ChemicalBook > CAS DataBase List > TRIACSIN C

TRIACSIN C

Product Name
TRIACSIN C
CAS No.
76896-80-5
Chemical Name
TRIACSIN C
Synonyms
WS1228A;FR-900190;TRIACSIN C;2,4,7-Undecatrienal;Triacsincapprox.90%;Antibiotic WS-1228A;Antibiotic FR-900190;from Streptomyces aureofaciens;2E,4E,7E-undecatriene-1-triazine;triacsin c from streptomyces sp.
CBNumber
CB0199054
Molecular Formula
C11H17N3O
Formula Weight
207.27
MOL File
76896-80-5.mol
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TRIACSIN C Property

Boiling point:
320.7±45.0 °C(Predicted)
Density 
0.94±0.1 g/cm3(Predicted)
storage temp. 
-20°C
solubility 
methanol: soluble4.90 - 5.10 mg/mL, clear (Pale yellow to yellow)
form 
Liquid. In DMSO.
pka
-0.10±0.70(Predicted)
color 
clear (Pale yellow to yellow) Solution in DMSO
Stability:
Stable for 1 year from date of purchase as supplied. Solutions further diluted with DMSO may be stored at -20° for up to 2 months.
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Safety

WGK Germany 
3
HS Code 
29299090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
T4540
Product name
Triacsin C from Streptomyces sp.
Packaging
1mg
Price
$636
Updated
2024/03/01
Cayman Chemical
Product number
10007448
Product name
Triacsin C
Purity
≥95%
Packaging
500μg
Price
$287
Updated
2024/03/01
Cayman Chemical
Product number
10007448
Product name
Triacsin C
Purity
≥95%
Packaging
1mg
Price
$515
Updated
2024/03/01
Tocris
Product number
2472
Product name
TriacsinC
Purity
≥95%(HPLC)
Packaging
100U
Price
$173
Updated
2021/12/16
Usbiological
Product number
256968
Product name
Triacsin C
Packaging
100ug
Price
$432
Updated
2021/12/16
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TRIACSIN C Chemical Properties,Usage,Production

Description

Triacsin C (76896-80-5) is a long-chain fatty acyl CoA synthetase inhibitor (IC50=3.6-8.7 μM).1?Inhibits mouse macrophage-derived foam cell formation2 and displays anti-atherosclerotic activity3. Cell permeable.

Chemical Properties

Solid

Uses

Triacsin, a fatty acyl CoA synthetase inhibitor, reduces myocardial infarct size, attenuates loss of post-reperfusion cardiac function, increases intravascular nitric oxide (NO) concentration, and inhibits leukocyte recruitment. Triacsin C analogs can also be used as potential antivirals against rotavirus infections.

Definition

ChEBI: Triacsin C is a nitroso compound that is N-undecylnitrous hydrazide carrying double bonds at positions 1,2,4, and 7. It is a long-chain fatty acyl CoA synthetase inhibitor and interferes with lipid metabolism by inhibiting the de novo synthesis of glycerolipids and cholesterol esters. It has a role as an EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor, a vasodilator agent, an apoptosis inhibitor, a bacterial metabolite, an EC 3.1.1.64 (retinoid isomerohydrolase) inhibitor and an antimalarial. It is a nitroso compound, an olefinic compound and a hydrazone.

General Description

Triacsin C belongs to a family of fungal metabolites all having an 11-carbon alkenyl chain with a common N-hydroxytriazene moiety at the terminus.

Biochem/physiol Actions

Triacsin C is a potent inhibitor of long-chain fatty acyl CoA synthetase. It blocks β-cell apoptosis, induced by fatty acids (lipoapoptosis) in a rat model of obesity. In addition, it blocks the de novo synthesis of triglycerides, diglycerides, and cholesterol esters, thus interfering with lipid metabolism.

storage

Store at -20°C

References

1) Hartman et al. (1989), Triacsin C: a differential inhibitor of arachidonoyl-CoA synthetase and nonspecific long chain acyl-CoA synthetase; Prostaglandins, 37 655 2) Namatame et al. (1999), Complete inhibition of mouse macrophage-derived foam cell formation by triacsin C; J. Biochem, 125 319 3) Matsuda et al. (2008), Anti-atherosclerotic activity of triacsin C, an acyl-CoA synthetase inhibitor; J. Antibiot. (Tokyo), 61 318

TRIACSIN C Preparation Products And Raw materials

Raw materials

Preparation Products

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76896-80-5, TRIACSIN CRelated Search:


  • TRIACSIN C
  • WS1228A
  • 2,4,7-UNDECATRIENAL NITROSOHYDRAZONE
  • 2E, 4E, 7E-UNDECATRIENE-1-TRIAZENE
  • Triacsincapprox.90%
  • 2,4,7-Undecatrienal
  • triacsin c from streptomyces sp.
  • 2E,4E,7E-undecatriene-1-triazine
  • 2,4,7-Undecatrienal nitrosohydrazone, WS1228A
  • (2E,4E,7E)-2,4,7-Undecatrienal N2-nitroso hydrazone
  • Antibiotic FR-900190
  • Antibiotic WS-1228A
  • FR-900190
  • Transfection Reagents-Biofection
  • (2E,4E,7E)-2,4,7-Undecatrienal nitrosohydrazone
  • 2,4,7-Undecatrienal, nitrosohydrazone, (2E,4E,7E)-
  • from Streptomyces aureofaciens
  • Triacsin C, acyl-CoA synthetase inhibitor
  • 76896-80-5
  • Antibiotics T-Z
  • Antibiotics A to Z
  • Antibiotics
  • BioChemical
  • antibiotic