Abstract
It is generally accepted that saturated polycyclic hydrocarbons such as steranes and triterpanes, present in crude oils and sediments, originate from naturally occurring steroids and triter-penoids. The occurrence of individual steranes and triterpanes can be used to relate the oil or sediment sample to the biological material from which it is derived. All previously known saturated C30 pentacyclic hydrocarbons could be related to a naturally occurring triterpenoid. Here we report that the structure of a novel C30H52 pentacyclic isoprenoid hydrocarbon present in some Far Eastern crude oils has been established as 2,6a,12-trimethyl-4,9-diisopropyl-perhydrobenzo[de]naphthacene by joint application of Chromatographie methods, mass spectrometry (MS), nuclear magnetic resonance (NMR), molecular mechanics and X-ray diffraction. As far as we know, this is the first report of the occurrence in nature of a pentacyclic C30 isoprenoid compound with a perhy-drobenzo[de]naphthacene skeleton. It can be considered as a dimer of the sesquiterpane cadinane. A biosynthesis of the skeleton by direct cyclization of squalene seems impossible in this case.
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Cox, H., de Leeuw, J., Schenck, P. et al. Bicadinane, a C30 pentacyclic isoprenoid hydrocarbon found in crude oil. Nature 319, 316–318 (1986). https://doi.org/10.1038/319316a0
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DOI: https://doi.org/10.1038/319316a0
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