Skip to main content

Thank you for visiting nature.com. You are using a browser version with limited support for CSS. To obtain the best experience, we recommend you use a more up to date browser (or turn off compatibility mode in Internet Explorer). In the meantime, to ensure continued support, we are displaying the site without styles and JavaScript.

  • Letter
  • Published:

Carbon-13 NMR Study of the Stereochemistry of Steranes from Oil Shale of the Green River Formation (Eocene)

Abstract

THE presence of steranes and triterpanes in oils and sediments is especially significant as they possess the appropriate chemical stability for preservation throughout terrestrial diagenesis. They also contain a high degree of molecular order in their carbon skeleton and so the probability of their being synthesized by abiological processes is minimized. The high level of latent information in the structure and stereochemistry of these compounds renders them ideal biological markers1–6.

This is a preview of subscription content, access via your institution

Access options

Buy this article

Prices may be subject to local taxes which are calculated during checkout

Similar content being viewed by others

References

  1. Bendoraitis, J. G., Brown, G. L., and Hepner, L. S., Anal. Chem., 34, 49 (1962); Bendoraitis, J. G., Brown, G. L., and Hepner, L. S., Sixth World Petrol. Cong., Frankfurt (June, 1963).

    Article  CAS  Google Scholar 

  2. Eglinton, G., Scott, P. M., Belsky, T., Burlingame, A. L., Richter, W. J., and Calvin, M., Adv. Org. Geochem., 41 (Pergamon Press, London, 1964).

  3. Gelpi, E., Han, J., Nooner, D. W., and Oro, J., Geochim. Cosmochim. Acta, 34, 965 (1970).

    Article  ADS  CAS  Google Scholar 

  4. Johns, R. B., Belsky, T., McCarthy, E. D., Burlingame, A. L., Haug, P., Schnoes, H. K., Richter, W. J., and Calvin, M., Geochim. Cosmochim. Acta, 30, 1191 (1966).

    Article  ADS  CAS  Google Scholar 

  5. McCarthy, E. D., and Calvin, M., Nature, 216, 642 (1967).

    Article  ADS  CAS  Google Scholar 

  6. Studier, H. M., Hayatsu, R., and Anders, E., Geochim. Cosmochim. Acta, 34, 965 (1970).

    Article  Google Scholar 

  7. Eschenmoser, A., Ruzicka, L., Jeger, O., and Arigoni, D., Helv. Chim. Acta, 38, 1890 (1955).

    Article  CAS  Google Scholar 

  8. Ruzicka, L., Proc. Chem. Soc., 341 (1959).

  9. Clayton, R. B., Quart. Rev., 19, 168 (1965).

    Article  CAS  Google Scholar 

  10. Van Tamelen, E. E., Willet, J. D., Clayton, R. B., and Lord, K. E., J. Amer. Chem. Soc., 88, 4752 (1966).

    Article  CAS  Google Scholar 

  11. Johnson, W. S., Accounts of Chem. Research, 1, 1 (1968).

    Article  Google Scholar 

  12. Van Tamelen, E. E., Sharpless, K. B., Willet, J. D., Clayton, R. B., and Burlingame, A. L., J. Amer. Chem. Soc., 89, 3920 (1968).

    Article  Google Scholar 

  13. Van Tamelen, E. E., Sharpless, K. B., Hanzlik, R., Clayton, R. B., Burlingame, A. L., and Wszolek, P. C., J. Amer. Chem. Soc., 89, 7150 (1967).

    Article  CAS  Google Scholar 

  14. Van Tamelen, E. E., Hanzlik, R. P., Sharpless, K. B., Clayton, R. B., Richter, W. J., and Burlingame, A. L., J. Amer. Chem. Soc., 90, 3283 (1969).

    Google Scholar 

  15. Van Tamelen, E. E., Hanzlik, R. P., Clayton, R. B., and Burlingame, A. L., J. Amer. Chem. Soc., 92, 2137 (1970).

    Article  CAS  Google Scholar 

  16. Burlingame, A. L., Haug, P., Belsky, T., and Calvin, M., Proc. US. Nat. Acad. Sci., 54, 1406 (1965).

    Article  ADS  CAS  Google Scholar 

  17. Murphy, M. T. J., McCormick, A., and Eglinton, G., Science, 157, 1040 (1967).

    Article  ADS  CAS  Google Scholar 

  18. Hills, I. R., Whitehead, E. V., Anders, D. E., Cummins, J. J., and Robinson, W. E., Chem. Comm., 752 (1966).

  19. Henderson, W., Wollrab, V., and Eglinton, G., Chem. Comm., 710 (1968).

  20. Henderson, W., Wollrab, V., and Eglinton, G., Advances in Organic Geochemistry (edit. by Schenk, P. A., and Havenaar, I.), 181 (Pergamon Press, 1968).

    Google Scholar 

  21. Gallegos, E. J., Div. Petrol. Chem., 15, (Chicago, September 1970).

  22. Anders, D. E., and Robinson, W. E., Geochim. Cosmochim. Acta, 35, 661 (1971).

    Article  ADS  CAS  Google Scholar 

  23. Hills, I. R., Smith, G. W., and Whitehead, E. V., Div. Petrol. Chem., 13, B5 (Atlantic City, New Jersey, September, 1968).

    CAS  Google Scholar 

  24. Burlingame, A. L., and Schnoes, H. K., in Mass Spectrometry in Organic Geochemistry (edit. by Eglinton, G., and Murphy, M. T. J.), 89 (Springer, New Jersey, 1969).

    Google Scholar 

  25. Schnoes, H. K., and Burlingame, A. L., in Topics in Organic Mass Spectrometry (edit. by Burlingame, A. L.), 369 (Wiley–Interscience, New York, 1970).

    Google Scholar 

  26. Gelpi, E., Wszolek, P. C., Yang, E., and Burlingame, A. L., J. Chrom. Sci., 9, 147 (1971).

    Article  CAS  Google Scholar 

  27. Gelpi, E., Wszolek, P. C., Yang, E., and Burlingame, A. L., Anal. Chem., 43, 864 (1971).

    Article  CAS  Google Scholar 

  28. Jones, D. E., thesis, Univ. California, Berkeley (1970).

  29. Wilson, D. M., thesis, Univ. California, Berkeley (1971).

  30. Dalling, D. K., thesis, Univ. Utah, Salt Lake City (1969).

  31. Reich, H. J., Jautelat, M., Messe, M. T., Weigert, F. J., and Roberts, J. D., J. Amer. Chem. Soc., 91, 7445 (1969).

    Article  CAS  Google Scholar 

  32. Jautelat, M., Grutzner, J. B., and Roberts, J. D., Proc. US Nat. Acad. Sci., 65, 288 (1970).

    Article  ADS  CAS  Google Scholar 

  33. Cheney, B. V., and Grant, D. M., J. Amer. Chem. Soc., 89, 5319 (1967).

    Article  CAS  Google Scholar 

  34. Grant, D. M., and Cheney, B. V., J. Amer. Chem. Soc., 89, 5315 (1967).

    Article  CAS  Google Scholar 

  35. Grant, D. M., and Paul, E. G., J. Amer. Chem. Soc., 86, 2984 (1964).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

BALOGH, B., WILSON, D. & BURLINGAME, A. Carbon-13 NMR Study of the Stereochemistry of Steranes from Oil Shale of the Green River Formation (Eocene). Nature 233, 261–263 (1971). https://doi.org/10.1038/233261a0

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1038/233261a0

This article is cited by

Comments

By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.

Search

Quick links

Nature Briefing

Sign up for the Nature Briefing newsletter — what matters in science, free to your inbox daily.

Get the most important science stories of the day, free in your inbox. Sign up for Nature Briefing