gamma-Irone

Title: g-Irone
CAS Registry Number: 79-68-5
CAS Name: 4-(2,2,3-Trimethyl-6-methylenecyclohexyl)-3-buten-2-one
Molecular Formula: C14H22O
Molecular Weight: 206.32
Percent Composition: C 81.50%, H 10.75%, O 7.75%
Literature References: Principal fragrant constituent of natural iris oil. Isoln from irone mixture: Ruzicka et al., Helv. Chim. Acta 30, 1807 (1947); Ruzicka et al., ibid. 31, 257 (1948). Synthesis of dl-g-irone: Favre, Schinz, ibid. 41, 1368 (1958). Synthesis of (±)-cis- and trans-g-irone: F. Leyendecker, M.-T. Comte, Tetrahedron 43, 85 (1987); T. Kawanobe et al., Agric. Biol. Chem. 51, 791 (1987). Stereoselective synthesis of (±)-cis-g-irone: C. Nussbaumer, G. Fráter, Helv. Chim. Acta 71, 619 (1988). Stereochemistry: See a-irone.
Properties: Oil. bp0.06 85-88°. bp2 114-116°. d415 0.939; nD15 1.505. [a]D20 +2° (methylene chloride). uv max: 230 nm (log e 4.2).
Boiling point: bp0.06 85-88°; bp2 114-116°
Optical Rotation: [a]D20 +2° (methylene chloride)
Index of refraction: nD15 1.505
Absorption maximum: uv max: 230 nm (log e 4.2)
Density: d415 0.939
Use: In perfumery.
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