Erythritol

• I- erythritol
• Meso -1 ,2,3,4- tetrahydroxybutane
• E 968

Colorless, sweet-tasting crystals

Fixed

1.45 g · cm -3

120-123 ° C

329-331 ° C

• Moderately in water (100 g · l-1 at 20 ° C)
• Poorly in ethanol
• Insoluble in diethyl ether

Template: Infobox chemical / molecular formula search available

Erythritol ( meso -1 ,2,3,4- Butantetrol ) is a sweet-tasting compound, is a chemical of the sugar alcohols. It is used as a sugar substitute.

Molecular construction

The molecular formula of erythritol and threitol are identical. However, the two diastereomers of erythritol having a different spatial arrangement of the hydroxyl groups on the second or third carbon atom. Unlike threitol these molecules have in the lowest energy conformation of an inversion center ( the only element of symmetry ) between the centers of 2 and 3, the two theoretically possible, identical enantiomers can therefore be converted into itself by inversion. The oppositely configured centers rotate the plane of polarized light Shin Gung with the same amount in opposite way, so that a rotation angle of 0 results. It thus is a typical meso compound. The Fischer projection accordingly shows a mirror symmetry of the molecule with a mirror plane (red dashed line), which runs through the center of inversion:

Production and representation

Producing erythritol can be performed chemically by catalytic hydrogenation of tartaric acid of Raney nickel catalysts. Here, however, also arises threitol. A further possibility for the preparation is the conversion of dialdehyde starch to an equimolar mixture of glycol and erythritol. However, since these processes all are very expensive and complicated, erythritol is today produced by microbial transformation of low molecular weight carbohydrates ( preferably glucose and sucrose ) by osmophilic fungi. Possible side products of this fermentation are ribitol, glycerol and ethanol as well as lower oligosaccharides.

Erythritol as compared to other sugar alcohols such as sorbitol, maltitol, lactitol and isomalt have the advantage of particularly high digestive tolerance (about 1 g / kg body weight). Because erythritol is added already to 90 % higher than the small intestine and excreted by the kidney, the usual sugar alcohols side effects such as bloating and diarrhea are greatly reduced.

Trade names

Erylite (D), Sukrin (D), erythritol (D), New Sweetness (D), Serapur (D), Sucolin (D, AT), Xucker Light (D, AT), Sweetery (D) Next sugar, extra light (AT), Snake for sweetening (AT), Eryfly (D, aT), Wiezucker diet (D, F)