beta-Damascenone
Title: b-Damascenone
CAS Registry Number: 23726-93-4; 23696-85-7 (stereo unspecified)
CAS Name: (2E)-1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one
Additional Names: trans-2,6,6-trimethyl-1-crotonylcyclohexa-1,3-diene
Trademarks: Doricenone (Firmenich)
Molecular Formula: C13H18O
Molecular Weight: 190.28
Percent Composition: C 82.06%, H 9.53%, O 8.41%
Literature References: Terpenic ketone; odorant in fruits, vegetables, honey, wine and beer. Isoln from Bulgarian rose oil, Rosa damascena Mill., and synthesis: E. Demole et al., Helv. Chim. Acta 53, 541 (1970). Synthetic studies: G. Büchi, H. Wüest, ibid. 54, 1767 (1971); K. S. Ayyar et al., J. Chem. Soc. Perkin Trans. 1 1975, 1727. Identification in grapes: T. E. Acree et al., J. Agric. Food Chem. 29, 688 (1981); in tomato volatiles: R. G. Buttery et al., Chem. Ind. (London) 1988, 238. Quantitative determn in foods: A. Sen et al., J. Agric. Food Chem. 39, 757 (1991); in beers: F. Chevance et al., ibid. 50, 3818 (2002). Reactivity in wine: M. A. Daniel et al., ibid. 52, 8127 (2004).
Properties: Pale yellow to yellow liquid; powerful floral, fruity odor. bp0.001 57°. bp0.08 51°. bp13 116-118°. d420 0.942. nD20 1.5123. Flash pt (closed cup): >100°C. uv max (cyclohexane): 220, 253, 302 nm (e 10000, 4120, 2270). uv max (ethanol): 228, 255, 310 nm (e 12000, 500, 2000). Sol in ethanol (95°). Odor threshold in water: 0.02-0.09 ng/g.
Boiling point: bp0.001 57°; bp0.08 51°; bp13 116-118°
Flash point: Flash pt (closed cup): >100°C
Index of refraction: nD20 1.5123
Absorption maximum: uv max (cyclohexane): 220, 253, 302 nm (e 10000, 4120, 2270); uv max (ethanol): 228, 255, 310 nm (e 12000, 500, 2000)
Density: d420 0.942
Use: In perfumery.

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