meso-Octamethylporphyrinogen

*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
CAS Number	4475-42-7;
3D model (JSmol)	Interactive image;
Beilstein Reference	365398
ChEBI	CHEBI:51701;
ChemSpider	550696;
ECHA InfoCard	100.152.255
EC Number	623-589-1;
Gmelin Reference	2142403
PubChem CID	634396;
CompTox Dashboard (EPA)	DTXSID00348292 ;
	InChI 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;
	SMILES 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
Chemical formula	C28H36N4
Molar mass	428.624 g·mol−1
Appearance	white solid
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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

^ Gale, Philip A.; Sessler, Jonathan L.; Král, Vladimír (1998). "Calixpyrroles". Chemical Communications: 1–8. doi:10.1039/A706280J.
^ Baeyer, Adolf (1886). "Ueber ein Condensationsproduct von Pyrrol mit Aceton". Berichte der Deutschen Chemischen Gesellschaft. 19 (2): 2184–2185. doi:10.1002/cber.188601902121.
^ 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.
^ 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.
^ 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.

[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.

[1]

[2]

[3]

[4]

[5]