Δ-Decalactone

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.

Quick facts Names, Identifiers ...

δ-Decalactone
Names

Preferred IUPAC name 6-Pentyloxan-2-one
Other names delta-Decalactone 5-Decanolide δ-pentyl-δ-valerolactone
Identifiers
CAS Number	705-86-2^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:87327
ChEMBL	ChEMBL3182189
ChemSpider	12282
ECHA InfoCard	100.010.810
EC Number	211-889-1
PubChem CID	12810
UNII	CNA0S5T234^Y
CompTox Dashboard (EPA)	DTXSID0044496
InChI InChI=1S/C10H18O2/c1-2-3-4-6-9-7-5-8-10(11)12-9/h9H,2-8H2,1H3 Key: GHBSPIPJMLAMEP-UHFFFAOYSA-N
SMILES CCCCCC1CCCC(=O)O1
Properties
Chemical formula	C₁₀H₁₈O₂
Molar mass	170.252 g·mol⁻¹
Density	0.954 g/cm³
Melting point	−21 °C (−6 °F; 252 K)
Boiling point	281 °C (538 °F; 554 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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]

[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.

See also

References

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