4450. d-Glucaric Acid
Nomenclature
CAS number: 87-73-0
Saccharic acid; d-glucosaccharic acid; d-tetrahydroxyadipic acid. C6H10O8; mol wt 210.14.
C 34.29%, H 4.80%, O 60.91%.
Description and 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. [α]D19 +6.86° → +20.60° (H2O). Ka1 = 1.0 × 105 at 25°. Soluble in water, ethanol. Sparingly sol in ether.Derivative
1,4-Lactone.Nomenclature
Saccharolactone.Description and references
Strong inhibitor of β-glucuronidase: Levvy, Biochem. J. 52, 464 (1952); Boyland, Williams, ibid. 64, 578 (1956).