δ-癸内酯

δ-癸内酯
	IUPAC名; 6-Pentyloxan-2-one
识别
CAS号	705-86-2
PubChem	12810
ChemSpider	12282
SMILES	CCCCCC1CCCC(=O)O1;
ChEBI	87327
性质
化学式	C10H18O2
摩尔质量	170.25 g·mol−1
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

δ-癸内酯，简称DDL，是一种内酯，化学式 C₁₀H₁₈O₂。它天然微量存在于水果^[1]和奶制品中。^[2]它可以从化学和生物来源获得。^[3]^[4]从化学方法获得的方法是2-戊基环戊酮的拜耳－维立格氧化反应；^[5]而生物质方法是通过6-戊基-α-吡喃酮的氢化产生。^[4] DDL应用于食品、^[6]聚合物^[7]和农业^[8]。

δ-癸内酯的S-对映异构体很香，而R-对映异构体则是北美豪猪的警告性恶臭的主要成分。^[9]

参见

γ-癸内酯

参考资料

^ Tamura, Hirotoshi; Appel, Markus; Richling, Elke; Schreier, Peter. 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. 2005, 53 (13): 5397–5401. PMID 15969525. doi:10.1021/jf0503964.
^ Karagül-Yüceer, Yonca; Drake, Maryanne; Cadwallader, Keith R. Aroma-Active Components of Nonfat Dry Milk. Journal of Agricultural and Food Chemistry. 2001, 49 (6): 2948–2953. PMID 11409991. doi:10.1021/jf0009854.
^ Corma, Avelino; Iborra, Sara; Mifsud, María; Renz, Michael; Susarte, Manuel. A New Environmentally Benign Catalytic Process for the Asymmetric Synthesis of Lactones: Synthesis of the Flavouringδ-Decalactone Molecule. Advanced Synthesis & Catalysis. 2004, 346 (23): 257–262. doi:10.1002/adsc.200303234.
^ ^4.0 ^4.1 Alam, Md. Imteyaz; Khan, Tuhin S.; Haider, M. Ali. Alternate Biobased Route to Produce δ-Decalactone: Elucidating the Role of Solvent and Hydrogen Evolution in Catalytic Transfer Hydrogenation. ACS Sustainable Chemistry & Engineering. 2019, 7 (3): 2894–2898. doi:10.1021/acssuschemeng.8b05014.
^ Corma, Avelino; Iborra, Sara; Mifsud, María; Renz, Michael; Susarte, Manuel. A New Environmentally Benign Catalytic Process for the Asymmetric Synthesis of Lactones: Synthesis of the Flavouring δ-Decalactone Molecule. Advanced Synthesis & Catalysis. 2004, 346 (23): 257–262. doi:10.1002/adsc.200303234.
^ The forty-ninth meeting of the Joint FAO/WHO Expert Committee on Food Additives; WHO food additive series 40; WHO: Geneva, 1998
^ Martello, Mark T.; Burns, Adam; Hillmyer, Marc. Bulk Ring-Opening Transesterification Polymerization of the Renewable δ-Decalactone Using an Organocatalyst. ACS Macro Letters. 2012, 1: 131–135. doi:10.1021/mz200006s.
^ Menger, D. J.; Van Loon, J. J. A.; Takken, W. Assessing the efficacy of candidate mosquito repellents against the background of an attractive source that mimics a human host. Medical and Veterinary Entomology. 2014, 28 (4): 407–413. PMID 24797537. S2CID 13106405. doi:10.1111/mve.12061.
^ 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. Bibcode:1997JSP....23.2737L. S2CID 36405223. doi:10.1023/A:1022511026529.

[1] Tamura, Hirotoshi; Appel, Markus; Richling, Elke; Schreier, Peter. 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. 2005, 53 (13): 5397–5401. PMID 15969525. doi:10.1021/jf0503964.

[2] Karagül-Yüceer, Yonca; Drake, Maryanne; Cadwallader, Keith R. Aroma-Active Components of Nonfat Dry Milk. Journal of Agricultural and Food Chemistry. 2001, 49 (6): 2948–2953. PMID 11409991. doi:10.1021/jf0009854.

[3] Corma, Avelino; Iborra, Sara; Mifsud, María; Renz, Michael; Susarte, Manuel. A New Environmentally Benign Catalytic Process for the Asymmetric Synthesis of Lactones: Synthesis of the Flavouringδ-Decalactone Molecule. Advanced Synthesis & Catalysis. 2004, 346 (23): 257–262. doi:10.1002/adsc.200303234.

[#1-4] 4.0 ^4.1 Alam, Md. Imteyaz; Khan, Tuhin S.; Haider, M. Ali. Alternate Biobased Route to Produce δ-Decalactone: Elucidating the Role of Solvent and Hydrogen Evolution in Catalytic Transfer Hydrogenation. ACS Sustainable Chemistry & Engineering. 2019, 7 (3): 2894–2898. doi:10.1021/acssuschemeng.8b05014.

[5] Corma, Avelino; Iborra, Sara; Mifsud, María; Renz, Michael; Susarte, Manuel. A New Environmentally Benign Catalytic Process for the Asymmetric Synthesis of Lactones: Synthesis of the Flavouring δ-Decalactone Molecule. Advanced Synthesis & Catalysis. 2004, 346 (23): 257–262. doi:10.1002/adsc.200303234.

[6] The forty-ninth meeting of the Joint FAO/WHO Expert Committee on Food Additives; WHO food additive series 40; WHO: Geneva, 1998

[7] Martello, Mark T.; Burns, Adam; Hillmyer, Marc. Bulk Ring-Opening Transesterification Polymerization of the Renewable δ-Decalactone Using an Organocatalyst. ACS Macro Letters. 2012, 1: 131–135. doi:10.1021/mz200006s.

[8] Menger, D. J.; Van Loon, J. J. A.; Takken, W. Assessing the efficacy of candidate mosquito repellents against the background of an attractive source that mimics a human host. Medical and Veterinary Entomology. 2014, 28 (4): 407–413. PMID 24797537. S2CID 13106405. doi:10.1111/mve.12061.

[9] 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. Bibcode:1997JSP....23.2737L. S2CID 36405223. doi:10.1023/A:1022511026529.

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