Protoporphyrin IX dimethyl ester

Base Information

• Chemical Name: Protoporphyrin IX dimethyl ester
• CAS No.: 5522-66-7
• Molecular Formula: C36H38N4O4
• Molecular Weight: 590.722
• Mol file: 5522-66-7.mol

Synonyms:2,18-Porphinedipropionicacid, 3,7,12,17-tetramethyl-8,13-divinyl-, dimethyl ester (8CI);21H,23H-Porphine-2,18-dipropanoic acid, 7,12-diethenyl-3,8,13,17-tetramethyl-,dimethyl ester (9CI);Protoporphyrin IX di-Me ester (6CI);Protoporphyrindimethyl ester (7CI);NSC 19666;Protoporphyrin IX dimethyl ester;ProtoporphyrinIX methyl ester;

Chemical Property of Protoporphyrin IX dimethyl ester

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 225-228 °C(lit.)
• Refractive Index: 1.63
• Boiling Point: 1016.967 °C at 760 mmHg
• Flash Point: 568.841 °C
• PSA: 108.90000
• Density: 1.221 g/cm³
• LogP: 4.21740
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble

Purity/Quality:

99%, ^*data from raw suppliers

Protoporphyrin IX dimethyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: Protoporphyrin IX Dimethyl Ester is a derivative of Protoporphyrin IX (P839138), which is an important precursor to biologically essential prosthetic groups such as heme, cytochrome c, and chlorophylls.

Technology Process of Protoporphyrin IX dimethyl ester

There total 89 articles about Protoporphyrin IX dimethyl ester 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: 99.0%

methanol (67-56-1) + hemin (13496-05-4,16009-13-5) → 3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester (5522-66-7,6164-53-0)

Guidance literature:

With pyridine; diammonium iron(II) sulfate hexahydrate; acetyl chloride; In dichloromethane; for 1h; Cooling;

DOI:10.1016/j.mencom.2020.03.027

Reference yield: 98.0%

methanol (67-56-1) + protoporphyrin IX (553-12-8) → 3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester (5522-66-7,6164-53-0)

Guidance literature:

at 20 ℃; for 6h;

DOI:10.1142/S1088424615500650

Reference yield: 79.0%

protoporphyrin IX (553-12-8) → 3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester (5522-66-7,6164-53-0)

Guidance literature:

With sulfuric acid; In methanol; for 12h; Darkness;

DOI:10.1016/j.dyepig.2017.06.011

upstream raw materials:

diazomethane

protoporphyrin IX

hematoporphyrin-dimethyl ester

protoporphyrin

Downstream raw materials:

mesoporphyrin IX

3,4-dimethylmaleimide

3-ethyl-4-methyl-pyrrole-2,5-dione

phthalimide

Refernces

• 1、 O'Brien, Jessica M.,Sitte, Elisabeth,Flanagan, Keith J.,Kühner, Hannes,Hallen, Lukas J.,Gibbons, Dáire,Senge, Mathias O.. "Functionalization of Deutero- and Protoporphyrin IX Dimethyl Esters via Palladium-Catalyzed Coupling Reactions". . p. 6158 - 6173. Retrieved 2019.
• 2、 Sylvain,Zerrouki,Granet,Huang,Lagorce,Guilloton,Blais,Krausz. "Synthesis and biological evaluation of thioglycosylated porphyrins for an application in photodynamic therapy". . p. 57 - 69. Retrieved 2002.
• 3、 Gubarev, Yury A.,Kiselev, Aleksey N.,Lebedeva, Natalya Sh.,Syrbu, Sergey A.,Yurina, Elena S.. "Albumin aggregation promoted by protoporphyrin in vitro". . p. 211 - 213. Retrieved 2020.
• 4、 Moss et al.. "-". . p. 263. Retrieved 1972.
• 5、 Ponomarev et al.. "-". . . Retrieved 1973.
• 6、 Pandey, Ravindra K.,Shiau, Fuu-Yau,Medforth, Craig J.,Dougherty, Thomas J.,Smith, Kevin M.. "Syntheses, stability, and tumorcidal activity of porphyrin dimers and trimers with ether linkages". . p. 7399 - 7402. Retrieved 1990.
• 7、 Tachikawa, Shoji,El-Zaria, Mohamed E.,Inomata, Ryu,Sato, Shinichi,Nakamura, Hiroyuki. "Synthesis of protoporphyrin-lipids and biological evaluation of micelles and liposomes". . p. 4745 - 4751. Retrieved 2014.
• 8、 Byrne,Ward. "The identification of a carbon linked oligomer in hematoporphyrin derivative and Photofrin II". . p. 6211 - 6214. Retrieved 1989.
• 9、 Miyata, Kota,Yasuda, Satoru,Masuya, Takuto,Ito, Satoshi,Kinoshita, Yusuke,Tamiaki, Hitoshi,Oba, Toru. "Facile iodination of the vinyl groups in protoporphyrin IX dimethyl ester and subsequent transformation of the iodinated moieties". supporting information. p. 3707 - 3711. Retrieved 2018/05/28.