Formation mechanism of p-methylacetophenone from citral via a tert-alkoxy radical intermediate

Journal of Agricultural and Food Chemistry
Toshio UenoChi-Tang Ho

Abstract

The aim of this study was to clarify the formation mechanism of a potent off-odorant, p-methylacetophenone, from citral under acidic aqueous conditions. An acidic aqueous solution (pH 3.0) containing 10 mg/L of citral was stored at 40 degrees C for 2 weeks. Among the compounds detected in the stored citral solution, 4-(2-hydroxy-2-propyl)benzaldehyde was identified for the first time as a degradation product from citral. The formation of p-methylacetophenone and 4-(2-hydroxy-2-propyl)benzaldehyde behaved the same when antioxidants were added to the citral solution. In addition, both compounds were formed by the Fe(2+)-induced decomposition of 8-hydroperoxy-p-cymene, another compound identified in the stored citral solution. These results suggested that both p-methylacetophenone and 4-(2-hydroxy-2-propyl)benzaldehyde can be formed via the same radical intermediate [p-CH3C6H4C(CH3)2O*] that can be derived from the O-O bond homolysis of 8-hydroperoxy-p-cymene. On the other hand, the degradation of 8-hydroperoxy-p-cymene without Fe2+ under acidic aqueous conditions did not yield p-methylacetophenone and 4-(2-hydroxy-2-propyl)benzaldehyde, but the degradation of citral without Fe2+ did. Therefore, other than the decomposition of 8-h...Continue Reading

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Citations

Apr 27, 2011·Journal of Agricultural and Food Chemistry·Xiaoqing YangQingrong Huang
Dec 14, 2011·Journal of Agricultural and Food Chemistry·Xiaoqing YangQingrong Huang
Jul 17, 2013·Journal of Agricultural and Food Chemistry·Qin ZhaoQingrong Huang
Oct 13, 2014·Food Chemistry·Sung Joon ParkSeung Jun Choi
Aug 21, 2010·Journal of Food Science·Seung Jun ChoiDavid Julian McClements
Oct 24, 2015·Journal of the Science of Food and Agriculture·Chi Rac HongSeung Jun Choi
Sep 7, 2016·Molecular Oncology·Margaret Lois ThomasPaola Marcato
Dec 17, 2014·Journal of Agricultural and Food Chemistry·Bethany J HauschKeith R Cadwallader
Jan 18, 2017·Bioscience, Biotechnology, and Biochemistry·Sarunya PhunpeeApinan Soottitantawat
Oct 20, 2012·Journal of the Science of Food and Agriculture·María J Cejudo-BastanteCarmelo García-Barroso
Dec 12, 2017·Journal of Dairy Science·Hope FaulknerKieran N Kilcawley
Nov 11, 2010·Prikladnaia biokhimiia i mikrobiologiia·T A MisharinaI B Medvedeva
Jun 1, 2015·Journal of Food and Drug Analysis·Monthana WeerawatanakornChi-Tang Ho
Jul 10, 2019·Food Science and Technology International = Ciencia Y Tecnología De Los Alimentos Internacional·C RochaL M Cunha
May 17, 2019·Food Science and Biotechnology·Sung Hwa KimSeung Jun Choi
Jul 4, 2017·Journal of Agricultural and Food Chemistry·Robert J CannonMichael Z Chen
Mar 12, 2019·Journal of Agricultural and Food Chemistry·Emel AyJacques Lalevée
Apr 13, 2006·Journal of Agricultural and Food Chemistry·Toshio UenoHideki Masuda

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