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Significance Methyl-branched hydrocarbons (MBCHs) are widely used for inter- and intraspecific communication by insects. MBCHs can exist as two or more stereoisomers, but it remains unknown which stereoisomer(s) insects produce, nor is it clear whether insects can distinguish MBCH stereoisomers. To address these questions, we developed a generic method for isolation of MBCHs (and other lipids) from a range of insect species. Polarimetric analyses of 36 isolated MBCHs showed that their stereochemistry is conserved across nine orders of Insecta, with all compounds having the (R )-configuration, regardless of methyl branch position or chain length. These results will enable further explorations of the role of stereochemistry in contact chemical communication, and the molecular mechanisms involved in recognition of hydrocarbons.

Isolation and determination of absolute configurations of insect-produced methyl-branched hydrocarbons