3-(hydroxyimino)butan-2-one

• ChemBase ID: 102404
• Molecular Formular: C4H7NO2
• Molecular Mass: 101.10388
• Monoisotopic Mass: 101.04767847
• SMILES: CC(=O)/C(=N/O)/C
• Canonical SMILES: C/C(=N\O)/C(=O)C
• InChI: InChI=1S/C4H7NO2/c1-3(5-7)4(2)6/h7H,1-2H3
• InChIKey: FSEUPUDHEBLWJY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(hydroxyimino)butan-2-one; (3E)-3-(hydroxyimino)butan-2-one
• IUPAC Traditional name: 2,3-butanedione monoxime; diacetylmonoxime
• Synonyms: 2,3-Butanedione monoxime; BDM; Biacetyl monoxime; DIACETYL MONOXIME; 2,3-Butanedione monoxime; DIACETYLMONOXIME; Diacetyl monoxime; 二乙酰一肟; 联乙酰一肟; 2,3-丁二酮一肟

Database IDs

• CAS Number: 57-71-6
• EC Number: 200-348-5
• MDL Number: MFCD00002116
• Beilstein Number: 605582
• PubChem SID: 162088185; 24858995; 24277826
• PubChem CID: 6409633

CALCULATED PROPERTIES

• Acid pKa: 6.504975
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.364179
• LogD (pH = 7.4): -0.52803445
• Log P: 0.40497926
• Molar Refractivity: 25.3625 cm^3
• Polarizability: 9.643563 Å^3
• Polar Surface Area: 49.66 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 75-76 °C; 75-78 °C(lit.); 75-78°C
• Boiling Point: 185-186 °C(lit.); 185-186°C

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: EK3150000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... KCNB1(3745)

Product Information

• Purity: ≥98%; ≥99.0%; ≥99.0% (N); 97%
• Ignition Residue: ≤0.05% (as SO4)
• Quality: for spectrophotometric det. of urea
• Linear Formula: CH3C(=NOH)COCH3

DETAILS

MP Biomedicals - 05209991

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02101530

Crystalline
For the determination of urea; protector in cholinesterase inhibition.

Sigma Aldrich - B0753

包装
1 kg in poly bottle
25, 100, 500 g in poly bottle
Biochem/physiol Actions
DRK1 is a delayed rectifier (Kv2.1) cloned K+ channel from rat brain with consensus sites for protein kinase-dependent phosphorylation that might be expected to be functionally regulated by phosphorylation. 2,3-Butanedione monoxime (BDM) chemically removes phosphate groups from many proteins, and its action on DRK1 channels was examined after expression of DRK1 cRNA in Xenopus oocytes. In two-microelectrode voltage-clamp experiments, the application of 2,3-Butanedione monoxime to the bath inhibited DRK1 current (ki = 16.6 mM, H = 0.96) rapidly and reversibly, with a time course similar to the time course of solution change within the bath. DRK1 current was inhibited at all potentials; the time course of current activation, deactivation and inactivation were unaffected by 2,3-Butanedione monoxime. In inside-out patch-clamp experiments, the application of 2,3-Butanedione monoxime to the cytoplasmic surface similarly inhibited channel activity rapidly and reversibly (ki = 10.7 mM, H = 1.01) in the absence of rephosphorylating substrates. These results are inconsistent with a phosphatase effect, because such an effect should be irreversible in cell-free, ATP-free patches. Instead, the results suggest that 2,3-Butanedione monoxime can inhibit DRK1 channels directly from inside or outside of the membrane.

Sigma Aldrich - 112135

Packaging
500 g in poly bottle

Sigma Aldrich - 31550

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-compounds1; Spectrometric reagent for Co(II), Ni(II), Pd(II) and Re(VII)2; Reagent for the gravimetric determination of Ni(II)3