiling point 224 °C (435 °F; 497 K)
Insoluble
Solubility in Ethanol
Ether
Chloroform
Miscible
Hazards
Safety data sheet MSDS[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☑Y verify (what is ☑Y☒N ?)
Infobox references

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.

Contents

ToxicologyEdit

It was reported that the chemical is toxic to rats if a large quantity is consumed.[5] 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.[6]

Pulegone is also an insecticide − the most powerful of three insecticides naturally occurring in many mint species.[7]

As of October 2018, the FDA withdrew authorization for the use of pulegone as a synthetic flavoring substance for use in food, without regard to its continuing stance that this substance does not pose a risk to public health under the conditions of its intended use.[8]

Plants that contain the chemicalEdit

See alsoEdit

ReferencesEdit

  1. ^ Merck Index, 11th Edition, 7955.
  2. ^ Universiti Malaysia Pahang. "Safety data sheet" (PDF). Retrieved 8 June 2009.[permanent dead link]
  3. ^ Grundschober, F. (1979). "Literature review of pulegone". Perfum. Flavorist. 4: 15–17.
  4. ^ Sullivan, J.B., Rumack, B.H., Thomas, H., Peterson, R.G. & Brysch, P. (1979). "Pennyroyal oil poisoning and hepatotoxicity". J. Am. Med. Assoc. 242 (26): 2873–2874. doi:10.1001/jama.1979.03300260043027.CS1 maint: Multiple names: authors list (link)
  5. ^ 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.
  6. ^ a b 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.
  7. ^ Franzios, G; Mirotsou M; Hatziapostolou E; Kral J; Scouras ZG; Mavragani-Tsipidou P (16 July 1997). "Insecticidal and genotoxic activities of mint essential oils". Journal of Agricultural and Food Chemistry. 45 (7): 2690–2694. doi:10.1021/jf960685f. Retrieved 19 October 2012.
  8. ^ 83 FR 50490
  9. ^ Gordon, W. Perry; Valerie Howland; 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.
  10. ^ Farley, Derek R.; Valerie Howland (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.