Γ-Lactone
{{DISPLAYTITLE:γ-Lactone}}
γ-Lactones are a family of organic compounds with the formula cyclo-{{chem2|O\dCOCHRCH2CH2}}. 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.{{cite book |doi=10.1002/14356007.t11_t02 |chapter=Flavors and Fragrances, 3. Aromatic and Heterocyclic Compounds |title=Ullmann's Encyclopedia of Industrial Chemistry |date=2016 |last1=Panten |first1=Johannes |last2=Surburg |first2=Horst |pages=1–45 |isbn=978-3-527-30673-2 }}
| class="wikitable"
|+ Some γ-lactone fragrances | |||
| Name | Formula | Registry number | Notes |
|---|---|---|---|
| γ-Octalactone | {{chem2|C8H14O2}} | 104-50-7 | fruity |
| γ-Nonalactone | {{chem2|C9H16O2}} | 104-61-0 | coconut-like |
| γ-Decalactone | {{chem2|C10H18O2}} | 706-14-9 | peach flavors |
| γ-Undecalactone | {{chem2|C11H20O2}} | 104-67-6 | peach flavors |
| β-Methyl-γ-octalactone | {{chem2|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.{{cite journal |doi=10.1007/s00253-010-2945-0 |title=Biochemistry of lactone formation in yeast and fungi and its utilisation for the production of flavour and fragrance compounds |date=2011 |last1=Romero-Guido |first1=Cynthia |last2=Belo |first2=Isabel |last3=Ta |first3=Thi Minh Ngoc |last4=Cao-Hoang |first4=Lan |last5=Alchihab |first5=Mohamed |last6=Gomes |first6=Nelma |last7=Thonart |first7=Philippe |last8=Teixeira |first8=Jose A. |last9=Destain |first9=Jacqueline |last10=Waché |first10=Yves |journal=Applied Microbiology and Biotechnology |volume=89 |issue=3 |pages=535–547 |pmid=20981417 }} In terms of chemical routes, fatty alcohols undergo free radical addition to acrylic acid, giving hydroxy carboxylic acids, which spontaneously lactonize.
References
{{reflist}}
External links
- {{cite journal
| last = Poisson
| first = L.
| title = Characterization of the most odor-active compounds in an American Bourbon whisky by application of the aroma extract dilution analysis.
| journal = J Agric Food Chem
| volume =56
| issue = 14
| pages = 5813–9
| date = July 23, 2008
| doi =10.1021/jf800382m| pmid = 18570373
}}
{{DEFAULTSORT:Lactone, γ-}}