1730. Camphene

Nomenclature

CAS number: 79-92-5
2,2-Dimethyl-3-methylenebicyclo[2.2.1]heptane; 2,2-dimethyl-3-methylenenorbornane; 3,3-dimethyl-2-methylenenorcamphane.
C10H16; mol wt 136.23.
C 88.16%, H 11.84%.

Description and references

Occurs in many essential oils, such as turpentine (levo and dextro forms), in cypress oil (dextro form), in camphor oil from species of Lauraceae (dextro), in bergamot oil, in oil of citronella, neroli, ginger, valerian. Reviews on isolation, preparation and properties: J. L. Simonsen, The Terpenes vol. II (Cambridge Univ. Press, 1949) pp 280-322; E. Guenther, The Essential Oils vol. II (Van Nostrand, 1949) pp 66-70. Synthesis: G. W. Hana, H. Koch, Ber. 111, 2527 (1968).

Chemical structure

Derivative

dl-Form.

Properties

Cubic crystals from alcohol. Large dodecahedra by slow sublimation. Volatilizes on exposure to air. Insipid odor. mp 51-52°. bp760 158.5-159.5°; bp100 92.4°; bp16 55-56°. d454 0.8422. nD54 1.45514. Practically insol in water. Moderately sol in alcohol; sol in ether, cyclohexane, cyclohexene, dioxane, chloroform.

Derivative

d-Form.

Properties

mp 52°. [α]D17 +103.5° (c = 9.67 in ether). d450 0.8486. nD50 1.4605.

Derivative

l-Form.

Properties

mp 52°. [α]D21 -119.11° (c = 2.33 in benzene). d454 0.8422. nD40 1.4620.