Carvone

Title: Carvone
CAS Registry Number: 99-49-0
CAS Name: 2-Methyl-5-(1-methylethenyl)-2-cyclohexene-1-one
Additional Names: p-mentha-6,8-dien-2-one; 1-methyl-4-isopropenyl-D6-cyclohexen-2-one; carvol
Molecular Formula: C10H14O
Molecular Weight: 150.22
Percent Composition: C 79.95%, H 9.39%, O 10.65%
Literature References: d-Carvone is found in caraway seed and dill seed oils: Schweizer, J. Prakt. Chem. 24, 257 (1841); Gladstone, J. Chem. Soc. 25, 1 (1872). Isoln of d-carvone from mandarin peel oil (Citrus reticulata Blanco, Rutaceae): Kugler, Kováts, Helv. Chim. Acta 46, 1480 (1963). l-Carvone is found in spearmint and kuromoji oils: Kwaenick, Ber. 24, 82 (1891). dl-Carvone is found in gingergrass oil: Walbaum, Hüthig, J. Prakt. Chem. 71, 459 (1905). Prepn from a-pinene: Booth, Klein, US 2796428 (1957 to Glidden). Structure: Wagner, Ber. 27, 2270 (1894); Tiemann, Semmler, ibid. 28, 2147 (1895). Synthesis of l-carvone: Royals, Horne, J. Am. Chem. Soc. 73, 5856 (1951); Shono et al., Chem. Lett. 1975, 4330. Synthesis of dl-carvone: Suga, Bull. Chem. Soc. Jpn. 31, 569 (1958); I. Fleming, I. Patterson, Synthesis 1979, 736. Toxicity study: P. M. Jenner et al., Food Cosmet. Toxicol. 2, 327 (1964). Review: J. L. Simonsen, The Terpenes vol. I (University Press, Cambridge, 2nd ed., 1947) pp 394-408; B. Singaram, J. Verghese, Perfum. Flavor. 2, 47 (1977).
Derivative Type: d-Form
Properties: Liquid, bp755 230°; bp5-6 91°. d420 0.965. nD20 1.4989. [a]D20 +61.2°.
Boiling point: bp755 230°; bp5-6 91°
Optical Rotation: [a]D20 +61.2°
Index of refraction: nD20 1.4989
Density: d420 0.965
Derivative Type: l-Form
Properties: Liquid, bp763 230-231°. d1515 0.9652. nD20 1.4988. [a]D20 -62.46°.
Boiling point: bp763 230-231°
Optical Rotation: [a]D20 -62.46°
Index of refraction: nD20 1.4988
Density: d1515 0.9652
Derivative Type: dl-Form
Properties: Liquid, bp 230-231°. d1515 0.9645. nD20 1.5003. Practically insol in water. Misc with alc. LD50 orally in rats: 1640 mg/kg (Jenner).
Boiling point: bp 230-231°
Index of refraction: nD20 1.5003
Density: d1515 0.9645
Toxicity data: LD50 orally in rats: 1640 mg/kg (Jenner)
Use: As oil of caraway; also for flavoring liqueurs; in perfumery and soaps.
Therap-Cat: Carminative.
Carzenide Carzinophilin A Casanthranol Cascara Amara Cascara Sagrada

Carvone
Carvone
S-carvone-stickModel.png (R)-(−)-carvone-from-xtal-3D-balls-B.png
Identifiers
CAS number 99-49-0 (racemic) YesY, 6485-40-1 ((R)-Carvone), 2244-16-8 ((S)-Carvone)
ChemSpider 21106424 (racemic) YesY, 15855 (S-(+) enantiomer), 388655 (R-(-) enantiomer)
UNII 75GK9XIA8I YesY
KEGG C01767 YesY
ChEBI CHEBI:38265 YesY
ChEMBL CHEMBL15676 YesY
RTECS number OS8650000 (R)
OS8670000 (S)
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C10H14O
Molar mass 150.22 g/mol
Appearance Clear, colorless liquid
Density 0.96 g/cm3
Melting point 25.2 °C
Boiling point 231 °C
91 °C (@ 5 mmHg)
Solubility in water Insoluble (cold)
Slightly soluble (hot)/soluble in trace amounts
Solubility in Ethanol soluble
Solubility in Diethyl ether soluble
Solubility in Chloroform soluble
Chiral rotation [α]D −61° (R)-Carvone
61° (S)-Carvone
Hazards
MSDS External MSDS
R-phrases R22
S-phrases S36
Main hazards inflammable
NFPA 704
NFPA 704.svg
2
1
0
Related compounds
Related ketone menthone
dihydrocarvone
carvomenthone
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Carvone is a member of a family of chemicals called terpenoids.[2] Carvone is found naturally in many essential oils, but is most abundant in the oils from seeds of caraway (Carum carvi) and dill.[3]