142. Actinorhodine

Nomenclature

CAS number: 1397-77-9
C32H26O14; mol wt 634.54.
C 60.57%, H 4.13%, O 35.30%.

Description and references

Antibiotic pigment produced by Streptomyces coelicolor, found in woods near Gttingen, Germany: Brockmann, Pini, Naturwissenschaften 34, 190 (1947); Brockmann et al., Ber. 83, 161 (1950). Tentative structure: Brockmann, Hieronymus, Ber. 88, 1379 (1955); Brockmann et al., Naturwissenschaften 49, 131 (1962). Structure: Brockmann, Angew. Chem. 76, 863 (1964); Brockmann et al., Ann. 698, 209 (1966). Stereochemistry: Zeeck, Christiansen, Ann. 724, 172 (1969). Biosynthesis and determn of point of dimerization: C. P. Gorst-Allman et al., J. Org. Chem. 46, 455 (1981).

Chemical structure

Properties

Fine red needles from dioxane, dec 270°. Absorption max (dioxane): 560, 523 nm. Sol in pyridine, piperidine, tetrahydrofuran, dioxane, phenol; slightly sol in alcohol, acetic acid, acetone. Red soln with acetone, blue soln with pyridine. Practically insol in aq acid; sol in aq alkali with bright blue color.