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Porphine

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Porphine
Names
Other names
Porphin
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard100.002.690Edit this at Wikidata
UNII
  • 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
  • C1=CC2=CC5=CC=C(C=C4C=CC(C=C3C=CC(=CC1=N2)N3)=N4)N5
Properties
C20H14N4
Molar mass310.35196 g/mol
AppearanceDark red, shiny leaflets
Melting pointN/A
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Porphine orporphin is anorganic compound ofempirical formulaC20H14N4. It isheterocyclic andaromatic. The molecule is a flatmacrocycle, consisting of fourpyrrole-like rings joined by fourmethine bridges, which makes it the simplest of thetetrapyrroles.[1]

Thenonpolar tetrapyrrolic ring structure of porphine means it is poorly soluble in most organic solvents and hardly water soluble.[2] As a result, porphine is mostly of theoretical interest. It has been detected inGC-MS of certain fractions ofPiper betle.[3]

Porphine derivatives: porphyrins

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Further information:Porphyrin

Substituted derivatives of porphine are called porphyrins. Many porphyrins are found in nature with the dominant example beingprotoporphyrin IX.[4] Many synthetic porphyrins are also known, includingoctaethylporphyrin[5] andtetraphenylporphyrin.[6]

  • Common porphyrins
  • Derivatives of protoporphyrin IX are common in nature, the precursor to hemes.
    Derivatives ofprotoporphyrin IX are common in nature, the precursor tohemes.
  • 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.
Two resonance structures of porphine.

Further reading

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References

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  1. ^"Porphyrin".Encyclopedia of Inorganic and Bioinorganic Chemistry. Wiley-VCH. 2011.doi:10.1002/9781119951438.eibd0638.ISBN 9781119951438.
  2. ^Senge, Mathias O.; Davis, Mia (2010)."Porphyrin (porphine) — A neglected parent compound with potential"(PDF).Journal of Porphyrins and Phthalocyanines.14 (07):557–567.doi:10.1142/s1088424610002495.ISSN 1088-4246.
  3. ^Karak S, Das S, Biswas M, Choudhury A, Dutta M, Chaudhury K, De B (December 2019)."Phytochemical composition, β-glucuronidase inhibition, and antioxidant properties of two fractions of Piper betle leaf aqueous extract".Journal of Food Biochemistry.43 (12): e13048.doi:10.1111/jfbc.13048.PMID 31581322.S2CID 203661105.
  4. ^Paul R. Ortiz de Montellano (2008). "Hemes in Biology".Wiley Encyclopedia of Chemical Biology. John Wiley & Sons.doi:10.1002/9780470048672.wecb221.ISBN 978-0470048672.
  5. ^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.
  6. ^Lindsey, Jonathan S. (2000). "Synthesis of meso-substituted porphyrins". In Kadish, Karl M.; Smith, Kevin M.; Guilard, Roger (eds.).Porphyrin Handbook. Vol. 1. pp. 45–118.ISBN 0-12-393200-9.
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