Octaethylporphyrin
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Names | |
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Other names
2,3,7,8,12,13,17,18-Octaethyl-21H,23H-porphine
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Identifiers | |
3D model (JSmol)
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379798 | |
ChEBI | |
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EC Number |
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PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
C36H46N4 | |
Molar mass | 534.792 g·mol−1 |
Appearance | purple solid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Octaethylporphyrin (H2OEP) is an organic compound that is a relative of naturally occurring heme pigments. The compound is used in the preparation of models for the prosthetic group in heme proteins. It is a dark purple solid that is soluble in organic solvents. When treated with ferric chloride in hot acetic acid solution, it forms the square pyramidal complex Fe(OEP)Cl.[1] It also forms the square planar complexes Ni(OEP) and Cu(OEP).
![](http://upload.wikimedia.org/wikipedia/commons/thumb/6/69/H2OEP_in_DCM.jpg/114px-H2OEP_in_DCM.jpg)
Unlike naturally occurring porphyrins, the conjugate base of H2OEP has four-fold symmetry, which simplifies spectroscopic analysis. In contrast to tetraphenylporphyrin and related analogues, H2OEP features unprotected meso positions. In this way, it is a more accurate model for naturally occurring porphyrins.
H2OEP is prepared by condensation of 3,4-diethylpyrrole with formaldehyde.[2]
References
- ^ Chang, C. K.; DiNello, R. K.; Dolphin, D. (1980). "Iron Porphines". Inorg. Synth. 20: 147. doi:10.1002/9780470132517.ch35.
- ^ Jonathan L. Sessler; Azadeh Mozaffari; Martin R. Johnson (1992). "3,4-Diethylpyrrole and 2,3,7,8,12,13,17,18-Octaethylporphyrin". Org. Synth. 70: 68. doi:10.15227/orgsyn.070.0068.