Lactobionic Acid
Title: Lactobionic Acid
CAS Registry Number: 96-82-2
CAS Name: 4-O-b-D-Galactopyranosyl-D-gluconic acid
Additional Names: 4-(b-D-galactosido)-D-gluconic acid
Molecular Formula: C12H22O12
Molecular Weight: 358.30
Percent Composition: C 40.23%, H 6.19%, O 53.58%
Literature References: Obtained by oxidation of lactose: Fischer, Meyer, Ber. 22, 362 (1889); Ruff, Ollendorff, ibid. 33, 1806 (1900); Isbell, J. Res. Natl. Bur. Stand. 11, 713 (1933); Margariello, US 2746916 (1956 to Nat. Dairy Res. Labs.); Eddy, Nature 181, 904 (1958); Nishizuka et al., J. Biol. Chem. 235, PC13 (1960). Manuf from lactose: Y. Sato et al., DE 2038230 (1971 to Hayashibara Co.), C.A. 74, 142296c (1971). Crystal structure of calcium salt: W. J. Cook, C. E. Bugg, Acta Crystallogr. B29, 215 (1973). NMR studies: T. Taga et al., Bull. Chem. Soc. Jpn. 51, 2278 (1978). For therapeutic use see Erythromycin Lactobionate.
Properties: Syrup. Freely sol in water, slightly sol in methanol, ethanol, glacial acetic acid. Dehydration by distillation with dioxane yields lactobionic d-lactone, C12H20O11, non-deliquescent crystals, dec 195-196°. Shows mutarotation. [a]D20 +53.0° initial (c = 8.8) ® [a]D20 +22.6° final (240 minutes).
Optical Rotation: [a]D20 +53.0° initial (c = 8.8) ® [a]D20 +22.6° final (240 minutes)
 
Derivative Type: Calcium salt
Additional Names: Calcium lactobionate
Molecular Formula: C24H42CaO24
Molecular Weight: 754.65
Percent Composition: C 38.20%, H 5.61%, Ca 5.31%, O 50.88%
Properties: Pentahydrate, hairlike needles in brushlike groups. When anhydr, slender needles from small amts of anhydr ethanol. [a]D20 +23.7° (c = 6.28). nD20 1.4583 (concd syrup just before crystallization). Freely sol in water.
Optical Rotation: [a]D20 +23.7° (c = 6.28)
Index of refraction: nD20 1.4583 (concd syrup just before crystallization)

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