35998-29-9

Basic information

• Product Name: HBED
• Synonyms: HBED;N,N'-DI(2-HYDROXYBENZYL)ETHYLENEDIAMINE-N,N'-DIACETIC ACID HCL;N,N-BIS[2-HYDROXYBENZYL]ETHYLENEDIAMINE-N,N-DIACETIC ACID;chelii;n,n’-1,2-ethanediylbis(n-((2-hydroxyphenyl)methyl)-glycin;n,n’-1,2-ethanediylbis(n-((2-hydroxyphenyl)methyl)glycine);n,n’-ethylenebis(n-salicyl-glycin;[Ethylenebis(2-hydroxybenzylimino)]diacetic acid
• CAS NO: 35998-29-9
• Molecular Formula: C₂₀H₂₄N₂O₆
• Molecular Weight: 388.41
• Mol File: 35998-29-9.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 614.7°Cat760mmHg
• Flash Point: 325.6°C
• Appearance: /
• Density: 1.374g/cm³
• PKA: 1.77±0.10(Predicted)
• CAS DataBase Reference: HBED(CAS DataBase Reference)
• NIST Chemistry Reference: HBED(35998-29-9)
• EPA Substance Registry System: HBED(35998-29-9)

Safety Data

• Hazardous Substances Data: 35998-29-9(Hazardous Substances Data)

Upstream product

• 18653-98-0 N,N'-bis(2-hydroxybenzyl)ethylenediamine 
• 94-93-9 N,N'-ethylenebis(2-hydroxybenzylideneimine) 
• 298-12-4 Glyoxilic acid 
• 50-00-0 formaldehyd 
• 5657-17-0 ethylenediaminediacetic acid 
• 108-95-2 phenol 
• 1073169-23-9 (HO)2BC₆H₄CHNCH₂CH₂NCHC₆H₄B(OH)2 
• 40138-16-7 2-formylbenzene boronic acid 
• 36053-27-7 N,N'-di(2-hydroxybenzyl)ethylenediamine-N,N'-diacetonitrile 
• 103334-86-7 N,N'-di(2-hydroxybenzyl)ethylenediamine-N,N'-diacetamide 

Downstream Products

• 98318-32-2 N,N'-bis(2-hydroxybenzyl)ethylenediamine-N,N'-diacetic acid dipentyl ester 
• 102212-12-4 N,N'-bis(2-hydroxybenzyl)ethylenediamine-N,N'-diacetic acid dibenzyl ester 
• 220961-63-7 N,N'-bis(2-hydroxybenzyl)ethylenediamine-N,N'-diacetic acid hydrochloride 
• 102212-13-5 N,N'-bis(2-hydroxybenzyl)ethylenediamine-N,N'-diacetic acid dimethyl ester diacetate 
• 102212-11-3 N,N'-bis(2-hydroxybenzyl)ethylenediamine-N,N'-diacetic acid diisopropyl ester 
• 102212-10-2 N,N'-bis(2-hydroxybenzyl)ethylenediamine-N,N'-diacetic acid diethyl ester 
• 85120-52-1 N,N'-bis(2-hydroxybenzyl)ethylenediamine-N,N'-diacetic acid dimethyl ester 

Relevant articles and documents

Novel double prodrugs of the iron chelator N,N'-bis(2-hydroxybenzyl)ethylenediamine-N,N'-diacetic acid (HBED): Synthesis, characterization, and investigation of activation by chemical hydrolysis and oxidation

The development of iron chelators suitable for the chronic treatment of diseases where iron accumulation and subsequent oxidative stress are implicated in disease pathogenesis is an active area of research. The clinical use of the strong chelator N,N'-bis(2-hydroxybenzyl)ethylenediamine-N,N'-diacetic acid (HBED) and its alkyl ester prodrugs has been hindered by poor oral bioavailability and lack of conversion to the parent chelator, respectively. Here, we present novel double prodrugs of HBED that have the carboxylate and phenolate donors of HBED masked with carboxylate esters and boronic acids/esters, respectively. These double prodrugs were successfully synthesized as free bases (7a-f) or as dimesylate salts (8a-c,e), and were characterized by 1H, 13C, and 11B NMR; MP; MS; and elemental analysis. The crystal structure of 8a was solved. Three of the double prodrugs (8a-c) were selected for further investigation into their abilities to convert to HBED by stepwise hydrolysis and H2O2 oxidation. The serial hydrolysis of the pinacol and methyl esters of N,N'-bis(2-boronic acid pinacol ester benzyl)ethylenediamine-N,N'-diacetic acid methyl ester dimesylate (8a) was verified by LC-MS. The macro half-lives for the hydrolyses of 8a-c, measured by UV, ranged from 3.8 to 26.3 h at 37 °C in pH 7.5 phosphate buffer containing 50% MeOH. 9, the product of hydrolysis of 8a-c and the intermediate in the conversion pathway, showed little-to-no affinity for iron or copper in UV competition experiments. 9 underwent a serial oxidative deboronation by H2O2 in N-methylmorpholine buffer to generate HBED (k Combining double low line 10.3 M-1min-1). The requirement of this second step, oxidation, before conversion to the active chelator is complete may confer site specificity when only localized iron chelation is needed. Overall, these results provide proof of principle for the activation of the double prodrugs by chemical hydrolysis and H2O2 oxidation, and merit further investigation into the protective capabilities of the prodrugs against H2O2-induced cell death.

PROCESS TO PREPARE PHENOLIC ETHYLENEDIAMINE DIACETIC ACID COMPOUNDS

The present invention relates to a process to prepare N,N'-di(2-hydroxybenzyl) ethylenediamine-N,N'-diacetic acid and salts thereof comprising a reaction between formaldehyde, ethylenediamine diacetic acid or a salt thereof and phenol at a pH of between 3 and 7 and a temperature below 60°Cwherein the reaction mixture contains 0.2 to 1.1 molar equivalents of alkali metalions on the molar amount of EDDA.

A process for the preparation of N,N'-bis(2-hydroxybenzyl)ethylenediamine-N,N'-diacetic acid and its derivatives

The invention relates to a process for the preparation of N,N'-bis(2-hydroxybenzyl)-ethylenediamine-N,N'-diacetic acid and its derivatives of general formula I, wherein both R have the same meaning and are selected from H, C1-C4alkyl, CH2OH, SO3M, and COOM; and all M have the same meaning and represent hydrogen atom, Na, K or NH4; which comprises reductive amination of glyoxylic acid with a salan compound of general formula (II), in the presence of an amine proton acceptor. The compounds of formula (I) can be used as chelating agents for micronutrients in fertilizer preparations for plants.