meso-Octamethylporphyrinogen
Names
IUPAC name
5,5,10,10,15,15,20,20-octamethyl-21,22,23,24-tetrahydroporphyrin
Other names
acetonepyrrole, octamethylcalix[4]pyrrole
Identifiers
3D model (JSmol)
365398
ChEBI
ChemSpider
ECHA InfoCard 100.152.255
EC Number
  • 623-589-1
2142403
  • InChI=1S/C28H36N4/c1-25(2)17-9-11-19(29-17)26(3,4)21-13-15-23(31-21)28(7,8)24-16-14-22(32-24)27(5,6)20-12-10-18(25)30-20/h9-16,29-32H,1-8H3
    Key: XZCHDFOYWDLFEY-UHFFFAOYSA-N
  • CC1(C2=CC=C(N2)C(C3=CC=C(N3)C(C4=CC=C(N4)C(C5=CC=C1N5)(C)C)(C)C)(C)C)C
Properties
C28H36N4
Molar mass 428.624 g·mol−1
Appearance white solid
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

meso-Octamethylporphyrinogen, usually referred to simply as octamethylporphyrinogen, is an organic compound with the formula (Me2C-C4H2NH)4 (Me = CH3. It is one of the simplest porphyrinogens, a family of compounds that occur as intermediates in the biosynthesis of hemes and chlorophylls. In contrast to those rings, porphyrinogens are colorless since they lack extended conjugation. The prefix meso-octamethyl indicates that the eight methyl groups are located on the carbon centers that interconnect the four pyrrole rings. Also unlike porphyrins, the porphyrinogens are highly ruffled.[1]

Preparation

The compound was first reported by Adolph Bayer.[2] It is made by condensation of pyrrole with acetone.[3]

Structure of octamethylporphyrinogen.[4]

Reactions

The pyrrolic N-H centers of ctamethylporphyrinogen can be deprotonated, and the resulting tetraanion functions as a tetradentate ligand for a variety of metal ions.[5]

References

  1. ↑ Gale, Philip A.; Sessler, Jonathan L.; Král, Vladimír (1998). "Calixpyrroles". Chemical Communications: 1–8. doi:10.1039/A706280J.
  2. ↑ Baeyer, Adolf (1886). "Ueber ein Condensationsproduct von Pyrrol mit Aceton". Berichte der Deutschen Chemischen Gesellschaft. 19 (2): 2184–2185. doi:10.1002/cber.188601902121.
  3. ↑ Sobral, Abilio J.F.N. (2005). "Synthesis of Meso-Octamethylporphyrinogen: An Undergraduate Laboratory Mini-Scale Experiment in Organic Heterocyclic Chemistry". Journal of Chemical Education. 82 (4): 618. Bibcode:2005JChEd..82..618S. doi:10.1021/ed082p618.
  4. ↑ Allen, William E.; Gale, Philip A.; Brown, Christopher T.; Lynch, Vincent M.; Sessler, Jonathan L. (1996). "Binding of Neutral Substrates by Calix[4]pyrroles". Journal of the American Chemical Society. 118 (49): 12471–12472. doi:10.1021/ja9632217.
  5. ↑ Bachmann, Julien; Hodgkiss, Justin M.; Young, Elizabeth R.; Nocera, Daniel G. (2007). "Ground- and Excited-State Reactivity of Iron Porphyrinogens". Inorganic Chemistry. 46 (3): 607–609. doi:10.1021/ic0616636. PMID 17256999.
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