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Cas Database |
| Name |
L(-)-Carvone |
EINECS | 229-352-5 |
| CAS No. | 6485-40-1 | Density | 0.94 g/cm3 |
| PSA | 17.07000 | LogP | 2.48790 |
| Solubility | practically insoluble in water | Melting Point |
25.2oC |
| Formula | C10H14O | Boiling Point | 230.5 °C at 760 mmHg |
| Molecular Weight | 150.22 | Flash Point | 88.9 °C |
| Transport Information | N/A | Appearance | clear colorless to pale yellow liquid |
| Safety | 36 | Risk Codes | 22 |
| Molecular Structure |
|
Hazard Symbols |
 Xn
|
| Synonyms |
2-Cyclohexen-1-one,2-methyl-5-(1-methylethenyl)-, (R)-;p-Mentha-6,8-dien-2-one, (R)-(-)- (8CI);(-)-(5R)-Carvone;(-)-(R)-Carvone; |
Article Data | 88 |
L(-)-Carvone Synthetic route
- 6485-40-1
(+)-carvone
- 56423-45-1
2-methyl-5-(1-methyl-1-oxiranyl)-2-cyclohexen-1-one
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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
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: 
Xn
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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