Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Pulegone: Difference between pages

{{Use dmy dates|date=September 2021}}

{{Chembox

| Watchedfields = changed

| verifiedrevid = 464376356

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

| OtherNames = ''p''-Menth-4(8)-en-3-one; <br>δ-4(8)-''p''-Menthen-3-one; <br>(''R'')-2-Isopropylidene-5-methylcyclohexanone; <br>(''R'')-''p''-Menth-4(8)-en-3-one; <br>(''R'')-(+)-Pulegone

|Section1={{Chembox Identifiers

}}

|Section2={{Chembox Properties

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

| MeltingPt_notes =

| BoilingPt_notes =

| 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]<ref name=sds>{{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 }}</ref>

| NFPA-S =

| HPhrases =

| PPhrases =

| GHS_ref =

| AutoignitionPt =

| PEL =

}}

'''Pulegone''' is a naturally occurring [[organic compound]] obtained from the [[essential oil]]s of a variety of plants such as ''[[Nepeta cataria]]'' ([[catnip]]), ''[[Mentha piperita]]'', and [[Mentha pulegium|pennyroyal]].<ref>{{cite journal | author = Grundschober, F. | year = 1979 | title = Literature review of pulegone | journal = Perfum. Flavorist | volume = 4 | pages = 15–17}}</ref><ref>{{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 }}</ref> It is classified as a [[monoterpene]].

Pulegone is a clear colorless oily liquid and has a pleasant odor similar to pennyroyal, [[peppermint]] and [[camphor]]. It is used in flavoring agents, in [[perfumery]], and in [[aromatherapy]].

==Toxicology==

It was reported that the chemical is toxic to rats if a large quantity is consumed.<ref name=stts>{{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}}</ref><ref name=edmq>{{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}}</ref>

Pulegone is also an insecticide − the most powerful of three insecticides naturally occurring in many mint species.<ref>{{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}}</ref>

As of October 2018, the [[Food and Drug Administration|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.<ref>{{Federal Register|83|50490}}</ref>

==Sources==

* [[Glechoma hederacea|Creeping charlie]]

* ''[[Mentha longifolia]]''<ref name=edmq />

* ''[[Mentha suaveolens]]''<ref name="pmid25985361">{{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 }}</ref>

* [[Mentha pulegium|Pennyroyal]]<ref name=hptp>{{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

}}</ref>

* [[Peppermint]]<ref name=nvpc>{{cite journal

| last = Farley

| first = Derek R.

| author2=Valerie Howland

| title = The natural variation of the pulegone content in various oils of peppermint

| journal = Journal of the Science of Food and Agriculture

| volume = 31

| issue = 11

| pages = 1143–1151

| year = 2006

| doi = 10.1002/jsfa.2740311104

}}</ref>

*''[[Schizonepeta| Schizonepeta tenuifolia]]''

*''[[Bursera graveolens]]''

== See also ==

* [[Menthofuran]]

* [[Menthol]]

== References ==

{{reflist}}

{{Terpenoids}}

[[Category:Ketones]]

[[Category:Flavors]]

[[Category:Cooling flavors]]

[[Category:Perfume ingredients]]

[[Category:Monoterpenes]]

[[Category:IARC Group 2B carcinogens]]