protoporphyrin IX

Base Information

• Chemical Name: protoporphyrin IX
• CAS No.: 553-12-8
• Deprecated CAS: 1818-68-4,37188-04-8,42183-71-1,50312-31-7,61320-51-2,63872-77-5,68034-48-0,75440-82-3,75460-41-2,75599-49-4,75750-98-0,227475-00-5,263148-77-2,392312-74-2,562103-89-3,673437-82-6,720672-66-2,942418-20-4,1005309-17-0,1018811-74-9,1057726-94-9,885267-29-8,1185235-79-3,1564276-52-3,880014-89-1,1650010-82-4,2234266-25-0,1005309-17-0,1057726-94-9,227475-00-5,263148-77-2,37188-04-8,392312-74-2,42183-71-1,50312-31-7,562103-89-3,61320-51-2,63872-77-5,673437-82-6,68034-48-0,720672-66-2,75440-82-3,75460-41-2,75599-49-4,75750-98-0,885267-29-8,942418-20-4
• Molecular Formula: C34H34N4O4
• Molecular Weight: 562.668
• European Community (EC) Number: 209-033-7
• NSC Number: 757839,2632
• UNII: C2K325S808
• DSSTox Substance ID: DTXSID4048353
• Nikkaji Number: J1.130.119C,J1.756.122G,J136.582G,J15.490C
• Wikipedia: Protoporphyrin_IX
• Wikidata: Q619815
• NCI Thesaurus Code: C785
• Metabolomics Workbench ID: 50071
• ChEMBL ID: CHEMBL267548,CHEMBL1618319,CHEMBL1325592,CHEMBL4463327,CHEMBL1907972,CHEMBL1907974
• Mol file: 553-12-8.mol

Synonyms:PPIX;protoporphyrin;protoporphyrin IX;protoporphyrin IX dihydride;protoporphyrin IX, disodium salt

Chemical Property of protoporphyrin IX

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: >300 °C(Solv: acetone (67-64-1))
• Refractive Index: 1.654
• Boiling Point: 1122.015 °C at 760 mmHg
• Flash Point: 632.372 °C
• PSA: 130.90000
• Density: 1.299 g/cm³
• LogP: 4.04060
• Storage Temp.: 2-8°C
• Sensitive.: light sensitive
• Solubility.: DMSO (Slightly)
• Water Solubility.: 106.9mg/L(25 oC)
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 562.25800558
• Heavy Atom Count: 42
• Complexity: 1010

Purity/Quality:

98%,99%, ^*data from raw suppliers

Zinc protoporphyrin IX ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C2=CC3=NC(=CC4=NC(=CC5=C(C(=C(N5)C=C1N2)C=C)C)C(=C4CCC(=O)O)C)C(=C3C)CCC(=O)O)C=C
• Uses: Protoporphyrin IX has been used:as a standard in protoporphyrin assaysin fluorescence spectra analysisto treat cells in cell culture to study heme-mediated ferroportin 1 transcription

Technology Process of protoporphyrin IX

There total 41 articles about protoporphyrin IX which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

hemin → protoporphyrin IX (553-12-8)

Guidance literature:

With formic acid; iron; at 60 - 125 ℃; for 0.5h; Reflux;

Reference yield: 76.6%

protoporphyrin IX dimethyl ester (5522-66-7,6164-53-0) → protoporphyrin IX (553-12-8)

Guidance literature:

With potassium hydroxide; In methanol; Reflux; Inert atmosphere; Darkness;

Reference yield:

hemin → protoporphyrin IX (553-12-8)

Guidance literature:

With ammonium hydroxide; phosphoric acid tributyl ester; sulfuric acid; In benzene; at 40 ℃; for 1.5h;

DOI:10.1016/j.reactfunctpolym.2020.104530

upstream raw materials:

pyridine

acetic acid

3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester

hematoporphyrin

Downstream raw materials:

protoporphyrin-dibenzyl ester

mesoporphyrin IX

mesoporphyrin IX dimethyl ester

hemin

Refernces

• 1、 Cox, G. Sidney,Krieg, Marianne,Whitten, David G.. "Self-Sensitized Photooxidation of Protoporphyrin IX Derivatives in Aqueous Surfactant Solutions: Product and Mechanistic Studies". . p. 6930 - 6937. Retrieved 1982.
• 2、 Wang, Nan,Jin, Xin,Guo, Dongbo,Tong, Gangsheng,Zhu, Xinyuan. "Iron Chelation Nanoparticles with Delayed Saturation as an Effective Therapy for Parkinson Disease". . p. 461 - 474. Retrieved 2017.
• 3、 Carr et al.. "-". . p. 1025. Retrieved 1967.
• 4、 Bonnett, Raymond,Ridge, Richard J.,Scourides, Panayiotis A.,Berenbaum, Morris C.. "Haematoporphyrin Derivative". . p. 1198 - 1199. Retrieved 1980.
• 5、 Donegan, Rebecca K.,Moore, Courtney M.,Hanna, David A.,Reddi, Amit R.. "Handling heme: The mechanisms underlying the movement of heme within and between cells". . p. 88 - 100. Retrieved 2018/08/21.
• 6、 -. "TARGETED ANTIMICROBIAL PHOTODYNAMIC THERAPY". Paragraph 0177. . Retrieved 2019/10/29.