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Merck
CN

T4540

Triacsin C

From Streptomyces sp., long-chain fatty acyl CoA synthetase inhibitor, powder

Synonym(s):

2,4,7-Undecatrienal nitrosohydrazone, WS1228A

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About This Item

Empirical Formula (Hill Notation):
C11H17N3O
CAS Number:
76896-80-5
Molecular Weight:
207.27
UNSPSC Code:
51111800
PubChem Substance ID:
24900214
NACRES:
NA.77
MDL number:
MFCD00798237

Key Documents

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Product Name

Triacsin C from Streptomyces sp.,

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

biological source

Streptomyces sp.

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

Quality Level

200

Related Categories

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.

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.

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000406514
0000398574
0000195910
0000154368
0000144971

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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
R A Igal et al.
The Biochemical journal, 324 ( Pt 2), 529-534 (1997-06-01)
The trafficking of acyl-CoAs within cells is poorly understood. In order to determine whether newly synthesized acyl-CoAs are equally available for the synthesis of all glycerolipids and cholesterol esters, we incubated human fibroblasts with [14C]oleate, [3H]arachidonate or [3H]glycerol in the
Hua-wei Wang et al.
Biology of reproduction, 87(3), 74-74 (2012-07-13)
In most vertebrates, fully grown oocytes are arrested in meiotic prophase I and only resume the cell cycle upon external stimuli, such as hormones. The proper arrest and resumption of the meiotic cycle is critical for reproduction. A Galpha(S) signaling
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