76896-80-5

Basic information

• Product Name: TRIACSIN C
• Synonyms: 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
• CAS NO: 76896-80-5
• Molecular Formula: C11H17N3O
• Molecular Weight: 207.27
• EINECS: 616-408-2
• Product Categories: antibiotic
• Mol File: 76896-80-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 320.657 °C at 760 mmHg
• Flash Point: 147.728 °C
• Appearance: /
• Density: 0.941 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.485
• Storage Temp.: −20°C
• Solubility: methanol: soluble4.90 - 5.10 mg/mL, clear (Pale yellow to yellow
• PKA: -0.10±0.70(Predicted)
• 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.
• CAS DataBase Reference: TRIACSIN C(CAS DataBase Reference)
• NIST Chemistry Reference: TRIACSIN C(76896-80-5)
• EPA Substance Registry System: TRIACSIN C(76896-80-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 76896-80-5(Hazardous Substances Data)

Usage

Description

Triacsin C, with the chemical formula (76896-80-5), is a long-chain fatty acyl CoA synthetase inhibitor that belongs to a family of fungal metabolites. These metabolites are characterized by an 11-carbon alkenyl chain and a common N-hydroxytriazene moiety at the terminus. Triacsin C is a solid substance with potent biological activities, including its ability to reduce myocardial infarct size, attenuate loss of post-reperfusion cardiac function, increase intravascular nitric oxide (NO) concentration, and inhibit leukocyte recruitment.

Uses

Used in Pharmaceutical Industry:
Triacsin C is used as a therapeutic agent for cardiovascular diseases due to its ability to reduce myocardial infarct size and attenuate loss of post-reperfusion cardiac function. Its anti-atherosclerotic activity and inhibition of mouse macrophage-derived foam cell formation make it a promising candidate for the treatment of atherosclerosis.
Used in Antiviral Applications:
Triacsin C analogs are used as potential antivirals against rotavirus infections, providing a new avenue for the development of antiviral drugs to combat rotavirus-related illnesses.
Used in Nitric Oxide Regulation:
Triacsin C is used as a regulator of intravascular nitric oxide (NO) concentration, which can have implications in various physiological processes and medical conditions where NO levels play a crucial role.
Used in Immunology:
Triacsin C is used as an immunomodulatory agent due to its ability to inhibit leukocyte recruitment, which can be beneficial in managing inflammatory responses and autoimmune diseases.

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.

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

InChI:InChI=1/C11H17N3O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15/h4-5,7-11H,2-3,6H2,1H3,(H,13,15)/b5-4+,8-7+,10-9+,12-11+

Upstream product

• 80599-06-0 [(2E,4E,7E)-Undeca-2,4,7-trien-(E)-ylidene]-hydrazine 
• 80612-69-7 C₁₄H₂₆N₂Si 

Relevant articles and documents

Structure and synthesis of a new hypotensive vasodilator isolated from Streptomyces aureofaciens

-