6683. Nopol

Nomenclature

CAS number: 35836-73-8; 128-50-7 ((±)-form)
(1R,5S)-6,6-Dimethylbicyclo[3.1.1]hept-2-ene-2-ethanol.
C11H18O; mol wt 166.26.
C 79.46%, H 10.91%, O 9.62%.

Description and references

Bicyclic primary alcohol found in carrot root oil; synthesized from β-pinene, q.v. Prepn: J. P. Bain, J. Am. Chem. Soc. 68, 638 (1946). Thermal isomerization: idem et al., ibid. 74, 4292 (1952). Isoln from carrot root oil: D. M. Alabran et al., J. Agric. Food Chem. 23, 229 (1975). Applications as a polymer substrate: J. V. Crivello, S. S. Liu, J. Polym. Sci. A 37, 1199 (1999). Improved syntheses: U. R. Pillai, E. Sahle-Demessie, Chem. Commun. 2004, 826; A. L. Villa de P et al., Catal. Today 107-108, 942 (2005).

Chemical structure

Properties

bp10 110.5°. nD25 1.4920. d425 0.9647. [α]D25 -36.5°.

Use

In the synthesis of pesticides, soaps, detergents and other household products.