Threit

Structural formula
(2R, 3R) -Threit and (2S, 3S) -Threit ( Fischer projection )
General
Surname	Threit
other names	1,2,3,4-butanetetrol Threitol
Molecular formula	C 4 H 10 O 4
External identifiers / databases
CAS number 7493-90-5 2418-52-2 (2 R , 3 R ) 2319-57-5 (2 S , 3 S ) 6968-16-7 (racemate) EC number 621-282-7 ECHA InfoCard 100.150.149 PubChem 169019 ChemSpider 147828 DrugBank DB03278 Wikidata Q415347
properties
Molar mass	122.12 g mol −1
Physical state	firmly
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 315-319-335 P: 261-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Threit ( 1,2,3,4-butanetetrol ) is a chemical compound with a sweet taste that belongs to the group of sugar alcohols (alditols). There are two enantiomers of Threit , (2R, 3R) -Threitol and (2S, 3S) -Threitol. The molecules of the two Threit forms relate to one another like an image and a mirror image. A mixture of these two compounds is also called threitol . Another sugar alcohol with the same molecular formula as the Threit is erythritol .

properties

Both enantiomeric forms are optically active because they are built chirally . Threitol has with the second and third carbon - Atom 2 chiral centers in the Fischer-projections are shown as points of intersection of the vertical and horizontal linkages (crosses). The two enantiomers differ in the spatial position of their hydroxyl groups on these carbon atoms. The designations (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 Threit, but differs in configuration . In the Fischer projection of erythritol, the hydroxyl groups on the second and third carbon atoms are on the same side.

Manufacturing

Threit can be made from the sugar threose by reducing the aldehyde group to the hydroxyl group. In the laboratory this is quite possible with sodium borohydride as a reducing agent. Furthermore, threose can be reduced with hydrogen, with nickel (Ni) serving as a catalyst ( catalytic hydrogenation) . Another possibility is the catalytic hydrogenation of erythrulose , which creates both configurations. Furthermore, Threit can be produced biotechnologically from erythritol. This reaction is z. B. catalyzed by Bordetella avium .

Individual evidence

1. ↑ ^{a b} data sheet DL-Threitol from Sigma-Aldrich , accessed on April 24, 2011 ( PDF ).