4587. Hadacidin

Nomenclature

CAS number: 689-13-4
N-Formyl-N-hydroxyglycine; N-formyl-N-hydroxyaminoacetic acid; N-hydroxyformamidoacetic acid.
C3H5NO4; mol wt 119.08.
C 30.26%, H 4.23%, N 11.76%, O 53.74%.

Description and references

Antitumor antibiotic originally isolated from cultures of Penicillium frequentans Westling. Synthesis: Kaczka et al., Biochemistry 1, 340 (1962); Kinnel, Schoenewaldt, US 3154578 (1964 to Merck & Co.). Biosynthesis: Stevens, Emery, Biochemistry 5, 74 (1966). Review: Shigeura, “Hadacidin” in Antibiotics I, D. Gottlieb, P. Shaw, Eds. (Springer-Verlag, New York, 1967) pp 451-456.

Chemical structure

Properties

Unstable crystals, mp 119-120°. Turns brown and liquefies on standing. The decompn products are formic acid and N-hydroxyglycine. Dibasic acid, potentiometric titration shows pH peak at 3.5 and 9.1. Soluble in water, methanol, ethanol, acetone, ether.

Derivative

Monosodium salt.
C3H4NNaO4; mol wt 141.06.
C 25.54%, H 2.86%, N 9.93%, Na 16.30%, O 45.37%.

Properties

Crystals. Easily forms a hydrate, very freely sol in water.