18-(2-Carboxyethyl)-20-(carboxymethyl)-12-ethenyl-7-ethyl-3,8,13,17-tetramethyl-17,18,22,23-tetrahydroporphyrin-2-carboxylic acid

Base Information

• Chemical Name: 18-(2-Carboxyethyl)-20-(carboxymethyl)-12-ethenyl-7-ethyl-3,8,13,17-tetramethyl-17,18,22,23-tetrahydroporphyrin-2-carboxylic acid
• CAS No.: 19660-77-6
• Molecular Formula: C34H36N4O6
• Molecular Weight: 596.683
• Hs Code.: 2933998090
• European Community (EC) Number: 243-209-4
• ChEMBL ID: CHEMBL4166417
• Nikkaji Number: J195.874G
• Wikidata: Q110185473
• Mol file: 19660-77-6.mol

Synonyms:13-carboxy-17-(2-carboxyethyl)-15-carboxymethyl-17,18-trans-dihydro-3-vinyl-8-ethyl-2,7,12,18-tetramethylporphyrin;2-porphinepropionic acid, 18-carboxy-20-(carboxymethyl)-13-ethyl-2beta,3-dihydro-3beta,7,12,17-tetramethyl-8-vinyl-;21H,23H-porphine-2-propanoic acid, 18-carboxy-20-(carboxymethyl)-8-ethenyl-13-ethyl-2,3-dihydro-3,7,12,17-tetramethyl-, (2S-trans);21h,23h-porphine-7-propanoic acid, 3-carboxy-5-(carboxymethyl)-13-ethenyl-18-ethyl-7,8-dihydro-2,8,12,17-tetramethyl-, (7S,8S)-;BLC 1010;BLC-1010;BLC1010;chlorin A6;chlorin e6;chlorine A6;chlorine e6;fotolon;photochlorine;Photolon;phytochlorin

Chemical Property of 18-(2-Carboxyethyl)-20-(carboxymethyl)-12-ethenyl-7-ethyl-3,8,13,17-tetramethyl-17,18,22,23-tetrahydroporphyrin-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 2.11E-25mmHg at 25°C
• Refractive Index: 1.674
• Boiling Point: 1048.3 ºC at 760 mmHg
• Flash Point: 587.8 ºC
• PSA: 168.20000
• Density: 1.321 g/cm³
• LogP: 3.72630
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Isopropanol (Slightly, Heated, Sonicated)
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 596.26348488
• Heavy Atom Count: 44
• Complexity: 1090

Purity/Quality:

97% ^*data from raw suppliers

ChlorinE6 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1=C(C2=CC3=C(C(=C(N3)C=C4C(C(C(=N4)C(=C5C(=C(C(=N5)C=C1N2)C)C(=O)O)CC(=O)O)CCC(=O)O)C)C)C=C)C
• Recent EU Clinical Trials: An open-label phase IIb study to evaluate the safety, tolerability and efficacy of Fotolon? as a photosensitising agent for the local treatment of airway-obstructing non small cell lung cancer (NSCLC) with photodynamic therapy (PDT)
• Description: Chlorin E6 is a natural molecule and a promising photosensitizer. Chlorin E6 is isolated from renewable natural sources. Chlorin E6 is an attractive photodynamic therapy (PDT) drug candidate because of (1) its high absorption in the red spectral region, and (2) its low cost to make compared to other porphyrin-based PDT drugs. Chlorin E6 exhibits advantageous photophysical properties for PDT such as having long lifetimes in their photoexcited triplet states and high molar absorption in the red region of the visible spectrum. Moreover, a 664-nm laser light can penetrate tissue deeper that the 630-nm laser light used for other PDT drugs. Chlorin E6 is an important starting material for making PDT drug Talaporfin sodium (mono-L-aspartyl chlorin e6 or NPe6). PDT is currently being used as an alternative therapeutic modality for a variety of malignant tumors. Studies have examined antitumor activity of Ce6-induced PDT (Ce6-PDT) both in vitro and in vivo using a rat tumor models. In one study three-week-old male Sprague-Dawley (SD) rats were inoculated s.c. on the right flank with 5x106 RK3E-ras cells. The animals were administered i.v. with Ce6 (10 mg/kg) and 24 h later, PDT was performed using a laser diode at a light dose of 100 J/cm2. Ce6-PDT generated reactive oxygen species and led to significant growth inhibition in RK3E-ras cell. In addition, Ce6-PDT induced apoptosis through the activation of caspase-3 and its downstream target, PARP cleavage. The protein level of anti-apoptotic bcl-2 was also reduced by Ce6-PDT in RK3E-ras cells. In in vivo experiments, application of Ce6- PDT led to a significant reduction of tumor size. PCNA immunostaining and TUNEL assay revealed that Ce6-PDT inhibited tumor cell proliferation and increased apoptosis. (source: Oncology Reports, 2009, 22(5). 1085-1091.)
• Uses: Chlorin E6 is a photosensitizer.The conjugates of gold nanorods and chlorin e6 enhance the fluorescence detection and photodynamic therapy (PDT) of cancers.

Technology Process of 18-(2-Carboxyethyl)-20-(carboxymethyl)-12-ethenyl-7-ethyl-3,8,13,17-tetramethyl-17,18,22,23-tetrahydroporphyrin-2-carboxylic acid

There total 12 articles about 18-(2-Carboxyethyl)-20-(carboxymethyl)-12-ethenyl-7-ethyl-3,8,13,17-tetramethyl-17,18,22,23-tetrahydroporphyrin-2-carboxylic acid 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:

pheophorbide-a (15664-29-6) → chlorin e6 (19660-77-6)

Guidance literature:

With pyridine; potassium hydroxide; diethyl ether;

DOI:10.1021/ja01370a070

Reference yield:

pheophytin a (603-17-8,47907-36-8,74984-11-5,74984-81-9,75598-38-8) → chlorin e6 (19660-77-6)

Guidance literature:

pheophytin a; With sodium hydroxide; In ethanol; water; for 12h; pH=13 - 14;

With hydrogenchloride; In ethanol; water;

Reference yield:

chlorin e6 trimethyl ester (15592-17-3,35038-32-5) → chlorin e6 (19660-77-6)

Guidance literature:

With hydrogenchloride; water; In chloroform; for 4h;

DOI:10.5935/0103-5053.20150290

upstream raw materials:

pheophorbide-a

pheophytin b

pheophytin a

pheophytin a

Downstream raw materials:

rhodoporphyrin-15-acetic acid

chlorin e6 trimethyl ester

15-methoxycarbonylmethyl-rhodoporphyrin-dimethyl ester

15-methylrhodoporphyrin