γ-Lactone
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γ-Lactones are a family of organic compounds with the formula cyclo-O=COCHRCH2CH2. 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.
| Name | Formula | Registry number | Notes |
|---|---|---|---|
| γ-Octalactone | C8H14O2 | 104-50-7 | fruity |
| γ-Nonalactone | C9H16O2 | 104-61-0 | coconut-like |
| γ-Decalactone | C10H18O2 | 706-14-9 | peach flavors |
| γ-Undecalactone | C11H20O2 | 104-67-6 | peach flavors |
| β-Methyl-γ-octalactone | C9H16O2 | 39212-23-2 | whisky 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.
