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δ-Decalactone

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δ-Decalactone
Names
Preferred IUPAC name 6-Pentyloxan-2-one
Other names
  • delta-Decalactone
  • 5-Decanolide
  • δ-pentyl-δ-valerolactone
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.010.810 Edit this at Wikidata
EC Number
  • 211-889-1
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H18O2/c1-2-3-4-6-9-7-5-8-10(11)12-9/h9H,2-8H2,1H3Key: GHBSPIPJMLAMEP-UHFFFAOYSA-N
SMILES
  • CCCCCC1CCCC(=O)O1
Properties
Chemical formula C10H18O2
Molar mass 170.252 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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

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

See also

References

  1. Tamura, Hirotoshi; Appel, Markus; Richling, Elke; Schreier, Peter (2005). "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. doi:10.1021/jf0503964. PMID 15969525.
  2. Karagül-Yüceer, Yonca; Drake, Maryanne; Cadwallader, Keith R. (2001). "Aroma-Active Components of Nonfat Dry Milk". Journal of Agricultural and Food Chemistry. 49 (6): 2948–2953. doi:10.1021/jf0009854. PMID 11409991.
  3. Corma, Avelino; Iborra, Sara; Mifsud, María; Renz, Michael; Susarte, Manuel (2004). "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. doi:10.1002/adsc.200303234.
  4. Alam, Md. Imteyaz; Khan, Tuhin S.; Haider, M. Ali (2019). "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. doi:10.1021/acssuschemeng.8b05014. S2CID 104343740.
  5. Corma, Avelino; Iborra, Sara; Mifsud, María; Renz, Michael; Susarte, Manuel (2004). "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. doi:10.1002/adsc.200303234.
  6. Alam, Md. Imteyaz; Khan, Tuhin S.; Haider, M. Ali (2019). "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. doi:10.1021/acssuschemeng.8b05014. S2CID 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. Martello, Mark T.; Burns, Adam; Hillmyer, Marc (2012). "Bulk Ring-Opening Transesterification Polymerization of the Renewable δ-Decalactone Using an Organocatalyst". ACS Macro Letters. 1 (1): 131–135. doi:10.1021/mz200006s. PMID 35578491.
  9. Menger, D. J.; Van Loon, J. J. A.; Takken, W. (2014). "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. doi:10.1111/mve.12061. PMID 24797537. S2CID 13106405.
  10. "delta-decalactone, 705-86-2". www.thegoodscentscompany.com. Retrieved 2023-11-05.
  11. Li, Guang; Roze, Uldis; Locke, David C. (December 1997). "Warning Odor of the North American Porcupine(Erethizon dorsatum)". Journal of Chemical Ecology. 23 (12): 2737–2754. Bibcode:1997JSP....23.2737L. doi:10.1023/A:1022511026529. S2CID 36405223.
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