Carvone, (+)-
Basic information
- CAS
2244-16-8- Standard SMILES
C=C(C)[C@H]1CC=C(C)C(=O)C1- InChIKey
ULDHMXUKGWMISQ-VIFPVBQESA-N- Molecular formula
- C10H14O
- Average molar mass
- 150.22 g/mol
- Monoisotopic mass
- 150.10446507
Overview
D-carvone appears as pale yellow or colorless liquid. (NTP, 1992)
Names & identifiers
- Preferred name
- Carvone, (+)-
- IUPAC
- (5S)-2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one
- English name
- 2-Methyl-4-(1 -methylethenyl)-2-cyclohexene-1 -one
- Molecular formula
- C10H14O
- Molecular weight
- 150.21756
Names & synonyms
d-Carvone2244-16-8(S)-(+)-Carvone(+)-Carvone(S)-CarvoneCarvone, (+)-D(+)-CarvoneD-(+)-CarvoneS-(+)-carvone(S)-(+)-p-Mentha-6,8-dien-2-oned-Carvone (natural)(5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one
Show more names
(+)-(S)-Carvonep-Mentha-6,8-dien-2-one, (S)-(+)-CCRIS 2385DTXSID8020256UNII-4RWC1CMS3X2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (S)-4RWC1CMS3X(S)-d-p-Mentha-6,8,(9)-dien-2-one
Database identifiers
- CAS
2244-16-8- PubChem CID
- 16724
- DTXSID
DTXSID8020256- ChEMBL
CHEMBL501949- ChEBI
CHEBI:15399- UNII
- 4RWC1CMS3X
- EC Number
- 218-827-2
- Nikkaji
- J9.490K
Properties
Computed structural properties
- XLogP
- 2.4
- Topological polar surface area
- 17.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 1
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 223
Experimental & physicochemical properties
CosmeticsCosmetics ingredient -> Flavor; Fragrance; Other (Specify)
FragrancesFragrance Ingredient (d-Carvone) -> IFRA transparency List
LogP
1.267
2.71
Density
0.965 at 68 °F (NTP, 1992) - Less dense than water; will float
0.956-0.961
Flavoring AgentsEU Flavoring substances
Solubility
less than 1 mg/mL at 77 °F (NTP, 1992)
1300 mg/L at 18 °C
soluble in propylene glycol and most fixed oils; insoluble in glycerol; miscible with alcohol
1 ml in 5 ml 60% alcohol (in ethanol)
Flash Point192 °F (NTP, 1992)
Boiling Point
446 °F at 760 mmHg (NTP, 1992)
231.00 °C. @ 760.00 mm Hg
230 °C
Melting Point
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H317: 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 0.1% (2 of 1654) of reports.
Warning
H302 (16.3%): Harmful if swallowed [Warning Acute toxicity, oral]
Hazard information
Regulatory Information
Chemical: 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (S)-
Regulation (EC) No 1831/2003 (amended)
REACH registered substance: (S)-2-methyl-5-(1-methylvinyl)cyclohex-2-en-1-one (EC: 218-827-2)
2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (5S)-: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
DOT LabelPoison
Fire HazardsThis chemical is combustible. (NTP, 1992)
Health HazardsSYMPTOMS: Symptoms of exposure to this compound may include irritation.
Reactive GroupKetones
Reactivity ProfileD-CARVONE may be sensitive to prolonged exposure to light and air. Incompatible with strong oxidizing agents and strong reducing agents (NTP, 1992)
Air and Water Reactions
Chemistry & industry
Pharmacology
Cellular LocationsExtracellular
Uses & manufacturing
IFRA Fragrance Standards
Carvone
99-49-0 (Carvone):; p-Mentha-6,8-dien-2-one; 1-Methyl-4-isopropenyl-6-cyclohexen-2-one; 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-; 5-Isopropenyl-2-methylcyclohex-2-en-1-one; 6,8(9)-p-Menthadien-2-one.; 2244-16-8 (d-Carvone):; (S)-2-Methyl-5-(1-methylvinyl)cyclohex-2-en-1-one; d-p-Mentha-6,8(9)-dien-2-one; d-1-Methyl-4-isopropenyl-6-cyclohexen-2-one; 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (S)-.; 6485-40-1 (l-Carvone):; l-p-Mentha-1(6),8-dien-2-one; l-p-Mentha-6,8(9)-dien-2-one; l-1-Methyl-4-isopropenyl-6-cyclohexen-2-one; 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (R)-; 5-Isopropenyl-2-methylcyclohex-2-en-1-one.
IFRA_STD_016.pdf
49
IFRA 51st Amendment - Guidance for the use of IFRA Standards
Restriction: This material should be used only in the limited quantity as stated in the Standard
Household Products
Cosmetics product ingredient: 2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one; (5R)-2-Methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one;(5S)-2-Methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one (Carvone)
Information on 2 consumer products that contain D-Carvone in the following categories is provided:
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
General Manufacturing Information2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (5S)-: ACTIVE
Restriction Limits in the Finished Product (%)
0.2 [Products applied to the lips]
0.06 [Products applied to the axillae]
0.02 [Products applied to the face/body using fingertips]
Suppliers
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Related reactions
1 records
Compound notes
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