2-Keto-L-gulonic Acid
Title: 2-Keto-L-gulonic Acid
CAS Registry Number: 526-98-7
CAS Name: L-xylo-2-Hexulosonic acid
Additional Names: 2-oxo-L-gulonic acid
Molecular Formula: C6H10O7
Molecular Weight: 194.14
Percent Composition: C 37.12%, H 5.19%, O 57.69%
Literature References: Important intermediate in vitamin C manufacture. Prepn from sorbitol: Reichstein, Grüssner, Helv. Chim. Acta 17, 311 (1934); Reichstein, US 2301811 (1942); from L-sorbose: Haworth et al., GB 443901 (1936); by microbial conversion: Huang, US 3043749 (1962 to Pfizer); Motizuki et al., US 3234105 (1966 to Takeda); Z. Y. Yuan et al., Ann. N.Y. Acad. Sci. 672, 628 (1992). Biosynthesis and metabolism in bacteria: S. Makover et al., Biotechnol. Bioeng. 17, 1485 (1975). NMR structure determn: T. C. Crawford et al., J. Am. Chem. Soc. 102, 2220 (1980). HPLC separation in fermentation broth: R. A. Lazarus, J. L. Seymour, Anal. Biochem. 157, 360 (1986). Review of early syntheses: T. C. Crawford, S. A. Crawford, Adv. Carbohydr. Chem. Biochem. 37, 79-159 (1980).
Properties: Crystals from water (may be washed with acetone). mp 171° (slight dec). [a]D18 -48° (c = 1). Moderately sol in water. Strong acid. Reduces boiling Fehling's soln rapidly.
Melting point: mp 171° (slight dec)
Optical Rotation: [a]D18 -48° (c = 1)
 
Derivative Type: Methyl ester
Properties: Crystals, mp 155-157°. [a]D18 -25° (c = 1 in methanol).
Melting point: mp 155-157°
Optical Rotation: [a]D18 -25° (c = 1 in methanol)
 
Derivative Type: Ethyl ester
Properties: Crystals, [a]D20 -14.5° (c = 0.63 in abs alc).
Optical Rotation: [a]D20 -14.5° (c = 0.63 in abs alc)

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