12-04442. Gladiolic Acid [Archived]
Nomenclature
CAS number: 478-05-7
2,3-Diformyl-6-methoxy-5-methylbenzoic acid; 4-methoxy-5-methyl-o-phthalaldehyde-3-carboxylic
acid. C11H10O5; mol wt 222.19.
C 59.46%, H 4.54%, O 36.00%.
Description and references
Fungistatic antibiotic produced by Penicillium gladioli Machacek: Brian et al., Nature 157, 697 (1946). Active only in the form shown; the lactol form, 4-formyl-3-hydroxy-7-methoxy-6-methylphthalide, is inactive. Structure: Grove, Biochem. J. 50, 648 (1952); 54, 664 (1953); J. Chem. Soc. 1952, 3345; Raistrick, Ross, Biochem. J. 50, 635 (1952). Synthesis: Brown, Newbold, J. Chem. Soc. 1954, 1076.
Properties
Silky needles from water, mp 160°. pK 4.4. uv max: 214, 271, 304 nm (ε 18500, 6900, 3200). Sol in hot water.Status
This monograph has been retired and is no longer subject to revision or update.