| 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, Rollbackers770,662 editsm Disambiguating links to Polycyclic (link changed to Polycyclic compound) using DisamAssist. |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 406731331 |
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|Reference=<ref name="Merck">'']'', 11th Edition, '''7443''</ref> |
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| verifiedrevid = 424976837 |
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|ImageFile=Piperitone.png |
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| Reference =<ref name="Merck">'']'', 11th Edition, '''7443''</ref> |
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|ImageSize=120px |
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| ImageFile =Piperitone.png |
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|IUPACName=6-Isopropyl-3-methyl-1-cyclohex-2-enone |
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| ImageSize =120px |
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|OtherNames=3-Carvomenthenone; ''p''-Menth-1-en-3-one |
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| IUPACName =6-Isopropyl-3-methyl-1-cyclohex-2-enone |
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| OtherNames =3-Carvomenthenone; ''p''-Menth-1-en-3-one |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=89-81-6 |
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| CASNo = 89-81-6 |
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| CASOther = (<small>D</small>/<small>L</small>)<br>6091-50-5 (<small>D</small>)<br>4573-50-6 (<small>L</small>) |
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| CASNo_Comment = (<small>D</small>/<small>L</small>) |
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| PubChem=6987 |
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| CASNo2_Ref = {{cascite|correct|CAS}} |
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| SMILES=CC1=CC(=O)C(CC1)C(C)C |
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| CASNo2 = 6091-50-5 |
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| CASNo2_Comment =(<small>D</small>) |
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| CASNo3_Ref = {{cascite|correct|CAS}} |
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| CASNo3 = 4573-50-6 |
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| CASNo3_Comment = (<small>L</small>) |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 1VZ8RG269R |
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| UNII2_Ref = {{fdacite|correct|FDA}} |
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| UNII2 = 8ZZ2GU5WBU |
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| UNII2_Comment = (<small>D</small>) |
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| UNII3_Ref = {{fdacite|correct|FDA}} |
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| UNII3 = 8GZY0Q0N20 |
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| UNII3_Comment = (<small>L</small>) |
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| PubChem =6987 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 48933 |
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| SMILES =CC1=CC(=O)C(CC1)C(C)C |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 6721 |
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| InChI = 1/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9H,4-5H2,1-3H3 |
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| InChIKey = YSTPAHQEHQSRJD-UHFFFAOYAC |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9H,4-5H2,1-3H3 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = YSTPAHQEHQSRJD-UHFFFAOYSA-N |
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|Section2={{Chembox Properties |
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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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| Formula =C<sub>10</sub>H<sub>16</sub>O |
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| MolarMass=152.23 g/mol |
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| MolarMass =152.23 g/mol |
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| Appearance= |
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| Density=0.9331 g/cm<sup>3</sup> |
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| Density =0.9331 g/cm<sup>3</sup> |
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| MeltingPt=232-233 °C |
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| MeltingPtC = 232 to 233 |
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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards= |
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| FlashPt= |
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| FlashPt = |
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| AutoignitionPt = |
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'''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"/> |
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'''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"/> |
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== Occurrence == |
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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> |
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] |
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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" /> |
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== Properties == |
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Piperitone is a colorless liquid with a distinct ] odor.<ref name=":1" /> |
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== Production == |
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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> |
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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> |
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== Reactions == |
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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> |
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==References== |
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