Enantioselective syntheses and sensory properties of the 3-mercapto-2-methylpentanols.
3-Mercapto-2-methylpentanol, a new powerful flavor compound, exhibits two stereocenters giving rise to two pairs of diastereomers. To determine differences in the sensory properties, all four diastereomers and enantiomers were stereo- and enantioselectively synthesized. A highly diastereoselective aldol reaction using a chiral auxiliary was one of the key steps in the synthesis. Further derivatization yielded the enantiopure compounds. Odor thresholds in air and water were determined.
Sabater Lüntzel
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Corporate Research, DRAGOCO Gerberding & Company, AG D-37601, Holzminden, Germany.
Widder
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Vössing
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Pickenhagen
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D008956:Models, Chemical; D009812:Odorants; D000439:Pentanols / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis*; D013649:Taste
D000439:Pentanols; D013438:Sulfhydryl Compounds; C406689:3-mercapto-2-methylpentan-1-ol