Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2004-12-08
2008-05-20
Oh, Taylor Victor (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C424S745000
Reexamination Certificate
active
07375239
ABSTRACT:
A method of separating ZE-nepetalactone and EZ-nepetalactone from catnip oil involving mixing catnip oil dissolved in at least one water immiscible, non-halogenated organic solvent with at least one inorganic base dissolved in water to form a biphasic mixture, stirring the biphasic mixture to hydrolyze ZE-nepetalactone to form ZE-nepetalic acid, separating the aqueous phase containing ZE-nepetalic acid from the organic phase containing EZ-nepetalactone in the biphasic mixture, and optionally acidifying the aqueous phase to about pH 4.5 and adding at least one water immiscible, non-halogenated organic solvent to azeotropically lactonize the ZE-nepetalic acid in the presence of a catalytic amount of p-toluene sulfonic acid to form ZE-nepetalactone.
REFERENCES:
patent: 4663346 (1987-05-01), Coulston et al.
patent: 6524605 (2003-02-01), Coats et al.
patent: 6562332 (2003-05-01), Baker et al.
patent: 6841570 (2005-01-01), Haenke
patent: 2003/0138471 (2003-07-01), Coats et al.
patent: 2003/0235601 (2003-12-01), Hallahan
patent: 2004/0127553 (2004-07-01), Hallahan
McElvain et al , J. Am. Chem. Soc., 1941, vol. 63, p. 1558-1563.
Smith et al , March's Advanced Organic Chemistry, Reactions, Mechanisms, and Structure, John Wiley & Sons, Inc. 2001, p. 484 and (a total of 3 pages).
Birkett, Michael A. et al., “Molecules of Interest Aphid Sex Pheromones: From Discovery to Commercial Production,”Photochemistry, 2003, vol. 62, pp. 651-656.
Chauhan, Kamlesh R. et al., “Iridodials: Enantiospecific Synthesis and Stereochemical Assignment of the Pheromone for the Golden-Eyed Lacewing,Chrysopa oculata,”Tetrahedron Letters, 2004, vol. 45, pp. 3339-3340.
Dawson, Glenn W. et al., “The Aphid Sex Pheromone Cyclopentanoids: Synthesis in the Elucidation of Structure and Biosynthetic Pathways,”Bioorganic&MedicinalChemistry, 1996, vol. 4, No. 3, pp. 351-361.
Hooper, A.M. et al., “Characterization of (1R,4S,4aR, 7S, 7aR)- Dihydronepetalactol as a Semiochemical for Lacewings, IncludingChrysopaspp. AndPeyerimhoffina gracilis,”Journal of Chemical Ecology, Apr. 2002, vol. 28, No. 4, pp. 849-864.
Tucker, Arthur O. et al., “Catnip and the Catnip Response,”Economic Botany, 1988, vol. 42, No. 2, pp. 214-231.
Zhang, Qing-He et al., “Semiochemistry of the Golden-eyed LacewingChrysopa oculata: Attraction of Males to a Male-Produced Pheromone,”Journal of Chemical Ecology, Sep. 2004, vol. 30 No. 9, pp. 1849-1870.
Oliver, James E. et al., “(S)(+)-Linalool from Oil of Coriander,”J. Essent. Oil Research, Jan./Feb. 2003, vol. 15, pp. 31-33.
Eisenbraun, Edmund J. et al., “(4aS,7S,7aR)-2-(3R,4R,4aR,7S,7aR)-Octahydro-4, 7-dimethyl-1-oxocyclopenta[c] pyran-3yl] nepetalactam: Nitrogen Analogues of Nepetalactone and Nepalic Anhydride,”J. Org. Chem., 1988, vol. 53, pp. 3968-3972.
Bottini, Albert T. et al., “(7R)-Trans, Tans-Nepetalactone from Nepeta Elliptica,”Photochemistry, 1987, vol. 26, No. 4, pp. 1200-1202.
Eisenbraun, Edmund J. et al., “Structure and Stereochemistry of 4aB, 7a,7aB-Nepetalactone fromNepeta mussiniand its Relationship to the 4aa,7a,7aa-and 4aa,7a,7aB-Nepetalactones fromN. cataria,” J. Org. Chem., 1980, vol. 45, pp. 3811-3814.
Peterson, C.J. et al., “Catnip Essential Oil as a Barrier to Subterranean Termites (Isoptera: Rhinotermitidae) in the Laboratory,”J. Econ. Entomol, 2003, vol. 96, No. 4, pp. 1275-1282.
Peterson, C.J., et al., “Catnip Essential Oil as a Barrier to Subterranean Termites (Isoptera: Rhinotermitidae) in the Laboratory”, J. Economic Entomology, vol. 96(4), pp. 1275-1282, Aug. 2003.
Tucker, A.O., et al., “Catnip and the Catnip Response”, Economic Botany, vol. 42(2), pp. 214-231, 1988.
Zhang, Q., et al., “Semiochemistry of the Goldeneyed LacewingChrysopa oculata: Attraction of Males to a Male-Produced Pheromone”,J. Chemical Ecology, vol. 30(9), pp. 1831-1853, Sep. 2004.
Oliver, James E., “(S) (+)-Linalool from Oil of Coriander”,J. Essent. Oil Res., vol. 15, pp. 31-33, Jan./Feb. 2003.
Birkett, M.A., et al., “Aphid Sex Pheromones: From Discovery to Commercial Production”,Phytochemistry, vol. 62, pp. 651-656, 2003.
Chauhan, K.R., et al., “Iridodials: Enantiospecific Synthesis and Stereochemical Assignment of the Pheromone for the Golden-Eyed Lacewing,Chrysopa oculata”,Tetrahedron Letters, vol. 45, pp. 3339-3340, 2004.
Dawson, G.W., et al., “The Aphid Sex Pheromone Cyclopentanoids: Synthesis in the Elucidation of Structure and Biosynthetic Pathways”,Bioorganic&Medicinal Chemistry, vol. 4(3), pp. 351-361, 1996.
Hooper, A.M., et al., “Characterization of (1R, 4S,4aR,7S,7aR)—Dihydronepetalactol as a Semiochemical for Lacewings, IncludingChrysopaspp. ANDPeyerimhoffina gracilis”,J. Chemical Ecology, vol. 28(4), pp. 849-864, Apr. 2002.
Chauhan Kamlesh R.
Zhang Aijun
Fado John D.
Oh Taylor Victor
Stover G. Byron
The United States of America as represented by the Secretary of
LandOfFree
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