5055-99-2

Upstream product

• 1845-59-6 (1S,2S,4S)-(+)-carvomenthol 
• 98-59-9 p-toluenesulfonyl chloride 
• 22567-21-1 (1S,2S,5S)-5-isopropenyl-2-methylcyclohexan-1-ol 

Downstream Products

• 5056-00-8 (3S,6R)-3-methyl-6-(1-methylethyl)cyclohexene 
• 1845-59-6 (1S,2S,4S)-(+)-carvomenthol 
• 5563-78-0 (-)neocarvomenthol 
• 499-94-5 (S)-carvomenthene 
• 87001-64-7 (-)neocarvomenthyl carbonitrile 
• 61585-35-1 p-menth-1-ene 

Relevant academic research and scientific papers

Structure-Odor Activity Studies on Monoterpenoid Mercaptans Synthesized by Changing the Structural Motifs of the Key Food Odorant 1-p-Menthene-8-thiol

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.

Synthesis and reactions of enantiomerically pure dialkyl diselenides from the p-menthane group

A convenient route for the synthesis of optically active dialkyl diselenides from the p-menthane system utilizing a reaction of alkyl tosylates and chlorides with sodium diselenide is reported. The diselenides obtained have been used for asymmetric methoxyselenenylation of styrene. Quantum chemical calculations of the chair conformers stability of the terpeneselenenyl bromides from the p-menthane group have also been carried out using density functional theory (DFT, at the B3LYP/6-311G(d) level). The influence of the diselenides structure on the stereoselectivity in the methoxyselenenylation reaction is also discussed.