δ-癸内酯

化合物

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-戊基环戊酮拜耳-维立格氧化反应[5]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
IUPAC名
6-Pentyloxan-2-one
识别
CAS号 705-86-2  checkY
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

参考资料

  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. 
  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.