223653-15-4Relevant articles and documents
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.
Chirality transfer through sulfur or selenium to chiral propellers
Skowronek, Pawel,cianowski, Jacek,Pacula, Agata J.,Gawroski, Jacek
, p. 69441 - 69444 (2015/09/01)
The mechanism of chirality transfer from a chiral alkyl substituent to a trityl moiety through sulfur or selenium atoms is analysed and discussed on the basis of ECD measurements, DFT structure and ECD spectra calculations. It is shown that the presence o
The use of sulfides derived from carane, p -menthane, pinane, and bornane in the synthesis of optically active epoxides
Banach, Anna,Scianowski, Jacek,Ozimek, Piotr
, p. 274 - 284 (2014/01/06)
Convenient routes for the synthesis of optically active methyl, phenyl, and dimonoterpenyl sulfides derived from carane, p-menthane, pinane, and bornane were developed. Methyl and dimonoterpenyl sulfides have been obtained by the reaction of the corresponding monoterpene thiolates with methyl iodide or monoterpene tosylates. The reactions of monoterpene tosylates with sodium benzenethiolate gave the corresponding phenyl monoterpenyl sulfides. These sulfides were used for the sulfur ylide-mediated reaction to yield epoxides. Good diastereoselectivities up to 99:1 and low to moderate enantioselectivities were observed for the enantioselective synthesis of chiral epoxides.
Asymmetric synthesis of new optically active sulfinamides of menthane series and their derivatives
Izmest'ev,Sudarikov,Rubtsova,Slepukhin,Kuchin
, p. 184 - 192 (2012/06/01)
Asymmetric syntheses were performed of neomenthanesulfi namide in the yield of 60% and de 74%, of neomenthanesulfi naldimines and N-substituted neomenthanesulfi namides in 22-80 and 40-90% yields respectively. Pleiades Publishing, Ltd., 2012.
Synthesis of several optically active menthane disulfides and thiosulfinates
Sudarikov,Rubtsov,Kuchin
experimental part, p. 46 - 50 (2011/07/09)
Symmetric and asymmetric disulfides were synthesized from mixtures of menthyl- and neomenthylthiols and were oxidized asymmetrically. Dineomenthyldisulfide, dimenthyldisulfide, and menthylneomenthyldisulfide were synthesized in yields of 47-48%, 24-25, an
Stereoselective synthesis of δ-lactones from 5-oxoalkanals via one-pot sequential acetalization, tishchenko reaction, and lactonization by cooperative catalysis of samarium ion and mercaptan
Hsu,Fang
, p. 8573 - 8584 (2007/10/03)
By the synergistic catalysis of samarium ion and mercaptan, a series of 5-oxoalkanals was converted to (substituted) δ-lactones in efficient and stereoselective manners. This one-pot procedure comprises a sequence of acetalization, Tishchenko reaction and lactonization. The deliberative use of mercaptan, by comparison with alcohol, is advantageous to facilitate the catalytic cycle. The reaction mechanism and stereochemistry are proposed and supported by some experimental evidence. Such samarium ion/mercaptan cocatalyzed reactions show the feature of remote control, which is applicable to the asymmetric synthesis of optically active δ-lactones. This study also demonstrates the synthesis of two insect pheromones, (2S,5R)-2-methylhexanolide and (R)-hexadecanolide, as examples of a new protocol for asymmetric reduction of long-chain aliphatic ketones.
One pot rapid synthesis of thiols from alcohols under mild conditions
Bandgar,Sadavarte
, p. 908 - 910 (2007/10/03)
Thiols are prepared in high yields from corresponding alcohols using Ph3P, NBS in acetone and followed by addition of polymer supported hydrosulfide under mild condition.
Remarkably fast direct synthesis of thiols from alcohols under mild conditions
Bandgar,Sadavarte,Uppalla
, p. 1304 - 1305 (2007/10/03)
One pot rapid synthesis of thiols from alcohols via trifluoroacetates using polymer supported hydrosulfide in acetonitrile under mild conditions has been described.
Syntheses of Chiral Menthyl and Neomenthyl Sulfides, Sulfoxides and Sulfones
Blanco, Jose Manuel,Caamano, Olga,Fernandez, Franco,Nieto, Isabel
, p. 538 - 541 (2007/10/03)
Attempts to synthesize stereospecifically menthanethiol (2) and menthyl thiocyanate (3) from suitable electrophilic neomenthyl substrates (4a-c) and a variety of sulfur nucleophiles failed or predominatly led to β-elimination products.Almost quantitative
Separation of racemic binaphthol into enantiomers. Synthesis of neomenthylthioacetic acid chloride - A new chiral resolving agent
Pakulsi,Zamojski
, p. 111 - 114 (2007/10/02)
Treatment of racemic binaphthol (1) with neomenthylthioacetic acid chloride (2) gave monoesters 7 and 8. Their separation by column chromatography followed by reduction afforded enantiometrically pure binaphthols.
