ACETYLENEDICARBOXAMIDE

ACETYLENEDICARBOXAMIDE Basic information
Product Name:ACETYLENEDICARBOXAMIDE
Synonyms:Acetylendicarbonsaeureamid;Acetylenedicarboxylic acid diamide;acetylenedicarboxylicaciddiamide;Aquamycin;Lenamycin;Renamycin;2-BUTYNEDIAMIDE;ACETYLENEDICARBOXAMIDE
CAS:543-21-5
MF:C4H4N2O2
MW:112.09
EINECS:684-490-7
Product Categories:
Mol File:543-21-5.mol
ACETYLENEDICARBOXAMIDE Structure
ACETYLENEDICARBOXAMIDE Chemical Properties
Melting point 179 °C
Boiling point 209.98°C (rough estimate)
density 1.4421 (rough estimate)
refractive index 1.4610 (estimate)
storage temp. Store at -20°C
solubility DMF: 10 mg/ml; DMSO: 20 mg/ml; DMSO:PBS (pH 7.2) (1:7): 0.12 mg/ml
pka13.01±0.50(Predicted)
form Fine Crystalline Powder
color Cream to beige
EPA Substance Registry System2-Butynediamide (543-21-5)
Safety Information
Hazard Codes T
Risk Statements 25-21
Safety Statements 45-36/37-28A
HS Code 29241900
ToxicityLD50 i.v. in mice: 11 mg/kg (Suzuki)
MSDS Information
ProviderLanguage
ACROS English
ACETYLENEDICARBOXAMIDE Usage And Synthesis
DescriptionCellocidin is an antibiotic originally isolated from S. chibaensis. It is active against various bacterial strains including M. tuberculosis and against the trypanosomes T. brucei and T. rhodesiense (IC50s = 150 and 30 ng/ml, respectively). It inhibits proliferation of LCL1 and LCL2 cells transformed by Epstein-Barr virus (EBV), activates the c-Myc and NF-κB pathways in BC3 and LCL1 cells, and induces necrotic cell death in B cells infected with gammaherpes virus. Cellocidin (100-200 ppm) is protective against bacterial leaf blight in rice plants and inhibits α-ketoglutarate oxidation in X. oryzae, the bacterium that causes leaf blight, when used at a concentration of 1 ppm, suggesting that it inhibits the citric acid cycle. Formulations containing cellocidin have been used as agricultural pesticides.
Chemical PropertiesCREAM TO BEIGE FINE CRYSTALLINE POWDER
UsesCellocidin is a small neutral alkyne produced by a number of Streptomyces species, first discovered by Suzuki and colleagues in 1958. Cellocidin has a broad antibacterial, antifungal and antitumor profile due to its ability to react with endogenous thiols like cysteine and glutathione. Cellocidin occurs as a weak active in many bioassays using actinomycete crude extracts and is thus a useful standard for chemical and bioassay dereplication.
DefinitionChEBI: A dicarboxylic acid diamide resulting from the formal condensation of both of the carboxy groups of butynedioic acid with ammonia. An antibacterial agent produced by Streptomyces chibaensis.
Purification MethodsAcetylenedicarboxamide crystallises from MeOH and H2O [m 190-192o(dec) as hemihydrate]. When prepared from the ester + NH3 it has m 213o(dec). Also a melting point of 290-292o(dec) has been reported. [Saggimo J Org Chem 22 1171 1857, Kharash et al. J Org Chem 10 392 1945, Blomquist & Winslow J Org Chem 10 156 1945, Beilstein 2 I 317, 2 III 1995, 2 IV 2295.]
ACETYLENEDICARBOXAMIDE Preparation Products And Raw materials
Preparation ProductsCyanoacetylene
Diphenylacetylene Acetylenedicarboxylic acid PROPYNOIC ACID AMIDE ACETYLENEDICARBOXAMIDE PROPARGYLAMINE

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