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Pulegone





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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]
Names
Preferred IUPAC name

(5R)-5-Methyl-2-(propan-2-ylidene)cyclohexan-1-one

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=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3/t8-/m1/s1 checkY

    Key: NZGWDASTMWDZIW-MRVPVSSYSA-N checkY

  • InChI=1/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3/t8-/m1/s1

    Key: NZGWDASTMWDZIW-MRVPVSSYBS

  • O=C1/C(=C(/C)C)CC[C@@H](C)C1

Properties

Chemical formula

C10H16O
Molar mass 152.237 g·mol−1
Appearance Colorless oil
Density 0.9346 g/cm3
Boiling point 224 °C (435 °F; 497 K)

Solubility in water

Insoluble
SolubilityinEthanol
Ether
Chloroform
Miscible
Hazards
Safety data sheet (SDS) MSDS[2]

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

checkY verify (what is checkY☒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.

Toxicology

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It was reported that the chemical is toxic to rats if a large quantity is consumed.[5][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, but that naturally-occurring pulegone can continue to be used.[8]

Sources

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See also

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References

edit
  1. ^ Merck Index, 11th Edition, 7955.
  • ^ Universiti Malaysia Pahang. "Safety data sheet" (PDF). Retrieved 8 June 2009.[permanent dead link]
  • ^ Grundschober, F. (1979). "Literature review of pulegone". Perfum. Flavorist. 4: 15–17.
  • ^ 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. PMID 513258.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  • ^ 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.
  • ^ 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.
  • ^ 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. Archived from the original on 23 December 2012. Retrieved 19 October 2012.
  • ^ 83FR 50490
  • ^ Božović M, Pirolli A, Ragno R (May 2015). "Mentha suaveolens Ehrh. (Lamiaceae) Essential Oil and Its Main Constituent Piperitenone Oxide: Biological Activities and Chemistry". Molecules (Basel, Switzerland). 20 (5): 8605–33. doi:10.3390/molecules20058605. PMC 6272761. PMID 25985361.
  • ^ 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.
  • ^ 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.

  • Retrieved from "https://en.wikipedia.org/w/index.php?title=Pulegone&oldid=1059988488"
     



    Last edited on 12 December 2021, at 21:12  





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    This page was last edited on 12 December 2021, at 21:12 (UTC).

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