Hyalobiuronic Acid
Title: Hyalobiuronic Acid
CAS Registry Number: 499-15-0
CAS Name: 2-Amino-2-deoxy-3-O-b-D-glucopyranuronosyl-D-glucose
Additional Names: 3-O-(b-D-glucopyranosyluronic acid)-2-amino-2-deoxy-D-glucose
Molecular Formula: C12H21NO11
Molecular Weight: 355.30
Percent Composition: C 40.57%, H 5.96%, N 3.94%, O 49.53%
Literature References: Disaccharide unit of hyaluronic acid. Isoln from hyaluronic acid: Rapport et al., Nature 168, 996 (1951). Structure: Weissman, Meyer, J. Am. Chem. Soc. 76, 1753 (1954). Synthesis: Takanashi et al., ibid. 84, 3029 (1962).
Properties: Rectangular prisms from water, darken at 190° with no characteristic melting or dec point. pK1¢ = 2.6, pK2¢ = 7.1. Shows mutarotation: [a]D20 +34° ® +30° (c = 1.08 in 0.1N HCl). Sparingly sol in hot water, dilute HCl, dil NaHCO3. Practically insol in water, glacial acetic acid, ethanol, methanol and pyridine.
pKa: pK1¢ = 2.6, pK2¢ = 7.1
Optical Rotation: [a]D20 +34° ® +30° (c = 1.08 in 0.1N HCl)
 
Derivative Type: N-Acetylhyalobiuronic acid
Molecular Formula: C14H23NO12
Molecular Weight: 397.33
Percent Composition: C 42.32%, H 5.83%, N 3.53%, O 48.32%
Properties: Amorphous. pK¢ = 3.3. [a]D24 -32° (c = 2.0 in water).
pKa: pK¢ = 3.3
Optical Rotation: [a]D24 -32° (c = 2.0 in water)

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