TOFA

Cayman Chemical Item Number 10005263

5-(Tetradecyloxy)-2-furoic Acid; RMI 14514 (CAS 54857-86-2)

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Description

Inhibition of fatty acid synthase (FAS) by the irreversible inhibitor cerulenin leads to cytotoxicity and apoptosis in human cancer cell lines.1 TOFA is an inhibitor of fatty acid synthesis blocking the synthesis of malonyl-CoA by acetyl-CoA carboxylase (ACC).2 Both cerulenin (at about 10 µg/ml) and TOFA (at about 1 µg/ml) are effective at blocking the incorporation of radiolabeled acetate into palmitate. However, TOFA reduces malonyl-CoA levels rather than elevating them, and TOFA is relatively non-toxic to various cancer cell lines. TOFA also attenuates the inhibition of feeding observed when FAS inhibitors such as cerulenin and C75 are administered to obese ob/ob mice.

1. Moche, M., Schneider, G., Edwards, P., et al. Structure of the complex between the antibiotic cerulenin and its target, β-ketoacyl-acyl carrier protein synthase. J Biol Chem 274(10) 6031-6034 (1999).

2. Loftus, T.M., Jaworsky, D.E., Frehywot, G.L., et al. Reduced food intake and body weight in mice treated with fatty acid synthase inhibitors. Science 288 2379-2381 (2000).

Synonyms
  • 5-(Tetradecyloxy)-2-furoic Acid
  • RMI 14514
Formal Name 5-​(tetradecyloxy)-​2-​furancarboxylic acid
CAS Number 54857-86-2
Molecular Formula C19H32O4
Formula Weight 324.5
Formulation A crystalline solid
Purity ≥98%
λmax 278 nm
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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CCCCCCCCCCCCCCOc1ccc(o1)​C(=O)​O
InCHI Code
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​1S/C19H32O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-22-18-15-14-17(23-18)​19(20)​21/h14-15H,2-13,16H2,1H3,(H,20,21)​
InCHI Key
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CZRCFAOMWRAFIC-UHFFFAOYSA-N

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TOFA is available in the following screening library:

Size Price Quantity Subtotal
5 mg $29.00 $0.00
10 mg $55.00 $0.00
50 mg $232.00 $0.00
100 mg $406.00 $0.00
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