39067-80-6Relevant articles and documents
Exploiting the Synthetic Potential of Sesquiterpene Cyclases for Generating Unnatural Terpenoids
Oberhauser, Clara,Harms, Vanessa,Seidel, Katja,Schr?der, Benjamin,Ekramzadeh, Kimia,Beutel, Sascha,Winkler, Sven,Lauterbach, Lukas,Dickschat, Jeroen S.,Kirschning, Andreas
, p. 11802 - 11806 (2018/09/10)
The substrate flexibility of eight purified sesquiterpene cyclases was evaluated using six new heteroatom-modified farnesyl pyrophosphates, and the formation of six new heteroatom-modified macrocyclic and tricyclic sesquiterpenoids is described. GC-O analysis revealed that tricyclic tetrahydrofuran exhibits an ethereal, peppery, and camphor-like olfactoric scent.
Macrocyclic lactone compound, preparation method thereof, and intermediate application
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Paragraph 0074; 0075, (2016/10/07)
The invention discloses macrolide compounds with the general structure represented by formula I, a preparation method thereof, an application thereof and an intermediate thereof. The macrolide compounds have very strong activities on most test G bacteria, wherein the activities of two types of compounds to partial gram-positive bacteria are higher than the activities of Azithromycin to the partial gram-positive bacteria.
Structure-Odor Activity Studies on Monoterpenoid Mercaptans Synthesized by Changing the Structural Motifs of the Key Food Odorant 1-p-Menthene-8-thiol
Schoenauer, Sebastian,Schieberle, Peter
, p. 3849 - 3861 (2016/06/01)
1-p-Menthene-8-thiol (1) has been discovered as the key odorant in grapefruit juice several decades ago and contributes to the overall odor of the fruit with an extremely low odor threshold of 0.000034 ng/L in air. This value is among the lowest odor thresholds ever reported for a food odorant. To check whether modifications in the structure of 1 would lead to changes in odor threshold and odor quality, 34 mercapto-containing p-menthane and 1-p-menthene derivatives as well as several aromatic and open-chain mercapto monoterpenoids were synthesized. Eighteen of them are reported for the first time in the literature, and their odor thresholds and odor qualities as well as analytical data are supplied. A comparison of the sensory data with those of 1 showed that hydrogenation of the double bond led to a clear increase in the odor threshold. Furthermore, moving the mercapto group into the ring always resulted in higher odor thresholds compared to thiols with a mercapto group in the side chains. Although all tertiary thiols always exhibited low odor thresholds, none of the 31 compounds reached the extremely low threshold of 1. Also, none of the synthesized mercapto monoterpenoids showed a similar odor quality resembling grapefruit. Although the saturated and aromatic analogues exhibited similar scents as 1, the aromas of the majority of the other compounds were described as sulfury, rubber-like, burned, soapy, or even mushroom-like. NMR and MS data as well as retention indices of the 23 newly reported sulfur-containing compounds might aid in future research to identify terpene-derived mercaptans possibly present in trace levels in foods.