9997. Violacein

Nomenclature

CAS number: 548-54-9
(E)-3-[1,2-Dihydro-5-(5-hydroxy-1H-indol-3-yl)-2-oxo-3H-pyrrol-3-ylidene]-1,3-dihydro-2H-indol-2-one; 3-[2-(5-hydroxyindol-3-yl)-5-oxo-2-pyrrolin-4-ylidene]-2-indolinone; 3-[2-(5-hydroxyindol-3-yl)-5-oxopyrrolin-4-ylidene]oxindole; 5-(5-hydroxy-3-indolyl)-3-(3-oxindolylidene)-2-oxopyrroline.
C20H13N3O3; mol wt 343.34.
C 69.96%, H 3.82%, N 12.24%, O 13.98%.

Description and references

Pigment isolated from Chromobacterium violaceum (Bacillus violaceus): Tobie, J. Bacteriol. 29, 223 (1935); Strong, Science 100, 287 (1944); Ballantine et al., J. Chem. Soc. 1958, 755. Structure and synthesis: Ballantine et al., ibid. 1960, 2292. Review: DeMoss in Antibiotics vol. 2, D. Gottlieb, P. D. Shaw, Eds. (Springer, New York, 1967).

Chemical structure

Properties

Purplish-black needles, prisms. Practically insol in water; slightly sol in alcohol; moderately sol in dioxane.