Pulegone

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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
89-82-7 YesY
ChEBI CHEBI:35596 YesY
ChemSpider 390923 YesY
Jmol-3D images Image
PubChem 442495
UNII 4LF2673R3G YesY
Properties
C10H16O
Molar mass 152.23 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
SDS MSDS[2]
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY verify (what isYesY/N?)
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[edit]

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[edit]

See also[edit]

References[edit]

  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. ^ 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. ^ 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.