Carvone, (+-)-
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
Identifiers & Physical Properties
| CAS No. | 22327-39-5 |
|---|---|
| Molecular formula | C10H14O |
| Average molar mass | 150.22 g/mol |
| Monoisotopic mass | 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 |
Chemical & Physical Properties
| XLogP | 2.4 |
|---|---|
| Topological polar surface area | 17.1 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 1 |
| Rotatable bonds | 1 |
| Heavy atoms | 11 |
| Formal charge | 0 |
| Complexity | 223 |
| Chemical classes | Biological Agents -> Plant Oils and Extracts |
| Cosmetics | Cosmetics ingredient -> FlavorFragranceMasking |
| Fragrances | Fragrance Ingredient (Carvone) -> IFRA transparency List |
| Pesticides | Agrochemicals -> Pesticide active substancesActive substance -> EU Pesticides database: Approved |
| Food additives | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Density | 0.956-0.9610.956-0.9600.963 g/cm3 (15℃) |
| Flavoring agents | EU Flavoring substances |
| Color/Form | Pale-yellowish or colorless liquid |
| Solubility | 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 |
| Boiling point | 230-231 °C230 °C232℃ (760.0 Torr) |
| Melting point | 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℃ |
| FLAVIS Number | 07.012 | Carvone |
| Refractive index | 1.710 |
| FEMA | 2249 | CARVONE |
| Storage conditions | 2-8°C |
| Physical state | Oil |
| Color | Light Orange to Light Brown |
| Odor | at 100.00 %. minty licorice |
| Odor type | minty |
| JECFA Number | 380 |
| Henry's law constant | 1.3×10-1 mol/(m3Pa) at 25℃, HSDB (2015) |
| Dielectric constant | 11.0(22℃) |
| Stability | Light Sensitive |
| Cosmetics Ingredients Functions | PERFUMINGFLAVOURINGFRAGRANCE |
| LogP (partition coefficient) | 3.07 |
| CAS DataBase Reference | 99-49-0 |
| Substances Added to Food (formerly EAFUS) | CARVONE |
| EWG's Food Scores | 1-2 |
| FDA UNII | 75GK9XIA8I |
| EPA Substance Registry System | 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)- (99-49-0) |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H317 |
| GHS precautionary statements | P261-P272-P280-P302+P352-P333+P313-P321-P363-P501 |
| TSCA inventory status | TSCA listed |
| Hazardous substances data | 99-49-0(Hazardous Substances Data) |
Safety & Regulations
| GHS classification | 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] |
|---|---|
| Regulatory information | 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 |
| Hazards summary | 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 requirements | 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 |
| Disposal methods |
Applications & Uses
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.
Uses
Carvone is useful for the treatment of various metabolic disorders and GI related disorders.
Uses
Flavoring, liqueurs, perfumery, soaps.
Preparation & Synthesis
Preparation
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.