| Identification | More | [Name]
Acetohydroxamic acid | [CAS]
546-88-3 | [Synonyms]
ACETOHYDROXAMIC ACID
ACETYL HYDROXYAMINE
N-ACETYLHYDROXYLAMINE
N-HYDROXYACETAMIDE
Acetamide,N-hydroxy-
acethydroxamsaeure
Acethydroxamsaure
Acetic acid, oxime
aceticacid,oxime
acetohydroxamicacid(INN)
Acetohydroxamsαure
Acetohydroximic acid
acetohydroximicacid
Acetyl hydroxyamino
Acetylhydroxamic acid
acetylhydroxamicacid
Acetylhydroxylamine
AHA
cetohyroxamic acid
Hydroxylamine, N-Acetyl- | [EINECS(EC#)]
208-913-8 | [Molecular Formula]
C2H5NO2 | [MDL Number]
MFCD00009994 | [Molecular Weight]
75.07 | [MOL File]
546-88-3.mol |
| Chemical Properties | Back Directory | [Appearance]
White Crystalline Solid | [Melting point ]
88-90 °C (lit.) | [Boiling point ]
133.7°C (rough estimate) | [density ]
1.2269 (rough estimate) | [refractive index ]
1.4264 (estimate) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [solubility ]
Methanol (Sparingly), Water (Sparingly) | [form ]
Crystalline Solid | [pka]
8.70(at 25℃) | [color ]
White to pale yellow | [Water Solubility ]
Soluble in water. | [Sensitive ]
Hygroscopic | [Usage]
A urease inhibitor | [Merck ]
14,63 | [BRN ]
1739019 | [Stability:]
Moisture and Temperature Sensitive | [InChI]
1S/C2H5NO2/c1-2(4)3-5/h5H,1H3,(H,3,4) | [InChIKey]
RRUDCFGSUDOHDG-UHFFFAOYSA-N | [SMILES]
CC(NO)=O | [CAS DataBase Reference]
546-88-3(CAS DataBase Reference) | [NIST Chemistry Reference]
Acetamide,N-hydroxy(546-88-3) | [EPA Substance Registry System]
546-88-3(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS08 | [Signal word ]
Danger | [Hazard statements ]
H360 | [Precautionary statements ]
P201-P280-P308+P313 | [Hazard Codes ]
T | [Risk Statements ]
R61:May cause harm to the unborn child.
R40:Limited evidence of a carcinogenic effect. | [Safety Statements ]
S53:Avoid exposure-obtain special instruction before use .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S22:Do not breathe dust . | [RIDADR ]
3263 | [WGK Germany ]
3
| [RTECS ]
AK8157000
| [Hazard Note ]
Toxic | [PackingGroup ]
II | [HS Code ]
29225090 | [Storage Class]
6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | [Hazard Classifications]
Repr. 1B | [Hazardous Substances Data]
546-88-3(Hazardous Substances Data) | [Toxicity]
mmo-sat 160 mmol/plate JOPHDQ 3,557,80 |
| Hazard Information | Back Directory | [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. | [Chemical Properties]
White Crystalline Solid | [Originator]
Research Organics; Baylor Unk. (USA) | [Uses]
A urease inhibitor. Used in the synthesis | [Uses]
urease inhibitor, antiurolithic, antbacterial | [Definition]
ChEBI: Acetohydroxamic acid is a member of the class of acetohydroxamic acids that is acetamide in which one of the amino hydrogens has been replaced by a hydroxy group. It has a role as an EC 3.5.1.5 (urease) inhibitor and an algal metabolite. It is functionally related to an acetamide. It is a tautomer of a N-hydroxyacetimidic acid. | [Manufacturing Process]
3 Methods of producing of acetohydroxamic acid:
1. Ethyl acetic acid ether was treated with hydroxylamine and
acetohydroxamic acid was obtained.
2. Acetohydroxamic acid was obtained in the result of reaction of acetamide
with hydroxylamine.
3. Acetohydroxamic acid was obtained by treatment of acetaldehyde with
nitrohydroxylamine. | [Brand name]
Lithostat (Mission). | [Therapeutic Function]
Urease inhibitor | [General Description]
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. | [Side effects]
Get emergency medical help if you have any of these signs of an allergic reaction: hives; difficulty breathing; swelling of your face, lips, tongue, or throat.
Call your doctor at once if you have:
pounding heartbeats or fluttering in your chest;
signs of a blood clot in your leg --pain, swelling, warmth, or redness in one or both legs;
signs of a red blood cell disorder --pale or yellowed skin, dark colored urine, fever, confusion or weakness.
Common side effects may include:
headache during the first 2 days of treatment;
skin rash, warmth, tingling or redness (especially if you drink alcohol while taking acetohydroxamic acid);
upset stomach, nausea, loss of appetite;
depressed mood;
anxiety, tremors, nervousness;
hair loss. | [Safety Profile]
Moderately toxic by intraperitonealroute. An experimental teratogen. Other experimentalreproductive effects. Mutation data reported. When heatedto decomposition it emits toxic fumes of NOx. | [Synthesis]
Acetohydroxamic acid (AHA) can be prepared by chemical synthesis and enzymatic methods (biocatalysis).
(1) Chemical synthesis
Using a 50% hydroxylamine hydrate solution (25 mL, 0.42 mol, diluted with 25 mL water) as the starting material, acetic anhydride (45 mL, 49.3 g, 0.42 mol) is added dropwise under magnetic stirring, during which the reaction temperature rises to 80 °C. After complete addition, the clear liquid is cooled to room temperature whilst continuing to stir. The product is then extracted with ethyl acetate (4 × 70 mL); the combined extracts are concentrated under reduced pressure to ~90 mL, cooled, and crystallised from acetone to yield 17.0 g of colourless AHA in a 55% yield with 98% purity[1].
(2) Enzymatic method (biocatalysis)
With acetamide (400 mM, 100 mL, in 0.1 M potassium phosphate buffer, pH 7.0) as the acyl donor and hydroxylamine (1.5 M, 50 mL) as the co-substrate, resting cells of Bacillus smithii IIIMB2907 (100 mg dcw) are incubated at 50 °C, pH 7.0, for 90 min (150 mL batch reaction), exploiting the acyltransferase activity of the amidase to transfer the acyl group of the amide to hydroxylamine. The reaction mixture is centrifuged (10,000 g, 10 min), the supernatant concentrated by rotary evaporation, purified by silica gel (60–120 mesh) column chromatography (chloroform elution), and dried under reduced pressure to afford 1.9 g AHA with 85% conversion and ~81% purification recovery[2].
| [Veterinary Drugs and Treatments]
Acetohydroxamic acid can be used in dogs as adjunctive therapy
in some cases of recurrent urolithiasis or in the treatment of persistent
urinary tract infections caused by the following bacteria:
E. coli, Klebsiella, Morganella morganii, Staphylococci spp., and
Pseudomonas aeruginosa. Adverse effects limit its usefulness. | [References]
[1]
Sukumar, S., Rao, R. V. S., & Natarajan, R. (2014). Improved Preparation of Acetohydroxamic Acid. Organic Preparations and Procedures International, 46(1), 85–87. https://doi.org/10.1080/00304948.2014.866477
[2]
Singh, R. V. (2023). Enzymatic Catalysts for Hydroxamic Acid Formation: A Mini‐Review. ChemBioEng Reviews, 11(2), 339–347. https://doi.org/10.1002/cben.202300059
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J & K SCIENTIFIC LTD.
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https://www.jkchemical.com |
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Alfa Aesar
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400-6106006 |
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http://chemicals.thermofisher.cn |
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Energy Chemical
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400-0056266 |
| Website: |
www.energy-chemical.com |
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