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159034

Sigma-Aldrich

Acetohydroxamic acid

98%

Synonym(s):

AHA

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About This Item

Linear Formula:
CH3CONHOH
CAS Number:
546-88-3
Molecular Weight:
75.07
Beilstein/REAXYS Number:
1739019
EC Number:
208-913-8
MDL number:
MFCD00009994
UNSPSC Code:
12352100
PubChem Substance ID:
24849786
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

100

assay

98%

mp

88-90 °C (lit.)

functional group

amine

SMILES string

CC(NO)=O

InChI

1S/C2H5NO2/c1-2(4)3-5/h5H,1H3,(H,3,4)

InChI key

RRUDCFGSUDOHDG-UHFFFAOYSA-N

Gene Information

human ... CA2(760), MMP3(4314)

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This Item
1006506308560189400
Acetohydroxamic acid 98%

159034

Acetohydroxamic acid

Acetohydroxamic acid United States Pharmacopeia (USP) Reference Standard

1006506

Acetohydroxamic acid

4-Amino-6-chloro-1,3-benzenedisulfonamide 98%

308560

4-Amino-6-chloro-1,3-benzenedisulfonamide

Aurintricarboxylic Acid A cell-permeable polyanionic, polyaromatic compound used as a powerful inhibitor of cellular processes that are dependent on the formation of protein-nucleic acid complexes.

189400

Aurintricarboxylic Acid

assay

98%

assay

-

assay

98%

assay

≥85% (titration)

Quality Level

100

Quality Level

-

Quality Level

100

Quality Level

100

mp

88-90 °C (lit.)

mp

88-90 °C (lit.)

mp

257-261 °C (lit.)

mp

-

functional group

amine

functional group

-

functional group

chloro

functional group

-

Gene Information

human ... CA2(760), MMP3(4314)

Gene Information

-

Gene Information

human ... CA1(759), CA2(760), CA5A(763), CA5B(11238), CA9(768)

Gene Information

-

General description

Acetohydroxamic acid is a potent inhibitor of bacterial urease activity and reduces urinary ammonia levels.[1] 2-Acetohydroxamic acid loaded floating microspheres forms an efficient drug delivery system for the treatment of Helicobacter pylori.[2]

Application

Acetohydroxamic acid was used:
  • to study the mechanism of complexation of iron (III) with acetohydroxamic acid[3]
  • to study the inhibitory mechanism of lansoprazole and omeprazole on Helicobacter pyloni[4]
  • in urease inhibition studies[5][6]
  • for in situ generation of nitrosocarbonylmethane as a Diels-Alder dienophile[7]
Used in urease inhibition studies[5][6] and for in situ generation of nitrosocarbonylmethane as a Diels-Alder dienophile.[7]

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H360

Hazard Classifications

Repr. 1B

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

ppe

Eyeshields, Gloves, type P2 (EN 143) respirator cartridges

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    Certificates of Analysis (COA)

    Lot/Batch Number
    MKCQ1871
    MKCP8530
    MKCL1213
    MKCK1237
    MKCH3896

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    K Nagata et al.
    Antimicrobial agents and chemotherapy, 37(4), 769-774 (1993-04-01)
    The gastric proton pump inhibitor lansoprazole, its active analog AG-2000, and omeprazole dose dependently inhibited urease activity extracted with distilled water from Helicobacter pylori cells; the 50% inhibitory concentrations were between 3.6 and 9.5 microM, which were more potent than
    Zbl. Bakt., 275, 63-63 (1991)
    D P Griffith et al.
    The Journal of urology, 140(2), 318-324 (1988-08-01)
    Acetohydroxamic acid is known to inhibit bacterial urease activity, thus, reducing urinary ammonia levels. A double-blind placebo-controlled clinical trial of acetohydroxamic acid was conducted at 12 Veterans Administration spinal cord injury units. A total of 210 male spinal cord injury
    Journal of the Chemical Society. Perkin Transactions 1, 1001-1001 (1991)
    Mechanism of iron (III) complex formation. Activation volumes for the complexation of the iron (III) ion with thiocyanate ion and acetohydroxamic acid.
    Funahashi S, et al.
    Inorganic Chemistry, 22(14), 2070-2073 (1983)
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