Porphine

Porphine

File:Porphyrin.svg
File:Porphyrin3D.png
Names
IUPAC name Porphyrin
Other names Porphin
Identifiers
CAS Number	101-60-0 checkY
3D model (JSmol)	Interactive image
ChEBI	CHEBI:8337 checkY
ChemSpider	10447586 checkY
ECHA InfoCard
E number
PubChem CID	66868
UNII	604BGD9J5B checkY
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI InChI=1S/C20H14N4/c1-2-14-10-16-5-6-18(23-16)12-20-8-7-19(24-20)11-17-4-3-15(22-17)9-13(1)21-14/h1-12,21,24H/b13-9-,14-10-,15-9-,16-10-,17-11-,18-12-,19-11-,20-12- checkY Key: RKCAIXNGYQCCAL-CEVVSZFKSA-N checkY InChI=1/C20H14N4/c1-2-14-10-16-5-6-18(23-16)12-20-8-7-19(24-20)11-17-4-3-15(22-17)9-13(1)21-14/h1-12,21,24H/b13-9-,14-10-,15-9-,16-10-,17-11-,18-12-,19-11-,20-12- Key: RKCAIXNGYQCCAL-CEVVSZFKBA
SMILES C1=CC2=CC5=CC=C(C=C4C=CC(C=C3C=CC(=CC1=N2)N3)=N4)N5
Properties
Chemical formula	C20H14N4
Molar mass	310.35196 g/mol
Appearance	Dark red, shiny leaflets
Melting point	N/A
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). checkY verify (what is checkY☒N ?) Infobox references

Porphine or porphin is an organic compound of empirical formula C₂₀H₁₄N₄. 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

Further information: Porphyrin

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.

• Common porphyrins
• Derivatives of protoporphyrin IX are common in nature, the precursor to hemes.
  Derivatives of protoporphyrin IX are common in nature, the precursor to hemes.
• Octaethylporphyrin (H2OEP) is a synthetic analogue of protoporphyrin IX. Unlike the natural porphyrin ligands, OEP2− is highly symmetrical.
  Octaethylporphyrin (H₂OEP) is a synthetic analogue of protoporphyrin IX. Unlike the natural porphyrin ligands, OEP²⁻ is highly symmetrical.
• 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.
  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.

File:Porphin resonance structures.PNG

Two resonance structures of porphine.