Δ-Decalactone Explained

δ-Decalactone (DDL) is a chemical compound, classified as a lactone, that naturally occurs in fruit[1] and milk products[2] in traces. It can be obtained from both chemical and biological sources.[3] [4] Chemically, it is produced from Baeyer–Villiger oxidation of delfone.[5] From biomass, it can be produced via the hydrogenation of 6-pentyl-α-pyrone.[6] DDL has applications in food,[7] polymer,[8] and agricultural[9] industries to formulate important products.

The S-enantiomer has a nutty odor with a fruity undertone.[10] The R-enantiomer is the main component of the warning stench of the North American porcupine.[11]

See also

Notes and References

  1. 10.1021/jf0503964 . 15969525 . Authenticity Assessment of γ- and δ-Decalactone from Prunus Fruits by Gas Chromatography Combustion/Pyrolysis Isotope Ratio Mass Spectrometry (GC-C/P-IRMS) . Journal of Agricultural and Food Chemistry . 53 . 13 . 5397–5401 . 2005 . Tamura . Hirotoshi . Appel . Markus . Richling . Elke . Schreier . Peter.
  2. 10.1021/jf0009854 . 11409991 . Aroma-Active Components of Nonfat Dry Milk . Journal of Agricultural and Food Chemistry . 49 . 6 . 2948–2953 . 2001 . Karagül-Yüceer . Yonca . Drake . Maryanne . Cadwallader . Keith R. .
  3. 10.1002/adsc.200303234 . A New Environmentally Benign Catalytic Process for the Asymmetric Synthesis of Lactones: Synthesis of the Flavouringδ-Decalactone Molecule . Advanced Synthesis & Catalysis . 346 . 23 . 257–262 . 2004 . Corma . Avelino . Iborra . Sara . Mifsud . María . Renz . Michael . Susarte . Manuel.
  4. 10.1021/acssuschemeng.8b05014 . Alternate Biobased Route to Produce δ-Decalactone: Elucidating the Role of Solvent and Hydrogen Evolution in Catalytic Transfer Hydrogenation . ACS Sustainable Chemistry & Engineering . 7 . 3 . 2894–2898 . 2019 . Alam . Md. Imteyaz . Khan . Tuhin S. . Haider . M. Ali. 104343740 .
  5. 10.1002/adsc.200303234 . A New Environmentally Benign Catalytic Process for the Asymmetric Synthesis of Lactones: Synthesis of the Flavouring δ-Decalactone Molecule . Advanced Synthesis & Catalysis . 346 . 23 . 257–262 . 2004 . Corma . Avelino . Iborra . Sara . Mifsud . María . Renz . Michael . Susarte . Manuel .
  6. 10.1021/acssuschemeng.8b05014 . Alternate Biobased Route to Produce δ-Decalactone: Elucidating the Role of Solvent and Hydrogen Evolution in Catalytic Transfer Hydrogenation . ACS Sustainable Chemistry & Engineering . 7 . 3 . 2894–2898 . 2019 . Alam . Md. Imteyaz . Khan . Tuhin S. . Haider . M. Ali. 104343740 .
  7. The forty-ninth meeting of the Joint FAO/WHO Expert Committee on Food Additives; WHO food additive series 40; WHO: Geneva, 1998
  8. 10.1021/mz200006s . Bulk Ring-Opening Transesterification Polymerization of the Renewable δ-Decalactone Using an Organocatalyst . ACS Macro Letters . 1 . 131–135 . 2012 . Martello . Mark T. . Burns . Adam . Hillmyer . Marc. 1 . 35578491 .
  9. 10.1111/mve.12061 . 24797537 . Assessing the efficacy of candidate mosquito repellents against the background of an attractive source that mimics a human host . Medical and Veterinary Entomology . 28 . 4 . 407–413 . 2014 . Menger . D. J. . Van Loon . J. J. A. . Takken . W.. 13106405 .
  10. Web site: delta-decalactone, 705-86-2 . 2023-11-05 . www.thegoodscentscompany.com . en-US.
  11. Li. Guang. Roze. Uldis. Locke. David C.. Warning Odor of the North American Porcupine(Erethizon dorsatum). Journal of Chemical Ecology. December 1997. 23. 12. 2737–2754. 10.1023/A:1022511026529. 1997JSP....23.2737L. 36405223.

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