Γ-Lactone Explained
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.[1]
Some γ-lactone fragrances| Name | Formula | Registry number | Notes |
|---|
| γ-Octalactone | | 104-50-7 | fruity |
| | 104-61-0 | coconut-like |
| γ-Decalactone | | 706-14-9 | peach flavors |
| γ-Undecalactone | | 104-67-6 | peach flavors |
| β-Methyl-γ-octalactone | | 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.[2] In terms of chemical routes, fatty alcohols undergo free radical addition to acrylic acid, giving hydroxy carboxylic acids, which spontaneously lactonize.[1]
External links
- Poisson . L. . Characterization of the most odor-active compounds in an American Bourbon whisky by application of the aroma extract dilution analysis. . J Agric Food Chem . 56 . 14 . 5813–9 . July 23, 2008 . 10.1021/jf800382m. 18570373 .
Notes and References
- Book: 10.1002/14356007.t11_t02 . Flavors and Fragrances, 3. Aromatic and Heterocyclic Compounds . Ullmann's Encyclopedia of Industrial Chemistry . 2016 . Panten . Johannes . Surburg . Horst . 1–45 . 978-3-527-30673-2 .
- 10.1007/s00253-010-2945-0 . Biochemistry of lactone formation in yeast and fungi and its utilisation for the production of flavour and fragrance compounds . 2011 . Romero-Guido . Cynthia . Belo . Isabel . Ta . Thi Minh Ngoc . Cao-Hoang . Lan . Alchihab . Mohamed . Gomes . Nelma . Thonart . Philippe . Teixeira . Jose A. . Destain . Jacqueline . Waché . Yves . Applied Microbiology and Biotechnology . 89 . 3 . 535–547 . 20981417 .
