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.^[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^[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	89-82-7 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:35596 Y
ChemSpider	390923 Y
ECHA InfoCard	100.001.767
PubChem CID	442495
UNII	4LF2673R3G Y
CompTox Dashboard (EPA)	DTXSID2025975
InChI InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3/t8-/m1/s1 Y Key: NZGWDASTMWDZIW-MRVPVSSYSA-N Y 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
SMILES 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
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). Y verify (what is YN ?) Infobox references

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

• Creeping charlie
• Mentha longifolia^[7]
• Mentha suaveolens^[10]
• Pennyroyal^[11]
• Peppermint^[12]
• Schizonepeta tenuifolia
• Bursera graveolens

See also

• Menthofuran
• Menthol