Skip to main content

Ioxaglic acid

ADVERTISEMENT
Identification
Molecular formula
C19H13I3N2O6
CAS number
59017-53-7
IUPAC name
3-acetamido-5-[acetyl(methyl)amino]-2,4,6-triiodo-benzoic acid
State
State

At room temperature, ioxaglic acid is typically solid. It is used in aqueous solutions, particularly as a contrast medium in medical imaging, allowing it to be administered intravenously.

Melting point (Celsius)
220.00
Melting point (Kelvin)
493.15
Boiling point (Celsius)
300.00
Boiling point (Kelvin)
573.15
General information
Molecular weight
821.94g/mol
Molar mass
821.9410g/mol
Density
2.3000g/cm3
Appearence

Ioxaglic acid appears as a crystalline white or off-white solid. It is often supplied as a powder and may exhibit a slight yellowish tint depending on the purity and specific formulation. The compound is typically used in solution form when applied as a contrast agent for radiographic imaging.

Comment on solubility

Solubility of 3-acetamido-5-[acetyl(methyl)amino]-2,4,6-triiodo-benzoic acid (C19H13I3N2O6)

The solubility of 3-acetamido-5-[acetyl(methyl)amino]-2,4,6-triiodo-benzoic acid can be quite complex due to its unique chemical structure, which includes multiple functional groups and iodine substitutions. Here are some key points to consider:

  • Polarity: The presence of the acetamido and acetyl groups typically increases the polarity of the compound, which may enhance its solubility in polar solvents like water.
  • Hydrophobic Character: However, the three iodine substituents significantly contribute to hydrophobic characteristics, which may hinder solubility in aqueous environments.
  • Organic Solvents: This compound is likely to be more soluble in organic solvents such as dimethyl sulfoxide (DMSO) or methanol due to the balance of hydrophilic and hydrophobic regions.
  • pH Influence: The solubility may also vary with pH levels, as benzoic acid derivatives can dissociate in basic conditions, potentially increasing solubility.

In conclusion, while 3-acetamido-5-[acetyl(methyl)amino]-2,4,6-triiodo-benzoic acid may exhibit some degree of solubility in polar solvents, its hydrophobic segments strongly influence its overall solubility profile. As a result, the practical application of this compound often involves dissolution in specifically chosen organic solvents to achieve the necessary concentration for studies or formulations.

Interesting facts

Interesting Facts About 3-Acetamido-5-[Acetyl(methyl)amino]-2,4,6-triiodo-benzoic Acid

3-Acetamido-5-[acetyl(methyl)amino]-2,4,6-triiodo-benzoic acid represents a fascinating intersection of organic chemistry and medicinal applications. Known for its unique structure, this compound features multiple iodine atoms incorporated into a benzoic acid framework, which greatly influences its chemical behavior and potential uses.

Chemical Significance

  • Halogenation: The presence of three iodine atoms can enhance the compound's stability and lipophilicity, making it potentially useful in pharmaceutical formulations.
  • Amide Bonds: With both acetamido and acetyl(methyl)amino functional groups, this compound showcases the versatility of amide linkages in organic synthesis.
  • Radiological Applications: Iodine-containing compounds are vital in medical imaging techniques, particularly in radiology, due to their ability to absorb X-rays.

Potential Applications

The unique properties of this compound open doors to several exciting applications:

  • Imaging Agents: Its iodine content makes it a prime candidate for use in contrast agents in imaging.
  • Antimicrobial Activity: Some iodine compounds demonstrate antimicrobial properties, potentially offering therapeutic benefits.
  • Drug Design: The compound could serve as a lead structure for the development of new pharmaceuticals targeting various diseases.

Conclusion

3-Acetamido-5-[acetyl(methyl)amino]-2,4,6-triiodo-benzoic acid highlights just how complex and multifunctional organic compounds can be. Its combination of halogens, amide groups, and a robust aromatic system invite further exploration in chemistry, medicinal research, and material science. As researchers continue to unravel its potential, this compound may play a significant role in the future of therapeutics and diagnostics.

Synonyms
Metrizoic acid
1949-45-7
Metrizoate
Acide metrizoique
Acidum metrizoicum
3-acetamido-2,4,6-triiodo-5-(N-methylacetamido)benzoic acid
Metrizoic Acid [JAN]
Isopaque
Triosil
3-Acetamido-2,4,6-triiodo-5-N-methylacetamidobenzoic acid
Benzoic acid, 3-(acetylamino)-5-(acetylmethylamino)-2,4,6-triiodo-
3-acetamido-5-[acetyl(methyl)amino]-2,4,6-triiodobenzoic acid
CM1N99QR1M
CHEBI:34847
3-(acetylamino)-5-(acetylmethylamino)-2,4,6-triiodobenzoic acid
V08AA02
3-(acetylamino)-5-[acetyl(methyl)amino]-2,4,6-triiodobenzoic acid
Isopaque 440
SMR001550298
NSC107431
METRIZOIC ACID, METRIZOIC ACID 610.4MG
NCGC00181093-01
EINECS 217-761-1
UNII-CM1N99QR1M
BRN 2822724
metrizoic-acid
3-(Acetylamino)-5-(acetyl(methyl)amino)-2,4,6-triiodobenzoic acid
3-(Acetylamino)-5-(acetylmethylamino)-2,4,6-triiodobenzoic Acid; 3-Acetamido-2,4,6-triiodo-5-(N-methylacetamido)benzoic Acid; 3,5-Diacetamido-N-methyl-2,4,6-triiodobenzoic Acid; Metrizoate;
MFCD00867964
3-Acetamido-5-(N-methylacetamido)-2,4,6-triiodobenzoic Acid
BENZOIC ACID, 3-ACETAMIDO-2,4,6-TRIIODO-5-(N-METHYLACETAMIDO)-
Sodium Metrizoate (USAN)
CHEMBL1736
METRIZOIC ACID [MI]
SCHEMBL37641
MLS004773979
MLS006010899
METRIZOIC ACID [MART.]
DTXSID6023311
METRIZOIC ACID [WHO-DD]
GGGDNPWHMNJRFN-UHFFFAOYSA-N
3-acetamido-5-[acetyl(methyl)amino]-2,4,6-triiodo-benzoic acid
HY-B1699
METRIZOIC ACID [ORANGE BOOK]
AKOS016846123
DB09346
AS-70791
CS-0013692
M1363
NS00026356
D91491
SBI-0654051.0001
EN300-6731075
SR-01000939781
Q6824400
SR-01000939781-2
BRD-K99241550-001-03-5
Z2417556930
3-Acetamido-2,4, 6-triiodo-5-(N-methylacetamido)benzoate-
Sodium 3-acetamido-2,4, 6-triiodo-5-(N-methylacetamido)benzoate
3-ACETAMIDO-2,4,6-TRI-IODO-5-(N-METHYLACETAMIDO)BENZOIC ACID
Benzoic acid, 3-(acetylamino)-5-(acetylmethylamino)-2,4, 6-triiodo-, monosodium salt
Benzoic acid, 3-acetamido-2,4, 6-triiodo-5-(N-methylacetamido)-, monosodium salt