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Porphine

Porphine

Porphine or porphin is an organic compound of empirical formula . It is heterocyclic and aromatic. The molecule is a flat macrocycle, consisting of four pyrrole-like rings joined by four methine bridges, which makes it the simplest of the tetrapyrroles.

The nonpolar tetrapyrrolic ring structure of porphine means it is poorly soluble in most organic solvents and hardly water soluble. As a result, porphine is mostly of theoretical interest. It has been detected in GC-MS of certain fractions of Piper betle.

Porphine derivatives: porphyrins

Substituted derivatives of porphine are called porphyrins. Many porphyrins are found in nature with the dominant example being protoporphyrin IX. Many synthetic porphyrins are also known, including octaethylporphyrin and tetraphenylporphyrin.

File:Protoporphyrin IX neutral.svg|Derivatives of protoporphyrin IX are common in nature, the precursor to hemes. File:H2octaethylporphyrin.png |Octaethylporphyrin (H2OEP) is a synthetic analogue of protoporphyrin IX. Unlike the natural porphyrin ligands, OEP2− is highly symmetrical. File:H2TPP.png|Tetraphenylporphyrin (H2TPP)is another synthetic analogue of protoporphyrin IX. Unlike the natural porphyrin ligands, TPP2− is highly symmetrical. Another difference is that its methine centers are occupied by phenyl groups.

Two resonance structures of porphine.

References

References

  1. "TP-0 and TP-1".
  2. {{cite encyclopedia. (2011). Wiley-VCH
  3. Senge, Mathias O.. (2010). "Porphyrin (porphine) — A neglected parent compound with potential". Journal of Porphyrins and Phthalocyanines.
  4. (December 2019). "Phytochemical composition, β-glucuronidase inhibition, and antioxidant properties of two fractions of Piper betle leaf aqueous extract". [[Journal of Food Biochemistry]].
  5. {{cite encyclopedia. Paul R. Ortiz de Montellano. (2008). John Wiley & Sons
  6. (1992). "3,4-Diethylpyrrole and 2,3,7,8,12,13,17,18-Octaethylporphyrin". Org. Synth..
  7. Lindsey, Jonathan S.. (2000). "Synthesis of meso-substituted porphyrins".
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biomolecules chelating-agents macrocycles tetrapyrroles
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