Abstract
Juvocimene I and II are potent juvenile hormone mimics isolated from the essential oil of sweet basil,Ocimum basilicum L. The structures given by the formula I and II have been confirmed by synthesis withtrans-β-ocimene andp-methoxycinnamyl chloride. Biological activity of the natural and synthetic juvocimenes was found to be identical.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Bowers, W.S. 1968. Juvenile hormone: Activity of natural and synthetic synergists.Science 161: 895–897.
Bowers, W.S., andNishida, R. 1980. Juvocimenes: Potent juvenile hormone mimics from sweet basil.Science 209:1030–1032.
Bowers, W.S., Fales, H.M., Thompson, M.J., andUebel, E.C. 1966. Juvenile hormone: Identification of an active compound from balsam fir.Science 154:1020–1022.
Černý, V., Dolejš, L., Lábler, L., šorm, F. andSláma, K. 1967. Dehydrojuvabione-a new compound with juvenile hormone activity from balsam fir.Coll. Czech. Chem. Commun. 32:3926–3933.
Crawford, R.J., Erman, F., andBroaddus, C.D. 1972. Metalation of limonene. A novel method for the synthesis of bisabolane sesquiterpenes.J. Am. Chem. Soc. 94:4298–4306.
Deshpande, R.S., andTipnis, H.P. 1977. Insecticidalactivity ofOcimum basilicum L.Pesticides 11:11–12.
Erman, W.F. 1967. Photochemical transformations of unsaturated bicyclic ketones. Verbenone and its photodynamic products of ultraviolet irradiation.J. Am. Chem. Soc. 89:3828–3841.
Fieser, M., andFieser, L.F. 1974. Reagents for Organic Synthesis, Vol. 4. pp. 485–489. John Wiley & Sons, New York.
Frank, G. 1968. Photosensitized reaction of α-pinene.J. Chem. Soc. (B) Part I:130–132.
Kropp, P.J. 1969. Photochemistry of cycloalkanes. V. Effects of ring size and substitution.J. Am. Chem. Soc. 91:5783–5791.
Lawrence, B.M., Terhune, S.J., andHogg, J.W. 1971. Essential oils and their constituents. VI. The co-called “exotic” oil ofOcimum basilicum L.Flavour Ind. 2(3): 173–176.
Ohloff, G., Seibl, J., andKovats, E. 1964. Zur Kenntnis atherische Öle, III. Die α-Verbindungen acyclischer Monoterpene.Liebigs Ann. Chem. 675:83–101.
Thomas, B.R. 1966. The chemistry of the order Araucariales, Part 4. The bled resins ofAgathis australis.Acta Chem. Scand. 20:1074–1081.
Whitham, G.H., 1961. The reaction of α-pinene with lead tetra-acetate.J. Chem. Soc. Part II:2232–2236.
White, W.N., andFife, W.K. 1961. The ortho-Claisen rearrangement IV. The rearrangement of X-cinnamylp-tolyl ethers.J. Am. Chem. Soc. 83:3846–3853.
Wigfield, D.C., Feiner, S., Malbacho, G., andTaymaz, K. 1974. Investigations on the question of multiple mechanisms in the Cope rearrangement.Tetrahedron 30:2949–2959.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Nishida, R., Bowers, W.S. & Evans, P.H. Synthesis of highly active juvenile hormone analogs, juvocimene I and II, from the oil of sweet basil,Ocimum basilicum L.. J Chem Ecol 10, 1435–1451 (1984). https://doi.org/10.1007/BF00990314
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00990314