Meso-octamethylporphyrinogen

Meso-octamethylporphyrinogen
Names
	IUPAC name 5,5,10,10,15,15,20,20-octamethyl-21,22,23,24-tetrahydroporphyrin
	Other names 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 pictograms
GHS Signal word	Warning
GHS hazard statements	H315, H319, H335
GHS precautionary statements	P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, 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 eight methyl groups are located on the carbon centers that interconnect the four pyrrole rings. Also unlike porphyrins, the porphyrinogens are highly ruffled. The compound is made by condensation of pyrrole with acetone.[1]

Structure of octamethylporphyrinogen.[2]

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.[3]

References

Sessler, Jonathan L.; Anzenbacher, Pavel Jr.; Miyaji, Hidekazu; Jursikova, Karolina; Bleasdale, Ellen R.; Gale, Philip A. (2000). "Modified Calix[4]pyrroles". Industrial & Engineering Chemistry Research. 39 (10): 3471–3478. doi:10.1021/ie000102y.
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.

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[sessler-1] Sessler, Jonathan L.; Anzenbacher, Pavel Jr.; Miyaji, Hidekazu; Jursikova, Karolina; Bleasdale, Ellen R.; Gale, Philip A. (2000). "Modified Calix[4]pyrroles". Industrial & Engineering Chemistry Research. 39 (10): 3471–3478. doi:10.1021/ie000102y.

[2] 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.

[3] 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.