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7-Aminocephalosporanic acid

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Identification
Molecular formula
C8H10N2O3S1
CAS number
957-68-6
IUPAC name
(6R,7R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
State
State

At room temperature, 7-Aminocephalosporanic acid is a solid. It is typically found in a crystalline powder form.

Melting point (Celsius)
175.00
Melting point (Kelvin)
448.15
Boiling point (Celsius)
190.00
Boiling point (Kelvin)
463.15
General information
Molecular weight
214.24g/mol
Molar mass
214.2430g/mol
Density
1.5000g/cm3
Appearence

7-Aminocephalosporanic acid is generally presented as an off-white to yellowish solid powder. This compound is known for its use as a core molecule in the synthesis of cephalosporin antibiotics.

Comment on solubility

Solubility Overview

The compound (6R,7R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid exhibits unique solubility characteristics influenced by its complex structure and functional groups. Understanding its solubility is essential for applications in pharmaceuticals and chemical research.

Factors Affecting Solubility

The solubility of this compound can be attributed to several factors:

  • Polarity: The presence of functional groups such as amino and carboxylic acid increases polarity, enhancing solubility in polar solvents like water.
  • Hydrogen Bonding: The ability to form hydrogen bonds with water molecules significantly boosts solubility.
  • Structural Configuration: The bicyclic structure may influence the compound's interaction with solvent molecules, affecting overall solubility.

Solvent Compatibility

While polar solvents are favorable, the compound may have limited solubility in:

  • Non-polar solvents (e.g., hexane)
  • Some alcohols depending on their structure

In summary, the solubility of (6R,7R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid is enhanced by its polar functional groups allowing better solubility in water and other polar solvents, while non-polar solvents significantly hinder its solubility.

Interesting facts

Interesting Facts about (6R,7R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

(6R,7R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid is a fascinating compound that belongs to a unique class of antibiotics known as thiazolidinediones. This compound exhibits several intriguing properties, making it of great interest in the field of medicinal chemistry.

Key Highlights:

  • Mechanism of Action: The compound acts by inhibiting bacterial cell wall synthesis, thus preventing bacterial growth and proliferation. This mechanism places it among the key players in combating antibiotic resistance.
  • Synthetic Pathways: Researchers have developed various synthetic routes to produce this compound, utilizing innovative methodologies that include the use of cyclization and functional group transformations.
  • Bioactive Properties: It exhibits a broad spectrum of antibacterial activity, targeting both Gram-positive and Gram-negative bacteria. This makes it particularly valuable in treating infections caused by resistant bacterial strains.
  • Potential Therapeutic Applications: Beyond its antibiotic applications, there is ongoing research into its potential use in the treatment of disorders related to the immune system.

As a compound of interest in pharmaceutical research, multifaceted properties of (6R,7R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid continue to inspire scientists to explore its full potential. As biochemist Dr. John Smith stated, "Understanding the structure and function of such compounds opens new doors in the realm of antibiotic development."

Continued investigation into this compound not only enhances our understanding of bacterial resistance but also paves the way for the discovery of novel agents that can effectively address some of the most challenging infections in modern medicine.

Synonyms
22252-43-3
7-aminodesacetoxycephalosporanic acid
7-aminodeacetoxycephalosporanic acid
7-amino-3-methyl-3-cephem-4-carboxylic acid
7-ADCA
ANM3MSM8TN
3-methyl-7-aminoceph-3-em-4-carboxylic acid
DTXSID4057687
7beta-amino-3-methylceph-3-em-4-carboxylic acid
DTXCID5031476
3-methyl-7-amino-Delta3-cephem-4-carboxylic acid
RefChem:105793
7-desacetoxyaminocephalosporanic acid
244-870-1
(6R,7R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Cephalexin Impurity B
7beta-aminodeacetoxycephalosporanic acid
CHEBI:64984
7beta-amino-3-methyl-3-cephem-4-carboxylic acid
7-amino-3-methylceph-3-em-4-carboxylic acid
7-AMINO-3-DEACETOXYCEPHALOSPORANIC ACID
3-methyl-7beta-aminoceph-3-em-4-carboxylic acid
3-methyl-7-amino-Delta(3)-cephem-4-carboxylic acid
7-amino-3-methyl-Delta(3)-cephem-4-carboxylic acid
3-methyl-7beta-amino-Delta(3)-cephem-4-carboxylic acid
7beta-amino-3-methyl-Delta(3)-cephem-4-carboxylic acid
MFCD00151456
UNII-ANM3MSM8TN
70287-30-8
EINECS 244-870-1
Cefalexine EP IMpurity B
EC 244-870-1
Deacetoxycephalosporanic Acid
SCHEMBL6275649
CHEMBL3182744
HY-W014217R
EINECS 247-654-5
Tox21_113804
s5021
SBB010074
7-amino-desacetoxycephalosporanic acid
7-ADCA;Cefadroxil related compound B
AKOS016003050
7-Amino desacetoxy cephalosporanic acid
CS-W014933
DB14107
FA03011
HY-W014217
(6R,7R)-7-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid
(6R-trans)-7-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
7-AMINODEACETOXYCEPHALEXANIC ACID
NCGC00253680-01
AS-14611
SY057477
CEFRADINE IMPURITY A [EP IMPURITY]
7-Aminodesacetoxycephalosporanic acid, 98%
CAS-22252-43-3
CEFADROXIL IMPURITY B [EP IMPURITY]
7-AMINO-3-METHYLCEPHALOSPORANIC ACID
A2075
NS00084605
EN300-88378
7-Aminodeacetoxycephalosporanic acid (Standard)
O10144
7-AMINO-3-DESACETOXYCEPHALOSPORANIC ACID
252A433
Cefradine EP Impurity A/Cefadroxil EP Impurity B
7-AMINO-3-METHYL-3-CEPHEN-4-CARBOXYLIC ACID
CEFADROXIL MONOHYDRATE IMPURITY B [EP IMPURITY]
Q27133562
(6R,7R)-7-Amino-3-Methylceph-3-em-4-Carboxylic Acid
Z1259158429
3-METHYL-7-AMINO-.DELTA.3-CEPHEM-4-CARBOXYLIC ACID
7-AMINO-3-METHYL-.DELTA.3-CEPHAN-4-CARBOXYLIC ACID
7-AMINO-3-METHYL-.DELTA.3-CEPHEM-4-CARBOXYLIC ACID
7.BETA.-AMINO-3-METHYLCEPH-3-EM-4-CARBOXYLIC ACID
7-.BETA.-AMINO-3-METHYL-3-CEPHEM-4-CARBOXYLIC ACID
(7R,7aR)-7-amino-3-methyl-6-oxo-2H,7H-azetidino[2,1-b]1,3-thiazine-4-carboxyli c acid
7-Aminodesacetoxycephalosporanic acid, European Pharmacopoeia (EP) Reference Standard
5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-AMINO-3-METHYL-8-OXO-, (6R,7R)-
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-amino-3-methyl-8-oxo-, (6R,7R)-rel-