Physicochemical Properties
| Molecular Formula | C4H7NO2 |
| Molecular Weight | 101.1039 |
| Exact Mass | 101.047 |
| CAS # | 57-71-6 |
| PubChem CID | 6409633 |
| Appearance | White to off-white solid powder |
| Density | 1.1±0.1 g/cm3 |
| Boiling Point | 185.5±9.0 °C at 760 mmHg |
| Melting Point | 75-78 °C(lit.) |
| Flash Point | 66.0±18.7 °C |
| Vapour Pressure | 0.3±0.7 mmHg at 25°C |
| Index of Refraction | 1.452 |
| LogP | -0.47 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 1 |
| Heavy Atom Count | 7 |
| Complexity | 106 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | C/C(=N\O)/C(=O)C |
| InChi Key | FSEUPUDHEBLWJY-HWKANZROSA-N |
| InChi Code | InChI=1S/C4H7NO2/c1-3(5-7)4(2)6/h7H,1-2H3/b5-3+ |
| Chemical Name | (3E)-3-hydroxyiminobutan-2-one |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | In both 6 and 48 hours, Diacetone monoxime (50 mM) decreases C's cellulase secretion. cinerea [1]. Endoplasmic reticulum localization is not affected by diethyl monoxime (50 mM, 2 and 4 hours), although the Golgi apparatus is [1]. Without the use of efflux inhibitors, dialethylmonoxime (0–30 mM) causes the concentration-dependent release of SR Ca2+, which is maximally reduced by 72% at pCa 6.0 [2]. Diacetyl monoxime functions as a chemical phosphatase, which has led to theories that its contraction-inhibiting effect may be due to the dephosphorylation of important Ca2+ channel proteins [2]. Neither myosin-V nor myosin-VI, the two distinct myosin-I isoforms, had their ATPase activity inhibited by dialetyl monoxime [3]. In isolated single cardiomyocytes from SHR and WKY rats, diethyl monooxime (0–50 mM) suppresses L-type Ca2+ currents [4]. In cultured newborn rat cardiomyocytes, dialetyl monooxime dramatically shortens the length of both electrically triggered and spontaneous action potentials [4]. |
| ln Vivo | Hypotensive effects can be caused by intravenous injection of dialetyl monoxime (0-200 mg/kg) once [4]. Picrotoxin-induced convulsions can be treated with diacetyl monoxime (0-205 mg/kg; intraperitoneal injection; once) to prevent convulsions [5]. |
| Animal Protocol |
Animal/Disease Models: Male SHR and age-matched WKY rats [4] Doses: 5, 30, 100 and 200 mg/kg Route of Administration: intravenous (iv) (iv)administration, 1 mL/kg, once Experimental Results: Arterial blood pressure of both strains were the same By lowering the SHR, the response speed is Dramatically improved. Animal/Disease Models: Male mice (20 to 25 g) [5] Doses: 51, 103 and 205 mg/kg combined with intraperitoneal (ip) injection of 3.0 mg/kg Picrotoxin Route of Administration: one intraperitoneal (ip) injection Experimental Results: demonstrated dose-dependent resistance Convulsions caused by picrotoxins. |
| References |
[1]. The myosin ATPase inhibitor, 2,3-butanedione 2-monoxime, prevents protein secretion by the basidiomycete Coprinopsis cinerea. Biotechnol Lett. 2011 Apr;33(4):769-75. [2]. 2,3-Butanedione 2-monoxime (BDM) induces calcium release from canine cardiac sarcoplasmic reticulum. Biochem Biophys Res Commun. 1996 Dec 4;229(1):154-7. [3]. Ostap EM. 2,3-Butanedione monoxime (BDM) as a myosin inhibitor. J Muscle Res Cell Motil. 2002;23(4):305-8. [4]. Effects of 2,3-butanedione monoxime on blood pressure, myocardial Ca2+ currents, and action potentials of rats. Am J Hypertens. 1995 Dec;8(12 Pt 1):1232-40. [5]. 2,3-Butanedione monoxime protects mice against the convulsant effect of picrotoxin by facilitating GABA-activated currents. Brain Res. 1995 Apr 24;678(1-2):110-6. |
| Additional Infomation |
2-oxime 2,3-butanedione is a cream-colored powder. (NTP, 1992) Diacetylmonoxime is a ketoxime obtained via formal condensation of butane-2,3-dione with hydroxylamine. It is a reversible myosin ATPase inhibitor. It has a role as a cholinesterase reactivator, a chromogenic compound and an EC 3.6.1.3 (adenosinetriphosphatase) inhibitor. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~100 mg/mL (~989.12 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (20.57 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (20.57 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.08 mg/mL (20.57 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 9.8912 mL | 49.4560 mL | 98.9120 mL | |
| 5 mM | 1.9782 mL | 9.8912 mL | 19.7824 mL | |
| 10 mM | 0.9891 mL | 4.9456 mL | 9.8912 mL |