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Extended hopanes up to C40 in Thornton bitumen

Abstract

Gas-chromatographic and mass-spectrometric investigation of the saturated hydrocarbon fraction of a distillation cut of Thornton bitumen has revealed the presence of diastereomeric pairs of side-chain-extended 17α(H)-hopanes with carbon numbers ranging up to C40. Pentacyclic triterpanes of the hopane type are ubiquitous in sediments and related fossil fuels1. Commonly, besides the parent hydrocarbon itself, 17α(H)-hopane(C30), compounds with degraded (C27, C29) and extended side-chains (C31–C35) are detected2. While hopanes with 30 or fewer carbon atoms can easily be interpreted as diagenetic products of C30 hopanoids, for example, hop-22(29)-ene, known in several living organisms3, the extended hopanes (C31–C35) have recently been related to a C35 precursor, bacteriohopanetetrol, which was found to be a constituent of several microorganisms1,4–6. We report here that the new C36–C40 hopanes are of the same structural type as the well-known extended hopanes ranging up to C35.

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Rullkötter, J., Philip, P. Extended hopanes up to C40 in Thornton bitumen. Nature 292, 616–618 (1981). https://doi.org/10.1038/292616a0

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