6448. Neocembrene

Nomenclature

CAS number: 31570-39-5
(1E,5E,9E,12R)-1,5,9-Trimethyl-12-(1-methylethenyl)-1,5,9-cyclotetradecatriene; cembrene A; neocembrene A.
C20H32; mol wt 272.47.
C 88.16%, H 11.84%.

Description and references

Termite trail pheromone with all-trans configuration isolated from Nasutitermes exitiosus (Hill): B. P. Moore, Nature 211, 746 (1966). Structure: A. J. Birch et al., J. Chem. Soc. Perkin Trans. 1 1972, 2653; V. D. Patil et al., Tetrahedron 29, 341 (1973). Synthesis: M. Kodama et al., Tetrahedron Lett. 1975, 3065; Y. Kitahara et al., Chem. Lett. 1976, 219; H. Takayanagi et al., Chem. Commun. 1978, 359. Synthesis of neocembrene and isomers: T. Kato et al., J. Org. Chem. 45, 1126 (1980).

Chemical structure

Properties

Colorless oil, faint wax-like odor. bp0.8 150-152°. nD30 1.5102.