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ACETYLENEDICARBOXAMIDE

CAS No.
543-21-5
Chemical Name:
ACETYLENEDICARBOXAMIDE
Synonyms
Renamycin;Lenamycin;Aquamycin;4-Dioxane-2;2-BUTYNEDIAMIDE;but-2-ynediaMide;ACETYLENEDICARBOXAMIDE;1,2-Ethynedicarboxamide;Acetylendicarbonsaeureamid;acetylenedicarboxylicaciddiamide
CBNumber:
CB7103786
Molecular Formula:
C4H4N2O2
Molecular Weight:
112.09
MDL Number:
MFCD00017146
MOL File:
543-21-5.mol
Last updated:2023-06-08 09:02:06

ACETYLENEDICARBOXAMIDE 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
form Fine Crystalline Powder
pka 13.01±0.50(Predicted)
color Cream to beige
EWG's Food Scores 1
FDA UNII 1K327HA41T
EPA Substance Registry System 2-Butynediamide (543-21-5)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P264-P270-P301+P312-P330-P501
Hazard Codes  T
Risk Statements  25-21
Safety Statements  45-36/37-28A
HS Code  29241900
Toxicity LD50 i.v. in mice: 11 mg/kg (Suzuki)
NFPA 704
0
1 0

ACETYLENEDICARBOXAMIDE price More Price(7)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Cayman Chemical 23637 Cellocidin ≥95% 543-21-5 5mg $97 2024-03-01 Buy
Cayman Chemical 23637 Cellocidin ≥95% 543-21-5 10mg $156 2024-03-01 Buy
Cayman Chemical 23637 Cellocidin ≥95% 543-21-5 25mg $340 2024-03-01 Buy
Cayman Chemical 23637 Cellocidin ≥95% 543-21-5 50mg $631 2024-03-01 Buy
TRC C255953 Cellocidin 543-21-5 5mg $305 2021-12-16 Buy
Product number Packaging Price Buy
23637 5mg $97 Buy
23637 10mg $156 Buy
23637 25mg $340 Buy
23637 50mg $631 Buy
C255953 5mg $305 Buy

ACETYLENEDICARBOXAMIDE Chemical Properties,Uses,Production

Description

Cellocidin 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 Properties

CREAM TO BEIGE FINE CRYSTALLINE POWDER

Uses

Cellocidin 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.

Definition

ChEBI: 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 Methods

Acetylenedicarboxamide 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

Raw materials

Preparation Products

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Acetylendicarbonsaeureamid Acetylenedicarboxylic acid diamide acetylenedicarboxylicaciddiamide Aquamycin Lenamycin Renamycin 2-BUTYNEDIAMIDE ACETYLENEDICARBOXAMIDE ACETYLENEDICARBOXAMIDE (PRACT), 95% 1,2-Ethynedicarboxamide Acetylenedicarboxamide,95%,pract. Acetylenedicarboxamide2-Butynediamide but-2-ynediaMide AquaMycin, ButynesiaMide, LenaMycin 4-Dioxane-2 543-21-5