Pulegone

{{Chembox

| Watchedfields = changed

| verifiedrevid = 464376356

| Reference = Merck Index, 11th Edition, 7955.

| ImageFile = Pulegon.svg

| ImageSize = 150px

| PIN = (5R)-5-Methyl-2-(propan-2-ylidene)cyclohexan-1-one

| OtherNames = 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

|Section1={{Chembox Identifiers

| Abbreviations =

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 390923

| InChI = 1/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3/t8-/m1/s1

| InChIKey = NZGWDASTMWDZIW-MRVPVSSYBS

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3/t8-/m1/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = NZGWDASTMWDZIW-MRVPVSSYSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 89-82-7

| EINECS =

| PubChem = 442495

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 4LF2673R3G

| SMILES = O=C1/C(=C(/C)C)CC[C@@H](C)C1

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| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 35596

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG =

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|Section2={{Chembox Properties

| C=10 | H=16 | O=1

| Appearance = Colorless oil

| Density = 0.9346 g/cm³

| MeltingPt =

| MeltingPt_notes =

| BoilingPtC = 224

| BoilingPt_notes =

| Solubility = Insoluble

| SolubleOther = Miscible

| Solvent = organic solvent

| pKa =

| pKb =

}}

|Section7={{Chembox Hazards

| ExternalSDS = [http://notes.ump.edu.my/fkksa/FKKSA/Archive/Technical%20Unit/Warehouse%20Unit/Chemical/MSDS/MERCK_EN/8186/818665.pdf MSDS]{{cite web| last =Universiti Malaysia Pahang| title =Safety data sheet| url =http://notes.ump.edu.my/fkksa/FKKSA/Archive/Technical%20Unit/Warehouse%20Unit/Chemical/MSDS/MERCK_EN/8186/818665.pdf| access-date =8 June 2009}}{{dead link|date=April 2018 |bot=InternetArchiveBot |fix-attempted=yes }}

| MainHazards =

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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.{{cite journal | author = Grundschober, F. | year = 1979 | title = Literature review of pulegone | journal = Perfum. Flavorist | volume = 4 | pages = 15–17}}{{cite journal | author = Sullivan, J.B., Rumack, B.H., Thomas, H., Peterson, R.G. & Brysch, P. | year = 1979 | title = Pennyroyal oil poisoning and hepatotoxicity | journal = J. Am. Med. Assoc. | volume = 242 | pages = 2873–2874 | doi = 10.1001/jama.1979.03300260043027 | issue = 26| pmid = 513258 }} 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.{{cite book |doi=10.1002/0471238961.2005181602120504.a01.pub2|chapter=Terpenoids |title=Kirk-Othmer Encyclopedia of Chemical Technology |year=2006 |last1=Sell |first1=Charles S. |isbn=0471238961 }}

Toxicology

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

| last1 = Thorup

| first1 = I.

| title = Short term toxicity study in rats dosed with pulegone and menthol

| journal = Toxicology Letters

| volume = 19

| issue = 3

| pages = 207–210

| year = 1983

| doi = 10.1016/0378-4274(83)90120-0

| pmid = 6658833

| last2 = Würtzen

| first2 = G

| last3 = Carstensen

| first3 = J

| last4 = Olsen

| first4 = P|display-authors=etal}}{{cite journal

| last1 = Asekun

| first1 = O.T.

| title = Effects of drying methods on the quality and quantity of the essential oil of Mentha longifolia L. subsp. Capensis

| journal = Food Chemistry

| volume = 101

| issue = 3

| pages = 995–998

| year = 2006

| doi = 10.1016/j.foodchem.2006.02.052

| last2 = Grierson

| first2 = D

| last3 = Afolayan

| first3 = A|display-authors=etal}}

Pulegone is also an insecticide − the most powerful of three insecticides naturally occurring in many mint species.{{cite journal|last=Franzios|first=G|author2=Mirotsou M|author3=Hatziapostolou E|author4=Kral J|author5=Scouras ZG|author6=Mavragani-Tsipidou P|title=Insecticidal and genotoxic activities of mint essential oils|journal=Journal of Agricultural and Food Chemistry|date=16 July 1997|pages=2690–2694|doi=10.1021/jf960685f|url=http://ukpmc.ac.uk/abstract/AGR/IND21242689/reload=0;jsessionid=IzuDur4k1KjWolRsRlm2.0|archive-url=https://archive.today/20121223054744/http://ukpmc.ac.uk/abstract/AGR/IND21242689/reload=0;jsessionid=IzuDur4k1KjWolRsRlm2.0|url-status=dead|archive-date=23 December 2012|access-date=19 October 2012|volume=45|issue=7}}

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.{{Federal Register|83|50490}}

Sources

Creeping charlie
Mentha longifolia
Mentha suaveolens{{cite journal |vauthors=Božović M, Pirolli A, Ragno R |title=Mentha suaveolens Ehrh. (Lamiaceae) Essential Oil and Its Main Constituent Piperitenone Oxide: Biological Activities and Chemistry |journal=Molecules (Basel, Switzerland) |volume=20 |issue=5 |pages=8605–33 |date=May 2015 |pmid=25985361 |pmc=6272761 |doi=10.3390/molecules20058605 |doi-access=free }}
Pennyroyal{{cite journal

| last = Gordon

| first = W. Perry

| author2=Valerie Howland

| title = Hepatotoxicity and pulmonary toxicity of pennyroyal oil and its constituent terpenes in the mouse

| journal = Toxicology and Applied Pharmacology

| volume = 65

| issue = 3

| pages = 413–424

| year = 1982

| doi = 10.1016/0041-008X(82)90387-8

| pmid = 7157374|display-authors=etal

}}