Acetohydroxamic acid

Base Information

• Chemical Name: Acetohydroxamic acid
• CAS No.: 546-88-3
• Molecular Formula: C2H5NO2
• Molecular Weight: 75.0672
• Hs Code.: 29225090
• European Community (EC) Number: 208-913-8
• NSC Number: 755855,176136,5073
• UNII: 4RZ82L2GY5
• DSSTox Substance ID: DTXSID7022546
• Nikkaji Number: J1.012.476J,J23.285H
• Wikipedia: Acetohydroxamic_acid
• Wikidata: Q481822
• NCI Thesaurus Code: C47381
• RXCUI: 16728
• Metabolomics Workbench ID: 42887
• ChEMBL ID: CHEMBL734
• Mol file: 546-88-3.mol

Synonyms:acetohydroxamic acid;Lithostat;N-hydroxyacetamide;N-hydroxyacetamidine;Uronefrex

Chemical Property of Acetohydroxamic acid

Chemical Property:

• Appearance/Colour: White crystalline solid
• Vapor Pressure: 0.0118mmHg at 25°C
• Melting Point: 88-90 °C(lit.)
• Refractive Index: 1.42
• Boiling Point: 231.4 °C at 760 mmHg
• PKA: 8.70(at 25℃)
• Flash Point: 127.6 °C
• PSA: 49.33000
• Density: 1.155 g/cm³
• LogP: -0.09740
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Sensitive.: Hygroscopic
• Solubility.: Methanol (Sparingly), Water (Sparingly)
• Water Solubility.: Soluble in water.
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 75.032028402
• Heavy Atom Count: 5
• Complexity: 42.9

Purity/Quality:

99% ^*data from raw suppliers

Acetohydroxamic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 61-40
• Safety Statements: 53-45-36/37/39-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NO
• Recent ClinicalTrials: Manipulating the Gut Microbiome Study
• Description: Acetohydroxamic acid is a potent, non-competitive and irreversible inhibitor of bacterial urease (Ki≈lO-7M). This enzyme, which is widely distributed in plants and bacteria, but not in mammalian cells, catalyzes the decomposition of urea to ammonia. Elevated urinary ammonia levels can reduce the antibacterial effectiveness of a number of agents. Thus, acetohydroxamic acid is useful as adjunctive therapy to decrease urinary ammonia and alkalinity in patients with chronic urea-splitting urinary infection. Such infections are a leading cause of recurring complications and death in paraplegics.
• Uses: Acetohydroxamic acid is a potent inhibitor of bacterial urease activity and reduces urinary ammonia levels. 2-Acetohydroxamic acid loaded floating microspheres forms an efficient drug delivery system for the treatment of Helicobacter pylori.Acetohydroxamic acid was used:to study the mechanism of complexation of iron (III) with acetohydroxamic acid.to study the inhibitory mechanism of lansoprazole and omeprazole on Helicobacter pyloni.in urease inhibition studies.for in situ generation of nitrosocarbonylmethane as a Diels-Alder dienophile.Used in urease inhibition studies and for in situ generation of nitrosocarbonylmethane as a Diels-Alder dienophile. A urease inhibitor. Used in the synthesis Urease inhibitorAcetohydroxamic acid acts as a drug, as an inhibitor of bacterial and plant urease, which is used for urinary tract infections. It is also used in organic synthesis. It acts as an antiurolithic and antibacterial agent. It is involved in the study of complexation of iron(III) with acetohydroxamic acid as well as in the inhibition study of lansoprazole and omeprazole on Helicobacter pyloni. It plays an important role in the insitu generation of nitrosocarbonylmethane as a Diels-Alder dienophile. In addition to this, it is used in the treatment of kidney stones and urinary tract infections.
• Therapeutic Function: Urease inhibitor

Technology Process of Acetohydroxamic acid

There total 87 articles about Acetohydroxamic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

hydroxylamine hydrochloride (5470-11-1) + ethyl acetate (141-78-6) → acetylhydroxamic acid (546-88-3)

Guidance literature:

hydroxylamine hydrochloride; With sodium hydroxide; In water; at 20 - 25 ℃; for 0.15h;

ethyl acetate; at 30 - 35 ℃; for 0.25h; Temperature;

Reference yield: 97.1%

ethyl acetate (141-78-6) → acetylhydroxamic acid (546-88-3)

Guidance literature:

With hydroxyammonium sulfate; sodium ethanolate; In ethanol; at 25 ℃; for 2h; Concentration;

Reference yield: 92.0%

acetamide (60-35-5) → acetylhydroxamic acid (546-88-3)

Guidance literature:

With hydrogenchloride; iron(III) chloride; amidase from Pseudomonas aeruginosa strain L₁₀; hydroxylamine; cetyltrimethylammonium bromide; In octanol; n-heptane; water; for 0.5h; aq. buffer; Enzymatic reaction;

DOI:10.1016/j.procbio.2011.11.001

upstream raw materials:

acetamide

Ketene

Acetaldehyde oxime

Nitroethane

Downstream raw materials:

12-acetyl-9,10-dimethyl-9,10-dihydro-10,9-oxaazaethano-anthracene

Acetamino-(1,3,5-tri-tert-butyl-4-oxo-cyclohexa-2,5-dienyl)-ether

3-methyl-5-(2-nitro-benzyl)-[1,4,2]dioxazole

4-methoxyacetanilide

Refernces

• 1、 Bergmann. "". . p. 1367. Retrieved 1952.
• 2、 Fragoso, Ana,Pacheco, Rita,Karmali, Amin. "Investigation of structural effects and behaviour of Pseudomonas aeruginosa amidase encapsulated in reversed micelles". . p. 264 - 272. Retrieved 2012.
• 3、 Bruice et al.. "". . p. 4886,4891. Retrieved 1964.
• 4、 Hoare,Olson,Koshland Jr.. "The reaction of hydroxamic acids with water-soluble carbodiimides. A Lossen rearrangement.". . p. 1638 - 1643. Retrieved 1968.
• 5、 Dai, Peng,Jiao, Jian,Wang, Qing-Qing,Zhang, Shu-Guang,Zhang, Wei-Hua. "Novel fluorinated 7-hydroxycoumarin derivatives containing an oxime ether moiety: Design, synthesis, crystal structure and biological evaluation". . . Retrieved 2021/06/28.
• 6、 F?hrmann, Jan,Hilt, Gerhard. "Alternating Current Electrolysis as Efficient Tool for the Direct Electrochemical Oxidation of Hydroxamic Acids for Acyl Nitroso Diels–Alder Reactions". supporting information. p. 20313 - 20317. Retrieved 2021/08/12.