7599. Porphine

Nomenclature

CAS number: 101-60-0
21H,23H-Porphine; porphin.
C20H14N4; mol wt 310.35.
C 77.40%, H 4.55%, N 18.05%.

Description and references

Parent substance of the porphyrins, a group of compounds found in all living matter which are the basis of respiratory pigments in animals and plants. In porphyrins, side chains are substituted for the hydrogens in the porphine pyrrole rings. Chlorins are dihydroporphyrins. See also: chlorophyll, hemoglobin, vitamin B12, hematin. Prepn of porphine: Fischer, Gleim, Ann. 521, 157 (1935); Rothemund, J. Am. Chem. Soc. 58, 625 (1936); Krol, J. Org. Chem. 24, 2065 (1959). Study of porphyrin analogs: C. L. Honeybourne et al., Tetrahedron 36, 1833 (1980). Review of biosyntheses of porphyrins and chlorins: A. R. Battersby, E. McDonald in Porphyrins Metalloporphyrins, K. M. Smith, Ed. (Elsevier, New York, 1975) pp 61-122. Review of porphyrin syntheses: R. P. Evstigneeva, Pure Appl. Chem. 53, 1129-1140 (1981). Comprehensive seven volume treatise: The Porphyrins, D. Dolphin, Ed. (Academic Press, New York, 1978).

Chemical structure

Properties

Dark red, shiny leaflets from chloroform-methanol. Darkens at 360° but does not melt. The absorption bands are those characteristic of the substituted porphyrins, details in Fischer-Orth, Die Chemie des Pyrrols vol. II, 1, 175 (1937). Sol in pyridine, dioxane, and phenol; slightly sol in chloroform, bromoform, glacial acetic acid. Almost insol in acetone, methanol, ether. HCl number: 1.7 (Fischer); 3.3 (Rothemund).

Derivative

Iron salt.
C20H12N4.FeCl; mol wt 399.63.
C 60.11%, H 3.03%, N 14.02%, Fe 13.97%, Cl 8.87%.

Properties

Brown cubes from ether.

Derivative

Magnesium salt.
C20H12MgN4; mol wt 332.64.
C 72.21%, H 3.64%, Mg 7.31%, N 16.84%.

Properties

Red needles.

Derivative

Copper salt.
C20H12N4Cu; mol wt 371.88.
C 64.59%, H 3.25%, N 15.07%, Cu 17.09%.

Properties

Brown needles.