γ-Lactone
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.[1]
| 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
[edit]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]
References
[edit]- ^ a b Panten, Johannes; Surburg, Horst (2016). "Flavors and Fragrances, 3. Aromatic and Heterocyclic Compounds". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–45. doi:10.1002/14356007.t11_t02. ISBN 978-3-527-30673-2.
- ^ 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 (2011). "Biochemistry of lactone formation in yeast and fungi and its utilisation for the production of flavour and fragrance compounds". Applied Microbiology and Biotechnology. 89 (3): 535–547. doi:10.1007/s00253-010-2945-0. PMID 20981417.
External links
[edit]- Poisson, L. (July 23, 2008). "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. doi:10.1021/jf800382m. PMID 18570373.