Synonym: Protoporphyrin IX; Kammerer’s porphyrin, NSC 177389, NSC 2632, Ooporphyrin, Protoporphyrin, Protoporphyrin IX;

IUPAC/Chemical Name: 3,3'-(3,8,13,17-tetramethyl-7,12-divinylporphyrin-2,18-diyl)dipropionic acid

InChi Key: KSFOVUSSGSKXFI-UJJXFSCMSA-N

InChi Code: InChI=1S/C34H34N4O4/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25/h7-8,13-16,35,38H,1-2,9-12H2,3-6H3,(H,39,40)(H,41,42)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-

SMILES Code: O=C(O)CCC=1C=2N=C(C=C3NC(=CC4=NC(=CC=5NC(C2)=C(C5C)CCC(=O)O)C(C=C)=C4C)C(C=C)=C3C)C1C

Appearance: To be determined

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).

Solubility: Protoporphyrin IX is soluble in polar organic solvents, especially pyridine. Dissolve initially in 0.1M base (Tris base or NaOH). Add a water miscible organic solvent (EtOH, MeOH, DMSO, DMF) until the solution is 50/50 base/solvent. When a clear solution is obtained, it can be diluted into an aqueous medium and titrated or buffered to any pH >7. Use immediately. Protoporphyrin IX slowly degrades in solution.

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info: The compound is encountered in nature in the form of complexes where the two inner hydrogen atoms are replaced by a divalent metal cation. When complexed with an iron(II) (ferrous) cation Fe2+, the molecule is called heme. Hemes are prosthetic groups in some important proteins. These heme-containing proteins include hemoglobin, myoglobin, and cytochrome c. Complexes can also be formed with other metal ions, such as zinc. Protoporphyrin IX is active as a photosensitizer and is a component of nitric oxide synthase for NOS generation. Protoporphyrin IX is a substrate for heme oxygenases affording cellular protection and producing biliverdin and CO, a secondary messenger in cells, and metallated (Fe) versions of heme are one of the most abundant and widely used metalloporphyrins in the biosphere. Metallated protoporphyrin derivatives especially those containing tin and first row transition metals such as Zn, Mn, Cr, Ni are extensively used as experimental heme oxygenase inhibitors. Frontier Specialty Chemicals produces a wide range of metallated protoporphyrin derivatives for your experimental needs , including 54Fe and 57Fe protoporphyrin chlorides Gallium (III) protoporphyrin derivatives display potent photodynamic antimicrobial effects and is of current interest for the treatment of antibiotic resistant infections. Electrocatalytic reduction of CO2 to formic acid was demonstrated for various metallated protoporphyrins. Cobalt (III) protoporphyrin, when inserted into myoglobin serves as a catalyst for the reduction of N2O to N2. Co(III) and Sn(IV) protoporphyrin derivatives inactivate arboviruses including Chikungunya and Zika by targeting the viral envelope. Protoporphyrin is a potential biomarker for cancer screening. Aggregation behavior of protoporphyrin in water is complex and is dependent on pH and ionic strength. Magnesium (II) Protoporphyrin is the first intermediate in the biosynthesis of chlorophylls from protoporphyrin IX. Zinc (II) protoporphyrin IX is a potent competitive inhibitor of heme oxygenase and is formed naturally in the case of iron deficiency of lead poisoning. Copper (II) protoporphyrin IX does not inhibit heme oxygenase and is used as a negative control in inhibition studies. N-methyl protoporphyrin IX is a transition state analogue and a potent inhibitor of ferrochelatase, the enzyme that inserts iron into protoporphyrin IX and is commonly used to induce haem deficiency in cell cultures. Protoporphyrin is a reactive molecule and readily reacts with electrophilic reagents at the vinyl groups to produce new derivatives and is often an undesirable reaction pathway that is involved in its degradation in solution. Mesoporphyrin IX is very similar to protoporphyrin IX and is more stable for catalytic and material science applications that do not require the beta-vinyl groups.