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γ-Lactone

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(Redirected fromΓ-lactone)

γ-Lactones are a family oforganic compounds with the formula cyclo-O=COCHRCH2CH2. The parent member isγ-butyrolactone (R = H). A commercially important set of γ-lactones are derived from thefree radical addition offatty alcohols andacrylic acid. They are all weakly volatile liquids, which are colorless when pure, but typical samples are not.[1]

Some γ-lactone fragrances
NameFormulaRegistry numberNotes
γ-OctalactoneC8H14O2104-50-7fruity
γ-NonalactoneC9H16O2104-61-0coconut-like
γ-DecalactoneC10H18O2706-14-9peach flavors
γ-UndecalactoneC11H20O2104-67-6peach flavors
β-Methyl-γ-octalactoneC9H16O239212-23-2whisky lactone

Production

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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 toacrylic acid, giving hydroxy carboxylic acids, which spontaneously lactonize.[1]

chemical route to gamma-lactones from fatty alcohols

References

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  1. ^abPanten, 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.
  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

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  • 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.
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