Protoporphyrin IX
Title: Protoporphyrin IX
CAS Registry Number: 553-12-8
CAS Name: 7,12-Diethenyl-3,8,13,17-tetramethyl-21H,23H-porphine-2,18-dipropanoic acid
Additional Names: 3,7,12,17-tetramethyl-8,13-divinyl-2,18-porphinedipropionic acid; 1,3,5,8-tetramethyl-2,4-divinylporphine-6,7-dipropionic acid; ooporphyrin; Kammerer's porphyrin
Molecular Formula: C34H34N4O4
Molecular Weight: 562.66
Percent Composition: C 72.58%, H 6.09%, N 9.96%, O 11.37%
Literature References: Biological precursor of blood and plant pigments. Prepd from hemin: Fischer-Orth, Die Chemie des Pyrrols II, 1, 396 (Leipzig, 1937); Ramsey, Biochem. Prep. 3, 39 (1953). Structure: Sparatore, Mauzerall, J. Org. Chem. 25, 1073 (1960). Synthesis: Carr et al., J. Chem. Soc. C 1971, 487. Crystal and molecular structure: W. S. Caughey, J. A. Ibers, J. Am. Chem. Soc. 99, 6639 (1977). Chelates with metals, esp iron, in the ferrous state to form heme, q.v., in the ferric state to form hematin, q.v. Review: Rimington, Kennedy, in M. Florkin, H. S. Mason, Comparative Biochemistry (Academic Press, New York, 1962) pp 557-614.
Properties: Monoclinic, brownish-yellow prisms from ether. Absorption max (25% HCl): 602.4, 582.2, 557.2 nm. Freely sol in chloroform, glacial acetic acid, alcohol contg HCl, ether contg some glacial acetic acid, hydrochloric acid. Somewhat sol in dil alkalies, aniline, pyridine. Forms sparingly sol disodium and dipotassium salts.
Absorption maximum: Absorption max (25% HCl): 602.4, 582.2, 557.2 nm
 
Derivative Type: Disodium salt
CAS Registry Number: 50865-01-5
Trademarks: Depocolin-S (Ohta)
Molecular Formula: C34H32N4Na2O4
Molecular Weight: 606.62
Percent Composition: C 67.32%, H 5.32%, N 9.24%, Na 7.58%, O 10.55%
 
Derivative Type: Dimethyl ester
CAS Registry Number: 5522-66-7
Molecular Formula: C36H38N4O4
Molecular Weight: 590.71
Percent Composition: C 73.20%, H 6.48%, N 9.48%, O 10.83%
Properties: Crystals from chloroform + methanol, mp 228-230°. Absorption max (25% HCl): 601, 556, 409 nm. Soluble in chloroform, slightly sol in methanol. Insol in sodium carbonate solns.
Melting point: mp 228-230°
Absorption maximum: Absorption max (25% HCl): 601, 556, 409 nm
 
Therap-Cat: In liver disease.
Keywords: Hepatoprotectant.

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