D-Glucaric Acid

Title: D-Glucaric Acid
CAS Registry Number: 87-73-0
Additional Names: Saccharic acid; D-glucosaccharic acid; D-tetrahydroxyadipic acid
Molecular Formula: C6H10O8
Molecular Weight: 210.14
Percent Composition: C 34.29%, H 4.80%, O 60.91%
Literature References: Best prepd by nitric acid oxidation of starch; yields as high as 65% are obtained in contrast to much lower yields from glucose or sucrose: Kiliani, Ber. 58, 2344 (1925); Schmidt et al., ibid. 70, 2402 (1937). Prepn from D-glucose: Mehltretter et al., US 2472168 (1949 to U.S. Secy. Agr.); Truchan, US 2809989 (1957 to Cowles Chem.); Phillips et al., J. Chem. Soc. 1958, 3522; BE 615023 (1962 to Ciba).
Properties: Needles from 95% ethanol, mp 125-126°. Shows mutarotation. [a]D19 +6.86° ® +20.60° (H2O). Ka1 = 1.0 ´ 10-5 at 25°. Soluble in water, ethanol. Sparingly sol in ether.
Melting point: mp 125-126°
Optical Rotation: [a]D19 +6.86° ® +20.60° (H2O)
Derivative Type: 1,4-Lactone
Additional Names: Saccharolactone
Literature References: Strong inhibitor of b-glucuronidase: Levvy, Biochem. J. 52, 464 (1952); Boyland, Williams, ibid. 64, 578 (1956).
Properties: Monohydrate, crystals, mp 90°.
Melting point: Monohydrate, crystals, mp 90°
D-Glucoascorbic Acid D-Glucuronic Acid D-Glucuronolactone D-Gulonic Acid D-Gulose