Skip to main content
Log in

Application of methoxymercuration-demercuration followed by mass spectrometry as a convenient microanalytical technique for double-bond location in insect-derived alkenes

  • Published:
Journal of Chemical Ecology Aims and scope Submit manuscript

Abstract

The positions of double bonds in olefins can be readily determined by a sodium borohydride reduction of their methoxymercuration products followed by mass spectrometry. Fragmentation of the methoxy derivative in the mass spectrometer results in cleavage on either side of the methoxy group to give intense fragment ions which are characteristic of each isomer. This simple and convenient microanalytical technique was applied to several synthetic standards and insect derived olefins, including the alkenes from the cuticular lipids of the honeybeeApis mellifera L.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • Abley, P., McQuillin, F.J., Minnikin, D.E., Kusamran, K., Maskens, K., andPolgar, N. 1970. Location of olefinic links in long-chain esters by methoxymercuration-demercuration followed by gas chromatography-mass spectrometry.Chem. Commun. 1970:348–349.

    Google Scholar 

  • Baker, G.L., Vroman, H.E., andPadmore, J. 1963. Hydrocarbons of the American cockroach.Biochem. Biophys. Res. Commun. 13:360–365.

    Google Scholar 

  • Baker, J.E., Sukkestad, D.R., Woo, S.M., andNelson, D.R. 1978. Cuticular hydrocarbons ofTribolium castaneum: Effects of the food additive tricalcium phosphate.Insect Biochem. 8:159–167.

    Google Scholar 

  • Beatty, I.M., andGilby, A.R. 1969. The major hydrocarbon of a cockroach cuticular wax.Naturwissenschaften 56:373.

    Google Scholar 

  • Beroza, M., andBierl, B.A. 1967. Rapid determination of olefin positions in organic compounds in microgram range by ozonolysis and gas chromatography.Anal. Chem. 39:1131–1135.

    Google Scholar 

  • Blomquist, G.J., andRies, M.K. 1979. The enzymatic synthesis of wax esters by a microsomal preparation from the honeybeeApis mellifera L.Insect Biochem. 9:183–188.

    Google Scholar 

  • Carlson, D.A., Mayer, M.S., Silhacek, D.L., James, J.D., Beroza, M., andBierl, B.A. 1971. Sex attractant pheromone of the housefly: Isolation, identification and synthesis. Science 174:76–78.

    Google Scholar 

  • Cavill, G.W.K., andHoughton, E. 1973. Hydrocarbon constituents of the Argentine ant,Iridomyrmex humitis.Aust. J. Chem. 26:1131–1135.

    Google Scholar 

  • Howard, R.W., McDaniel, C.A., andBlomquist, G.J. 1978. Cuticular hydrocarbons of the eastern subterranean termite,Reticulitermes flavipes (Kollar) (Isoptera: Rhinotermitidae).J. Chem. Ecol. 4:233–245.

    Google Scholar 

  • Jackson, L.L. 1972. Cuticular lipids of the insects-IV. Hydrocarbons of the cockroachesPeriplaneta japonica andPeriplaneta americana compared to other cockroach hydrocarbons.Comp. Biochem. Physiol. 418:331–336.

    Google Scholar 

  • Jackson, L.L., andArmold, M.T. 1977. Insect lipid analysis, pp. 171–206,in R.B. Turner, (ed.), Analytical Biochemistry of Insects. Elsevier, Amsterdam.

    Google Scholar 

  • Jackson, L.L., andBlomquist, G.J. 1976. Insect waxes, pp. 201–233,in P.E. Kolattukudy, (ed.), Chemistry and Biochemistry of Natural Waxes. Elsevier, Amsterdam.

    Google Scholar 

  • Kates, M. 1972. Techniques of lipidology—isolation, analysis and identification of lipids, pp. 267–610,in T.S. Work, and E. Work, (eds.), Laboratory Techniques in Biochemistry and Molecular Biology, Vol. 3. North Holland-American Elsevier, London.

    Google Scholar 

  • Mody, N.V., Hedin, P.A., Neel, W.W., andMiles, P.H. 1975. Hydrocarbons from males, females and larvae of pecan weevil:Curculio caryae (Horn).Lipids 10:117–119.

    Google Scholar 

  • Nakanishi, K. 1962. Infrared Absorption Spectroscopy—Practical. Page 233. Holden Day, San Francisco.

    Google Scholar 

  • Nelson, D.R. 1978. Long chain methyl branched hydrocarbons: Occurrence, biosynthesis and functions.Adv. Insect Physiol. 13:1–33.

    Google Scholar 

  • Plattner, R.D., Spencer, G.F., andKleiman, R. 1976. Double bond location in polyenoic fatty esters through partial oxymercuration.Lipids 11:222–227.

    Google Scholar 

  • Streibl, M., andStransky, K. 1968. Uber naturwachsen IX: vorkommen, isolierung und identifizierung der Olefine in Naturwachsen.Fette-Seifen Anstrichmittel 70:343–348.

    Google Scholar 

  • Uebel, E.C., Sonnet, P.E., Menzer, R.E., Miller, R.W., andBeroza, M., 1975a. Sex pheromone of the faceflyMusca autumnalis (De Geer) (Diptera: Muscidae).J. Chem. Ecol. 1:195–202.

    Google Scholar 

  • Uebel, E.C., Sonnet, P.E., Bierl, B.A., andMiller, R.W. 1975b. Sex pheromone of the stable fly: Isolation and preliminary identification of compounds that induce mating strike behavior.J. Chem. Ecol. 1:377–385.

    Google Scholar 

  • Uebel, E.C., Sonnet, P.E., andMiller, R.W. 1976. Housefly sex pheromone: Enhancement of mating strike activity by combination of (Z)-9-tricosene with branched saturated hydrocarbons.J. Econ. Entomol. 5:905–908

    Google Scholar 

  • Uebel, E.C., Sonnet, P.E., Menzer, R.E., Miller, R.W., andLusby, W.R. 1977. Matingstimulant pheromone and cuticular lipid constituents of the little house fly,Fannia canicularis (L.).J. Chem. Ecol. 3:269–278.

    Google Scholar 

  • Uebel, E.C., Schwarz, M., Menzer, R.E., andMiller, R.W. 1978a. Mating stimulant pheromone and cuticular lipid constituents ofFannia pusio (Wiedmann) (Diptera: Muscidae).J. Chem. Ecol. 4:73–81.

    Google Scholar 

  • Uebel, E.C., Schwarz, M., Miller, R.W., andMenzer, R.E. 1978b. Mating stimulant pheromone and cuticular constituents ofFannia femoralis (Stein) (Diptera: Muscidae).J. Chem. Ecol. 4:83–93.

    Google Scholar 

  • Von Endt, D.W., andWheeler, J.W. 1971. 1-Pentadecene production inTribolium confusum.Science 172:60–61.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Mention of trade names or companies is solely to identify materials used and does not imply endorsement by the USDA.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Blomquist, G.J., Howard, R.W., McDaniel, C.A. et al. Application of methoxymercuration-demercuration followed by mass spectrometry as a convenient microanalytical technique for double-bond location in insect-derived alkenes. J Chem Ecol 6, 257–269 (1980). https://doi.org/10.1007/BF00987544

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00987544

Key words

Navigation