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L(-)-Carvone
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  • Name L(-)-Carvone
  • EINECS229-352-5
  • CAS No. 6485-40-1
  • Density0.94 g/cm3
  • PSA17.07000
  • LogP2.48790
  • Solubilitypractically insoluble in water
  • Melting Point25.2oC
  • FormulaC10H14O
  • Boiling Point230.5 °C at 760 mmHg
  • Molecular Weight150.22
  • Flash Point88.9 °C
  • Transport InformationN/A
  • Appearanceclear colorless to pale yellow liquid
  • Safety36
  • Risk Codes22
  • Molecular Structure
    Molecular Structure of 6485-40-1 (L(-)-Carvone)
  • Hazard SymbolsHarmfulXn
  • SynonymsHarmfulXn
  • Article Data88

L(-)-Carvone Synthetic route

6485-40-1

(+)-carvone

56423-45-1

2-methyl-5-(1-methyl-1-oxiranyl)-2-cyclohexen-1-one

Conditions
ConditionsYield
With potassium superoxide; 2,4-dinitrobenzenesulfonyl chloride In acetonitrile at -35℃; for 4h;83%
With potassium superoxide; 2,4-dinitrobenzenesulfonyl chloride In acetonitrile at -35℃; for 4h; Product distribution; var. oxidation agent;83%
With Perbenzoic acid In chloroform at 20℃; for 14h;
6485-40-1

(+)-carvone

119-26-6

(2,4-dinitro-phenyl)-hydrazine

43231-17-0, 81679-69-8

8-Hydroxycarvotanaceton-dinitrophenylhydrazon

Conditions
ConditionsYield
With sulfuric acid; water 1.) from -10 deg C to 0 deg C, 70 h, 2.) H2O, C2H5OH; Yield given. Multistep reaction;
6485-40-1

(+)-carvone

81679-68-7

8,9-Dihydroxycarvotanaceton-dinitrophenylhydrazon

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: perbenzoic acid / CHCl3 / 14 h / 20 °C
2: H2O, H2SO4 / CHCl3; ethanol
View Scheme

L(-)-Carvone Chemical Properties

Molecular Structure of (-)-Carvone (CAS NO.6485-40-1):

IUPAC Name: (5R)-2-Methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one
Molecular Formula: C10H14O
Molecular Weight: 150.22 g/mol
EINECS: 229-352-5
Density: 0.94 g/cm3
Boiling Point: 227-230 °C
Flash Point: 88 °C
Storage Temp.: 2-8 °C
Water Solubility: practically insoluble
Index of Refraction: 1.481
Molar Refractivity: 45.48 cm3
Molar Volume: 159.7 cm3
Surface Tension: 29.8 dyne/cm 
XLogP3-AA: 2.4
H-Bond Acceptor: 1
Rotatable Bond Count: 1
Tautomer Count: 5
Exact Mass: 150.104465
MonoIsotopic Mass: 150.104465
Topological Polar Surface Area: 17.1
Heavy Atom Count: 11 
Canonical SMILES: CC1=CCC(CC1=O)C(=C)C
Isomeric SMILES: CC1=CC[C@H](CC1=O)C(=C)C
InChI: InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3/t9-/m1/s1
InChIKey: ULDHMXUKGWMISQ-SECBINFHSA-N
Product Categories: Aromatic Ketones (substituted); Biochemistry; Monocyclic Monoterpenes; Terpenes 

L(-)-Carvone History

Until Varrentrapp obtained it in 1841, (-)-Carvone was probably not isolated as a pure compound. It was originally called carvol by Schweizer. Goldschmidt and Z?rrer identified it as a ketone related to limonene, and the structure was finally elucidated by Wagner in 1894.

L(-)-Carvone Uses

 (-)-Carvone (CAS NO.6485-40-1) can be used  in foods such as chewing gum additives such as fragrance. And it is also the main raw material for spice to reconcile chicle and used in medicine and toothpaste, spices, etc.

L(-)-Carvone Production

 (-)-Carvone can be derived from the single of  neutral sulfite derivatives France France, or hydrogen sulfide from the Spearmint oil. And it is derived by the d-line.

L(-)-Carvone Toxicity Data With Reference

1.    

orl-rat LD50:1640 mg/kg

     FCTXAV    Food and Cosmetics Toxicology. 11 (1973),1057.
2.    

ivn-mus LD50:56 mg/kg

     CSLNX*    U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#02834 .
3.    

orl-gpg LD50:766 mg/kg

     FCTXAV    Food and Cosmetics Toxicology. 11 (1973),1057.

L(-)-Carvone Safety Profile

Hazard Codes: HarmfulXn
Risk Statements: 22 
R22:Harmful if swallowed.
Safety Statements: 36 
S36:Wear suitable protective clothing.
WGK Germany: 2
RTECS: OS8650000
F: 8-10-23
HS Code: 29142900
Poison by intravenous route. Moderately toxic by ingestion. When heated to decomposition it emits acrid smoke and irritating fumes.

L(-)-Carvone Specification

 (-)-Carvone (CAS NO.6485-40-1) is also named as (R)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-one ; (R)-Carvone ; AI3-36200 ; L(-)-Carvone ; UNII-5TO7X34D3D ; l-1-Methyl-4-isopropenyl-6-cyclohexen-2-one ; l-6,8(9)-p-Menthadien-2-one ; l-Carvone ; l-Carvone (natural) ; p-Mentha-6,8-dien-2-one, (-)- ; 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (5R)- ; 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (R)- (9CI) . (-)-Carvone (CAS NO.6485-40-1) is clear colorless to pale yellow liquid. S-(+)-carvone smells like caraway. Its mirror image, R-(-)-carvone, smells like spearmint.

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