Skip to Content
Merck
All Photos(1)

Documents

T4540

Sigma-Aldrich

Triacsin C from Streptomyces sp.

Synonym(s):

2,4,7-Undecatrienal nitrosohydrazone, WS1228A

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

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

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

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Y-L Xie et al.
Theriogenology, 78(9), 1917-1928 (2012-10-13)
In vivo and in vitro approaches were used to elucidate mechanisms of palmitate-induced cytotoxicity of follicle granulosa cells in fuel-overloaded broiler hens. In contrast to their energy-restricted counterparts, broiler breeder hens fed ad libitum for 2 wk had dyslipidemia, atresia
M Shimabukuro et al.
Proceedings of the National Academy of Sciences of the United States of America, 95(16), 9558-9561 (1998-08-05)
Obesity causes its complications through functional and morphologic damage to remotely situated tissues via undetermined mechanisms. In one rodent model of obesity, the Zucker diabetic fatty fa/fa rat, overaccumulation of triglycerides in the pancreatic islets may be responsible for a
Yulia Y Tyurina et al.
FEBS letters, 586(3), 235-241 (2012-01-03)
Peroxidation of cardiolipin in mitochondria is essential for the execution of apoptosis. We suggested that integration of oleic acid into cardiolipin generates non-oxidizable cardiolipin species hence protects cells against apoptosis. We synthesized mitochondria-targeted triphenylphosphonium oleic acid ester. Using lipidomics analysis
I Namatame et al.
Journal of biochemistry, 125(2), 319-327 (1999-02-17)
Primary mouse peritoneal macrophages effectively take up and metabolize phosphatidylcholine/cholesterol liposomes containing a small amount of phosphatidylserine, which results in the massive accumulation in the cytoplasm of oil red O positive lipid droplets consisting of cholesteryl ester (CE) and triacylglycerol
H Tomoda et al.
The Journal of biological chemistry, 266(7), 4214-4219 (1991-03-05)
Triacsins A, B, C, and D are new inhibitors of long chain acyl-CoA synthetase (EC 6.2.1.3) and possess different inhibitory potencies against the enzyme (Tomoda, H., Igarashi, K., and Omura, S. (1987) Biochim. Biophys. Acta 921, 595-598). Acyl-CoA synthetase activity
View All Related Papers

Articles

Discover Bioactive Small Molecules for Lipid Signaling Research

Discover Bioactive Small Molecules for Lipid Signaling Research

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service