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Triacsin C

Name: Triacsin C
Brand: SIGMA

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

Form:

powder

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Properties

Product Name

Triacsin C from Streptomyces sp.,

biological source

Streptomyces sp.

Quality Segment

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.

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This Item	T7765	M0440	T8902
Sigma-Aldrich T4540 Triacsin C from Streptomyces sp.	Sigma-Aldrich T7765 Tunicamycin from Streptomyces sp.	Sigma-Aldrich M0440 Mitomycin C from Streptomyces caespitosus	Sigma-Aldrich T8902 Thiostrepton from Streptomyces azureus
form powder	form -	form -	form -
Quality Level 200	Quality Level 300	Quality Level 200	Quality Level 200
storage temp. −20°C	storage temp. 2-8°C	storage temp. 2-8°C	storage temp. −20°C
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	solubility 95% ethanol: soluble 1 mg/mL, clear to faintly hazy, THF: soluble <1 mg/mL, dioxane: soluble <1 mg/mL, DMF: soluble >10 mg/mL, pyridine: >10 mg/mL, DMSO: soluble 4.9-5.1 mg/mL, clear to slightly hazy, colorless to yellow, methanol: slightly soluble 4.9-5.1 mg/mL, methanol: soluble 4.9-5.1 mg/mL, clear to slightly hazy, colorless to yellow, acetone: insoluble, aqueous base: insoluble, chloroform: insoluble, ethyl acetate: insoluble	solubility H₂O: 40 mg/mL, clear to very slightly hazy, colorless, H₂O: soluble	solubility acetic acid: soluble 25 mg/mL, clear to hazy, yellow to brownish-yellow
shipped in wet ice	shipped in -	shipped in -	shipped in -
mode of action enzyme \| inhibits	mode of action protein synthesis \| interferes	mode of action DNA synthesis \| interferes	mode of action protein synthesis \| interferes

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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