D-Erythritol, 赤藓糖醇

meso-Erythritol, belonging to the class of sugar alcohols, is identified in a variety of food products, fruits, vegetables, beverages and dietary supplements. It is known as a low glycemic food additive and plays an important role as a sweetener for diabetic patients, since it does not have glycemic or insulinemic effect due to its ability to not get metabolized but get absorbed in the small intestine. It is also reportedly used as a sugar substitute in toothpaste, chewing gums, confectionery food products, etc.

Erythritol is the meso-diastereomer of butane-1,2,3,4-tetrol. It has a role as an antioxidant, a plant metabolite and a human metabolite.

Erythritol is a four-carbon sugar that is found in algae, fungi, and lichens. It is twice as sweet as sucrose and can be used as a coronary vasodilator.

D-Threitol, also known as D-threo-tetritol, belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group. D-Threitol is very soluble (in water) and a very weakly acidic compound (based on its pKa). D-Threitol has been primarily detected in feces, urine, blood, and cerebrospinal fluid. D-Threitol has been linked to the inborn metabolic disorders including ribose-5-phosphate isomerase deficiency.

Title: Erythritol

CAS Registry Number: 149-32-6

CAS Name: (2R,3S)-rel-1,2,3,4-Butanetetrol

Additional Names: meso-erythritol; tetrahydroxybutane; erythrol; erythrite; antierythrite; erythroglucin; phycite

Molecular Formula: C4H10O4

Molecular Weight: 122.12

Percent Composition: C 39.34%, H 8.25%, O 52.41%

Literature 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).

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).

Melting point: mp 121.5°

Boiling point: bp 329-331°

pKa: pKa (18°): 13.903

Toxicity data: 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.