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Supelco

2,3-Butanedione monoxime

for spectrophotometric det. of urea, ≥99.0%

Synonym(s):

BDM, Biacetyl monoxime, Diacetyl monoxime

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About This Item

Linear Formula:
CH3C(=NOH)COCH3
CAS Number:
57-71-6
Molecular Weight:
101.10
Beilstein/REAXYS Number:
605582
EC Number:
200-348-5
MDL number:
MFCD00002116
UNSPSC Code:
41116105
PubChem Substance ID:
329753805
NACRES:
NA.21

Quality Level

100

assay

≥98.0% (N)
≥99.0%

form

solid

quality

for spectrophotometric det. of urea

technique(s)

UV/Vis spectroscopy: suitable

ign. residue

≤0.05% (as SO4)

bp

185-186 °C (lit.)

mp

75-76 °C
75-78 °C (lit.)

SMILES string

CC(=O)\C(C)=N\O

InChI

1S/C4H7NO2/c1-3(5-7)4(2)6/h7H,1-2H3/b5-3+

InChI key

FSEUPUDHEBLWJY-HWKANZROSA-N

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General description

2,3-Butanedione Monoxime (BDM) is also known as diacetyl monoxime, it is also a nucleophilic agent and it can dephosphorylates acetylcholinesterase poisoned with organophosphates. It is also a well-characterized, non-competitive inhibitor of skeletal muscle myosin-II, where it inhibits the chemical and motile activity.

Application


  • A novel method to extend viability and functionality of living heart slices.: This research introduces a novel application of 2,3-Butanedione monoxime for prolonging the functional lifespan of cardiac tissue samples in experimental settings, offering insights into cardiac biology and potential therapeutic targets (Ross et al., 2023).

  • Molecular Mechanisms of Deregulation of Muscle Contractility Caused by the R168H Mutation in TPM3 and Its Attenuation by Therapeutic Agents.: The study utilizes 2,3-Butanedione monoxime to investigate the molecular pathways affected by genetic mutations in muscle contractility, contributing to the understanding of muscle disorders and their management (Karpicheva et al., 2023).

  • Generation of myocyte agonal Ca(2+) waves and contraction bands in perfused rat hearts following irreversible membrane permeabilisation.: Research employing 2,3-Butanedione monoxime investigates its role in inducing specific cellular events in cardiac cells under stress, highlighting its potential in studies of heart disease mechanisms and therapies (Morishita et al., 2023).


Analysis Note

Solubility:
0.5 g are completely soluble and give a clear solution in 10 mL water or also in 10 mL ethanol.
Sensitivity test:
0.05 mg urea in 3 mL water and 5 mL conc. HCl together with a 3% solution in water of diacetylmonoxime heated on a water bath for 10 minutes give a light yellow color.

Other Notes

Reagent for the colorimetric determination of urea and ureido-compounds; Spectrometric reagent for Co(II), Ni(II), Pd(II) and Re(VII); Reagent for the gravimetric determination of Ni(II)

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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W.B. Guenther
Analytical Letters, 12A, 1305-1305 (1979)
Improvements on the Prescott-Jones method for the colorimetric analysis of ureido compounds.
D B Shindler et al.
Analytical biochemistry, 97(2), 421-422 (1979-09-01)
Multiple Effects of 2, 3-Butanedione Monoxime.
Sellin LC and McArdle JJ/
Pharmacology & Toxicology, 74 (4-5), 305-313 (1994)
2, 3-Butanedione monoxime (BDM) as a myosin inhibitor.
Ostap EM.
Journal of Muscle Research and Cell Motility, 23 (4), 305-308 (2002)
Chang Liu et al.
Molecular plant, 11(11), 1389-1399 (2018-10-09)
The process of pollen germination is crucial for flowering plant reproduction, but the mechanisms through which pollen grains establish polarity and select germination sites are not well understood. In this study, we report that a formin family protein, AtFH5, is localized
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