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Deferoxamine

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Identification
Molecular formula
C25H48N6O8
CAS number
138-14-7
IUPAC name
N-[(3S,7S,11S)-7,11-bis[(2,3-dihydroxybenzoyl)amino]-2,6,10-trioxo-1,5,9-trioxacyclododec-3-yl]-2,3-dihydroxy-benzamide
State
State

At room temperature, deferoxamine is typically in a solid state, provided in powder form for medicinal use.

Melting point (Celsius)
138.00
Melting point (Kelvin)
411.15
Boiling point (Celsius)
438.15
Boiling point (Kelvin)
711.30
General information
Molecular weight
560.64g/mol
Molar mass
560.6430g/mol
Density
0.9890g/cm3
Appearence

Deferoxamine appears as an off-white or slightly yellowish powder. It is typically supplied as a mesylate salt for pharmaceutical applications.

Comment on solubility

Solubility Characteristics of N-[(3S,7S,11S)-7,11-bis[(2,3-dihydroxybenzoyl)amino]-2,6,10-trioxo-1,5,9-trioxacyclododec-3-yl]-2,3-dihydroxy-benzamide

The solubility of the compound N-[(3S,7S,11S)-7,11-bis[(2,3-dihydroxybenzoyl)amino]-2,6,10-trioxo-1,5,9-trioxacyclododec-3-yl]-2,3-dihydroxy-benzamide can be influenced by several factors. Here are some important aspects to consider:

  • Polarity: The presence of multiple hydroxyl groups in the chemical structure can enhance polar interactions, potentially increasing solubility in polar solvents like water.
  • Hydrogen bonding: The compound has the capacity to form hydrogen bonds due to its hydroxyl groups, which can be beneficial for solubility in aqueous environments.
  • Solvent interactions: Depending on the solvent used, the compound may exhibit different solubility behaviors. It may show higher solubility in organic solvents that have similar polar characteristics.
  • Temperature: Solubility may also be temperature-dependent, generally increasing with rising temperatures, depending on the dissolution process.
  • pH dependency: Given the presence of functional groups that can either donate or accept protons, changes in pH can significantly impact solubility.

In summary, the solubility of this complex compound is likely to be highly variable and dependent on both the solvent environment and external conditions. Further studies are essential to elucidate precise solubility metrics and optimal conditions for application.

Interesting facts

Interesting Facts About N-[(3S,7S,11S)-7,11-bis[(2,3-dihydroxybenzoyl)amino]-2,6,10-trioxo-1,5,9-trioxacyclododec-3-yl]-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-dihydroxy-benzamide is a striking example of a compound that showcases the complexity and elegance of organic chemistry. This compound features multiple functional groups and a sophisticated molecular architecture that can vastly influence its reactivity and potential applications.

Key Features:

  • Chirality: The (3S,7S,11S) configuration denotes specific stereochemistry, which can have significant implications for the biological activity of the compound. Chirality affects how molecules interact with enzymes and receptors in biological systems.
  • Multiple Functional Groups: This compound contains multiple hydroxyl groups and amides, which enhance its potential as a ligand in coordination chemistry and medicinal applications. The presence of dihydroxybenzoyl moieties contributes to its reactivity and solubility characteristics.
  • Antioxidant Properties: Compounds with similar structural motifs often exhibit antioxidant properties, suggesting that this molecule might scavenge free radicals and protect against oxidative stress.
  • Potential Drug Candidate: Due to its structural complexity, this compound could serve as a lead compound in drug development, particularly in creating treatments for diseases where reactive oxygen species play a critical role.

In the world of medicinal chemistry, the ability to synthesize and modify such complex structures is pivotal. Each modification can lead to vastly different biological profiles, and scientists continually explore these compounds for novel therapeutic applications. As you study this compound, consider its potential pathways of action and methods for synthesis—opportunities abound in the realm of organic synthesis and pharmaceutical chemistry.

As scientists say, "The beauty of chemistry lies in the art of molecular manipulation and the quest for discovering the unknown."

Synonyms
enterobactin
28384-96-5
Enterochelin
CHEBI:28855
35C9R2N24F
tri-(2,3-dihydroxy-N-benzoyl-L-serine)-ester
DTXSID40182617
tri-(N-(2,3-dihydroxybenzoyl)-L-serine)-ester
Benzamide, N,N',N''-(2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris(2,3-dihydroxy-, (3S-(3R*,7R*,11R*)))-
N-[(3S,7S,11S)-7,11-bis[(2,3-dihydroxybenzoyl)amino]-2,6,10-trioxo-1,5,9-trioxacyclododec-3-yl]-2,3-dihydroxybenzamide
N-((3S,7S,11S)-7,11-bis((2,3-dihydroxybenzoyl)amino)-2,6,10-trioxo-1,5,9-trioxacyclododec-3-yl)-2,3-dihydroxybenzamide
RefChem:388954
DTXCID80105108
N-(7,11-bis((2,3-dihydroxybenzoyl)amino)-2,6,10-trioxo-1,5,9-trioxacyclododec-3-yl)-2,3-dihydroxybenzamide
N-((3S,7S,11S)-7,11-bis(2,3-dihydroxybenzamido)-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl)-2,3-dihydroxybenzamide
Enterochellin
MFCD16876395
N,N',N''-((3S,7S,11S)-2,6,10-Trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris(2,3-dihydroxybenzamide)
Cyclotris(N-2,3-dihydroxybenzoyl-L-seryl)
Chymosin preparation, Escherichia coli K-12
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''-(2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris[2,3-dihydroxy-, [3S-(3R*,7R*,11R*)]-
N,N',N''-((3S,7S,11S)-2,6,10- trioxo-1,5,9-trioxacyclododecane- 3,7,11-triyl)tris(2,3-dihydroxybenzamide)
UNII-35C9R2N24F
2xuz
H6ent
BENZAMIDE, N,N',N''-((3S,7S,11S)-2,6,10-TRIOXO-1,5,9-TRIOXACYCLODODECANE-3,7,11-TRIYL)TRIS(2,3-DIHYDROXY-
Benzamide, N,N',N''-(2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris(2,3-dihydroxy-, (3S-(3R*,7R*,11R*))-
benzamide, N,N',N''-[(3S,7S,11S)-2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl]tris[2,3-dihydroxy-
EB4
C30H27N3O15
ENTEROBACTIN [MI]
SCHEMBL263621
CHEMBL432995
orb1298062
SCHEMBL29427854
SERBHKJMVBATSJ-BZSNNMDCSA-N
GLXC-21659
Enterobactin from Escherichia coli
DA-73127
FE177921
SY253278
HY-128525
1,5,9-Trioxacyclododecane, benzamide deriv.
CS-0095342
C05821
F77042
Q523354
N-(2,3-DIHYDROXYBENZOYL)-L-SERINE TRIMOLECULAR CYCLIC ESTER
(3S-(3R*,7R*,11R*))-N,N',N''-(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- (9CI)
N,N inverted exclamation mark ,N inverted exclamation mark inverted exclamation mark -[(3S,7S,11S)-2,6,10-Trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl]tris(2,3-dihydroxybenzamide)
N-(2,3-dihydroxybenzoyl)-O-[N-(2,3-dihydroxybenzoyl)-O-[N-(2,3-dihydroxybenzoyl)-L-seryl]-L-seryl]-L-serine-(3->1(3))-lactone
N-[(3S,7S,11S)-7,11-bis[(2,3-dihydroxybenzene)amido]-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzamide
N-[(3S,7S,11S)-7,11-bis[(2,3-dihydroxybenzoyl)amino]-2,6,10-trioxo-1,5,9-trioxacyclododec-3-yl]-2,3-dihydroxy-benzamide
o-Pyrocatechuamide, N,N',N''-(2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris- (8CI)
Tri-(N-(2,3-Dihydroxybenzoyl)-L-serine)-ester; N,N',N''-((3S,7S,11S)-2,6,10- trioxo-1,5,9-trioxacyclododecane- 3,7,11-triyl)tris(2,3-dihydroxybenzamide)