Pyrophaeophorbide-a-monomethyl ester

Base Information

• Chemical Name: Pyrophaeophorbide-a-monomethyl ester
• CAS No.: 6453-67-4
• Molecular Formula: C34H36N4O3
• Molecular Weight: 548.685
• Mol file: 6453-67-4.mol

Synonyms:Methyl 3-(16-ethenyl-11-ethyl-4-hydroxy-12,17,21,26-tetramethyl-7,23,24,25-tetrazahexacyclo[18.2.1.15,8.110,13.115,18.02,6]hexacosa-1,4,6,8(26),9,11,13(25),14,16,18(24),19-undecaen-22-yl)propanoate;methyl 4-(16-ethenyl-11-ethyl-4-hydroxy-12,17,21-trimethyl-7,23,24,25-tetrazahexacyclo[18.2.1.15,8.110,13.115,18.02,6]hexacosa-1,4,6,8(26),9,11,13(25),14,16,18(24),19-undecaen-22-yl)butanoate;3-Phorbinepropanoic acid, 9-ethenyl-14-ethyl-4,8,13,18-tetramethyl-20-oxo-, methyl ester, (3S,4S)-;3-Phorbinepropanoic acid, 9-ethenyl-14-ethyl-4,8,13,18-tetramethyl-20-oxo-, methyl ester, (3S-trans)-;Pyrophaeophorbide-a-monomethyl ester;9-Ethenyl-14-ethyl-4,8,13,18-tetramethyl-20-oxophorbine-3-propanoicacid meth

Chemical Property of Pyrophaeophorbide-a-monomethyl ester

Chemical Property:

• Vapor Pressure: 3.37E-35mmHg at 25°C
• Refractive Index: 1.641
• Boiling Point: 924.1 °C at 760 mmHg
• Flash Point: 512.7 °C
• PSA: 99.67000
• Density: 1.28 g/cm³
• LogP: 4.22820
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated)
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 548.27874102
• Heavy Atom Count: 41
• Complexity: 1650

Purity/Quality:

99.0% ^*data from raw suppliers

Pyropheophorbide a methyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC1=C(C2=NC1=CC3=CC4=C(CC(=C5C(C(C(=CC6=NC(=C2)C(=C6C)C=C)N5)C)CCCC(=O)OC)C4=N3)O)C
• Uses: Pyropheophorbide A Methyl Ester is a chlorophyll (C379815) analog for studies of photosynthesis. Methyl pyropheophorbide a (Pyropheophorbide-a methyl ester), a chlorophyll-a derivative, and is a potent photosensitizer that can be used in photodynamic therapy (PDT) of cancer. Methyl pyropheophorbide a has photodynamic activity and can induce apoptosis and inhibit tumor growth.

Technology Process of Pyrophaeophorbide-a-monomethyl ester

There total 54 articles about Pyrophaeophorbide-a-monomethyl 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: 100.0%

pheophorbide a methyl ester (5594-30-9) → pyropheophorbide a methyl ester (6453-67-4)

Guidance literature:

With maleic anhydride; In toluene; at 150 ℃; for 2h; Inert atmosphere; Microwave irradiation;

DOI:10.1055/s-0034-1380176

Reference yield: 98.0%

methylpheophorbide a (5594-30-9,64070-09-3,138812-88-1) → methyl pyropheophorbide a (6453-67-4)

Guidance literature:

With 2,3,5-trimethyl-pyridine; for 1.5h; Heating;

DOI:10.1021/jo951854i

Reference yield: 88.0%

methyl bacteriopheophorbide-d (59954-18-6,61665-26-7,72937-56-5,98576-10-4) → methyl pyropheophorbide a (6453-67-4)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; water; benzene; Darkness; Inert atmosphere; Reflux;

DOI:10.1016/j.tet.2013.07.060

upstream raw materials:

pyropheophorbide a

methylpheophorbide a

dimethyl sulfate

pyropheophorbide-d methyl ester

Downstream raw materials:

C₅₀H₄₉N₅O₇

methyl mesopyropheophorbide a

methyl bacteriopheophorbide-d

3¹,3²-didehydro-15-carboxyrhodochlorin anhydride methyl ester

Refernces

• 1、 Hynninen, Paavo H.,Mesilaakso, Markku. "Protonation-deprotonation equilibria in tetrapyrroles Part 2:". . p. 39 - 46. Retrieved 2012.
• 2、 Trowitzsch. "-". . p. 59,60,61. Retrieved 1976.
• 3、 Chansakaow, Sunee,Ruangrungsi, Nijsiri,Ishikawa, Tsutomu. "Isolation of pyropheophorbide a from the leaves of Atalantia monophylla (Roxb.) Corr. (Rutaceae) as a possible antiviral active principle against herpes simplex virus type 2". . p. 1415 - 1417. Retrieved 1996.
• 4、 Sadaoka, Kana,Oba, Toru,Tamiaki, Hitoshi,Kashimura, Shigenori,Saga, Yoshitaka. "Demetalation kinetics of the zinc chlorophyll derivative possessing two formyl groups:". . p. 1120 - 1128. Retrieved 2013.
• 5、 Saga, Yoshitaka,Hojo, Sayaka,Hirai, Yuki. "Comparison of demetalation properties between zinc chlorin and zinc porphyrin derivatives: Effect of macrocyclic structures". . p. 5697 - 5700. Retrieved 2010.
• 6、 Ocakoglu, Kasim,Erten-Ela, Sule,Saleem Joya,Harputlu, Ersan. "Artificial zinc chlorin dyes for dye sensitized solar cell". . p. 30 - 34. Retrieved 2016.
• 7、 Kosaka, Nobuo,Tamiaki, Hitoshi. "Synthesis of a novel cyclic chlorophyll hetero-dyad as a model compound for stacked chlorophylls found in photosynthetic systems". . p. 2325 - 2330. Retrieved 2004.
• 8、 Mase, Kentaro,Ohkubo, Kei,Fukuzumi, Shunichi. "Much enhanced catalytic reactivity of cobalt chlorin derivatives on two-electron reduction of dioxygen to produce hydrogen peroxide". . p. 1808 - 1815. Retrieved 2015.
• 9、 Wang, Jin-Jun,Liu, Chun-Lin,Li, Jia-Zhu. "Synthesis of 3-pyrazolinyl chlorins related to chlorophyll by 1,3-dipolar cycloaddition reaction from methyl pheophorbide-a". . p. 487 - 496. Retrieved 2012.
• 10、 Mal'Shakova, Marina V.,Velegzhaninov, Ilya O.,Rasova, Elena E.,Belykh, Dmitry V.. "Novel chlorophyll a derivatives with ester-linked galactose fragments for photodynamic therapy and fluorescence diagnostics of cancer". . p. 135 - 144. Retrieved 2021/01/11.