Enterobactin

Product Name: Enterobactin
CAS No.: 28384-96-5
Chemical Name: Enterobactin
Synonyms: Enterobactin;Enterochelin;Enterochellin;Enterobactin from Escherichia coli;(3S,7S,11S)-3,7,11-Tris(2,3-dihydroxybenzoylamino)-1,5,9-trioxacyclododecane-2,6,10-trione;N-(2,3-Dihydroxybenzoyl)cyclo[L-Ser*-N-(2,3-dihydroxybenzoyl)-L-Ser*-N-(2,3-dihydroxybenzoyl)-L-Ser*-];N,N',N''-((3S,7S,11S)-2,6,10-Trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris(2,3-dihydroxybenzamide);Benzamide, N,N',N''-[(3S,7S,11S)-2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl]tris[2,3-dihydroxy-
CBNumber: CB81348374
Molecular Formula: C30H27N3O15
Formula Weight: 669.55
MOL File: 28384-96-5.mol

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Enterobactin Property

Melting point:: 202-203°
alpha: D25 +7.40° (ethanol)
Boiling point:: 1109.1±65.0 °C(Predicted)
Density: 1.72±0.1 g/cm3(Predicted)
storage temp.: -20°C
solubility: Acetonitrile: Slightly soluble: 0.1-1 mg/ml
form: Solid
pka: 7.46±0.35(Predicted)
color: White to off-white
biological source: Escherichia coli

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: E3910
Product name: Enterobactin
Purity: ≥98% (HPLC)
Packaging: 1mg
Price: $372
Updated: 2025/07/31

American Custom Chemicals Corporation

Product number: CCH0013192
Product name: ENTEROBACTIN
Purity: 95.00%
Packaging: 5MG
Price: $1897.16
Updated: 2021/12/16

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Enterobactin Chemical Properties,Usage,Production

Uses

Enterobactin has been used:

as a positive control in tryptophan fluorescence quenching experiments
as a reference standard in high performance liquid chromatography to quantify Kosakonia radicincitans culture medium siderophores
in the crystallization reservoir to remove iron contamination in the medium and in Fe-enterbactin binding studies

', 'This preparation of enterobactin is not bound to iron and will bind to Fe3+ and Fe2+ in solution.

Definition

ChEBI: Enterobactin is a macrotriolide produced by certain members of Enterobacteriaceae, e.g. Escherichia coli and Salmonella. It has a role as a bacterial metabolite and a siderophore. It is a crown compound, a member of catechols, a polyphenol and a macrotriolide. It is a conjugate acid of an enterobactin(6-) and an enterobactin(1-).

Biological Activity

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.

References

[1] K POOLE S N L Young. Enterobactin-mediated iron transport in Pseudomonas aeruginosa.[J]. Journal of Bacteriology, 1990, 172 12: 6991-6996. DOI: 10.1128/jb.172.12.6991-6996.1990
[2] VISHAL SINGH. Interplay between enterobactin, myeloperoxidase and lipocalin 2 regulates E. coli survival in the inflamed gut.[J]. Nature Communications, 2015: 7113. DOI: 10.1038/ncomms8113
[3] MÉLISSA CAZA Charles M D François Lépine. Secretion, but not overall synthesis, of catecholate siderophores contributes to virulence of extraintestinal pathogenic Escherichia coli.[J]. Molecular Microbiology, 2011, 80 1: 266-282. DOI: 10.1111/j.1365-2958.2011.07570.x
[4] KRYSTYNA KONOPKA J. B N. Effect of serum albumin on siderophore-mediated utilization of transferrin iron[J]. Biochemistry Biochemistry, 1984, 23 10: 2122-2127. DOI: 10.1021/bi00305a003
[5] DAVID H GOETZ. The neutrophil lipocalin NGAL is a bacteriostatic agent that interferes with siderophore-mediated iron acquisition.[J]. Molecular Cell, 2002, 10 5: 1033-1043. DOI: 10.1016/s1097-2765(02)00708-6

Enterobactin Preparation Products And Raw materials

Raw materials

Preparation Products

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Enterobactin Suppliers

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28384-96-5, EnterobactinRelated Search:

Enterochelin

Enterobactin

(3S,7S,11S)-3,7,11-Tris(2,3-dihydroxybenzoylamino)-1,5,9-trioxacyclododecane-2,6,10-trione

Enterochellin

N-(2,3-Dihydroxybenzoyl)cyclo[L-Ser*-N-(2,3-dihydroxybenzoyl)-L-Ser*-N-(2,3-dihydroxybenzoyl)-L-Ser*-]

Benzamide, N,N',N''-[(3S,7S,11S)-2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl]tris[2,3-dihydroxy-

Enterobactin from Escherichia coli

N,N',N''-((3S,7S,11S)-2,6,10-Trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris(2,3-dihydroxybenzamide)

28384-96-5

C30H27N3O15