. The actinomycetes. Actinomycetales. DESCRIPTIONS OF ANTIBIOTICS 327 110°C (decomposition). Very soluble in methanol, ethanol, acetone, and butanol. Soluble in dilute aqueous acids and moderately soluble in water and ligroin. Insoluble in hexane, carbon tetra- chloride, and n-dibutyl ether. More soluble in aqueous alkaline solution than erythromycin or carbomycin. Ultraviolet absorption spectrum maximum at 290 to 295 m/u (e = 50), a broad, low intensity peak (4, 16, 18). Infrared spectnun given in references 1 and 4. [a]i, = —65° =b 1° (c = 2 per cent in methanol). Positive Fehling (slow) and
. The actinomycetes. Actinomycetales. DESCRIPTIONS OF ANTIBIOTICS 327 110°C (decomposition). Very soluble in methanol, ethanol, acetone, and butanol. Soluble in dilute aqueous acids and moderately soluble in water and ligroin. Insoluble in hexane, carbon tetra- chloride, and n-dibutyl ether. More soluble in aqueous alkaline solution than erythromycin or carbomycin. Ultraviolet absorption spectrum maximum at 290 to 295 m/u (e = 50), a broad, low intensity peak (4, 16, 18). Infrared spectnun given in references 1 and 4. [a]i, = —65° =b 1° (c = 2 per cent in methanol). Positive Fehling (slow) and Tollen tests. Negative and ninhydrin tests. Rf = on paper chromatography with benzene saturated with formamide. pK,.,' = 0,2N (12, 16): C = ; H = ; N = Molecular weight, about 715. Equivalent weight, 690 (1, 16, 18). Forms a crystalline solvate with chloroform, 120-122°C (decomposition) in which the chloroform is tenaciously bound, as well as other solvate-hydrate complexes. Methanolysis of oleandomycin under mild acidic concHtions gives "desoleandomycin," C2SH49NO9 , a colorless substance, 116-118°C, and CsHi604 , the methylglycositle of L-oleandrose (2-desoxy-L- glucomethylose-3-methyl ether). Acid hydrolysis products include desosamine (18). Oleandomycin hydrochloride (anhydrous): 125-128°C (1) or 134-135°C (4). Hydrochloride (Dihydrate): Crys- talline; 134-135°C. Very soluble in water. [a]o = ° (c = 2 per cent in methanol). Stable in aqueous solution at room temperature for several hours, over a wide range of pH. Stal)le in the dry state or in anhydrous solvents. Unstable to acid pH on heating (4,18). Sulfate: Long, white needles. Soluble in water (4). Phosphate: Crystalline; 150°C (decomposition). Water-soluble (16). Oleandmycin is composed of a polyhydroxy, polymethyl ketolactone ("oleandride") gly- cosidically bound with the desoxy sugars L- oleandrose and desosam
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