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Porphine

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Porphineorporphin is an organic compoundofempirical 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.^[1]

Porphine
Names


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

The nonpolar 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 in GC-MS of certain fractions of Piper betle.^[3]

Porphine derivatives: porphyrins

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Substituted derivatives of porphine are called porphyrins. Many porphyrins are found in nature with the dominant example being protoporphyrin IX.^[4] Many synthetic porphyrins are also known, including octaethylporphyrin^[5] and tetraphenylporphyrin.^[6]

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.

References

edit

^ "Porphyrin". Encyclopedia of Inorganic and Bioinorganic Chemistry. Wiley-VCH. 2011. doi:10.1002/9781119951438.eibd0638. ISBN 9781119951438.

^ 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.

^ 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.

^ 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.

^ 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.

^ 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.

Retrieved from "https://en.wikipedia.org/w/index.php?title=Porphine&oldid=1195947006" Last edited on 15 January 2024, at 22:03

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Porphine

Porphine derivatives: porphyrins

Further reading

References

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