T4540

Triacsin C from Streptomyces sp.

• Synonym(s): 2,4,7-Undecatrienal nitrosohydrazone, WS1228A
• Empirical Formula (Hill Notation): C₁₁H₁₇N₃O
• CAS Number: 76896-80-5
• Molecular Weight: 207.27
• MDL number: MFCD00798237
• UNSPSC Code: 51111800
• PubChem Substance ID: 24900214
• NACRES: NA.77

Properties

• biological source: Streptomyces sp.
• Quality Level: 200
• form: powder
• solubility: methanol: soluble 4.90-5.10 mg/mL, clear (Pale yellow to yellow); methanol: soluble 4.90-5.10 mg/mL, clear, pale yellow to yellow
• Mode of action: enzyme | inhibits
• shipped in: wet ice
• storage temp.: −20°C
• SMILES string: CCC\C=C\C\C=C\C=C\C=N\NN=O
• InChI: 1S/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+
• InChI key: NKTGCVUIESDXPU-YLEPRARLSA-N

Description

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.

Application

Triacsin C was found to induce maturation in mouse and Xenopus oocytes in the absence of long-chain acyl-CoA synthetase. Triacsin C can also block palmitoylation of the G-protein alpha S subunit⁶. Furthermore, triacsin C can stabilize1-oleoyl-2-acetyl-sn-glycerol (OAG) and enhance perilipin 3 recruitment to the endoplasmic reticulum (ER) in mouse cells⁷.

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.

Preparation Note

Triacsin C is soluble in methanol at 4.90 - 5.10 mg/ml and yields a clear, pale yellow to yellow solution.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable