Porphine

Porphine

Names
IUPAC name Porphyrin [1]
Other names Porphin
Identifiers
CAS Number	101-60-0  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:8337  Y
ChemSpider	10447586  Y
ECHA InfoCard	100.002.690
PubChem CID	66868
UNII	604BGD9J5B  Y
CompTox Dashboard (EPA)	DTXSID6059235
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- Y Key: RKCAIXNGYQCCAL-CEVVSZFKSA-N Y 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). Y  verify  (what is  YN ?) 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. ^[2]

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

Further information: Porphyrin

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]

• Common porphyrins
• 
  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.
• 
  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

• Budavari, Susan (1989). "7574. Porphine" . The Merck Index (11th ed.). Merck & Co., Inc. p.  1210. ISBN   0-911910-28-X. LCCN   89-60001.

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   978-1-119-95143-8.
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   978-0-470-04867-2.
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.