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Revision as of 15:04, 10 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,081 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'UNII', 'ChEBI').← Previous edit Latest revision as of 06:57, 4 December 2024 edit undoR. Henrik Nilsson (talk | contribs)Extended confirmed users8,457 editsm occuring > occurring 
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{{Use dmy dates|date=September 2021}}
{{chembox
{{Chembox
| verifiedrevid = 406166674
| Watchedfields = changed
| verifiedrevid = 464376356
| Reference = <ref>''Merck Index'', 11th Edition, '''7955'''.</ref> | Reference = <ref>''Merck Index'', 11th Edition, '''7955'''.</ref>
| ImageFile = Pulegone Structural Formulae.png | ImageFile = Pulegone Structural Formulae.png
| ImageSize = 220px | ImageSize = 220px
| IUPACName = (''R'')-5-Methyl-2-(1-methylethylidine)cyclohexanone | 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 | 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 |Section1={{Chembox Identifiers
| Abbreviations = | Abbreviations =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
Line 20: Line 22:
| EINECS = | EINECS =
| PubChem = 442495 | PubChem = 442495
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 4LF2673R3G | UNII = 4LF2673R3G
| SMILES = O=C1/C(=C(/C)C)CC(C)C1 | SMILES = O=C1/C(=C(/C)C)CC(C)C1
| InChI =
| RTECS = | RTECS =
| MeSHName = | MeSHName =
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| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = | KEGG =
}}
| ATCCode_prefix =
|Section2={{Chembox Properties
| ATCCode_suffix =
| C=10 | H=16 | O=1
| ATC_Supplemental =}}
| Section2 = {{Chembox Properties
| Formula = C<sub>10</sub>H<sub>16</sub>O
| MolarMass = 152.23 g/mol
| Appearance = Colorless oil | Appearance = Colorless oil
| Density = 0.9346 g/cm<sup>3</sup> | Density = 0.9346 g/cm<sup>3</sup>
| MeltingPt = | MeltingPt =
| Melting_notes = | MeltingPt_notes =
| BoilingPtC = 224 | BoilingPtC = 224
| Boiling_notes = | BoilingPt_notes =
| Solubility = Insoluble | Solubility = Insoluble
| SolubleOther = Miscible | SolubleOther = Miscible
| Solvent = organic solvent
| Solvent = ]<br>]<br>]
| pKa = | pKa =
| pKb = }} | pKb =
}}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| ExternalMSDS = <ref name=sds>{{cite web | ExternalSDS = <ref name=sds>{{cite web| last =]| 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>
| last = ]
| first =
| authorlink =
| coauthors =
| title = Safety data sheet
| work =
| publisher =
| date =
| url = http://notes.ump.edu.my/fkksa/FKKSA/Archive/Technical%20Unit/Warehouse%20Unit/Chemical/MSDS/MERCK_EN/8186/818665.pdf
| format =
| doi =
| accessdate = 8 June 2009 }}</ref>
| EUClass =
| EUIndex =
| MainHazards = | MainHazards =
| NFPA-H = | NFPA-H =
| NFPA-F = | NFPA-F =
| NFPA-R = | NFPA-R =
| NFPA-O = | NFPA-S =
| RPhrases = | HPhrases =
| SPhrases = | PPhrases =
| RSPhrases = | GHS_ref =
| FlashPt = | FlashPt =
| Autoignition = | AutoignitionPt =
| ExploLimits = | ExploLimits =
| PEL = }} | PEL =
}}
}} }}


'''Pulegone''' is a naturally occurring ] obtained from the ]s of a variety of plants such as '']'' (]), '']'', and ].<ref>Grundschober, F. (1979) Literature review of pulegone. Perfum. Flavorist, 4, 15–17.</ref><ref>Sullivan, J.B., Rumack, B.H., Thomas, H., Peterson, R.G. & Brysch, P. (1979) Pennyroyal oil poisoning and hepatotoxicity. J. Am. Med. Assoc., 242, 2873–2874.</ref> It is classified as a ]. '''Pulegone''' is a naturally occurring ] obtained from the ]s of a variety of plants such as '']'' (]), '']'', and ].<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 ], which means that it is an oxidized derivative of a terpene, a large class of naturally occurring C<sub>10</sub> hydrocarbons.


Pulegone is a clear colorless oily liquid and has a pleasant odor similar to pennyroyal, ] and ]. It is used in flavoring agents, in ], and in ]. Pulegone is a colorless oil with a pleasant odor similar to ], ], and ]. It is used in flavoring agents, in ], and in ].

==Isolation and some uses==
Pulegone comprises 75% of the oil pressed from ], which is cultivated for that purpose. ] of pulegone gives ]. Pulegone is also a precursor to ], another flavorant.<ref name=KO>{{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 }}</ref>


==Toxicology== ==Toxicology==
It was reported that the chemical is toxic to rats if a large quantity is consumed.<ref name=stts>{{cite journal It was reported that the chemical is toxic to rats if a large quantity is consumed.<ref name=stts>{{cite journal
| last = Thorup | last1 = Thorup
| first = I. ''et al.'' | first1 = I.
| title = Short term toxicity study in rats dosed with pulegone and menthol
| authorlink =
| journal = ]
| coauthors =
| volume = 19
| title = Short term toxicity study in rats dosed with pulegone and menthol
| issue = 3
| journal = Toxicology Letters
| volume = 19 | pages = 207–210
| issue = 3 | year = 1983
| doi = 10.1016/0378-4274(83)90120-0
| pages = 207–210
| pmid = 6658833
| publisher =
| last2 = Würtzen
| location =
| date = 1983 | first2 = G
| last3 = Carstensen
| url =
| issn = | first3 = J
| last4 = Olsen
| doi = 10.1016/0378-4274(83)90120-0
| first4 = P|display-authors=etal}}</ref><ref name=edmq>{{cite journal
| id =
| last1 = Asekun
| accessdate = 8 June 2009
| pmid = 6658833 | first1 = O.T.
| title = Effects of drying methods on the quality and quantity of the essential oil of ''Mentha longifolia'' L. subsp. ''Capensis''
| last2 = Würtzen
| journal = Food Chemistry
| first2 = G
| last3 = Carstensen | volume = 101
| first3 = J | issue = 3
| last4 = Olsen | pages = 995–998
| year = 2006
| first4 = P}}</ref> Asekun ''et al.'' found that the chemical content of '']'' L was decreased by the treatments at high temperatures, suggesting that the herb should be oven dried or thoroughly cooked before consumption.<ref name=edmq>{{cite journal
| doi = 10.1016/j.foodchem.2006.02.052
| last = Asekun
| last2 = Grierson
| first = O.T. ''et al.''
| authorlink = | first2 = D
| last3 = Afolayan
| coauthors =
| first3 = A|display-authors=etal}}</ref>
| 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
| publisher =
| location =
| date = 2006
| url =
| issn =
| doi = 10.1016/j.foodchem.2006.02.052
| id =
| accessdate = 29 June 2009
| last2 = Grierson
| first2 = D
| last3 = Afolayan
| first3 = A}}</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>
==Plants that contain the chemical==
* ] <ref name=edmq />
* ] <ref name=hptp>{{cite journal
| last = Gordon
| first = W. Perry ''et al.''
| authorlink =
| coauthors = 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
| publisher =
| location =
| date = 1982
| url =
| issn =
| doi = 10.1016/0041-008X(82)90387-8
| id =
| accessdate = 29 June 2009
| pmid = 7157374}}</ref>
* ] <ref name=nvpc>{{cite journal
| last = Farley
| first = Derek R.
| authorlink =
| coauthors = 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
| publisher =
| location =
| date = 2006
| url =
| issn =
| doi = 10.1002/jsfa.2740311104
| id =
| accessdate = 29 June 2009}}</ref>


As of October 2018, the ] 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>
==Notes and references==
<div style="font-size:88%;">
<references />
</div>


==See also== ==Sources==
* ]
* ]
* '']''<ref name=edmq />
* ]
* '']''<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=] |volume=20 |issue=5 |pages=8605–33 |date=May 2015 |pmid=25985361 |pmc=6272761 |doi=10.3390/molecules20058605 |doi-access=free }}</ref>
* ]
* ]<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 = ]
| volume = 65
| issue = 3
| pages = 413–424
| year = 1982
| doi = 10.1016/0041-008X(82)90387-8
| pmid = 7157374|display-authors=etal
}}</ref>
* ]<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>
* '' ]''
* '']''

== See also ==
* ] * ]
* ]
* ] * ]

* ]
== References ==
* ]
{{reflist}}
{{Use dmy dates|date=January 2011}}

{{Terpenoids}}


] ]
] ]
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