5-(Tetradecyloxy)-2-furoic acid

• CAT Number: M013983
• CAS Number: 54857-86-2
• Molecular Formula: C19H32O4
• Molecular Weight: 324.5
• Purity: ≥95%
• Synonyms: TOFA;5-(tetradecyloxy)-2-furancarboxylicaci;5-tetradecyloxy-2-furonicacid;mdl14514;RMI-14514;5-(TETRADECYLOXY)-2-FURANCARBOXYLIC ACID;5-(TETRADECYLOXY)-2-FUROIC ACID;TOFA (5-(Tetradecyloxy)-2-furoic acid)
• Storage: -20°C
• InChI: 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)
• InChIKey: CZRCFAOMWRAFIC-UHFFFAOYSA-N
• SMILES: CCCCCCCCCCCCCCOc1ccc(o1)C(=O)O

Inhibition of fatty acid synthase (FAS) by the irreversible inhibitor cerulenin leads to cytotoxicity and apoptosis in human cancer cell lines. TOFA is an inhibitor of fatty acid synthesis blocking the synthesis of malonyl-<wbr></wbr>CoA by acetyl-<wbr></wbr>CoA carboxylase (ACC). 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-<wbr></wbr>CoA levels rather than elevating them, and TOFA is relatively non-<wbr></wbr>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.