5-(TETRADECYLOXY)-2-FUROIC ACID Chemical Properties

Melting point:

112-115 °C

Boiling point:

441.7±25.0 °C(Predicted)

Density 

1.003±0.06 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

DMSO: 2.5 mg/mL

form 

solid

pka

3.55±0.10(Predicted)

color 

white to beige

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 month.

Safety Information

WGK Germany 

2

RTECS 

LU0288000

HS Code 

29321900

MSDS

• Language:English Provider:SigmaAldrich

5-(TETRADECYLOXY)-2-FUROIC ACID Usage And Synthesis

Description

TOFA (54857-86-2) interferes with fatty acid synthase via inhibition of acetyl Co-A carboxylase (ACC1).1 Induces apoptosis in a variety of tumor cell lines.2,3 Stimulates neurite outgrowth and neuronal differentiation in rat pheochromocytoma cells.4 TOFA impairs glucose-stimulated insulin secretion after chronic treatment.5

Uses

TOFA has been used as a lipid biosynthesis inhibitor in mesenchymal stromal cells (MSCs), human pluripotent stem cells., an acetyl-CoA carboxylase 1 inhibitor in murine adipocyte cell lines., a lipolysis inhibitor in cancer stem cells (CSCs).

Definition

ChEBI: A member of the class of furans that is 2-furoic acid in which the hydrogen at position 5 is replaced by a tetradecyloxy group.

Biochem/physiol Actions

5-(Tetradecyloxy)-2-furoic acid (TOFA) elicits hypolipidemic?functionality by favoring fatty acid breakdown and at the same time preventing biosynthesis. It induces apoptosis in pancreatic cancer cells and favors tumor suppression.

References

References/Citations: 1) Halvorson?et al. (1984),?Inhibition of fatty acid synthesis in isolated adipocytes by 5-tetradecyloxy)-2-furoic acid; Lipids,?19?851 2) Guseva?et al. (2011),?TOFA (5-tetradecyl-oxy-2-furoic acid) reduces fatty acid synthesis, inhibits expression of AR, neuropilin-1 and Mcl-1 and kills prostate cancer cells independent of p53 status; Cancer Biol. Ther.,?12?80 3) Zhou?et al. (2003),?Fatty acid synthesis inhibition triggers apoptosis during S phase in human cancer cells; Cancer Res.,?63?7330 4) Schmidt?et al. (1999),?Transcription control and neuronal differentiation by agents that activate the LXR nuclear receptor family; Mol. Cell. Endocrinol.,?155?51 5) Ronnebaum?et al. (2008),?Chronic suppression of acetyl-CoA carboxylase 1 in beta-cells impairs insulin secretion via inhibition of glucose rather than lipid metabolism; J. Biol. Chem.,?283?14248

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