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Cuticular waxes are complex mixtures consisting mostly of very-long-chain aliphatics with single, primary functional groups. However, the waxes of many plant species also include aliphatics with one or more functional groups residing on subterminal or mid-chain carbons. In the present work, the cuticular wax mixtures from flag leaf blades and peduncles of Triticum aestivum cv. Bethlehem were analyzed in a search for novel wax constituents with in-chain functionalities, potentially of polyketide origin. The structures of compounds belonging to six different compound classes were elucidated using gas chromatography–mass spectrometry of various derivatives. Among them, a series of 2,4-ketols was identified, with odd carbon numbers ranging from C₂₅ to C₃₇ and peaking at C₃₃. The analogous C₃₃ 2,4-diketone was identified as well, together with a pair of co-eluting C₃₁ mid-chain β-ketol isomers (16 …