Title: Hemin
CAS Registry Number: 16009-13-5
CAS Name: (SP-5-13)-Chloro[7,12-diethenyl-3,8,13,17-tetramethyl-21H,23H-porphine-2,18-dipropanoato(4-)-N21,N22,N23,N24]ferrate(2-) dihydrogen
Additional Names: chloro[dihydrogen 3,7,12,17-tetramethyl-8,13-divinyl-2,18-porphinedipropionato(2-)]iron; chlorohemin; 1,3,5,8-tetramethyl-2,4-divinylporphine-6,7-dipropionic acid ferrichloride; Teichmann's crystals; ferriheme chloride; ferriprotoporphyrin chloride; ferriporphyrin chloride
Molecular Formula: C34H32ClFeN4O4
Molecular Weight: 651.94
Percent Composition: C 62.64%, H 4.95%, Cl 5.44%, Fe 8.57%, N 8.59%, O 9.82%
Literature References: Prepd from hemoglobin soln by heating with acetic acid and sodium chloride. Practical procedure for its prepn from ox blood: Schalfejeff, J. Russ. Phys. Chem. Soc. 1885, 30; Ber. 18, 232 (1885); Gattermann-Wieland, Praxis des Organischen Chemikers 23rd ed., p 407; Fischer-Orth, Die Chemie des Pyrrols II, 1, 377 (Leipzig, 1937); H. Fischer, Org. Synth. coll. vol. III, 442 (1955); Labbe, Nishida, Biochim. Biophys. Acta 26, 437 (1957). Biosynthesis: Karlzeile, Angew. Chem. 66, 729 (1954). Review: Stoll, Experientia 4, 6 (1948); H. H. Inhoffen, Naturwissenschaften 55, 457 (1968); W. S. Caughey in Inorganic Biochemistry vol. 2, G. L. Eichhorn, Ed. (Elsevier, New York, 1973) pp 797-831.
Properties: Long, thin blades from glacial acetic acid or from chloroform-pyridine-acetic acid, appearing brown in transmitted light and steel-blue in reflected light. Sinters at 240° but is not melted at 300°. Absorption spectrum: Fischer-Orth, loc. cit. Freely sol in dil ammonia water, also in solns of sodium hydroxide with hematin formation, i.e., the chlorine is displaced by an OH group. Practically insol in carbonate solns, dil acid solns. Sol in strong organic bases such as trimethylamine, p-toluidine, dimethylaniline. Sol in concd H2SO4 with loss of Fe. Sparingly sol in 70-80% alc. Practically insol but stable in water.
Derivative Type: Dimethyl ester
Molecular Formula: C36H36ClFeN4O4
Molecular Weight: 679.99
Percent Composition: C 63.59%, H 5.34%, Cl 5.21%, Fe 8.21%, N 8.24%, O 9.41%
Properties: Needles from benzene, not melted at 300°. Freely sol in acetic acid, benzene, chloroform, acetone.
Derivative Type: Diethyl ester
Molecular Formula: C38H40ClFeN4O4
Molecular Weight: 708.05
Percent Composition: C 64.46%, H 5.69%, Cl 5.01%, Fe 7.89%, N 7.91%, O 9.04%
Properties: Crystals, freely sol in chloroform.
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