Gadobenate dimeglumine

Base Information

• Chemical Name: Gadobenate dimeglumine
• CAS No.: 113786-33-7
• Molecular Formula: C22H31N3O11
• Molecular Weight: 513.502
• European Community (EC) Number: 680-377-1
• DSSTox Substance ID: DTXSID40869572
• Nikkaji Number: J636.243E
• NCI Thesaurus Code: C77547
• RXCUI: 68173
• ChEMBL ID: CHEMBL107137
• Mol file: 113786-33-7.mol

Synonyms:3,6,9-triaza-12-oxa-3,6,9-tricarboxymethylene-10-carboxy-13-phenyltridecanoic acid, gadolinium;B 19036;B-19036;gadobenate dimeglumine;gadobenic acid;gadobenic acid, dimeglumine salt;gadolinium-benzyloxypropionyl tetraacetate;gadolinium-BOPTA-Dimeg;Gd(BOPTA)2;Gd-BOPTA;MultiHance

Chemical Property of Gadobenate dimeglumine

Chemical Property:

• PSA: 205.45000
• Density: 1.446
• LogP: -1.09920
• XLogP3: -7.1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 20
• Exact Mass: 513.19585881
• Heavy Atom Count: 36
• Complexity: 727

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COCC(C(=O)O)N(CCN(CCN(CC(=O)O)CC(=O)O)CC(=O)O)CC(=O)O
• Recent ClinicalTrials: Hybrid Molecular Imaging of ER in Breast Cancer Patients With DCIS
• Recent EU Clinical Trials: Prospective evaluation of potential effects of repeated gadolinium-based contrast agent (GBCA) administrations of the same GBCA on motor and cognitive functions in neurologically normal adults in comparison to a non-GBCA exposed control group—ODYSSEY

Technology Process of Gadobenate dimeglumine

There total 4 articles about Gadobenate dimeglumine 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: 66.0%

sodium N-[2-[(2-aminoethyl)amino]ethyl]-O-(phenylmethyl)serine + bromoacetic acid (79-08-3) → 4-carboxy-5,8,11-tris(carboxymethyl)-1-phenyl-2-oxa-5,8,11-triazatridecan-13-oic acid (113786-33-7)

Guidance literature:

sodium N-[2-[(2-aminoethyl)amino]ethyl]-O-(phenylmethyl)serine; bromoacetic acid; With sodium hydroxide; In water; at 10 - 62 ℃;

With hydrogenchloride; In water; at 20 - 25 ℃; pH=5.5; Product distribution / selectivity;

Reference yield: 21.0%

N-[2-[(2-aminoethyl)amino]ethyl]-O-(phenylmethyl)serine trihydrochloride + bromoacetic acid (79-08-3) → 4-carboxy-5,8,11-tris(carboxymethyl)-1-phenyl-2-oxa-5,8,11-triazatridecan-13-oic acid (113786-33-7)

Guidance literature:

With sodium hydroxide;

Reference yield:

N-[2-[(2-aminoethyl)amino]ethyl]-O-(phenylmethyl)serine (790633-35-1) + chloroacetic acid (79-11-8) → 4-carboxy-5,8,11-tris(carboxymethyl)-1-phenyl-2-oxa-5,8,11-triazatridecan-13-oic acid (113786-33-7)

Guidance literature:

N-[2-[(2-aminoethyl)amino]ethyl]-O-(phenylmethyl)serine; chloroacetic acid; With hydrogenchloride; sodium hydroxide; In water; at 0 - 75 ℃; pH=10.5 - 11.5;

In water; pH=2;

upstream raw materials:

bromoacetic acid

N-[2-[(2-aminoethyl)amino]ethyl]-O-(phenylmethyl)serine

chloroacetic acid

Downstream raw materials:

[Eu(4-carboxy-5,8-11-tris(carboxymethyl)-1-phenyl-2-oxa-5,8,11-triazatridecan-13-oic acid-5H)]^(2-)

Gd(4-carboxyl-5,6,11-tris(carboxymethyl)-1-phenyl-2-oxa-5,8,11-triazatridecane-13-oic acid^(5-))^(2-)

Refernces

• 1、 -. "PROCESS FOR THE PURIFICATION OF POLYAMINOCARBOXYLATES". Paragraph 0019. . Retrieved 2014/11/11.
• 2、 -. "A PROCESS FOR THE PREPARATION OF 4-CARBOXY- 5,8,11- TRIS(CARBOXYMETHYL)- 1-PHENYL- 2-OXA- 5,8,11- TRIAZATRIDECAN- 13-OIC ACID". Page/Page column 2-3. . Retrieved 2008/06/13.