Pulegone

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Contents

Pulegone [1]
Pulegon.svg
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
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.767 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3/t8-/m1/s1 Yes check.svgY
    Key: NZGWDASTMWDZIW-MRVPVSSYSA-N Yes check.svgY
  • 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
C10H16O
Molar mass 152.237 g·mol−1
AppearanceColorless oil
Density 0.9346 g/cm3
Boiling point 224 °C (435 °F; 497 K)
Insoluble
Solubility in organic solventMiscible
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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 monoterpenoid, which means that it is an oxidized derivative of a terpene, a large class of naturally occurring C10 hydrocarbons.

Pulegone is a colorless oil with a pleasant odor similar to pennyroyal, peppermint, and camphor. It is used in flavoring agents, in perfumery, and in aromatherapy.

Isolation and some uses

Pulegone comprises 75% of the oil pressed from pennyroyal, which is cultivated for that purpose. Hydrogenation of pulegone gives menthone. Pulegone is also a precursor to menthofuran, another flavorant. [5]

Toxicology

It was reported that the chemical is toxic to rats if a large quantity is consumed. [6] [7]

Pulegone is also an insecticide − the most powerful of three insecticides naturally occurring in many mint species. [8]

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. [9]

Sources

See also

References

  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. PMID   513258.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. ↑ Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN   0471238961.
  6. ↑ 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.
  7. 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.
  8. ↑ 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.
  9. ↑ 83 FR 50490
  10. ↑ 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.
  11. ↑ 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.
  12. ↑ 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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