616-16-0Relevant articles and documents
Influence of the Production Process on the Key Aroma Compounds of Rum: From Molasses to the Spirit
Franitza, Laura,Granvogl, Michael,Schieberle, Peter
, p. 9041 - 9053 (2016)
The production of rum consists of fermentation, distillation, and aging. To check the influence of each step on the final rum aroma, molasses, mash, distillate, and the final rum were analyzed using the sensomics concept. The changes in key aroma compounds were determined by application of aroma extract dilution analysis (AEDA) in combination with gas chromatography-mass spectrometry for identification and by stable isotope dilution assays (SIDAs) for quantitation. Odor activity values (OAVs; ratio of concentration to respective odor threshold) were calculated for the compounds determined in the rum and, finally, the rum aroma was successfully simulated by recombination. (E)-β-Damascenone showed by far the highest OAV (3280) in rum. Although this compound was determined already in molasses, its concentration increased significantly during distillation, indicating a thermolabile precursor. Vanillin, 4-ethylphenol, 2-methoxyphenol, 4-ethyl-2-methoxyphenol, and 2-methoxy-4-propylphenol are well-known compounds mainly stemming from the wood barrels used for aging and showed an OAV ≥ 1. Another important group of aroma-active compounds in rum were ethyl esters, for which a significant increase was determined during fermentation but also to a lesser extent during aging. Altogether, the concentrations of 68% of the aroma-active compounds increased during the process, demonstrating its influence on the overall rum aroma.
Structure-Elucidating Total Synthesis of the (Polyenoyl)tetramic Acid Militarinone C §
Brückner, Reinhard,Drescher, Christian,Hamburger, Matthias,Keller, Morris,Potterat, Olivier
supporting information, (2020/03/30)
The (polyenoyl)tetramic acid militarinone C (1) heads a family of seven members. Before our work, the configuration of C-5 was unknown whereas the configurations of C-8′ and C-10′ were either (R,R) or (S,S). We synthesized the four stereoisomers of constitution 1, which conform with these insights. This included cross-coupling both enantiomers of the western building block (8) with both enantiomers of the eastern building block (9). The specific rotations of the resulting 1 isomers suggested that natural 1 is configured like the coupling partners (S)-8 and (R,R)-9. This conclusion was corroborated by degrading natural 1 to alcohol 35 and by proving its configurational identity with synthetic (R,R)-35.
Synthesis method and application of diabrotica virgifera virgifera le conte sex pheromone
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Paragraph 0073; 0092; 0105-0107, (2018/07/15)
The invention belongs to the technical field of pesticide chemistry, and discloses a synthesis method and application of diabrotica virgifera virgifera le conte sex pheromone. The synthesis method comprises the steps of enabling chiral sulfone compounds, i.e., (S)-2-methylbutyl thiazolsulfone and (R)-2-methylbutyl thiazolsulfone to be respectively subjected to a Julia-Kocienski coupling reaction with chiral aldehyde compounds, i.e., (S)-6-aldehyde hexan-2-ol propionate and (R)-6-aldehyde hexan-2-ol propionate, and carrying out hydrogenation reduction on the product of the coupling reaction soas to obtain the diabrotica virgifera virgifera le conte sex pheromone. In addition, the diabrotica virgifera virgifera le conte sex pheromone prepared by the method can be applied to the prevention and control of diabrotica virgifera virgifera le conte. The synthetic route of the diabrotica virgifera virgifera le conte sex pheromone is simplified, fewer by-products are produced in the reaction, and the reaction yield is greatly increased.
Polyunsaturated C-Glycosidic 4-Hydroxy-2-pyrone Derivatives: Total Synthesis Shows that Putative Orevactaene Is Likely Identical with Epipyrone A
Preindl, Johannes,Schulthoff, Saskia,Wirtz, Conny,Lingnau, Julia,Fürstner, Alois
supporting information, p. 7525 - 7530 (2017/06/13)
Orevactaene and epipyrone A were previously thought to comprise the same polyunsaturated tail but notably different C-glycosylated 4-hydroxy-2-pyrone head groups. Total synthesis now shows that the signature bicyclic framework assigned to orevactaene is a chimera; the compound is almost certainly identical with epipyrone A, whose previously unknown stereochemistry has also been established during this study. Key to success was the ready formation of the bicyclic core of putative orevactaene by a sequence of two alkyne cycloisomerization reactions using tungsten and gold catalysis. Equally important was the flexibility in the assembly process gained by the use of heterobimetallic polyunsaturated modules whose termini could be selectively and consecutively addressed in a practical one-pot cross-coupling sequence.
