Prodigiosin
Title: Prodigiosin
CAS Registry Number: 82-89-3
CAS Name: 4-Methoxy-5-[(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl]-2,2¢-bi-1H-pyrrole
Additional Names: 2,2¢-[3-methoxy-4¢-amyl-5¢-methyl-5-(2¢¢-pyrryl)]dipyrrylmethene; prodigiosine
Molecular Formula: C20H25N3O
Molecular Weight: 323.43
Percent Composition: C 74.27%, H 7.79%, N 12.99%, O 4.95%
Literature References: Antibiotic pigment produced by Chromobacterium prodigiosum (Serratia marcescens). Exhibits antimicrobial and cytotoxic properties. Isoln: Wrede, Hettche, Ber. 62, 2678 (1929); Lasseur, Georges, Trav. Lab. Microbiol. Fac. Pharm. Nancy 9, 47 (1936); Lasseur, Melcion, ibid. 13, 192 (1944). Purification: Morgan, Tanner, J. Chem. Soc. 1955, 3305. Structure: Wrede, Rothhaas, Z. Physiol. Chem. 226, 95 (1934). Revised structure and synthesis: H. H. Wasserman et al., J. Am. Chem. Soc. 82, 506 (1960); H. Rapoport, K. G. Holden, ibid. 5510; ibid. 84, 635 (1962); A. J. Castro et al., J. Org. Chem. 28, 857 (1963). Total synthesis and in vitro cytotoxic activity: D. L. Boger, M. Patel, Tetrahedron Lett. 28, 2499 (1987); eidem, J. Org. Chem. 53, 1405 (1988). NMR studies: R. J. Cushley et al., Can. J. Chem. 53, 148 (1975). Antimalarial activity: A. J. Castro, Nature 213, 903 (1967). Review: R. P. Williams, W. R. Hearn in Antibiotics vol. 2, D. Gottlieb, P. D. Shaw, Eds. (Springer-Verlag, New York, 1967) pp 410-432, 449-451. Review of synthesis: A. H. Jackson, K. M. Smith, in The Total Synthesis of Natural Products vol. 1, J. ApSimon, Ed. (Wiley-Interscience, New York, 1973) pp 227-232; of biological activity and production: V. Alonzo, Ig. Mod. 81, 557-564 (1984), C.A. 101, 126398h (1984).
Properties: Lustrous square pyramids (dark red with green reflex) from petr ether, mp 151-152°. Almost insol in water. Moderately sol in alcohol, ether; freely sol in chloroform, bromoform, benzene. Alkaline or neutral solns are orange-yellow, acid solns are red. Absorption max (isopropanol): 466 nm (e 43000); 336, 280 nm.
Melting point: mp 151-152°
Absorption maximum: Absorption max (isopropanol): 466 nm (e 43000); 336, 280 nm
 
Derivative Type: Hydrochloride
CAS Registry Number: 112373-40-7
Molecular Formula: C20H26ClN3O
Molecular Weight: 359.89
Percent Composition: C 66.75%, H 7.28%, Cl 9.85%, N 11.68%, O 4.45%
Properties: Magenta crystals from benzene + petr ether, dec 148.5-150°. Absorption max (isopropanol): 540, 294 nm (e 70700, 10800).
Absorption maximum: Absorption max (isopropanol): 540, 294 nm (e 70700, 10800)

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