Threitol

• 7493-90-5
• 2418-52-2 (2R, 3R)
• 2319-57-5 (2S, 3S)
• 6968-16-7 (racemate )

Fixed

Attention

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Threitol (1,2,3,4 - Butantetrol ) refers to a chemical compound with a sweet taste, which belongs to the group of sugar alcohols ( alditols ). From threitol exist two enantiomers, (2R, 3R)- threitol and ( 2S, 3S)- threitol. The molecules of the two - threitol forms relate to each other as mirror images. A mixture of these two compounds is referred to as threitol. Another sugar alcohol with the same molecular formula as that threitol is the erythritol.

Properties

Both enantiomeric forms are optically active because they are built chiral. Threitol has the second and the third carbon atom of 2 chiral centers (crosses) are shown in the Fischer projection as the intersections of the vertical and horizontal linkages. The two enantiomers differ in the spatial orientation of their hydroxyl groups at this carbon atoms. The designations of (2R, 3R)- threitol and (2S, 3S)- threitol are based on the arrangement of the hydroxyl groups, and follow the Cahn -Ingold-Prelog - Convention.

Erythritol has the same molecular formula and the same constitution as threitol, but differs in the configuration. In the Fischer projection, the hydroxy groups of erythritol are the second and third carbon atom on the same side.

Production

Threitol may be made from the sugar threose by reduction of the aldehyde to the hydroxyl group. In the lab, this is quite possible with sodium borohydride as reducing agent. Furthermore, the reduction with hydrogen can be carried threose, wherein nickel (Ni ) is used as a catalyst (catalytic hydrogenation). A further possibility is the catalytic hydrogenation of erythrulose, This produces both conformations. Furthermore threitol can be biotechnologically produced from erythritol. This reaction is catalyzed by Bordetella avium eg.