6475. Nerol
Nomenclature
CAS number: 106-25-2
(Z)-3,7-Dimethyl-2,6-octadien-1-ol; cis-2,6-dimethyl-2,6-octadien-8-ol. C10H18O; mol wt 154.25.
C 77.87%, H 11.76%, O 10.37%.
Description and references
The cis-isomer of geraniol, q.v.; found in many essential oils. Readily loses water and cyclizes forming dipentene. Isoln from neroli oil: Hesse, Zeitschel, J. Prakt. Chem. 66, 502 (1902). Structure: Verley, Bull. Soc. Chim. Fr. 25, 68 (1919); J. L. Simonsen, The Terpenes vol. I (University Press, Cambridge, 2nd ed., 1947) pp 52-54. Stereochemistry: Burrell et al., Proc. Chem. Soc. London 1959, 263; Bates et al., J. Org. Chem. 28, 1086 (1963). Synthesis: Yukawa et al., Bull. Chem. Soc. Jpn. 37, 158 (1964). Stereochemistry and synthesis: Burrell et al., J. Chem. Soc. C 1966, 2144; K. Takabe et al., Chem. Lett. 1977, 1025.
Properties
Liquid. Odor of sweet rose. bp745 224-225°; bp25 125°. d15 0.8813. Optically inactive. uv max: 189-194 nm (ε 18000). Sol in abs alc.Derivative
Tetrabromide.C10H18Br4O; mol wt 473.87.
C 25.35%, H 3.83%, Br 67.45%, O 3.38%.
Properties
Crystals, mp 118°.Derivative
Allophanate.C12H20N2O3; mol wt 240.30.
C 59.98%, H 8.39%, N 11.66%, O 19.97%.