Misplaced Pages

Piperitone: Difference between revisions

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Browse history interactively← Previous editContent deleted Content addedVisualWikitext
Revision as of 05:45, 20 April 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (← Previous edit Latest revision as of 19:28, 16 November 2024 edit undoRodw (talk | contribs)Autopatrolled, Event coordinators, Extended confirmed users, New page reviewers, Pending changes reviewers, Rollbackers771,302 editsm Disambiguating links to Polycyclic (link changed to Polycyclic compound) using DisamAssist. 
(18 intermediate revisions by 13 users not shown)
Line 1: Line 1:
{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 406731331
| Watchedfields = changed
⚫ |Reference=<ref name="Merck">'']'', 11th Edition, '''7443''</ref>
⚫ | verifiedrevid = 424976837
⚫ |ImageFile=Piperitone.png
⚫ | Reference =<ref name="Merck">'']'', 11th Edition, '''7443''</ref>
⚫ |ImageSize=120px
⚫ | ImageFile =Piperitone.png
⚫ |IUPACName=6-Isopropyl-3-methyl-1-cyclohex-2-enone
⚫ | ImageSize =120px
⚫ |OtherNames=3-Carvomenthenone; ''p''-Menth-1-en-3-one
⚫ | IUPACName =6-Isopropyl-3-methyl-1-cyclohex-2-enone
⚫ | OtherNames =3-Carvomenthenone; ''p''-Menth-1-en-3-one
|Section1={{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=89-81-6 | CASNo = 89-81-6
| CASOther = &nbsp;(<small>D</small>/<small>L</small>)<br>6091-50-5 (<small>D</small>)<br>4573-50-6 (<small>L</small>)
| CASNo_Comment = (<small>D</small>/<small>L</small>)
| PubChem=6987
| CASNo2_Ref = {{cascite|correct|CAS}}
⚫ | SMILES=CC1=CC(=O)C(CC1)C(C)C
| 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 |Section2={{Chembox Properties
| Formula=C<sub>10</sub>H<sub>16</sub>O | Formula =C<sub>10</sub>H<sub>16</sub>O
| MolarMass=152.23 g/mol | MolarMass =152.23 g/mol
| Appearance= | Appearance =
| Density=0.9331 g/cm<sup>3</sup> | Density =0.9331 g/cm<sup>3</sup>
| MeltingPt=232-233 °C | MeltingPtC = 232 to 233
| MeltingPt_notes =
| BoilingPt=
| BoilingPt =
| Solubility=
| Solubility =
}} }}
|Section3={{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards =
| FlashPt= | FlashPt =
| AutoignitionPt =
| Autoignition=
}} }}
}} }}


'''Piperitone''' is a natural ] ] which is a component of some ]s. Both ]s, the <small>D</small>-form and the <small>L</small>-form, are known. The <small>D</small>-form has a ]-like aroma and has been isolated from the oils of plants from the genera '']'', '']'', and '']''.<ref name="Merck"/> The <small>L</small>-form has been isolated from ].<ref name="Merck"/> '''Piperitone''' is a natural ] ] which is a component of some ]s. Both ]s, the <small>D</small>-form and the <small>L</small>-form, are known. The <small>D</small>-form has a ]-like aroma and has been isolated from the oils of plants from the genera '']'', '']'', and '']''.<ref name="Merck"/> The <small>L</small>-form has been isolated from ].<ref name="Merck"/>


== Occurrence ==
⚫ Piperitone is used as the principal raw material for the production of ] ] and ]. The primary source of <small>D</small>/<small>L</small>-piperitone is from '']'', produced mainly in ].<ref>Boland, D.J., Brophy, J.J., and A.P.N. House, ''Eucalyptus Leaf Oils'', 1991, ISBN 0-909605-69-6</ref>
]
Piperitone is found in many ], including over thirty species of the genus '']''. High levels are present in certain species of ''Eucalyptus'' and '']''.<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 '']''.<ref name=":1">{{citation|author=John Read, Henry George Smith |date=1921 |doi=10.1039/CT9211900779 |issue=0 |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 ]s occur naturally. In Eucalyptus species, (-)-piperitone is present; in mint species, (+)-piperitone is found; and some plants contain ] piperitone.<ref name="Ravid 1994" />

== Properties ==
Piperitone is a colorless liquid with a distinct ] odor.<ref name=":1" />

== Production ==
Piperitone can be synthesized from ] and ].<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 '']'', produced mainly in ].<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 ] ] and ].<ref name=":2" /> The reduction to menthol is achieved using hydrogen and a ] catalyst. Oxidation to thymol is accomplished with ] and ]. It also forms adducts with ] and ] (an ]), which were historically useful for compound identification by the melting points of the derivatives.<ref name=":1" /> Under light exposure, piperitone undergoes ], forming a ] compound with a ] 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==
Line 37: Line 78:
] ]
] ]
]

]
]

Latest revision as of 19:28, 16 November 2024

Piperitone
Names
IUPAC name 6-Isopropyl-3-methyl-1-cyclohex-2-enone
Other names 3-Carvomenthenone; p-Menth-1-en-3-one
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.766 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9H,4-5H2,1-3H3Key: YSTPAHQEHQSRJD-UHFFFAOYSA-N
  • InChI=1/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9H,4-5H2,1-3H3Key: YSTPAHQEHQSRJD-UHFFFAOYAC
SMILES
  • CC1=CC(=O)C(CC1)C(C)C
Properties
Chemical formula C10H16O
Molar mass 152.23 g/mol
Density 0.9331 g/cm
Melting point 232 to 233 °C (450 to 451 °F; 505 to 506 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Piperitone is a natural monoterpene ketone which is a component of some essential oils. Both stereoisomers, the D-form and the L-form, are known. The D-form has a peppermint-like aroma and has been isolated from the oils of plants from the genera Cymbopogon, Andropogon, and Mentha. The L-form has been isolated from Sitka spruce.

Occurrence

Eucalyptus dives

Piperitone is found in many essential oils, including over thirty species of the genus eucalyptus. High levels are present in certain species of Eucalyptus and mentha. In the genus Eucalyptus, the highest concentrations are found in Eucalyptus dives. Both enantiomers occur naturally. In Eucalyptus species, (-)-piperitone is present; in mint species, (+)-piperitone is found; and some plants contain racemate piperitone.

Properties

Piperitone is a colorless liquid with a distinct peppermint odor.

Production

Piperitone can be synthesized from isopropyl acetoacetate and 3-buten-2-one.

The primary source of D/L-piperitone is from Eucalyptus dives, produced mainly in South Africa.

Reactions

Piperitone is used as the principal raw material for the production of synthetic menthol and thymol. The reduction to menthol is achieved using hydrogen and a nickel catalyst. Oxidation to thymol is accomplished with iron(III) chloride and acetic acid. It also forms adducts with benzaldehyde and hydroxylamine (an oxime), which were historically useful for compound identification by the melting points of the derivatives. Under light exposure, piperitone undergoes photodimerization, forming a polycyclic compound with a cyclobutane ring.

References

  1. ^ Merck Index, 11th Edition, '7443
  2. ^ Uzi Ravid, Eli Putievsky, Irena Katzir (March 1994), "Enantiomeric distribution of piperitone in essential oils of some mentha spp., calamintha incána (sm.) heldr. and artemisia judaica L", Flavour and Fragrance Journal, vol. 9, no. 2, pp. 85–87, doi:10.1002/ffj.2730090210{{citation}}: CS1 maint: multiple names: authors list (link)
  3. ^ John Read, Henry George Smith (1921), "LXXXVII.—Piperitone. Part I. The occurrence, isolation, and characterisation of piperitone", J. Chem. Soc., Trans., vol. 119, no. 0, pp. 779–789, doi:10.1039/CT9211900779
  4. ^ Fritz Eiden (August 2007), "Carl Hagemann ...ein Mensch von großer Güte, ein richtiger Chemiker...", Chemie in unserer Zeit, vol. 41, no. 4, pp. 316–323, doi:10.1002/ciuz.200700411
  5. Boland, D.J., Brophy, J.J., and A.P.N. House, Eucalyptus Leaf Oils, 1991, ISBN 0-909605-69-6
  6. H. Ziffer, N.E. Sharpless, R.O. Kan (January 1966), "Photodimers of piperitone", Tetrahedron, vol. 22, no. 9, pp. 3011–3020, doi:10.1016/S0040-4020(01)82280-8{{citation}}: CS1 maint: multiple names: authors list (link)
Categories: