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5522-66-7

  • Product Name:Protoporphyrin IX dimethyl ester
  • Molecular Formula:C36H38N4O4
  • Molecular Weight:590.722
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Product Details

pd_meltingpoint:225-228 °C(lit.)

Purity:99%

Top Quality Chinese Factory supply 5522-66-7 Protoporphyrin IX dimethyl ester

  • Molecular Formula:C36H38N4O4
  • Molecular Weight:590.722
  • 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 

Protoporphyrin IX dimethyl ester(Cas 5522-66-7) Usage

Purification Methods

The crude dimethyl ester (1g) in CHCl3 (200 mL) is mixed with pet ether (b 70-90o, 600mL), and any porphyrin (m > 260o) which is insoluble in this mixture is filtered off. The filtrate is passed through a column of CaCO3 [from CaCO3 (130g) which is kept overnight in a mixture of CHCl3/pet ether (b 70-90o, 1:3), and the slurry is poured into a glass tube (2.5 x 26cm) to form the column]. After all the filtrate is applied, the column is eluted with a solution of CHCl3/pet ether (b 70-90o, 1:3). All the coloured eluates are collected, evaporated at room temperature in a vacuum to give a residue (0.8g), m 208-211o. The residue (0.8g) in CHCl3 (66mL) is heated briefly to its boiling point, then boiling MeOH (198mL) is added immediately to it. The mixture is allowed to cool to room temperature, refrigerated for 2days and the solid is filtered off. The solid is washed on the filter funnel with CHCl3/MeOH (1:9, 50mL) and dried at 50o/vacuum (yield 0.62-0.66g). It can also be recrystallised by dissolving in as little hot dry *C6H6 as possible and left overnight at 20o, m 228-230o. It has also been purified by dissolving (0.4g) in CHCl3 (33mL) by boiling for a few minutes, then diluting with boiling MeOH (100mL) and refrigerating for 2days. The crystals are collected, washed with CHCl3/MeOH (1:9) and dried at 50o in a vacuum (yield 0.3g). The UV has max at 631, 576, 541, 506 and 407nm in CHCl3 and 601, 556 and 406nm in 25% HCl. [Ramsey Biochemical Preparations 3 39 1953, Beilstein 26 III/IV 3052.]

InChI:InChI=1/C36H38N4O4/c1-9-23-19(3)27-15-28-21(5)25(11-13-35(41)43-7)33(39-28)18-34-26(12-14-36(42)44-8)22(6)30(40-34)17-32-24(10-2)20(4)29(38-32)16-31(23)37-27/h9-10,15-18,37,40H,1-2,11-14H2,3-8H3/b27-15-,28-15-,29-16-,30-17-,31-16-,32-17-,33-18-,34-18-

5522-66-7 Relevant articles

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Clezy,Fookes

, p. 217,218,219,220 (1977)

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Functionalization of Deutero- and Protoporphyrin IX Dimethyl Esters via Palladium-Catalyzed Coupling Reactions

O'Brien, Jessica M.,Sitte, Elisabeth,Flanagan, Keith J.,Kühner, Hannes,Hallen, Lukas J.,Gibbons, Dáire,Senge, Mathias O.

, p. 6158 - 6173 (2019)

Herein, we report the functionalization ...

NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY OF PETROPORPHYRINS Self-Aggregation Effects, Nuclear Overhauser Enhancements, and Spin-Lattice Relaxation used in Structural Elucidation

Krane, Jostein,Skjetne, Tore,Telnaes, Nils,Bjoroy, Malvin,Solli, Hauk

, p. 4109 - 4120 (1983)

The substitution pattern of the two majo...

Synthesis and biological evaluation of thioglycosylated porphyrins for an application in photodynamic therapy

Sylvain,Zerrouki,Granet,Huang,Lagorce,Guilloton,Blais,Krausz

, p. 57 - 69 (2002)

The aim of this work is the synthesis of...

Microwave-Assisted Synthesis of α-Amino Phosphonates Derived from Formylporphyrins of Natural Origin

Pavlov, Vsevolod Yu.,Kabachnik, Maria M.,Zobnina, Elena V.,Timofeev, Vladimir P.,Konstantinov, Igor O.,Kimel, Boris G.,Ponomarev, Gelii V.,Beletskaya, Irina P.

, p. 2193 - 2197 (2003)

The first synthesis of α-amino phosphona...

Albumin aggregation promoted by protoporphyrin in vitro

Gubarev, Yury A.,Kiselev, Aleksey N.,Lebedeva, Natalya Sh.,Syrbu, Sergey A.,Yurina, Elena S.

, p. 211 - 213 (2020)

Protoporphyrin upon its binding with ser...

Photophysical properties of porphyrin derivatives: Influence of the alkyl chains in homogeneous and micro-heterogeneous systems

Santos, Sandra Cruz Dos,Moreira, Leonardo Marmo,Novo, Diogo La Rosa,Santin, Luiza Rosimeri Romano,Bianchini, Daniela,Bonacin, Juliano Alves,Romani, Ana Paula,Fernandes, Adjaci Uchoa,Baptista, Mauricio S.,De Oliveira, Hueder Paulo Moises

, p. 920 - 933 (2015)

This work is focused on the evaluation o...

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Moss et al.

, p. 263 (1972)

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Battersby et al.

, p. 441 (1973)

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Ponomarev et al.

, (1973)

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Light harvesting in silicon(111) surfaces using covalently attached protoporphyrin IX dyes

Alderman, Nicholas,Danos, Lefteris,Fang, Liping,Grossel, Martin C.,Markvart, Tom

, p. 12120 - 12123 (2017)

We report the photosensitization of crys...

Syntheses, stability, and tumorcidal activity of porphyrin dimers and trimers with ether linkages

Pandey, Ravindra K.,Shiau, Fuu-Yau,Medforth, Craig J.,Dougherty, Thomas J.,Smith, Kevin M.

, p. 7399 - 7402 (1990)

The first syntheses of a series of regio...

Induction of aminolevulinic acid synthase gene expression and enhancement of metabolite, protoporphyrin IX, excretion by organic germanium

Nakamura, Takashi,Saito, Miki,Shimada, Yasuhiro,Fukaya, Haruhiko,Shida, Yasuo,Tokuji, Yoshihiko

, p. 75 - 81 (2011)

Poly-trans-[(2-carboxyethyl) germasesqui...

Synthesis of protoporphyrin-lipids and biological evaluation of micelles and liposomes

Tachikawa, Shoji,El-Zaria, Mohamed E.,Inomata, Ryu,Sato, Shinichi,Nakamura, Hiroyuki

, p. 4745 - 4751 (2014)

Protoporphyrin IX (PPIX) lipids were syn...

Boron-containing protoporphyrin ix derivatives and their modification for boron neutron capture therapy: Synthesis, characterization, and comparative in vitro toxicity evaluation

El-Zaria, Mohamed E.,Ban, Hyun Seung,Nakamura, Hiroyuki

, p. 1543 - 1552 (2010)

A novel series of boronated porphyrins f...

The identification of a carbon linked oligomer in hematoporphyrin derivative and Photofrin II

Byrne,Ward

, p. 6211 - 6214 (1989)

The presence of carbon linked oligomeric...

Development of the sensitizer for generating higher-energy photons under diluted condition via the triplet-triplet annihilation-supported upconversion

Tanaka, Kazuo,Ohashi, Wataru,Inafuku, Kenichi,Shiotsu, Shohei,Chujo, Yoshiki

, (2019/08/26)

It was previously reported that photon u...

Facile iodination of the vinyl groups in protoporphyrin IX dimethyl ester and subsequent transformation of the iodinated moieties

Miyata, Kota,Yasuda, Satoru,Masuya, Takuto,Ito, Satoshi,Kinoshita, Yusuke,Tamiaki, Hitoshi,Oba, Toru

supporting information, p. 3707 - 3711 (2018/05/28)

Iodination of protoporphyrin IX dimethyl...

5522-66-7 Process route

methanol
67-56-1

methanol

hemin
13496-05-4,16009-13-5

hemin

3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21<i>H</i>,23<i>H</i>-porphine-2,18-diyl)-bis-propionic acid dimethyl ester
5522-66-7,6164-53-0

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

Conditions
Conditions Yield
With pyridine; diammonium iron(II) sulfate hexahydrate; acetyl chloride; In dichloromethane; for 1h; Cooling;
99%
methanol
67-56-1

methanol

protoporphyrin IX
553-12-8

protoporphyrin IX

3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21<i>H</i>,23<i>H</i>-porphine-2,18-diyl)-bis-propionic acid dimethyl ester
5522-66-7,6164-53-0

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

Conditions
Conditions Yield
at 20 ℃; for 6h;
98%
With sulfuric acid; at -10 ℃; for 18h; Inert atmosphere; Schlenk technique; Darkness;
95%
With trimethyl orthoformate; sulfuric acid; for 0.75h; Ambient temperature;
71 % Chromat.
With sulfuric acid;
With sulfuric acid; at -10 ℃; for 18h; Inert atmosphere; Darkness;
With sulfuric acid; at 20 ℃; for 12h; Darkness;
1.4 g
With hydrogenchloride;

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