Structural Formula Vector Image
Title: HON
CAS Registry Number: 4439-84-3
CAS Name: 5-hydroxy-4-oxonorvaline
Additional Names: 2-amino-5-hydroxylevulinic acid; d-hydroxy-g-oxo-L-norvaline; 2-amino-5-hydroxy-4-oxopentanoic acid
Molecular Formula: C5H9NO4
Molecular Weight: 147.13
Percent Composition: C 40.82%, H 6.17%, N 9.52%, O 43.50%
Literature References: Antitubercular antibiotic substance isolated from Streptomyces akiyoshiensis nova sp.: Tatsuoka et al., J. Antibiot. 14A, 39 (1961). Synthesis and structure: Miyake, Chem. Pharm. Bull. 8, 1071, 1074, 1079 (1960).
Properties: Needles from water + acetone, no definite mp. [a]D20 -6° (water); [a]D17 -8.2° (c = 3.4 in water). pKa 2.91. uv max (water): 271 nm (e 24). Stable in pure, dry state. Less stable in basic than in acidic solns. Colors red when heated in caustic soln, losing antibiotic activity. The DL-form is half as active as L-HON. LD50 in mice (mg/kg): 5200 i.v.; 8000 s.c.; 7600 orally (Tatsuoka).
pKa: pKa 2.91
Optical Rotation: [a]D20 -6° (water); [a]D17 -8.2° (c = 3.4 in water)
Absorption maximum: uv max (water): 271 nm (e 24)
Toxicity data: LD50 in mice (mg/kg): 5200 i.v.; 8000 s.c.; 7600 orally (Tatsuoka)

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