Pulegone
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| 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)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.001.767 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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) | 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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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
[edit]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
[edit]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
[edit]- Creeping charlie
- Mentha longifolia[7]
- Mentha suaveolens[10]
- Pennyroyal[11]
- Peppermint[12]
- Schizonepeta tenuifolia
- Bursera graveolens
See also
[edit]References
[edit]- ^ 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) - ^ Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN 0471238961.
- ^ 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.
- ^ 83 FR 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.