Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Pulegone: Difference between pages
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Saving copy of the {{chembox}} taken from revid 444074446 of page Pulegone for the Chem/Drugbox validation project (updated: ''). |
m →top: Chembox: fix unknown parameters, replaced: | RPhrases = | → | HPhrases = |, | SPhrases = | → | PPhrases = | GHS_ref = |, | EUClass = | → | (2) |
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{{Use dmy dates|date=September 2021}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid [{{fullurl:Pulegone|oldid=444074446}} 444074446] of page [[Pulegone]] with values updated to verified values.}} |
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{{ |
{{Chembox |
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| Watchedfields = changed |
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| verifiedrevid = 444072653 |
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| verifiedrevid = 464376356 |
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| Reference = <ref>''Merck Index'', 11th Edition, '''7955'''.</ref> |
| Reference = <ref>''Merck Index'', 11th Edition, '''7955'''.</ref> |
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| ImageFile = Pulegone Structural Formulae.png |
| ImageFile = Pulegone Structural Formulae.png |
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| ImageSize = 220px |
| ImageSize = 220px |
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| PIN = (5''R'')-5-Methyl-2-(propan-2-ylidene)cyclohexan-1-one |
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| OtherNames = ''p''-Menth-4(8)-en-3-one; <br>δ-4(8)-p- |
| 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 |
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|Section1={{Chembox Identifiers |
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| Abbreviations = |
| Abbreviations = |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| UNII = 4LF2673R3G |
| UNII = 4LF2673R3G |
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| SMILES = O=C1/C(=C(/C)C)CC[C@@H](C)C1 |
| SMILES = O=C1/C(=C(/C)C)CC[C@@H](C)C1 |
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| InChI = |
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| RTECS = |
| RTECS = |
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| MeSHName = |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = |
| KEGG = |
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}} |
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| ATCCode_prefix = |
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|Section2={{Chembox Properties |
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| ATCCode_suffix = |
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| C=10 | H=16 | O=1 |
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| ATC_Supplemental =}} |
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| Section2 = {{Chembox Properties |
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| Formula = C<sub>10</sub>H<sub>16</sub>O |
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| MolarMass = 152.23 g/mol |
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| Appearance = Colorless oil |
| Appearance = Colorless oil |
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| Density = 0.9346 g/cm<sup>3</sup> |
| Density = 0.9346 g/cm<sup>3</sup> |
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| MeltingPt = |
| MeltingPt = |
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| MeltingPt_notes = |
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| BoilingPtC = 224 |
| BoilingPtC = 224 |
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| BoilingPt_notes = |
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| Solubility = Insoluble |
| Solubility = Insoluble |
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| SolubleOther = Miscible |
| SolubleOther = Miscible |
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| Solvent = [[Ethanol]]<br>[[diethyl ether|Ether]]<br>[[Chloroform]] |
| Solvent = [[Ethanol]]<br>[[diethyl ether|Ether]]<br>[[Chloroform]] |
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| pKa = |
| pKa = |
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| pKb = }} |
| pKb = |
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}} |
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|Section7={{Chembox Hazards |
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| 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> |
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| last = [[Universiti Malaysia Pahang]] |
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| first = |
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| authorlink = |
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| coauthors = |
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| title = Safety data sheet |
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| work = |
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| publisher = |
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| date = |
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| url = http://notes.ump.edu.my/fkksa/FKKSA/Archive/Technical%20Unit/Warehouse%20Unit/Chemical/MSDS/MERCK_EN/8186/818665.pdf |
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| format = |
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| doi = |
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| accessdate = 8 June 2009 }}</ref> |
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| EUClass = |
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| EUIndex = |
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| MainHazards = |
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| NFPA-H = |
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| NFPA-S = |
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| HPhrases = |
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| PPhrases = |
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| GHS_ref = |
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| FlashPt = |
| FlashPt = |
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| AutoignitionPt = |
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| ExploLimits = |
| ExploLimits = |
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| PEL = }} |
| PEL = |
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}} |
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}} |
}} |
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'''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]]. |
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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]]. |
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==Toxicology== |
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It was reported that the chemical is toxic to rats if a large quantity is consumed.<ref name=stts>{{cite journal |
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| last1 = Thorup |
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| first1 = I. |
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| title = Short term toxicity study in rats dosed with pulegone and menthol |
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| journal = [[Toxicology Letters]] |
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| volume = 19 |
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| issue = 3 |
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| pages = 207–210 |
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| year = 1983 |
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| doi = 10.1016/0378-4274(83)90120-0 |
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| pmid = 6658833 |
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| last2 = Würtzen |
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| first2 = G |
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| last3 = Carstensen |
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| first3 = J |
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| last4 = Olsen |
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| first4 = P|display-authors=etal}}</ref><ref name=edmq>{{cite journal |
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| last1 = Asekun |
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| first1 = O.T. |
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| title = Effects of drying methods on the quality and quantity of the essential oil of ''Mentha longifolia'' L. subsp. ''Capensis'' |
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| journal = Food Chemistry |
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| volume = 101 |
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| issue = 3 |
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| pages = 995–998 |
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| year = 2006 |
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| doi = 10.1016/j.foodchem.2006.02.052 |
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| last2 = Grierson |
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| first2 = D |
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| last3 = Afolayan |
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| first3 = A|display-authors=etal}}</ref> |
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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> |
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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> |
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==Sources== |
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* [[Glechoma hederacea|Creeping charlie]] |
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* ''[[Mentha longifolia]]''<ref name=edmq /> |
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* ''[[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> |
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* [[Mentha pulegium|Pennyroyal]]<ref name=hptp>{{cite journal |
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| last = Gordon |
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| first = W. Perry |
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| author2=Valerie Howland |
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| title = Hepatotoxicity and pulmonary toxicity of pennyroyal oil and its constituent terpenes in the mouse |
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| journal = [[Toxicology and Applied Pharmacology]] |
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| volume = 65 |
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| issue = 3 |
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| pages = 413–424 |
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| year = 1982 |
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| doi = 10.1016/0041-008X(82)90387-8 |
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| pmid = 7157374|display-authors=etal |
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}}</ref> |
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* [[Peppermint]]<ref name=nvpc>{{cite journal |
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| last = Farley |
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| first = Derek R. |
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| author2=Valerie Howland |
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| title = The natural variation of the pulegone content in various oils of peppermint |
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| journal = Journal of the Science of Food and Agriculture |
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| volume = 31 |
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| issue = 11 |
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| pages = 1143–1151 |
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| year = 2006 |
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| doi = 10.1002/jsfa.2740311104 |
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}}</ref> |
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*''[[Schizonepeta| Schizonepeta tenuifolia]]'' |
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*''[[Bursera graveolens]]'' |
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== See also == |
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* [[Menthofuran]] |
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* [[Menthol]] |
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== References == |
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{{reflist}} |
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{{Terpenoids}} |
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[[Category:Ketones]] |
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[[Category:Flavors]] |
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[[Category:Cooling flavors]] |
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[[Category:Perfume ingredients]] |
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[[Category:Monoterpenes]] |
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[[Category:IARC Group 2B carcinogens]] |