γ-Lactones are a family of organic compounds with the formula cyclo-. The parent member is γ-butyrolactone (R = H). A commercially important set of γ-lactones are derived from the free radical addition of fatty alcohols and acrylic acid. They are all weakly volatile liquids, which are colorless when pure, but typical samples are not.
+ Some γ-lactone fragrances Name Formula Registry numberNotes γ-Octalactone 104-50-7fruity γ-Nonalactone 104-61-0coconut-like γ-Decalactone 706-14-9peach flavors γ-Undecalactone 104-67-6peach flavorsβ-Methyl-γ-octalactone39212-23-2whisky lactone
Production Chemical, biological, and hybrid routes have been developed for these fragrances. Some fungal enzymes hydroxylate fatty acids, leading to the corresponding lactones. In terms of chemical routes, fatty alcohols undergo free radical addition to acrylic acid, giving hydroxy carboxylic acids, which spontaneously lactonize.
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