Title: D-Glucaric Acid
CAS Registry Number: 87-73-0
Synonyms: 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
Synonyms: 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°