19958-66-8Relevant articles and documents
Structure-Odor Correlations in Homologous Series of Mercapto Furans and Mercapto Thiophenes Synthesized by Changing the Structural Motifs of the Key Coffee Odorant Furan-2-ylmethanethiol
Schoenauer, Sebastian,Schieberle, Peter
, p. 4189 - 4199 (2018/05/01)
Furan-2-ylmethanethiol (2-furfurylthiol; 2-FFT, 1) is long-known as a key odorant in roast and ground coffee and was also previously identified in a wide range of thermally treated foods such as meat, bread, and roasted sesame seeds. Its unique coffee-like odor quality elicited at very low concentrations, and the fact that only a very few compounds showing a similar structure have previously been described in foods make 1 a suitable candidate for structure-odor activity studies. To gain insight into the structural features needed to evoke a coffee-like odor at low concentrations, 46 heterocyclic mercaptans and thio ethers were synthesized, 32 of them for the first time, and their odor qualities and odor thresholds were determined. A movement of the mercapto group to the 3-position kept the coffee-like aroma but led to an increase in odor threshold. A separation of the thiol group from the furan ring by an elongation of the carbon side chain caused a loss of the coffee-like odor and also led to an increase in odor thresholds, especially for ω-(furan-2-yl)alkane-1-thiols with six or seven carbon atoms in the side chain. A displacement of the furan ring by a thiophene ring had no significant influence on the odor properties of most of the compounds studied, but the newly synthesized longer-chain 1-(furan-2-yl)- and 1-(thiophene-2-yl)alkane-1-thiols elicited interesting passion fruit-like scents. In total, only 4 out of the 46 compounds also showed a coffee-like odor quality like 1, but none showed a lower odor threshold. Besides the odor attributes, also retention indices, mass spectra, and NMR data of the synthesized compounds were elaborated, which are helpful in possible future identification of these compounds in trace levels in foods or other materials.
A rapid condensation between lysophosphorylcholine and fatty acids with an easily separable amine base
Acharya, Hukum P.,Kobayashi, Yuichi
, p. 2015 - 2018 (2007/10/03)
With 2,6-Cl2C6H3COCl and 1-methylimidazole, the title condensation completed at room temperature within 12 hours, which is shorter time than that with the standard DCC/DMAP system. Use of easily separable 1-methylimidazole from the crude product by chromatography is an additional advantage of the present reagent system. Georg Thieme Verlag Stuttgart.
A synthesis of oxolenes and furans via oxacyclopentylidene chromium and molybdenum complexes
Schmidt, Bernd,Kocienski, Philip,Reid, Gillian
, p. 1617 - 1630 (2007/10/03)
An easy and convenient preparation of substituted oxolenes and furans by metal-assisted cyclization of alkynols using labile pentacarbonylchromium and pentacarbonylmolybdenum complexes is described.
