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Carvone

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Name

Carvone

EINECS 202-759-5
CAS No. 99-49-0 Density 0.94 g/cm3
PSA N/A LogP N/A
Solubility N/A Melting Point 230℃
Formula C10H14O Boiling Point 230.5 °C at 760 mmHg
Molecular Weight 150.221 Flash Point 88.9 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 99-49-0 (CARVONE) Hazard Symbols N/A
Synonyms

p-Mentha-6,8-dien-2-one(8CI);2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-one;2-Methyl-5-isopropenyl-2-cyclohexenone;5-Isopropyl-2-methyl-2-cyclohexen-1-one;2-Cyclohexen-1-one,2-methyl-5-(1-methylethenyl)-;DL-Carvone;Karvon;NSC 6275;

Article Data 157

Carvone Consensus Reports

Reported in EPA TSCA Inventory.

Carvone Specification

The CAS registry number of p-Mentha-6,8-dien-2-one is 99-49-0. In addition, the molecular formula is C10H14O and the molecular weight is 150.22. The IUPAC name is 2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one. What's more, it is an oxidized derivative of limonene. And it is found naturally in many essential oils, but is most abundant in the oils from seeds of caraway and dill. In addition, it can be used as a food flavor.

Physical properties about this chemical are: (1)ACD/LogP: 2.27; (2)ACD/LogD (pH 5.5): 2.26; (3)ACD/LogD (pH 7.4): 2.26; (4)#H bond acceptors: 1; (5)#Freely Rotating Bonds: 1; (6)Polar Surface Area: 17.07 Å2; (7)Index of Refraction: 1.481; (8)Molar Refractivity: 45.48 cm3; (9)Molar Volume: 159.7 cm3; (10)Polarizability: 18.03 ×10-24cm3; (11)Surface Tension: 29.8 dyne/cm; (12)Density: 0.94 g/cm3; (13)Flash Point: 88.9 °C; (14)Enthalpy of Vaporization: 46.71 kJ/mol; (15)Boiling Point: 230.5 °C at 760 mmHg; (16)Vapour Pressure: 0.0656 mmHg at 25°C.

Preparation of p-Mentha-6,8-dien-2-one: it can be prepared by 2-Methyl-5-(2-methyloxiranyl)-2-cyclohexen-1-one. This reaction will need reagent AlI3 and solvents acetonitrile and benzene. The reaction time is 0.5 hour. And the yield is about 87%.

p-Mentha-6,8-dien-2-one can be prepared by 2-Methyl-5-(2-methyloxiranyl)-2-cyclohexen-1-one

Uses of p-Mentha-6,8-dien-2-one: it can react with 2-iodo-propane to get 5-isopropenyl-3-isopropyl-2-methyl-cyclohexanone. This reaction will need reagent Zn(Cu) and solvent ethanol and H2O. The yield is about 76% with ambient temperature.

p-Mentha-6,8-dien-2-one can react with 2-iodo-propane to get 5-isopropenyl-3-isopropyl-2-methyl-cyclohexanone

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1CC(C\C=C1\C)C(C)=C
(2)Std.InChI: InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3
(3)Std.InChIKey: ULDHMXUKGWMISQ-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral 766mg/kg (766mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.
mouse LD50 subcutaneous 2675mg/kg (2675mg/kg) BEHAVIORAL: ANTICONVULSANT

BEHAVIORAL: SLEEP
Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 46, Pg. 77, 1957.
rat LD50 oral 1640mg/kg (1640mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA
Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.

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