Porphine

Last updated
Porphine
Porphyrin.svg
Porphyrin3D.png
Names
IUPAC name
Porphyrin [1]
Other names
Porphin
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.690 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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- Yes check.svgY
    Key: RKCAIXNGYQCCAL-CEVVSZFKSA-N Yes check.svgY
  • 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 mass 310.35196 g/mol
AppearanceDark 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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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. [2]

Contents

The nonpolar tetrapyrrolic ring structure of porphine means it is poorly soluble in most organic solvents and hardly water soluble. [3] As a result, porphine is mostly of theoretical interest. It has been detected in GC-MS of certain fractions of Piper betle . [4]

Porphine derivatives: porphyrins

Substituted derivatives of porphine are called porphyrins. Many porphyrins are found in nature with the dominant example being protoporphyrin IX. [5] Many synthetic porphyrins are also known, including octaethylporphyrin [6] and tetraphenylporphyrin. [7]

Two resonance structures of porphine. Porphin resonance structures.PNG
Two resonance structures of porphine.

Further reading

References

  1. "TP-0 and TP-1". iupac.qmul.ac.uk. Retrieved 2025-08-25.
  2. "Porphyrin". Encyclopedia of Inorganic and Bioinorganic Chemistry. Wiley-VCH. 2011. doi:10.1002/9781119951438.eibd0638. ISBN   9781119951438.
  3. 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.
  4. 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.
  5. 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.
  6. 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.
  7. 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.