ENTEROBACTIN

Synonyms. Enterobactin; (3S-(3R',7R',11R'))-N,N',N''-(2,6,10-trioxo-1,5,9-trioxacyclododecane -3,7,11-triyl) tris(2,3-dihydroxy benzamide); N-((3S,7S,11S)-7,11-Bis((2,3-dihydroxybenzoyl) amino)- 2,6,10-trioxo -1,5,9-trioxacyclododec-3-yl)-2,3-dihydroxybenzamide;

ENTEROBACTIN

 

PRODUCT IDENTIFICATION

CAS RN

28384-96-5

EINECS RN

 

FORMULA

C30H27N3O15

MOLE WEIGHT

669.55

H.S CODE

 2932.20.3000

SMILES

 C1C(C(=O)OCC(C(=O)OCC(C(=O)O1)NC(=O)C2=C(C(=CC=C2) O)O)NC (=O)C3=C(C(=CC=C3)O)O)NC(=O)C4=C(C(=CC=C4)O)O

CLASSIFICATION

Chelating agent, Siderophore, Macrocycle

EXTRA NOTES

An iron-binding cyclic trimer of 2,3-dihydroxy-N-benzoyl-L-serine. It is produced by E COLI and other enteric bacteria.

 

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE.

white to off-white crystalline powder. Bright blue fluorescence under uv light.

MELTING POINT

202 ~ 203 C

BOILING POINT

 

DENSITY

 

SOLUBILITY IN WATER

Insoluble

SOLVENT SOLUBILITY

Soluble in acetone, dioxane, dimethyl sulfoxide, methanol.

VAPOR DENSITY

 

log P(octanol-water)

  

VAPOR PRESSURE

  

AUTOIGNITION TEMP

  
pK

 

REFRACTIVE INDEX

 

FLASH POINT

 

 

STABILITY AND REACTIVITY
STABILITY Stable under normal conditions.

INCOMPATIBLE MATERIALS

Strong oxidizing agents

POLYMERIZATION

Has not been reported

NFPA RATINGS

 

 

EXTERNAL LINKS & GENERAL DESCRIPTION

USA.gov - Enterobactin

Wikipedia Linking - Enterobactin

Google Scholar Search - Enterobactin

U.S. National Library of Medicine - Enterobactin

PubChem Compound Summary - Enterobactin

KEGG (Kyoto Encyclopedia of Genes and Genomes) -  Enterobactin

ChEBI (http://www.ebi.ac.uk/chebi/) -  Enterobactin

NCBI (http://www.ncbi.nlm.nih.gov/) -  Enterobactin

Hazardous Substances Data Bank - Enterobactin

Sigmaaldrich
Biochem/physiol Actions: Iron mobilization and uptake by microbes is mediated by low molecular weight complexing agents named siderophores. Enterobactin is a catechol (a benzenediol, C6H4(OH)2) type siderophore produced in small quantities by Escherichia coli and related enteric bacteria when grown on iron deficient media, and is one of the most powerful ferric ion complexing agents known. Enterobactin is a very effective sequestering agent for iron, able to remove iron from proteins, insoluble iron complexes, and other siderophores. Studies of the chemistry, regulation, synthesis, recognition, and transport of enterobactin make it the best-understood siderophore.

 

SALES SPECIFICATION

APPEARANCE

white to off-white crystalline powder

ASSAY

98% min

MELTING POINT

202 ~ 203 C

OPTICAL ACTIVITY

+7.40° (ethanol)

LOSS ON DRYING

0.5% max

 

TRANSPORT & REGULATORY INFORMATION

UN NO.

 

HAZARD CLASS

 

PACKING GROUP  

 

SAFETY INFORMATION (N/A)

HAZARD OVERVIEW

 

SIGNAL WORD  

PICTOGRAMS

 

HAZARD STATEMENTS

 

PRECAUTIONARY STATEMENTS

 

EC DIRECTIVES

 

HAZARD CODES

 

RISK PHRASES

 

SAFETY PHRASES

 

 

PACKING

Preserve in light-resistant and well-closed containers

 

PRICE INFORMATION