| Identification | Back Directory | [Name]
TRIACSIN C | [CAS]
76896-80-5 | [Synonyms]
WS1228A
FR-900190
TRIACSIN C
Triacsincapprox.90%
2,4,7-Undecatrienal
Antibiotic WS-1228A
Antibiotic FR-900190
from Streptomyces aureofaciens
Transfection Reagents-Biofection
triacsin c from streptomyces sp.
2E,4E,7E-undecatriene-1-triazine
2E, 4E, 7E-UNDECATRIENE-1-TRIAZENE
2,4,7-UNDECATRIENAL NITROSOHYDRAZONE
2,4,7-Undecatrienal nitrosohydrazone, WS1228A
(2E,4E,7E)-2,4,7-Undecatrienal nitrosohydrazone
2,4,7-Undecatrienal, nitrosohydrazone, (2E,4E,7E)-
(2E,4E,7E)-2,4,7-Undecatrienal N2-nitroso hydrazone | [EINECS(EC#)]
616-408-2 | [Molecular Formula]
C11H17N3O | [MDL Number]
MFCD00798237 | [MOL File]
76896-80-5.mol | [Molecular Weight]
207.27 |
| Chemical Properties | Back Directory | [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. |
| Hazard Information | Back Directory | [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 |
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