Erythritol

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.
Erythritol Anhydride Erythrityl Tetranitrate Erythrocentaurin Erythromycin Erythromycin Acistrate

Erythritol
Erythritol structure.svg
Identifiers
CAS number 10030-58-7 YesY
PubChem 222285
ChemSpider 192963 YesY
UNII RA96B954X6 YesY
DrugBank DB04481
KEGG D08915 YesY
ChEBI CHEBI:17113 YesY
ChEMBL CHEMBL349605 YesY
Jmol-3D images Image 1
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Properties
Molecular formula C4H10O4
Molar mass 122.12 g mol−1
Density 1.45 g/cm³
Melting point 121 °C; 250 °F; 394 K
Boiling point 329 to 331 °C; 624 to 628 °F; 602 to 604 K
Hazards
NFPA 704
NFPA 704.svg
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Erythritol ((2R,3S)-butane-1,2,3,4-tetraol) is a sugar alcohol (or polyol) that has been approved for use as a food additive in the United States[1] and throughout much of the world. It was discovered in 1848 by British chemist John Stenhouse.[2] It occurs naturally in some fruits and fermented foods.[3] At the industrial level, it is produced from glucose by fermentation with a yeast, Moniliella pollinis.[1] It is 60–70% as sweet as table sugar yet it is almost noncaloric, does not affect blood sugar, does not cause tooth decay, and is partially absorbed by the body, excreted in urine and feces. It is less likely to cause gastric side effects than other sugar alcohols because of its unique digestion pathway. Under U.S. Food and Drug Administration (FDA) labeling requirements, it has a caloric value of 0.2 kilocalories per gram (95% less than sugar and other carbohydrates), though nutritional labeling varies from country to country. Some countries, such as Japan and the United States, label it as zero-calorie, while European Union regulations currently label it and all other sugar alcohols at 0.24 kcal/g.