Photo credits: ScenTree SAS
L-carvone
(5R)-2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one ; (5R)-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-one ; L-p- mentha-1(6),8-dien-2-one ; L-para- mentha-6,8-dien-2-one ; 6,8,9-para- menthadien-2-one ; L-1-methyl-4-isopropenyl-6-cyclohexen-2-one ; (R)-2- methyl-5-(1-methyl ethenyl)-2-cyclohexen-1-one
Photo credits: ScenTree SAS
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General Presentation
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CAS N° : 6485-40-1
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EINECS number : 229-352-5
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FEMA number : 2249
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Density : 0,959
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Optical rotation : Donnée indisponible
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Allergens : This ingredient does not contain any allergen.
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Refractive Index @20°C : Donnée indisponible
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Volatility : Head/Heart
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Price Range : €€
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Appearance : Colorless liquid
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FLAVIS number : 07.147
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JECFA number : 380.2
Information on synthetic ingredients
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Acid Value : Donnée indisponible
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Boiling Point : 229°C
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Detection Threshold : 30 ppb environ (0,000003%)
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Molecular formula : C10H14O
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Log P : Donnée indisponible.
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Molecular Weight : 150,22 g/mol
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Fusion Point : Donnée indisponible.
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Flash Point : 94°C
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Vapor pressure : Donnée indisponible
Uses
Other comments :
Stability :
Terpenes tend to polymerize by oxydation.
Uses in perfumery :
L-Carvone is used in mint reconstitutions, for its fidelity to this raw material and for a vegetal-green minty note.
Year of discovery :
Data not available.
Isomerism :
L-Carvone is an enantiomer of D-Carvone, the main constituent of Caraway EO, with a less minty and much more spicy smell. Dimethyl Benzyl Carbinol and Thymol are constitutional isomers of L-Carvone. Their smell, more floral for one and more aromatic for the other, is very different from Carvone.
Synthesis precursor :
L-Carvone can be a precursor to the synthesis of other terpenes, by a Diels-Alder reaction for example.
Natural availability :
L-Carvone is obtained in its natural state from Spearmint EO, of which it is the majority compound (between 55 and 75% according to the varieties).
Synthesis route :
Originally, L-Carvone was separated from D-Carvone from Spearmint EO. Today, its synthesis is made from D-Limonene. The synthesis process reverses the optical activity of the final product. A first reaction consists of reacting D-Limonene with nitrosyl chloride. The resulting D-Limonene nitrosochloride is subjected to a treatment with a weak base, removing hydrochloric acid. Finally, an acid hydrolysis in the presence of acetone allows to obtain the final product. Another method synthesizes L-Carvone from the same D-Limonene, transforming it into its 1,2-epoxide, resulting in a regioselective rearrangement, making it possible to obtain L-Carveol. The catalysis of this first step is metallic and phenolic. An Oppenhauer oxidation allows to obtain the final L-Carvone. The advantage of this synthesis is that it is achievable inside of an unique reactor.
Regulations & IFRA
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IFRA 51th : This ingredient is restricted by IFRA
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Restriction type : RESTRICTION
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Cause of restriction : DERMAL SENSITIZATION AND SYSTEMIC TOXICITY
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Amendment : 49
- Quantitative limit on the use :
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Cat.1 Cat.2 Cat.3 Cat.4 Cat.5A B C DCat.6 0,2 % 0,06 % 0,02 % 0,59 % 0,2 % 0,039 % 0,059 % 0,013 %0,66 % Cat.5A B C DCat.6 0,2 % 0,039 % 0,059 % 0,013 %0,66 % Cat.7A BCat.8 Cat.9 Cat.10A BCat.11A BCat.12 0,039 % 0,039 %0,013 % 0,18 % 0,18 % 0,43 %0,013 % 0,013 %17 % Cat.10A BCat.11A BCat.12 0,18 % 0,43 %0,013 % 0,013 %17 %
Comments :
The natural contribution of Carvone is determined by the sum of the natural contributions of each of its isomers.
