3675. Erythritol

Nomenclature

CAS number: 149-32-6
(2R,3S)-rel-1,2,3,4-Butanetetrol; meso-erythritol; tetrahydroxybutane; erythrol; erythrite; antierythrite; erythroglucin; phycite.
C4H10O4; mol wt 122.12.
C 39.34%, H 8.25%, O 52.41%.

Description and references

All natural bulk sweetener found in various fruits and fermented foods; 60 to 70% as sweet as sucrose. Isoln from algae, lichens, grasses: Bamberger, Landsiedl, Monatsh. Chem. 21, 571 (1900); Hesse, J. Prakt. Chem. 92, 425 (1915); Hofmann, Ber. 7, 508 (1874). Prepn by Aspergillus niger: Yuill, Nature 162, 652 (1948); by Penicillium herquei: Galarraga et al., Biochem. J. 61, 456 (1955); from 2-butene-1,4-diol: Reppe, Schnabel, DE 734025 (1943 to I. G. Farbenind.); from periodate-oxidized starch: Jeanes, Hudson, J. Org. Chem. 20, 1565 (1955). Structure: Shimada, Acta Crystallogr. 11, 748 (1958). Review of metabolism, toxicology and clinical safety studies: I. C. Munro et al., Food Chem. Toxicol. 36, 1139-1174 (1998); of use in beverage industry: P. de Cock, C.-L. Bechert, Pure Appl. Chem. 74, 1281-1289 (2002).

Chemical structure

Properties

Tetragonal prisms, mp 121.5°. About twice as sweet as sucrose. bp 329-331°. Very sol in water (satd soln contains about 61% w/w); sol in pyridine (satd soln contains 2.5% w/w); slightly sol in alcohol. Practically insol in ether. pKa (18°): 13.903. LD50 in male, female rats (g/kg): 6.6, 9.6 i.v.; >16, >16 s.c.; 13.1, 13.5 orally (Munro).

Use

Non-nutritive sweetener in beverages.