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Carvone

Carvone
Carvone
(R)-(−)-carvone-from-xtal-3D-balls-B.png
S-carvone-stickModel.png
Names
Preferred IUPAC name
2-Methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one
Other names
2-Methyl-5-(prop-1-en-2-yl)cyclohex-2-enone
2-Methyl-5-(1-methylethenyl)-2-cyclohexenone
Δ6:8(9)-p-Menthadien-2-one
1-Methyl-4-isopropenyl-Δ6-cyclohexen-2-one
Carvol (obsolete)
Identifiers
99-49-0 (R/S) YesY
6485-40-1 (R) YesY
2244-16-8 (S) N
3D model (Jmol) (R): Interactive image
(S): Interactive image
ChEBI CHEBI:38265 YesY
ChEMBL ChEMBL15676 YesY
ChemSpider 21106424 (R/S) YesY
15855 (S) YesY
388655 (R) YesY
ECHA InfoCard 100.002.508
KEGG C01767 YesY
RTECS number OS8650000 (R)
OS8670000 (S)
UNII 75GK9XIA8I (R/S) YesY
5TO7X34D3D (R) N
4RWC1CMS3X (S) N
Properties
C10H14O
Molar mass 150.22 g/mol
Appearance Clear, colorless liquid
Density 0.96 g/cm3
Melting point 25.2 °C (77.4 °F; 298.3 K)
Boiling point 231 °C (448 °F; 504 K) (91 °C @ 5 mmHg)
Insoluble (cold)
Slightly soluble (hot)/soluble in trace amounts
Solubility in Ethanol soluble
Solubility in Diethyl ether soluble
Solubility in Chloroform soluble
−61° (R)-Carvone
61° (S)-Carvone
-92.2·10−6 cm3/mol
Hazards
Main hazards Flammable
Safety data sheet External MSDS
R-phrases R22
S-phrases S36
NFPA 704
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g., diesel fuel Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Related compounds
Related ketone
 menthone
dihydrocarvone
carvomenthone
Related compounds
 limonene, menthol,
p-cymene, carveol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

Carvone is a member of a family of chemicals called terpenoids. Carvone is found naturally in many essential oils, but is most abundant in the oils from seeds of caraway (Carum carvi), spearmint (Mentha spicata), and dill.

Both carvones are used in the food and flavor industry.R-(−)-Carvone is also used for air freshening products and, like many essential oils, oils containing carvones are used in aromatherapy and alternative medicine.

As the compound most responsible for the flavor of caraway, dill and spearmint, carvone has been used for millennia in food. Wrigley's Spearmint Gum and spearmint flavored Life Savers are major users of natural spearmint oil from Mentha spicata. Caraway seed is extracted with alcohol to make the European drink Kümmel.

S-(+)-Carvone is also used to prevent premature sprouting of potatoes during storage, being marketed in the Netherlands for this purpose under the name Talent.

(R)-(–)-Carvone has been proposed for use as a mosquito repellent, and the U.S. Environmental Protection Agency is reviewing a request to register it as a pesticide.

Carvone is available inexpensively in both enantiomerically pure forms, making it an attractive starting material for the asymmetric total synthesis of natural products. For example, (S)-(+)-carvone was used to begin a 1998 synthesis of the terpenoid quassin:

Carvone forms two mirror image forms or enantiomers: R-(–)-carvone smells like spearmint leaves. Its mirror image, S-(+)-carvone, smells like caraway seeds. The fact that the two enantiomers are perceived as smelling different is evidence that olfactory receptors must contain chiral groups, allowing them to respond more strongly to one enantiomer than to the other. Not all enantiomers have distinguishable odors. Squirrel monkeys have also been found to be able to discriminate between carvone enantiomers.


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Wikipedia

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