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.

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