# Piperitone

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Piperitone
> Markdown URL: https://mediated.wiki/source/Piperitone.md
> Source: https://en.wikipedia.org/wiki/Piperitone
> Source revision: 1347018100
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{Distinguish|4-Piperidone{{!}}Piperidone}}

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 424976837
| Reference =<ref name="Merck">''[Merck Index](/source/Merck_Index)'', 11th Edition, '''7443''</ref>
| ImageFile =Piperitone.png
| ImageSize =120px
| IUPACName =6-Isopropyl-3-methyl-1-cyclohex-2-enone
| OtherNames =3-Carvomenthenone; ''p''-Menth-1-en-3-one
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 89-81-6
| CASNo_Comment = (<small>D</small>/<small>L</small>)
| CASNo2_Ref = {{cascite|correct|CAS}}
| CASNo2 = 6091-50-5
| CASNo2_Comment =(<small>D</small>)
| CASNo3_Ref = {{cascite|correct|CAS}}
| CASNo3 = 4573-50-6
| CASNo3_Comment = (<small>L</small>)
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 1VZ8RG269R
| UNII2_Ref = {{fdacite|correct|FDA}}
| UNII2 = 8ZZ2GU5WBU
| UNII2_Comment = (<small>D</small>)
| UNII3_Ref = {{fdacite|correct|FDA}}
| UNII3 = 8GZY0Q0N20
| UNII3_Comment = (<small>L</small>)
| PubChem =6987
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 48933
| SMILES =CC1=CC(=O)C(CC1)C(C)C
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 6721
| InChI = 1/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9H,4-5H2,1-3H3
| InChIKey = YSTPAHQEHQSRJD-UHFFFAOYAC
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9H,4-5H2,1-3H3
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = YSTPAHQEHQSRJD-UHFFFAOYSA-N
  }}
|Section2={{Chembox Properties
| Formula =C<sub>10</sub>H<sub>16</sub>O
| MolarMass =152.23 g/mol
| Appearance =
| Density =0.9331 g/cm<sup>3</sup>
| MeltingPtC = 232 to 233
| MeltingPt_notes =
| BoilingPt =
| Solubility =
  }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
 }}
}}

'''Piperitone''' is a natural [monoterpene](/source/monoterpene) [ketone](/source/ketone) which is a component of some [essential oil](/source/essential_oil)s. Both [stereoisomer](/source/stereoisomer)s, the <small>D</small>-form and the <small>L</small>-form, are known.  The <small>D</small>-form has a [peppermint](/source/peppermint)-like aroma and has been isolated from the oils of plants from the genera ''[Cymbopogon](/source/Cymbopogon)'', ''[Andropogon](/source/Andropogon)'', and ''[Mentha](/source/Mentha)''.<ref name="Merck"/>  The <small>L</small>-form has been isolated from [Sitka spruce](/source/Sitka_spruce).<ref name="Merck"/>

== Occurrence ==
left|thumb|''Eucalyptus dives''
Piperitone is found in many [essential oils](/source/essential_oils), including over thirty species of the genus ''[Eucalyptus](/source/Eucalyptus)''. High levels are present in certain species of ''Eucalyptus'' and ''[Mentha](/source/Mentha)''.<ref name="Ravid 1994">{{citation|author=Uzi Ravid, Eli Putievsky, Irena Katzir |date=March 1994 |doi=10.1002/ffj.2730090210 |issue=2 |pages=85–87 |periodical=Flavour and Fragrance Journal |title=Enantiomeric distribution of piperitone in essential oils of some mentha spp., calamintha incána (sm.) heldr. and artemisia judaica L |volume=9}}<!-- auto-translated from German by Module:CS1 translator --></ref> In the genus Eucalyptus, the highest concentrations are found in ''[Eucalyptus dives](/source/Eucalyptus_dives)''.<ref name=":1">{{citation|author=John Read, Henry George Smith |date=1921 |doi=10.1039/CT9211900779 |pages=779–789 |periodical=J. Chem. Soc., Trans. |title=LXXXVII.—Piperitone. Part I. The occurrence, isolation, and characterisation of piperitone |volume=119}}<!-- auto-translated from German by Module:CS1 translator --></ref> Both [enantiomer](/source/enantiomer)s occur naturally. In Eucalyptus species, (-)-piperitone is present; in mint species, (+)-piperitone is found; and some plants contain [racemate](/source/racemate) piperitone.<ref name="Ravid 1994" />

== Properties ==
[Racemic](/source/Racemic) piperitone is a colorless liquid with a distinct [peppermint](/source/peppermint) odour ("herbal, minty, camphoreous, medicinal").<ref>{{cite web |title=piperitone|url=https://scentsandflavors.com/database/9dbb51c7-eef5-432d-8e67-2550733674d8|website=Scents and Flavors |publisher=Scents and Flavors |access-date=4 April 2026}}</ref><ref name=":1" />

== Production ==
Piperitone can be synthesized from [isopropyl acetoacetate](/source/isopropyl_acetoacetate) and [3-buten-2-one](/source/3-buten-2-one).<ref name=":2">{{citation|author=Fritz Eiden |date=August 2007 |doi=10.1002/ciuz.200700411 |issue=4 |pages=316–323 |periodical=Chemie in unserer Zeit |title=Carl Hagemann ...ein Mensch von großer Güte, ein richtiger Chemiker... |volume=41}}<!-- auto-translated from German by Module:CS1 translator --></ref>

The primary source of <small>D</small>/<small>L</small>-piperitone is from ''[Eucalyptus dives](/source/Eucalyptus_dives)'', produced mainly in [South Africa](/source/South_Africa).<ref>Boland, D.J., Brophy, J.J., and A.P.N. House, ''Eucalyptus Leaf Oils'', 1991, {{ISBN|0-909605-69-6}}</ref>

== Reactions ==
Piperitone is used as the principal raw material for the production of [synthetic](/source/chemical_synthesis) [menthol](/source/menthol) and [thymol](/source/thymol).<ref name=":2" /> The reduction to menthol is achieved using hydrogen and a [nickel](/source/nickel) catalyst. Oxidation to thymol is accomplished with [iron(III) chloride](/source/iron(III)_chloride) and [acetic acid](/source/acetic_acid). It also forms adducts with [benzaldehyde](/source/benzaldehyde) and [hydroxylamine](/source/hydroxylamine) (an [oxime](/source/oxime)), which were historically useful for compound identification by the melting points of the derivatives.<ref name=":1" /> Under light exposure, piperitone undergoes [photodimerization](/source/photodimerization), forming a [polycyclic](/source/Polycyclic_compound) compound with a [cyclobutane](/source/cyclobutane) ring.<ref>{{citation|author=H. Ziffer, N.E. Sharpless, R.O. Kan |date=January 1966 |doi=10.1016/S0040-4020(01)82280-8 |issue=9 |pages=3011–3020 |periodical=Tetrahedron |title=Photodimers of piperitone |volume=22}}<!-- auto-translated from German by Module:CS1 translator --></ref>

==References==
<references/>

Category:Ketones
Category:Monoterpenes
Category:Cyclohexenes

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Adapted from the Wikipedia article [Piperitone](https://en.wikipedia.org/wiki/Piperitone) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Piperitone?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.