L-Carvone
Naturelle - Synthétique
Herbal > Minty > Fatty
Crédits photo: ScenTree SAS
Other names :
(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
Volatility :
Head/Heart
Uses in perfumery :
Carvone-L is used in mint reconstitutions, for its fidelity to this raw material and for a vegetal-green minty note.
Natural availability :
Carvone-L is obtained in its natural state from Spearmint EO, of which it is the majority compound (between 55 and 75% according to the varieties).
Year of discovery :
Data not available.
Other comments :
Data not available.
Price Range :
€€
Stability :
Terpenes tend to polymerize by oxydation.
Crédits photo: ScenTree SAS
- Molecular formula :
- C10H14O
- Molecular Weight :
- 150,22 g/mol
- Density :
- 0,959
- Flash Point :
- 94°C
- Fusion Point :
- Donnée indisponible.
- Appearance :
- Colorless liquid
- Log P :
- Donnée indisponible,
- Boiling Point :
- 229°C
- Detection Threshold :
- 30 ppb environ (0,000003% !)
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.
Synthesis precursor :
Carvone-L can be a precursor to the synthesis of other terpenes, by a Diels-Alder reaction for example.
Isomerism :
Carvone-L is an enantiomer of Carvone-D, the main constituent of Caraway EO, with a less minty and much more spicy smell.
Dimethyl Benzyl Carbinol and Thymol are constitutional isomers of Carvone-L. Their smell, more floral for one and more aromatic for the other, is very different from Carvone.
- EINECS number :
- 229-352-5
- FEMA number :
- 2249
- JECFA number :
- 380.2
- FLAVIS number :
- 07.147
- Allergens :
- This ingredient does not contain any allergen.
- IFRA :
- This ingredient is restricted by IFRA
- Restriction type :
- RESTRICTION
- Cause of restriction :
- DERMAL SENSITIZATION AND SYSTEMIC TOXICITY
- Amendment :
- 49
- Comments :
- The natural contribution of Carvone is determined by the sum of the natural contributions of each of its isomers.
- Quantitative limit on the use :
-
Cat.1 Cat.2 Cat.3 Cat.4 Cat.5A Cat.5B Cat.5C Cat.5D Cat.6 0,2 % 0,06 % 0,02 % 0,59 % 0,2 % 0,039 % 0,059 % 0,013 % 0,66 % Cat.7A Cat.7B Cat.8 Cat.9 Cat.10A Cat.10B Cat.11A Cat.11B Cat.12 0,039 % 0,039 % 0,013 % 0,18 % 0,18 % 0,43 % 0,013 % 0,013 % 17 % - Restriction type :
- RESTRICTION QRA
- Cause of restriction :
- SENSITIZATION
- Amendment :
- 43
- Quantitative usage limits :
-
Cat.1 Cat.2 Cat.3 Cat.4 Cat.5 Cat.6 Cat.7 Cat.8 Cat.9 Cat.10 Cat.11 0,08 % 0,1 % 0,4 % 1,2 % 0,6 % 1,9 % 0,2 % 2 % 5 % 2,5 % Not Restricted
To learn more about IFRA's standards : https://ifrafragrance.org/safe-use/library
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