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	{{chembox		{{chembox
			| Verifiedfields = changed
	| verifiedrevid = 443506929
			| Watchedfields = changed
	| Name = Carvone
			| verifiedrevid = 443508171
	| ImageFile = Carvone.svg
	| ImageName = Carvone		| Name = Carvone
			| ImageFile = Carvone.svg
	| ImageFileL1 = S-carvone-stickModel.png
			| ImageName = Carvone
	| ImageSizeL1 = 120px
	| ImageFileR1 = (R)-(−)-carvone-from-xtal-3D-balls-B.png		| ImageFileL1 = (R)-(−)-carvone-from-xtal-3D-balls-B.png
			| ImageFileR1 = S-carvone-stickModel.png
	| ImageSizeR1 = 120px
			| PIN = 2-Methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one
	| IUPACName = 2-Methyl-5-(1-methylethenyl)-2-cyclohexenone<ref>Vollhardt, Peter and Neil Schore. Organic Chemistry, 5th ed. New York: Freeman, 2007. 173.</ref>
			| OtherNames = 2-Methyl-5-(prop-1-en-2-yl)cyclohex-2-enone<br />2-Methyl-5-(1-methylethenyl)-2-cyclohexenone<ref>{{cite book|last1 = Vollhardt|first1 = K. Peter C.|author-link2 = Neil E. Schore|last2 = Schore|first2 = Neil E.|title = Organic Chemistry|url = https://archive.org/details/studyguidesoluti00scho_0|url-access = registration|edition = 5th|location = New York|publisher = ]|year = 2007|page = }}</ref><br />Δ<sup>6:8(9)</sup>-''p''-Menthadien-2-one<br />1-Methyl-4-isopropenyl-Δ<sup>6</sup>-cyclohexen-2-one<br />Carvol (obsolete)
	| OtherNames = Δ<sup>6:8(9)</sup>-''p''-menthadien-2-one<br />1-methyl-4-isopropenyl-<br />Δ<sup>6</sup>-cyclohexen-2-one<br />carvol (obsolete)
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| ChEMBL_Ref = {{ebicite|correct|EBI}}		| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 15676		| ChEMBL = 15676
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
Line 18:		Line 18:
	| StdInChIKey = ULDHMXUKGWMISQ-UHFFFAOYSA-N		| StdInChIKey = ULDHMXUKGWMISQ-UHFFFAOYSA-N
	| CASNo = 99-49-0		| CASNo = 99-49-0
			| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo_Comment = (racemic)
			| CASNo_Comment = (''R''/''S'')
	| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo1 = 6485-40-1		| CASNo1 = 6485-40-1
			| CASNo1_Ref = {{cascite|correct|CAS}}
	| CASNo1_Comment = ((''R'')-Carvone)
			| CASNo1_Comment = (''R'')
	| UNII_Ref = {{fdacite|correct|FDA}}
			| CASNo2_Ref = {{cascite|correct|CAS}}
			| CASNo2 = 2244-16-8
			| CASNo2_Comment = (''S'')
			| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = 75GK9XIA8I		| UNII = 75GK9XIA8I
			| UNII_Comment = (''R''/''S'')
			| UNII1_Ref = {{fdacite|correct|FDA}}
			| UNII1 = 5TO7X34D3D
			| UNII1_Comment = (''R'')
			| UNII2_Ref = {{fdacite|correct|FDA}}
			| UNII2 = 4RWC1CMS3X
			| UNII2_Comment = (''S'')
	| InChI = 1/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3		| InChI = 1/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3
	| ChEBI_Ref = {{ebicite|correct|EBI}}		| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 38265		| ChEBI = 38265
			| InChIKey = ULDHMXUKGWMISQ-UHFFFAOYAB
	| SMILES = O=C1C(C\C=C1\C)C(C)=C (''R'')<br>O=C1C(C\C=C1\C)C(C)=C (''S'')
			| SMILES1 = O=C1C(C\C=C1\C)C(C)=C
	| InChIKey = ULDHMXUKGWMISQ-UHFFFAOYAB
			| SMILES1_Comment = (''R'')
	| SMILES1 = O=C1CC(C\C=C1\C)C(C)=C
			| SMILES2 = O=C1C(C\C=C1\C)C(C)=C
			| SMILES2_Comment = (''S'')
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID=21106424		| ChemSpiderID =21106424
	| ChemSpiderID_Comment=(racemic)		| ChemSpiderID_Comment =(''R''/''S'')
			| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID1=15855
			| ChemSpiderID1 =15855
	| ChemSpiderID1_Comment=(R-(-) enantiomer)
			| ChemSpiderID1_Comment =(''S'')
	| ChemSpiderID2=388655
			| ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID2_Comment=(S-(+) enantiomer)
			| ChemSpiderID2 =388655
	| RTECS = OS8650000 (''R'')<br />OS8670000 (''S'')
			| ChemSpiderID2_Comment =(''R'')
			| PubChem = 7439
			| RTECS = OS8650000 (''R'')<br />OS8670000 (''S'')
	| KEGG_Ref = {{keggcite|correct|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = C01767		| KEGG = C01767
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| Formula = C<sub>10</sub>H<sub>14</sub>O		| Formula = C<sub>10</sub>H<sub>14</sub>O
	| MolarMass = 150.22 g/mol		| MolarMass = 150.22 g/mol
	| Appearance = Clear, colorless liquid		| Appearance = Clear, colorless liquid
	| Density = 0.96 g/cm<sup>3</sup>		| Density = 0.96 g/cm<sup>3</sup>
	| Solubility = Insoluble (cold)<br />Slightly soluble (hot)/soluble in trace amounts		| Solubility = Insoluble (cold)<br />Slightly soluble (hot)/soluble in trace amounts
			| Solubility1 = Soluble
	| SolubilityOther = soluble
	| Solvent = Ethanol		| Solvent1 = ethanol
			| Solubility2 = Soluble
	| SolubilityOther = soluble
	| Solvent = Diethyl ether		| Solvent2 = diethyl ether
			| Solubility3 = Soluble
	| SolubilityOther = soluble
	| Solvent = Chloroform		| Solvent3 = chloroform
	| MeltingPt = 25.2 °C		| MeltingPtC = 25.2
			| BoilingPtC = 231
	| BoilingPt = 231 °C<br>91 °C (@ 5 mmHg)
			| BoilingPt_notes = (91&nbsp;°C @ 5{{nbsp}}mmHg)
	| pKa =
			| pKa =
	| SpecRotation = -61° (''R'')-Carvone<br />61° (''S'')-Carvone|
			| SpecRotation = −61° (''R'')-Carvone<br />61° (''S'')-Carvone
			| MagSus = −92.2×10<sup>−6</sup> cm<sup>3</sup>/mol
	}}		}}
	| Section7 = {{Chembox Hazards		|Section7={{Chembox Hazards
			| ExternalSDS =
	| ExternalMSDS =
	| MainHazards = inflammable		| MainHazards = Flammable
	| EUClass =		| NFPA-H = 1
	| NFPA-H = 1		| NFPA-F = 2
	| NFPA-F = 2		| NFPA-R = 0
	| NFPA-R = 0		| GHSSignalWord = Danger
			| GHSPictograms = {{GHS07}}{{GHS08}}{{GHS09}}
	| RPhrases = {{R22}}
	| SPhrases = {{S36}}		| HPhrases = {{H-phrases|304|315|317|411}}
			| PPhrases = {{P-phrases|261|264|270|272|273|280|301+310|301+312|302+352|321|330|331|332+313|333+313|362|363|391|405|501}}
	}}		}}
	| Section8 = {{Chembox Related		|Section8={{Chembox Related
	| Function = ketone		| OtherFunction_label = ketone
	| OtherFunctn = ]<br />]<br />]		| OtherFunction = ]<br />]<br />]
	| OtherCmpds = ], ],<br />], ]		| OtherCompounds = ], ],<br />], ]
	}}		}}
	}}		}}
	'''Carvone''' is a member of a family of chemicals called ].<ref name = simonsen>{{cite book | author = Simonsen, J. L. | year = 1953 | title = The Terpenes | edition = 2nd | volume = 1 | location = Cambridge | publisher = Cambridge University Press | pages = 394–408}}</ref> Carvone is found naturally in many ]s, but is most abundant in the oils from seeds of ] (''Carum carvi'') and ].<ref name = carvalho>De Carvalho, C. C. C. R; Da Fonseca, M. M. R. "Carvone: Why and how should one bother to produce this terpene" ''Food Chemistry'' '''2006''', 95, 413-422.</ref>		'''Carvone''' is a member of a family of chemicals called ]s.<ref name = simonsen>{{cite book | author = Simonsen, J. L. | year = 1953 | title = The Terpenes | edition = 2nd | volume = 1 | location = Cambridge | publisher = Cambridge University Press | pages = 394–408}}</ref> Carvone is found naturally in many ]s, but is most abundant in the oils from seeds of ] (''Carum carvi''), ] (''Mentha spicata''), and ].<ref name = carvalho>{{cite journal |author1= De Carvalho, C. C. C. R. |author2=Da Fonseca, M. M. R. | year = 2006 | title = Carvone: Why and how should one bother to produce this terpene | journal = Food Chemistry | volume = 95 | issue = 3| pages = 413–422 | doi = 10.1016/j.foodchem.2005.01.003 }}</ref>
			==Uses==
			===Food applications===
			Both carvones are used in the food and flavor industry. As the compound most responsible for the flavor of caraway, dill, and spearmint, carvone has been used for millennia in food.<ref name="carvalho"/> Food applications are mainly met by carvone made from limonene. ''R''-(−)-Carvone is also used for air freshening products and, like many ], oils containing carvones are used in ] and ].
			===Agriculture===
			''S''-(+)-Carvone is also used to prevent premature sprouting of potatoes during storage, being marketed in the Netherlands for this purpose under the name ''Talent''.<ref name="carvalho"/>
			===Insect control===
			''R''-(−)-Carvone has been approved by the ] for use as a ].<ref>{{Cite web|title=Document Display (PURL) {{!}} NSCEP {{!}} US EPA|url=https://nepis.epa.gov/Exe/ZyPURL.cgi?Dockey=P1007AOE.TXT|access-date=2020-11-10|website=nepis.epa.gov}}</ref>
	==Stereoisomerism and odor==		==Stereoisomerism and odor==
	Carvone forms two mirror image forms or ]: ''R''-(&ndash;)-carvone smells like ]. Its mirror image, ''S''-(+)-carvone, smells like ].<ref>{{cite journal | doi = 10.1021/jf60176a035 | title=Chemical and sensory data supporting the difference between the odors of the enantiomeric carvones | author= Theodore J. Leitereg, Dante G. Guadagni, Jean Harris, Thomas R. Mon, and Roy Teranishi | journal=] | volume=19 | issue=4 | year=1971 | pages=785}}</ref> The fact that the two enantiomers are perceived as smelling differently is proof that ]s must contain ] groups, allowing them to respond more strongly to one enantiomer than to the other. Not all enantiomers have distinguishable odors. ]s have also been found to be able to discriminate between carvone enantiomers.<ref>Laska, M.; Liesen, A.; Teubner, P. ''American Journal of Physiology- Regulatory Integrative and Comparative Physiology'', '''1999''', ''277'', R1098-R1103.</ref>		Carvone forms two mirror image forms or ]: ''R''-(−)-carvone, has a sweetish minty smell, like ] leaves. Its mirror image, ''S''-(+)-carvone, has a spicy aroma with notes of rye, like ] seeds.<ref>{{cite journal | doi = 10.1021/jf60176a035 | title=Chemical and sensory data supporting the difference between the odors of the enantiomeric carvones |author1=Theodore J. Leitereg |author2=Dante G. Guadagni |author3=Jean Harris |author4=Thomas R. Mon |author5=Roy Teranishi | journal=] | volume=19 | issue=4 | year=1971 | pages=785–787}}</ref><ref>{{Cite journal|doi=10.1016/B978-0-12-416641-7.00035-3|title=Carvone (Mentha spicata L.) Oils - Essential Oils in Food Preservation, Flavor and Safety - Chapter 35 | year=2016|journal=Essential Oils in Food Preservation, Flavor and Safety|pages=309–316 | last1 = Morcia | first1 = Caterina | last2 = Tumino | first2 = Giorgio | last3 = Ghizzoni | first3 = Roberta | last4 = Terzi | first4 = Valeria}}</ref> The fact that the two enantiomers are perceived as smelling different is evidence that ]s must respond more strongly to one enantiomer than to the other. Not all enantiomers have distinguishable odors. ]s have also been found to be able to discriminate between carvone enantiomers.<ref>{{cite journal | last1 = Laska | first1 = M. | last2 = Liesen | first2 = A. | last3 = Teubner | first3 = P. | year = 1999 | title = Enantioselectivity of odor perception in squirrel monkeys and humans| journal = American Journal of Physiology. Regulatory, Integrative and Comparative Physiology | volume = 277 | issue = 4| pages = R1098–R1103 | doi=10.1152/ajpregu.1999.277.4.r1098| pmid = 10516250 }}</ref>
	The two forms are also referred to by older names, with '']''-, ''d''- referring to ''R''-carvone, and '']''-, ''l''- referring to ''S''-carvone.		The two forms are also referred to, in older texts, by their optical rotations of ] referring to ''R''-(−)-carvone, and ] referring to ''S''-(+)-carvone. Modern naming refers to levorotatory isomers with the sign (-) and dextrorotatory isomers with the sign (+) in the systematic name.
	==Occurrence==		==Occurrence==
	''S''-(+)-Carvone is the principal constituent (50-70%) of the oil from caraway seeds (''Carum carvi''),<ref>Hornok, L. ''Cultivation and Processing of Medicinal Plants'', John Wiley & Sons, Chichester, UK, 1992.</ref> which is produced on a scale of about 10 tonnes per year.<ref name = carvalho/> It also occurs to the extent of about 40-60% in ] seed oil (from ''Anethum graveolens''), and also in ] peel oil. ''R''-(&ndash;)-Carvone is present at levels greater than 51% in spearmint oil ('']''), which is produced on a scale of around 1500 tonnes annually. This isomer also occurs in ] oil. Some oils, like ] oil, contain a mixture of both enantiomers. Many other natural oils, for example ] oil, contain lower concentrations of carvones.		''S''-(+)-Carvone is the principal constituent (60–70%) of the oil from caraway seeds (''Carum carvi''),<ref>Hornok, L. ''Cultivation and Processing of Medicinal Plants'', John Wiley & Sons, Chichester, UK, 1992.</ref> which is produced on a scale of about 10 tonnes per year.<ref name = carvalho/> It also occurs to the extent of about 40–60% in ] seed oil (from ''Anethum graveolens''), and also in ] peel oil. ''R''-(−)-Carvone is also the most abundant compound in the essential oil from several species of mint, particularly spearmint oil ('']''), which is composed of 50–80% ''R''-(−)-carvone.<ref name="Chemical composition of spearmint oil"> {{Webarchive|url=https://web.archive.org/web/20120410220726/http://scienceofacne.com/mint-essential-oil/|date=2012-04-10}}, Chemical composition of essential oil from several species of mint (''Mentha spp.'')</ref> Spearmint is a major source of naturally produced ''R''-(−)-carvone. However, the majority of ''R''-(−)-carvone used in commercial applications is synthesized from ''R''-(+)-limonene.<ref name=Ullmann>{{cite book |doi=10.1002/14356007.a11_141 |chapter=Flavors and Fragrances |title=Ullmann's Encyclopedia of Industrial Chemistry |year=2003 |last1=Fahlbusch |first1=Karl-Georg |last2=Hammerschmidt |first2=Franz-Josef |last3=Panten |first3=Johannes |last4=Pickenhagen |first4=Wilhelm |last5=Schatkowski |first5=Dietmar |last6=Bauer |first6=Kurt |last7=Garbe |first7=Dorothea |last8=Surburg |first8=Horst |isbn=978-3-527-30673-2}}</ref> The ''R''-(−)-carvone isomer also occurs in ] oil. Some oils, like ] oil, contain a mixture of both enantiomers. Many other natural oils, for example ] oil, contain trace quantities of carvones.
	==History==		==History==
	Caraway was used for medicinal purposes by the ancient Romans,<ref name = carvalho/> but carvone was probably not isolated as a pure compound until Varrentrapp obtained it in 1841.<ref name = simonsen/> It was originally called ''carvol'' by Schweizer. Goldschmidt and Zűrrer identified it as a ketone related to ], and the structure was finally elucidated by ] in 1894.<ref>Wagner, G. ''Chemische Berichte'' '''1894''', ''27'', 2270.</ref>		Caraway was used for medicinal purposes by the ancient Romans,<ref name = carvalho/> but carvone was probably not isolated as a pure compound until Franz Varrentrapp (1815–1877) obtained it in 1849.<ref name = simonsen/><ref>''Handwörterbuch der reinen und angewandten Chemie'' (Braunschweig, (Germany): Friedrich Vieweg und Sohn, 1849), vol. 4, . </ref> It was originally called ''carvol'' by Schweizer. Goldschmidt and Zürrer identified it as a ketone related to ],<ref>Heinrich Goldschmidt and Robert Zürrer (1885) ''Berichte der Deutschen Chemischen Gesellschaft'', '''18''' : 1729–1733.</ref> and the structure was finally elucidated by ] (1849–1903) in 1894.<ref>Georg Wagner (1894) (On the oxidation of cyclic compounds), ''Berichte der Deutschen chemischen Gesellschaft zu Berlin'', vol. 27, pages 2270-2276. .); (2) Wagner did not prove the structure of carvone in this paper; he merely proposed it as plausible; its correctness was proved later.]</ref>
	==Preparation==		==Preparation==
			Carvone can be obtained from natural sources but insufficient is available to meet demand. Instead most carvone is produced from ].
	The dextro-form is obtained practically pure by the fractional distillation of ] oil; the laevo-form from the oils containing it, by first forming its addition compound with ], decomposing this by ] in ], and distilling the product in a current of steam. It may be synthetically prepared from ], alcoholic converting this compound into 1-carvoxime, which on boiling with dilute ] yields l-carvone. The major use of d-limonene is as a precursor to carvone. The large scale availability of orange rinds, a byproduct in the production of orange juice, has made limonene cheaply available, and synthetic carvone correspondingly inexpensively prepared.<ref name=Ullmann>Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, Kurt Bauer, Dorothea Garbe, Horst Surburg “Flavors and Fragrances“ in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. {{DOI|10.1002/14356007.a11_141}}.</ref>
			The dextro-form, ''S''-(+)-carvone is obtained practically pure by the fractional distillation of ] oil. The levo-form obtained from the oils containing it usually requires additional treatment to produce high purity ''R''-(−)-carvone. This can be achieved by the formation of an addition compound with ], from which carvone may be regenerated by treatment with ] followed by steam distillation.
			Carvone may be synthetically prepared from limonene by first treating limonene ]. Heating this nitroso compound gives carvoxime. Treating carvoxime with ] yields carvone.<ref>{{cite journal | doi = 10.1021/ed057p741 | volume=57 | issue=10 | title=Conversion of (+)-Limonene to (−)-Carvone: An organic laboratory sequence of local interest | year=1980 | journal=Journal of Chemical Education | page=741 | last1 = Rothenberger | first1 = Otis S. | last2 = Krasnoff | first2 = Stuart B. | last3 = Rollins | first3 = Ronald B.| bibcode=1980JChEd..57..741R }}</ref> This procedure affords ''R''-(−)-carvone from ''R''-(+)-limonene.
			The major use of d-limonene is as a precursor to ''S''-(+)-carvone. The large scale availability of orange rinds, a byproduct in the production of orange juice, has made limonene cheaply available, and synthetic carvone correspondingly inexpensively prepared.<ref name=Ullmann2>Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, Kurt Bauer, Dorothea Garbe, Horst Surburg "Flavors and Fragrances" in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a11_141}}.</ref>
	The ] of carvone is by oxidation of ].		The ] of carvone is by oxidation of ].
	==Chemical properties==		==Chemical properties==
	===Reduction===		===Reduction===
			There are three double bonds in carvone capable of reduction; the product of reduction depends on the reagents and conditions used.<ref name="simonsen"/> Catalytic hydrogenation of carvone ('''1''') can give either ] ('''2''') or ] ('''3'''). ] and ] reduce carvone to give ] ('''4'''). ] using ] and ] effects reduction of the ] group only to provide ] ('''5'''); a combination of ] and ] (]) is also effective. ] and ] give ] ('''6''') via a ].
	There are three double bonds in carvone capable of reduction; the product of reduction depends on the reagents and conditions used.<ref name="simonsen"/> Catalytic hydrogenation of carvone ('''1''') can give either ] ('''2''') or ] ('''3'''). ] and ] reduce carvone to give ] ('''4'''). ] using ] and ] effects reduction of the ] group only to provide ] ('''5'''); a combination of ] and ] (]) is also effective. ] and ] give ] ('''6''') via a ].
	]		]
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	===Conjugate additions===		===Conjugate additions===
			As an ], carvone undergoes ] of nucleophiles. For example, carvone reacts with ] to place a ] group ''trans'' to the isopropenyl group with good ]. The resulting ] can then be allylated using ] to give ketone '''11'''.<ref name=Srikrishna1998>{{cite journal
	As an ], carvone undergoes ] of nucleophiles. For example, carvone reacts with ] to place a ] group ''trans'' to the isopropenyl group with good ]. The resulting ] can then be allylated using ] to give ketone '''11'''.<ref name=Srikrishna1998>{{cite journal
	| author = Srikrishna, A.		| author = Srikrishna, A.
	| coauthors = Jagadeeswar Reddy, T.		|author2=Jagadeeswar Reddy, T.
	| year = 1998		| year = 1998
	| title = Enantiospecific synthesis of (+)-(1S, 2R, 6S)-1, 2-dimethylbicyclo nonan-8-one and (-)-7-epibakkenolide-A		| title = Enantiospecific synthesis of (+)-(1S, 2R, 6S)-1, 2-dimethylbicyclo </nowiki> nonan-8-one and (−)-7-epibakkenolide-A
	| journal = Tetrahedron		| journal = Tetrahedron
	| volume = 54		| volume = 54
	| issue = 38		| issue = 38
	| pages = 11517–11524		| pages = 11517–11524
	| url = http://linkinghub.elsevier.com/retrieve/pii/S0040402098006723
	| accessdate = 2008-01-22
	| doi = 10.1016/S0040-4020(98)00672-3		| doi = 10.1016/S0040-4020(98)00672-3
	}}</ref>		}}</ref>
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	<!-- More to follow -->		<!-- More to follow -->
	==Uses==		===Other===
			Being available inexpensively in enantiomerically pure forms, carvone is an attractive starting material for the ] ] of ]. For example, (''S'')-(+)-carvone was used to begin a 1998 synthesis of the terpenoid ]:<ref>(a) Shing, T. K. M.; Jiang, Q; Mak, T. C. W. '']'' '''1998''', ''63'', 2056-2057. (b) Shing, T. K. M.; Tang, Y. ''J. Chem. Soc. Perkin Trans. 1'' '''1994''', 1625.</ref>
	Both carvones are used in the food and flavor industry.<ref name="carvalho"/> ''R''-(-)-Carvone is also used for air freshening products and, like many ], oils containing carvones are used in ] and ].
			:]
	===Food applications===
	As the compound most responsible for the flavor of caraway, dill and spearmint, carvone has been used for millennia in food.<ref name="carvalho"/> Wrigley's Spearmint Gum is soaked in ''R''-(&ndash;)-carvone and powdered with ].
	===Agriculture===
	''S''-(+)-Carvone is also used to prevent premature sprouting of potatoes during storage, being marketed in the Netherlands for this purpose under the name ''Talent''.<ref name="carvalho"/>
	===Insect Control===
	''R''-(–)-carvone has been proposed for use as a ], and the ] is reviewing a request to register it as a pesticide.<ref>{{cite journal|last=ENVIRONMENTAL PROTECTION AGENCY|date=March 4, 2009|title=Pesticide Products; Registration Application|journal=Federal Register|volume=74|issue=41|pages=9396–9397|url=http://frwebgate4.access.gpo.gov/cgi-bin/TEXTgate.cgi?WAISdocID=194285304687+0+1+0&WAISaction=retrieve}}</ref>
	===Organic synthesis===
	Carvone is available inexpensively in both enantiomerically pure forms, making it an attractive starting material for the ] ] of ]. For example, (''S'')-(+)-carvone was used to begin a 1998 synthesis of the terpenoid ]<ref>(a) Shing, T. K. M.; Jiang, Q; Mak, T. C. W. '']'' '''1998''', ''63'', 2056-2057. (b) Shing, T. K. M.; Tang, Y. ''J. Chem. Soc. Perkin Trans. 1 '''1994''', 1625.</ref>:
	]
	==Metabolism==		==Metabolism==
	In the body, ''in vivo'' studies indicate that both enantiomers of carvone are mainly metabolized into ], ] and ].<ref>Engel, W. ''J. Agric. Food Chem.'', '''2001''', ''49'' (8), 4069-4075.</ref> ] is also formed as a minor product via reduction by ]. (4''S'')-(+)-carvone is likewise converted to (4''S'',6''S'')-(+)-carveol.<ref>Jager, W.; Mayer, M.; Platzer, P.; Reznicek, G.; Dietrich, H.; Buchbauer, G.; ''Journal of Pharmacy and Pharmacology'' '''2000''', ''52'', 191-197.</ref> This mainly occurs in the liver and involves ] and ].		In the body, ''in vivo'' studies indicate that both enantiomers of carvone are mainly metabolized into ], ] and ].<ref>{{cite journal | author = Engel, W. | journal = J. Agric. Food Chem. | year = 2001 | volume = 49 | issue = 8 | pages = 4069–4075 | doi = 10.1021/jf010157q | pmid = 11513712 | title = In vivo studies on the metabolism of the monoterpenes ''S''-(+)- and ''R''-(−)-carvone in humans using the metabolism of ingestion-correlated amounts (MICA) approach}}</ref> ] is also formed as a minor product via reduction by ]. (+)-Carvone is likewise converted to (+)-carveol.<ref>{{cite journal |author1=Jager, W. |author2=Mayer, M. |author3=Platzer, P. |author4=Reznicek, G. |author5=Dietrich, H. |author6=Buchbauer, G. | journal = Journal of Pharmacy and Pharmacology | year = 2000 | volume = 52 | pages = 191–197 | doi = 10.1211/0022357001773841 | pmid = 10714949 | title = Stereoselective metabolism of the monoterpene carvone by rat and human liver microsomes | issue = 2|s2cid=41116690 | doi-access = free }}</ref> This mainly occurs in the liver and involves ] and ].
	==References==		==References==
			{{Reflist}}
	<references/>
	<!-- Dead note "Srikrishna": Srikrishna, A.; Jagadeeswar Reddy, T. ''Tetrahedron'', '''1998''', ''54'', 11517-11524. -->		<!-- Dead note "Srikrishna": Srikrishna, A.; Jagadeeswar Reddy, T. ''Tetrahedron'', '''1998''', ''54'', 11517-11524. -->
			==External links==
			* at '']'' (University of Nottingham)
			{{Authority control}}
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