ACETYLENEDICARBOXAMIDE

Product Name: 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
Formula Weight: 112.09
MOL File: 543-21-5.mol

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ACETYLENEDICARBOXAMIDE Property

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
EPA Substance Registry System: 2-Butynediamide (543-21-5)

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Safety

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)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P330Rinse mouth.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 23637
Product name: Cellocidin
Purity: ≥95%
Packaging: 5mg
Price: $97
Updated: 2024/03/01

Cayman Chemical

Product number: 23637
Product name: Cellocidin
Purity: ≥95%
Packaging: 10mg
Price: $156
Updated: 2024/03/01

Cayman Chemical

Product number: 23637
Product name: Cellocidin
Purity: ≥95%
Packaging: 25mg
Price: $340
Updated: 2024/03/01

Cayman Chemical

Product number: 23637
Product name: Cellocidin
Purity: ≥95%
Packaging: 50mg
Price: $631
Updated: 2024/03/01

TRC

Product number: C255953
Product name: Cellocidin
Packaging: 5mg
Price: $305
Updated: 2021/12/16

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ACETYLENEDICARBOXAMIDE Chemical Properties,Usage,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.]

References

[1] S SUZUKI. Cellocidin, a new antibiotic.[J]. Journal of Antibiotics, 1958, 11 3: 81-83.
[2] KAZUHIKO OTOGURO. Selective and Potent in Vitro Antitrypanosomal Activities of Ten Microbial Metabolites[J]. Journal of Antibiotics, 2008, 61 6: 372-378. DOI: 10.1038/ja.2008.52
[3] RICHARD K. DZENG . Small molecule growth inhibitors of human oncogenic gammaherpesvirus infected B-cells[J]. Molecular Oncology, 2015, 9 2: Pages 365-376. DOI: 10.1016/j.molonc.2014.09.006
[4] MISATO T. Mode of action of agricultural antibiotics developed in Japan.[J]. Residue reviews, 1969, 25: 93-106. DOI: 10.1007/978-1-4615-8443-8_8

ACETYLENEDICARBOXAMIDE Preparation Products And Raw materials

Raw materials

Preparation Products

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ACETYLENEDICARBOXAMIDE Suppliers

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543-21-5, ACETYLENEDICARBOXAMIDERelated Search:

Diphenylacetylene Acetylenedicarboxylic acid PROPARGYLAMINE PROPYNOIC ACID AMIDE ACETYLENEDICARBOXAMIDE

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