98954-25-7Relevant articles and documents
The Discovery of Citral-Like Thiophenes in Fried Chicken
Cannon, Robert J.,Curto, Nicole L.,Esposito, Cynthia M.,Payne, Richard K.,Janczuk, Adam J.,Agyemang, David O.,Cai, Tingwei,Tang, Xiao-Qing,Chen, Michael Z.
, p. 5690 - 5699 (2017/07/24)
The isomers of 3,7-dimethyl-2,6-octadienal, more commonly known together as citral, are two of the most notable natural compounds in the flavor and fragrance industry. However, both isomers are inherently unstable, limiting their potential use in various applications. To identify molecules in nature that can impart the fresh lemon character of citral while demonstrating stability under acidic and thermal conditions has been a major challenge and goal for the flavor and fragrance industry. In the study of fried chicken, several alkyl thiophenecarbaldehydes were identified by gas chromatography-mass spectrometry and gas chromatography-olfactometry that provided a similar citral-like aroma. The potential mechanism of formation in fried chicken is discussed. Furthermore, in order to explore the organoleptic properties of this structural backbone, a total of 35 thiophenecarbaldehyde derivatives were synthesized or purchased for evaluation by odor and taste. Certain organoleptic trends were observed as the length of the alkyl or alkenyl chain increased or when the chain was moved to different positions on the thiophene backbone. The 3-substituted alkyl thiophenecarbaldehydes, specifically 3-butyl-2-thiophenecarbaldehyde and 3-(3-methylbut-2-en-1-yl)-2-thiophenecarbaldehyde, exhibited strong citrus and citral-like notes. Several alkyl thiophenecarbaldehydes were tested in high acid stability trials (4 °C vs 38 °C) and outperformed citral both in terms of maintaining freshness over time and minimizing off-notes. Additional measurements were completed to calculate the odor thresholds for a select group of thiophenecarbaldehydes, which were found to be between 4.7-215.0 ng/L in air.
Palladium-catalyzed regioselective allylation of five-membered heteroarenes with allyltributylstannane
Zhang, Sheng,Yu, Xiaoqiang,Feng, Xiujuan,Yamamoto, Yoshinori,Bao, Ming
supporting information, p. 3842 - 3845 (2015/03/30)
Palladium-catalyzed allylation reactions of 2-(chloromethyl)thiophenes, 2-(chloromethyl)furans, and N-protected 2-(chloromethyl)-1H-pyrroles with allyltributylstannane were described in this study. This type of allylation reaction regioselectively occurred on the heteroarene rings to produce allylated dearomatization products or allylated heteroarenes with satisfactory yields.
The Synthesis and Liquid Crystal Properties of Some Series Homologues of 1,2,4-Oxadiazole Derivatives
Gallardo, H.,Begnini, I. M.
, p. 85 - 94 (2007/10/02)
Homologues series of some derivatives of 3,5-(4-substituted phenyl)-1,2,4-oxydiazole were synthesized and their phase behavior studied.Introduction of the pentagonal heteroaromatic ring leads to significant changes in mesomorphic behavior in comparison with analogous compounds containing the phenyl ring.The synthesised compounds exhibit smectic and nematic phases. - Keywords: 1,2,4-oxadiazole, nematic and smectic liquid crystals