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2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-on
DL-carvone · 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)- · Cavone · Karvon · p-Mentha-6(1),8-dien-2-one · 2-methyl-5-(1-methylethenyl)-2-Cyclohexen-1-one · 5-Isopropenyl-2-methyl-2-cyclohexen-1-one · (-)-2-Methyl-5-isopropenyl-2-cyclohexen-1-one
Identifikatoren & physikalische Daten
| CAS No. | 22327-39-5 |
|---|---|
| Summenformel | C10H14O |
| Durchschnittliche Molmasse | 150,22 g/mol |
| Monoisotopische Masse | 150,10446507 g/mol |
| SMILES | C=C(C)C1CC=C(C)C(=O)C1 |
| InChIKey | ULDHMXUKGWMISQ-UHFFFAOYSA-N |
| PubChem CID | 7439 |
| ChEMBL | CHEMBL15676 |
| ChEBI | CHEBI:38265 |
| EC No. | 202-759-5 |
| DTXSID | DTXSID8047426 |
| Lokaler Name | 2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-on |
Chemische & physikalische Eigenschaften
| XLogP | 2,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 17,1 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 11 |
| Formalladung | 0 |
| Komplexität | 223 |
| Stoffklassen | Biological Agents -> Plant Oils and Extracts |
| Kosmetika | Cosmetics ingredient -> FlavorFragranceMasking |
| Duftstoffe | Fragrance Ingredient (Carvone) -> IFRA transparency List |
| Pestizide | Agrochemicals -> Pesticide active substancesActive substance -> EU Pesticides database: Approved |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Dichte | 0.956-0.9610.956-0.9600.963 g/cm3 (15℃) |
| Aromastoffe | EU Flavoring substances |
| Color/Form | Pale-yellowish or colorless liquid |
| Löslichkeit | Colorless to pale straw colored liquidspearmint odorsolubility in 70% alcohol: 1:2 /L-Carvone/In water, 1300 mg/L at 25 °C /L-Carvone/Colorless to light yellow liquidsolubility in 60% alcohol: 1:5 /D-Carvone/Soluble in alcohol, ether, chloroform, propylene glycol, mineral oilsinsoluble in glycerolsoluble in propylene glycol and most fixed oilsmiscible with alcohol1 ml in 5 ml 60% alcohol (in ethanol)Chloroform (Slightly), Methanol (Slightly) |
| Human Drugs | Pharmaceuticals |
| Siedepunkt | 230-231 °C230 °C232℃ (760.0 Torr) |
| Schmelzpunkt | MP: 25.2 °C. Very soluble in ethanolsoluble in ether, carbon tetrachloride, chloroform /L-Carvone/MP: <15 °C. Very soluble in ethanolsoluble in ether, chloroform /D-Carvone/230℃ |
| Brechungsindex | 1.710 |
| FEMA | 2249 | CARVONE |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Oil |
| Farbe | Light Orange to Light Brown |
| Geruch | at 100.00 %. minty licorice |
| Geruchsart | minty |
| JECFA Number | 380 |
| Henry-Konstante | 1.3×10-1 mol/(m3Pa) at 25℃, HSDB (2015) |
| Dielektrizitätskonstante | 11.0(22℃) |
| Stabilität | Light Sensitive |
| Kosmetik-Inhaltsstoffe Funktionen | PERFUMINGFLAVOURINGFRAGRANCE |
| LogP (Verteilungskoeffizient) | 3.07 |
| CAS Datenbank | 99-49-0 |
| EPA chemische Informationen | 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)- (99-49-0) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH317: May cause an allergic skin reaction [Warning Sensitization, Skin]P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 0.2% (1 of 457) of reports.H302 (59.5%): Harmful if swallowed [Warning Acute toxicity, oral] |
|---|---|
| Regulatorische Informationen | Chemical: 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-Hazard Traits - Fragrance Allergen08/44/EC, Reg. (EU) 2018/917, Reg. (EU) 2019/706, Reg. (EU) 2020/653, Reg. (EU) No 540/2011Carvone: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | Included in list of established contact allergens in humans[EC: Scientific Committee on Consumer Safety: Fragrance allergens in cosmetic products (2011)] Emergency treatment: Essential oilsEssential oils can cause CNS depression and aspiration pneumonia after ingestionCommercial products of essential oils usually contain concentrations of 1% to 20%, and a potentially toxic exposure is 5-15 mL[HSDB] Causes somnolence and ataxia in lethal-dose feeding studies of rats[RTECS] |
| FDA-Anforderungen | Synthetic flavoring substances and adjuvants /for human consumption/ that are generally recognized as safe for their intended use, within the meaning of section 409 of the Act. d- or l-Carvone is included on this list.Synthetic flavoring substances and adjuvants /for animal drugs, feeds, and related products/ that are generally recognized as safe for their intended use, within the meaning of section 409 of the Act. d- or l-Carvone is included on this list. |
| Special Reports | DHHS/NTPToxicology & Carcinogenesis Studies of d-Carvone in B6C3F1 Mice (Gavage Studies) Technical Report Series No. 381 (1990) NIH Publication No. 90-2836 |
| Hazard Classes and Categories | Acute Tox. 4 (59.5%)Skin sensitisation - category 1Skin Sens. 1 |
| Entsorgungsverfahren | SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in air, soil or watereffects on animal, aquatic and plant lifeand conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. |
| Wechselwirkungen | The objective was to investigate the difference in penetration enhancing effect of R-carvone, S-carvone and RS-carvone on the in vitro transdermal drug permeation. In vitro permeation studies were carried out across neonatal rat epidermis from 2% w/v HPMC (hydroxypropyl methylcellulose) gel containing 4% w/v of nicorandil (a model drug) and a selected concentration (12% w/v) of either R-carvone, S-carvone, or RS-carvone against a control. The stratum corneum (SC) of rats was treated with vehicle (70 %v/v ethanol-water) or ethanolic solutions of 12% w/v R-carvone, S-carvone or RS-carvone. The enhancement ratio (ER) of R-carvone, S-carvone, and RS-carvone when compared to control was about 37.1, 31.2, and 29.9, respectively, indicating enantioselective penetration enhancing effect of carvone enantiomers. Furthermore, there was a significant decrease in the lag time required to produce a steady-state flux of nicorandil with S-carvone when compared to R-carvone and RS-carvone. DSC and FT-IR studies indicate that the investigated enantiomers of carvone exhibit a difference in their ability to affect the cellular organization of SC lipids and proteins thereby showing enantioselective transdermal drug permeation. It was concluded that R-carvone exhibited a higher penetration enhancing activity on transdermal permeation of nicorandil when compared to its S-isomer or racemic mixture.Naturally occurring compounds belonging to the two chemical groups were studies for their capacities to inhibit N-nitrosodiethylamine-induced carcinogenesis in female A/J mice. One group consists of organosulfur compounds found in Allium species, including garlic, onions, leeks, and shallots, and the other, two monoterpenes, i.e., D-limonene and D-carvone. In these experiments D-limonene and D-carvone were tested and reduced forestomach tumor formation by slightly over 60% and pulmonary adenoma formation by about 35%. The results of these studies provide evidence of an increasing diversity of naturally occurring compounds having the capacity to inhibit nitrosamine carcinogenesis.Carvone is a monoterpene that is present in spearmint (Mentha spicata) and caraway (Carum carvi) essential oils and has been shown to have anticonvulsant effects, likely through the blockade of voltage-gated sodium channels, and anxiolytic-like effects. Considering that some anticonvulsants that blocked voltage-gated sodium channels (e.g., sodium valproate and carbamazepine) exert clinical antimanic effects, the aim of the present study was to evaluate (R)-(-)-carvone and (S)-(+)-carvone in animal models of mania (i.e., hyperlocomotion induced by methylphenidate and sleep deprivation). Mice that were treated with methylphenidate (5 mg/kg) or sleep-deprived for 24 hr using a multiple-platform protocol exhibited an increase in locomotor activity in an automated activity box. This effect was blocked by pretreatment with acute (R)-(-)-carvone (50-100 mg/kg), (S)-(+)-carvone (50-100 mg/kg), and lithium (100 mg/kg, positive control). These doses did not alter spontaneous locomotor activity in the methylphenidate-induced experiments while (S)-(+)-carvone decreased spontaneous locomotor activity in sleep deprivation experiment, indicating a sedative effect. Chronic 21-day treatment with (R)-(-)-carvone (100 mg/kg), (S)-(+)-carvone (100 mg/kg), and lithium also prevented methylphenidate-induced hyperactivity. The present results suggest that carvone may have an antimanic-like effect. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 140(SRC), determined from a structure estimation method(2), indicates that carvone is expected to have high mobility in soil(SRC). Volatilization of carvone from moist soil surfaces may be an important fate process(SRC) given an estimated Henry's Law constant of 7.73X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Carvone has an estimated vapor pressure of 0.115 mm Hg(SRC), determined from a fragment constant method(2), and exists as a liquid under environmental conditionstherefore, carvone may volatilize from dry soil(SRC). Using the optically active form L-carvone in the Manometric Respirometry test, 90% biodegradation of L-carvone was reached in 4 weeks(4) suggesting that biodegradation of carvone may be an important environmental fate process in soil(SRC).[(1) Swann RL et alRes Rev 85: 17-28 (1983) (2) US EPAEstimation Program Interface (EPI) Suite. Ver. 4.1. Nov, 2012. Available from, as of June 14, 2016: http://www2.epa.gov/tsca-screening-tools (3) Meylan WM, Howard PHEnviron Toxicol Chem 10: 1283-93 (1991) (4) ECHARegistered Substances. L-p-mentha-1AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 140(SRC), determined from a structure estimation method(2), indicates that carvone is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 7.73X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 11 hours and 9 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 30(SRC), from an estimated log Kow of 3.07(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Using the optically active form L-carvone in the Manometric Respirometry test, 90% biodegradation of L-carvone was reached in 4 weeks(6) suggesting that biodegradation of carvone may be an important environmental fate process in water(SRC).[(1) Swann RL et alEstimation Program Interface (EPI) Suite. Ver. 4.1. Nov, 2012. Available from, as of June 14, 2016: http://www2.epa.gov/tsca-screening-tools (3) Lyman WJ et alHandbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990) (4) Meylan WM, Howard PHEnviron Toxicol Chem 10: 1283-93 (1991) (5) Franke C et alChemosphere 29: 1501-14 (1994) (6) ECHAATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), carvone, which has an estimated vapor pressure of 0.115 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase carvone is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 3 hours(SRC), calculated from its rate constant of 1.41X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Carvone contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). |
| Lebensmitteluntersuchungswerte | Carvone has been detected as a volatile component of roasted filberts(1) and in concentrated aqueous orange essences(2). |
| Unerwünschte Wirkungen | Neurotoxin - Acute solvent syndrome |
| Toxizitätsübersicht | IDENTIFICATION AND USE: Carvone is a pale-yellowish or colorless liquid. The following uses have been identified for carvone: pesticide, feed additive, veterinary medicine use, flavoring substance and natural food occurrence, personal care products: D- and L-carvone are used in a variety of non-food consumer products, including cosmetics and personal care products. Some of these, such as toothpaste and mouthwash may result in oral intake of carvone. It is also used as natural insect repellent. HUMAN EXPOSURE AND TOXICITY: The sensitizing potential of l-carvone has been considered low, but it has occasionally caused contact allergy in users of spearmint toothpaste and chewing gum. L-Carvone inhibited proliferation of MCF 7 and MDA MB 231 cells and inhibited the migration of breast cancer cell lines. L-carvone induced apoptosis as observed by nuclei fragmentation and the presence of apoptotic bodies in DAPI, AnnexinV/propidium iodide, and TUNEL assays. l-carvone exposure arrested MCF 7 cells in S phase of the cell cycle. DNA damage caused by L-carvone was apparent from the increased tail moment in comet assay, which could be induced by an increase in ROS that was measured using a fluorescence probe. ANIMAL STUDIES: Clinical signs after acute exposure in mice and rats were different depending on the route of exposure. After acute oral administration, these included hunched posture and lethargy and occasional body tremor with no abnormalities at necropsy. After acute dermal exposure no systemic or skin effects were observed whereas after inhalation of carvone, respiratory effects were noted as well as alopecia and impairment of body weight gain. Carvone caused transient depression of central nervous system activity in mice. In developmental study rats were given 0, 3, 10 or 30 mg/kg/day of D-carvone (95%) for 10 weeks prior to mating until termination. There were no differences between treated and control animals in any of the indices of reproductive performance or in the results of the sperm morphology and motility measurements. Males of the F0 generation given 30 mg/kg bw/day had increased relative kidney weights. Histopathology of the male kidneys showed changes typical of alpha2u-globulin nephropathy at all doses. No other histopathological changes were reported and no similar changes were observed in females. Males of the F1 generation given 30 and 90 mg/kg bw/day had increased mean relative liver and kidney weights. Histopathology of the male kidneys showed changes typical of alpha2u-globulin nephropathy at all doses. No differences were seen in females and no other histopathological changes were reported. Carvone showed equivocal results for mutagenicity in a sister chromatid exchange study and a chromosomal aberration study with Chinese hamster ovary cells. Results from an in vivo UDS assay in liver and an in vivo micronucleus test were negative while those of an in vitro test for chromosome aberrations were not clear-cut. It was concluded that carvone should not be considered genotoxic. Groups of 50 male and 50 female mice were administered 0, 375, or 750 mg/kg D-carvone in corn oil by gavage, 5 days/wk for 103 weeks. Under the conditions of these two yr gavage studies, there was no evidence for the carcinogenic activity of D-carvone for male or female mice. |
| Ökotoxizitätsauszüge | /OTHER TERRESTRIAL SPECIES/ The efficacy of 30 aromatic compounds and their mutual binary combinations was assessed for acute toxicity agains the larvae Culex quinquefasciatus. Based on comparison of the lethal doses, thymol and p-cymene were selected as the most effective (LD50 = 18 and 21 mg/L, respectively, and LD90 = 25 and 30 mg/L, respectively). Although the LD50 for terpinolene and trans-anethole was also estimated at 21 mg/L), their LD90 was significantly higher compared to the substances above (245 and 34 mg/L, respectively). In total, 435 binary combinations were tested, of which 249 combinations showed a significant synergistic effect, while 74 combinations showed a significant antagonistic effect on mortality. Only nine substances were identified as being able to create a synergistic effect with more than 20 substances: limonene, trans-anethole, 4-allylanisole, carvacrol, isoeugenol, menthone, carvone, borneol, and camphor. The highest synergistic effect on larval mortality was achieved for the combinations: eugenol and isoeugenol, carvone and carvacrol, carvone and 4-allylanisole, carvone and a-terpineol, carvone and menthone, limonene and trans-anethole, limonene and menthone, a-pinene and menthone, beta-citronellol and menthone, carvacrol and 4-allylanisole, carvacrol and terpineol, a-terpinene and trans-anethole, camphor and menthone, camphene and menthone, and 4-allylanisole and menthone. Significant differences between achieved mortality and the mutual mixing ratio were found for the five selected binary mixtures that had shown the most significant synergistic effect in the previous tests. The mixture of limonene and trans-anethole showed the highest mortality, with the mixing ratio 1:1the mixture of eugenol and isoeugenol caused 90.2% mortality, with the mixing ratio 1:3. One hundred percent mortality was achieved if carvacrol was contained in a mixture with carvone in a ratio >2. After a comparison of all our results, based on our experiments, we can choose two pairs that caused mortality higher than 90% in concentrations lower than 20 mg/L: limonene and trans-anethole (with the mixing ratio 1:1), and carvone and carvacrol (with the mixing ratio 1:2-3). The information gained can thus be used in the development of new botanical insecticides based on essential oils (EOs) and particularly in the creation of formulations. |
| Plant Concentrations | Carvone has been reported in over 140 plants(1).Ground caraway seed yields up to 7% of volatile oil, having up to 60% carvone as principal constituent...L-Carvone has been reported at 480 ppm in the plant of Chrysanthemum balsamita (Balsamite, CostmaryAsteraceae). It was detected, not quantified in Aloysia citrodora (Lemon VerbenaVerbenaceae)(1). /L-Carvone/D-Carvone has been reported at 325 ppm in the plant of Tagetes minuta (Dwarf MarigoldAsteraceae). It was detected, not quantified in Aralia cordata (UdoAraliaceae) and Pimpinella anisum (AniseApiaceae)(1). /D-Carvone/ |
| Ongoing Test Status | EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPAICSS Dashboard ApplicationAvailable from, as of July 7, 2016: http://actor.epa.gov/dashboard/] |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc of carvone can be estimated to be 140(SRC). According to a classification scheme(2), this estimated Koc value suggests that carvone is expected to have high mobility in soil. |
| Natural Pollution Sources | Carvone is found in gingergrass oil and is the main constituent of spearmint oil(1,2). The optically active form D-carvone is found in caraway seed and dill seed oil and it has been isolated from mandarin peel oil (Citrus reticulata blanco, Rutaceae)(1). Optically active form L-carvone is found in spearmint and kuromoji oils(1). The most significant natural sources of carvone are spearmint, dill, and caraway. The term spearmint is applied to various Mentha species including M. cardiaca, M. gracilis, M. spicata, and M. viridis and these usually contain 55-75% of the (R)-(-)-enantiomer. The (S)-(+)-enantiomer is found in dill (Anethum graveolens) at levels of 30-65% and at 50-75% in caraway (Carum carvi)(3).Carvone occurs in several plants and plant tissues(1). Optically active and inactive forms of carvone have been reported among constituents of about 70 essential oils(2). D-Carvone is present in Carvi sp., Anethum graveolens, Anethum sowa, Lippia carviodora, Mentha arvensis, etc. L-Carvone is present in Mentha viridis var crispa, Mentha longifolia from South Africa, Eucalyptus globulus, and several mint species. Racemic or DL-carvone is present in ginger grass, Litsea guatemaleusis, lavender, and Artemisia ferganensis(2). |
| Human Toxicity Excerpts | /HUMAN EXPOSURE STUDIES/ The terpene L-carvone is one of the main constituents of spearmint oil. The sensitizing potential of L-carvone has been considered low, but it has occasionally caused contact allergy in users of spearmint toothpaste and chewing gum. L-Carvone is also an oxidation product of D-limonene that occurs in solvents used increasingly in industry. We included L-carvone 5% pet. in the standard patch test series. In the 1st year, 541 patients were tested and 15 (2.77%) had positive, and 12 doubtful positive (?+) reactions to L-carvone. The strongest reactions were observed in 9 patients with concomitant Compositae sensitivity. The key clinical features and other contact allergies of the patients are presented. When re-testing with L-carvone in the same or lower concentrations, only 2 out of 8 patients had positive reactions. Possible reasons for this discrepancy are discussed in terms of cross-reactions, concomitant sensitization, excited skin syndrome, irritancy and facilitated immunological response. /L-Carvone//HUMAN EXPOSURE STUDIES/ A maximization test was carried out on 25 volunteers. The material was tested at a concentration of 1% in petrolatum and produced no sensitization reactions. /L-Carvone//HUMAN EXPOSURE STUDIES/ L-Carvone tested at concentration of 1% in petrolatum produced no irritation after a 48-hr closed-patch test in 25 human subjects. /L-Carvone//CASE REPORTS/ Food or flavoring intolerance has been demonstrated in 14 out of 80 patients with oro-facial granulomatosis. Provoking molecules include cinnamaldehyde, carvone, and piperitone, although a wide range of food or flavorings may be implicated. The nature of the reaction is not understood but does not seem to involve an IgE mediated response. At present the only reliable way of detecting specific provoking factors is by the use of an elimination diet.For more Human Toxicity Excerpts (Complete) data for CARVONE (7 total), please visit the HSDB record page. |
| Artificial Pollution Sources | Carvone's production and use as a flavoring agent, in perfumery and soaps, and as a carminative(1) may result in its release to the environment through various waste streams(SRC). The optically acrive form, L-carvone's production may result in its release to the environment through various waste streamsits use as a pesticide active ingredient(2) will result in its direct release to the environment(SRC). |
| TSCA-Inventar-Status | TSCA listed |
| Gefahrstoffdaten | 99-49-0(Hazardous Substances Data) |
Anwendungen & Verwendung
Occurrence
The optically active and inactive forms have been reported among the constituents of about 70 essential oils. The dextro form is present in carvi, Antheum graveolens, Antheum sowa, Lippia carviodora, Mentha arvensis, etc. The levo form is present in Metha vifidis var. crispa, Mentha longifolia from South Africa, Eucalyptus globules and several mint species. The racemic form is present in ginger grass, Litsea gutalemaleusis, lavender and Artemisia ferganensis. Reported found in citrus oil and juice (lemon, lime, orange), celery seed, anise, clove, coriander seed, calamus, caraway herb and dill seed.
Verwenden
Carvone is useful for the treatment of various metabolic disorders and GI related disorders.
Herstellung & Synthese
synthetische
In the past, (+)- and ()-carvones were isolated by fractional distillation of caraway oil and spearmint oil, respectively. However, these carvones are now prepared synthetically, the preferred starting materials being (+)- and ()- limonenes, which are converted into the corresponding optically active carvones. Since optical rotation is reversed in the process, (+)-limonene is the startingmaterial for ()-carvone. Thepreferred industrialmethod of carvone synthesis utilizes the selective addition of nitrosyl chloride to the endocyclic double bond of limonene. If a lower aliphatic alcohol is used as solvent, limonene nitrosochloride is obtained in high yield. It is converted into carvone oxime by elimination of hydrogen chloride in the presence of a weak base. Acid hydrolysis in the presence of a hydroxylamine acceptor, such as acetone, yields carvone. An alternative process for the production of ()-carvone has recently been commercialized. Starting from (+)-limonene 1,2-epoxide, a regioselective rearrangement of the epoxide leads to ()-carveol (trans- :[2102-58-1]; cis- :[2102-59-2]). Thereaction is effected by the use of a catalyst consisting of a combination of metal salts and phenolic compounds. ()-Carveol is subsequently oxidized to ()-carvone by anOppenauer oxidation or by dehydrogenation in the presence of special catalysts.The reaction may also be performed as a one-pot reaction.