34787-28-5

Basic information

• Product Name: N-desferriferrichrome
• Synonyms: N-desferriferrichrome;DesferrichroMe;Cyclo(glycylglycylglycyl-N5-acetyl-N5-hydroxy-L-ornithyl-N5-acetyl-N5-hydroxy-L-ornithyl-N5-acetyl-N5-hydroxy-L-ornithyl);Deferriferrichrome;Ferrichrome Iron-free;deferrichrome
• CAS NO: 34787-28-5
• Molecular Formula: C27H45N9O12
• Molecular Weight: 687.6993
• Product Categories: Chelating Agents & Ligands;Intermediates & Fine Chemicals;Pharmaceuticals;Chelating Agents & Ligands, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 34787-28-5.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.27g/cm³
• Refractive Index: 1.509
• Storage Temp.: 2-8°C
• Solubility: DMSO, Methanol
• CAS DataBase Reference: N-desferriferrichrome(CAS DataBase Reference)
• NIST Chemistry Reference: N-desferriferrichrome(34787-28-5)
• EPA Substance Registry System: N-desferriferrichrome(34787-28-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 34787-28-5(Hazardous Substances Data)

Usage

Uses

Used in Microbiology:
N-desferriferrichrome is used as a growth-promoting iron chelator for various microorganisms, including fungi and bacteria. It helps these organisms to chelate and uptake iron, which is essential for their growth and survival.
Used in Immunology:
N-desferriferrichrome is used as an immunomodulatory agent to inhibit the proliferation of murine spleen mononuclear cells induced by concanavalin A. It also reduces the number of concanavalin A-stimulated CD4+ T cells expressing the IL-2 receptor, which can be beneficial in controlling immune responses.
Used in Cardiovascular Research:
N-desferriferrichrome is used as an antioxidant to inhibit heme-catalyzed oxidation of LDL by hydrogen peroxide in a concentration-dependent manner. This property can be useful in studying the role of oxidative stress in cardiovascular diseases and developing potential therapeutic agents.

Biochem/physiol Actions

Growth-promoting iron chelator

InChI:InChI=1/C27H45N9O12/c1-16(37)34(46)10-4-7-19-25(43)30-14-23(41)28-13-22(40)29-15-24(42)31-20(8-5-11-35(47)17(2)38)26(44)33-21(27(45)32-19)9-6-12-36(48)18(3)39/h19-21,46-48H,4-15H2,1-3H3,(H,28,41)(H,29,40)(H,30,43)(H,31,42)(H,32,45)(H,33,44)/t19-,20+,21+/m1/s1

Upstream product

• 117652-75-2 N-(tert-butoxycarbonyl)diglycyltri(N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl)glycine methyl ester 
• 117652-85-4 [(S)-5-(Acetyl-benzyloxy-amino)-2-((S)-5-(acetyl-benzyloxy-amino)-2-{(S)-5-(acetyl-benzyloxy-amino)-2-[2-(2-tert-butoxycarbonylamino-acetylamino)-acetylamino]-pentanoylamino}-pentanoylamino)-pentanoylamino]-acetic acid 
• 117652-87-6 C₅₇H₇₆N₁₀O₁₇ 
• 31972-52-8 Boc-Gly-Gly-OH 
• 40332-33-0 cyclo(triglycyltri(N⁵-acetyl-N⁵-(benzyloxy)-L-ornithyl)) 

Relevant articles and documents

Synthesis and application of an Nδ-acetyl-N δ-hydroxyornithine analog: Identification of novel metal complexes of deferriferrichrysin

Synthesis of Fmoc-protected Nδ-acetyl-N δ-(tert-butoxy)-l-ornithine has revealed it to be a metal-chelating amino-acid precursor. This protected amino acid was compatible with the preparation of ferrichrome peptides by standard Fmoc-

N-Hydroxy Amides. 7. Synthesis and Properties of Linear and Cyclic Hexapeptides Containing Three N5-Acetyl-N5-hydroxy-L-ornithine Residues as Models for Ferrichrome

As sequence-modified analogues of desferriferrichrome (1), linear and cyclic peptides have been prepared.They are (OrnAH-Gly)3 (2), Ac-Gly2-OrnAH3-Gly-OMe (3), Ac-(OrnAH-Gly)3-OMe (4), and Ac-Gly-OrnAH-(OrnAH-Gly)2-OMe (5), where OrnAH stands for an Nsup