L(-)-Carvone

Names

[ Name ]:
L(-)-Carvone

[Synonym ]:
Carvone
UNII:75GK9XIA8I
2-Methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-on
5-Isopropenyl-2-methyl-2-cyclohexen-1-one
(5R)-2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one
2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-
Levo-carvone
EINECS 229-352-5
MFCD00001578
2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one
L(-)-Carvone

Biological Activity

[Description]:

(-)-Carvone is an insect neurotoxin and a irreversible acetylcholinesterase (AChE) inhibitor. (-)-Carvone can be used as a bird repellent, inhibits larval growth, decreases pupatation rate, and increases mortality of larvae[1][2].

[Related Catalog]:

Research Areas >> Neurological Disease

Signaling Pathways >> Neuronal Signaling >> AChE

[Target]

eel AChE:2.19 mM (Ki)

[In Vitro]

(-)-Carvone (3.04 mM; 30 min) inactivates eel AChE with Ki value of 2.19 mM[1].

[In Vivo]

(-)-Carvone (5% in absolute ethanol v/v, 20 μL; application to the thoraces ventral surfaces) inhibits AChE such as horse serum cholinesterase, house fly head cholinesterases, and head and thorax cholinesterases from the Madagascar roach in vitro[1]. (-)-Carvone (0.05%-0.1% w/v; p.o.; 7 d) inhibits E. insulana larvae growth, decreases weight of larvae[2]. Animal Model: Female roaches (Gromphadorhina portentosa) (6.4 g-6.8 g)[1] Dosage: 5% in absolute ethanol v/v, 20 μL Administration: Application to the ventral surfaces of their thoraces; decapitated and crude at various time intervals (0, 2, 4, 5, 20, 24, and 26 hr) Result: Inhibited the activity of AChE in the extracts of both the head and thorax.

[References]

[1]. Grundy D L, et al. Inhibition of acetylcholinesterases by pulegone-1, 2-epoxide[J]. Pesticide biochemistry and physiology, 1985, 23(3): 383-388.

[2]. Meisner J, et al. The response of Earias insulana Boisd. larvae to phagodeterrent (–)‐carvone incorporated in an artificial diet 1[J]. Zeitschrift für Angewandte Entomologie, 1980, 90(1‐5): 80-82.

Chemical & Physical Properties

[ Density]:
0.958

[ Boiling Point ]:
227-230 ºC

[ Melting Point ]:
25.2ºC

[ Molecular Formula ]:
C₁₀H₁₄O

[ Molecular Weight ]:
150.218

[ Flash Point ]:
88 ºC

[ Exact Mass ]:
150.104462

[ PSA ]:
17.07000

[ LogP ]:
2.27

[ Vapour density ]:
5.2 (vs air)

[ Vapour Pressure ]:
0.1±0.5 mmHg at 25°C

[ Index of Refraction ]:
1.481

[ Water Solubility ]:
PRACTICALLY INSOLUBLE

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: OS8650000

CHEMICAL NAME :: p-Mentha-6,8-dien-2-one, (R)-(-)-

CAS REGISTRY NUMBER :: 6485-40-1

LAST UPDATED :: 199701

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C10-H14-O

MOLECULAR WEIGHT :: 150.24

WISWESSER LINE NOTATION :: L6V BUTJ B1 EY1&U1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1640 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 11,1057,1973

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 56 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) Volume(issue)/page/year: NX#02834

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 766 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 11,1057,1973 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X8585 No. of Facilities: 459 (estimated) No. of Industries: 8 No. of Occupations: 39 No. of Employees: 19245 (estimated) No. of Female Employees: 10383 (estimated)

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ Hazard Codes ]:
Xn:Harmful;

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
OS8650000

[ HS Code ]:
29142900

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914299000

[ Summary ]:
2914299000. other cyclanic, cyclenic or cyclotherpenic ketones without other oxygen function. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:5.5%. General tariff:30.0%

Articles

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Related Compounds

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