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Quantitative Determination of Sulfur Containing Wine Odorants at Sub-PPB Levels. 1. Synthesis of the Deuterated Analogues

Quantitative Determination of Sulfur Containing Wine Odorants at Sub-PPB Levels. 1. Synthesis of the Deuterated Analogues

Y Kotseridis, J L Ray, C Augier, R Baumes

J Agric Food Chem. 2000 Dec;48(12):5819-23.

PMID: 11141254

Abstract:

[2H10]-4-Sulfanyl-4-methylpentan-2-one (d10-SMP), [2H2]-3-sulfanylhexan-1-ol (d2-3SH), and [2H5]-3-sulfanylhexyl acetate (d5-3SHAc), the labeled analogues of impact odorants of wines and other foods, were synthesized to be used for the quantitative determination of the natural compounds in white and red wines by stable isotope dilution assay. The sulfidation was achieved by Michael addition, on mesityl oxide or ethyl hex-2-enoate, respectively, of the sulfhydryl anion generated in situ from triphenylsilanethiol and potassium fluoride under phase transfer conditions. The labeling of 4-sulfanyl-4-methylpentan-2-one (SMP) was obtained from the commercial starting material, [2H6]acetone, so that this method could be used to synthesize 13C-labeled SMP from 13C-labeled acetone. The labeling of 3-sulfanylhexan-1-ol (3SH) and 3-sulfanylhexyl acetate (3SHAc) was obtained from reduction with lithium aluminum deuteride of the Michael adduct ethyl 3-sulfanylhexanoate and [2H3]-acetylation. During the synthesis, 3SH and 3SHAc were partially oxidized to their disulfide, which were reduced back to the thiols by an additional reduction step; the tertiary thiol SMP was less sensitive to this oxidation.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP14606429	Triphenylsilanethiol		14606-42-9	Price

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