Article · Wikipedia archive · Last revised Jul 27, 2026

Pulegone

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. 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.

Last revised
Jul 27, 2026
Read time
≈ 3 min
Length
675 w
Citations
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Source
Wikipedia ↗

Pulegone1
source ↗
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
UNII
  • 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
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 organic solvent Miscible
Hazards
Safety data sheet (SDS) MSDS2
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.34 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

Biochemistry

The enzyme (+)-pulegone reductase from peppermint catalyses a reduction reaction which gives a mixture of (–)-menthone and (+)-isomenthone:

2D representation of the chemical structure of pulegone.
(+)-pulegone
+ NADPH
 
 
H+
 
Rightward reaction arrow with minor substrate(s) from top and bottom left
H+
 
 
2D representation of the chemical structure of Q424902.
70% (–)-menthone
+
 
2D representation of the chemical structure of Q27104366.
30% (+)-isomenthone
+ NADP+
 


It uses nicotinamide adenine dinucleotide phosphate (NADPH) as its cofactor.6

Toxicology

It was reported that the chemical is toxic to rats if a large quantity is consumed.78

Pulegone is also an insecticide − the most powerful of three insecticides naturally occurring in many mint species.9

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.10

Sources

Sources

See also

See also

References

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. 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. Ringer KL, McConkey ME, Davis EM, Rushing GW, Croteau R (October 2003). "Monoterpene double-bond reductases of the (−)-menthol biosynthetic pathway: isolation and characterization of cDNAs encoding (−)-isopiperitenone reductase and (+)-pulegone reductase of peppermint". Archives of Biochemistry and Biophysics. 418 (1): 80–92. doi:10.1016/s0003-9861(03)00390-4. PMID 13679086.
  7. 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.
  8. 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.
  9. 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.{{cite journal}}: CS1 maint: deprecated archival service (link)
  10. 83 FR 50490
  11. 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.
  12. 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.
  13. 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.