Pulegone

Pulegone[1]
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
89-82-7 YesY
ChEBI CHEBI:35596 YesY
ChemSpider 390923 YesY
Jmol interactive 3D Image
PubChem 442495
UNII 4LF2673R3G YesY
Properties
C10H16O
Molar mass 152.24 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).
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Infobox references

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 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.[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]

Plants that contain the chemical

See also

References

  1. ↑ Merck Index, 11th Edition, 7955.
  2. ↑ Universiti Malaysia Pahang. "Safety data sheet" (PDF). Retrieved 8 June 2009.
  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.
  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. 1 2 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. ↑ 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.
  9. ↑ 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.
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