| Identification | Back Directory | [Name]
5-(TETRADECYLOXY)-2-FUROIC ACID | [CAS]
54857-86-2 | [Synonyms]
TOFA
mdl14514
RMI-14514
TOFA (RMI14514
RMI14514; MDL14514
TOFA (RMI14514:MDL14514)
5-tetradecyloxy-2-furonicacid
5-(TETRADECYLOXY)-2-FUROIC TOFA
5-(TETRADECYLOXY)-2-FUROIC ACID
TOFA - CAS 54857-86-2 - Calbiochem
5-(tetradecyloxy)-2-furancarboxylicaci
TOFA (5-(Tetradecyloxy)-2-furoic acid)
5-(TETRADECYLOXY)-2-FURANCARBOXYLIC ACID
2-Furancarboxylic acid,5-(tetradecyloxy)- | [Molecular Formula]
C19H32O4 | [MDL Number]
MFCD01726059 | [MOL File]
54857-86-2.mol | [Molecular Weight]
324.45 |
| Chemical Properties | Back Directory | [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. |
| Hazard Information | Back Directory | [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. | [in vivo]
TOFA inhibits COC1/DDP cell growth in ovarian tumor mouse xenografts. The tumor growth rate is signifi cantly inhibited by TOFA compared with the DMSO treated control mice (1649±356.3 vs. 5128±390.4 mm3. No toxicity is observed in the heart, liver, spleen, lung, kidney and intestinal tissues. By inhibiting ACC, TOFA may be a promising small molecule agent for ovarian cancer therapy[2]. | [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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