Pulegone
Chemical compound
From Wikipedia, the free encyclopedia
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.
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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 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:
-pulegone.svg)
-menthone.svg)
-isomenthone.svg)
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.[7][8]
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]