Name | 5-(tetradecyloxy)furan-2-carboxylic acid |
Synonyms | TOFA mdl14514 RMI-14514 5-tetradecyloxy-2-furonicacid 5-(TETRADECYLOXY)-2-FUROIC ACID TOFA (5-(Tetradecyloxy)-2-furoic acid) 5-(tetradecyloxy)-2-furancarboxylicaci 5-(tetradecyloxy)furan-2-carboxylic acid 5-(TETRADECYLOXY)-2-FURANCARBOXYLIC ACID |
CAS | 54857-86-2 |
InChI | InChI=1/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) |
Molecular Formula | C19H32O4 |
Molar Mass | 324.45 |
Density | 1.003g/cm3 |
Melting Point | 112-115°C |
Boling Point | 441.7°C at 760 mmHg |
Flash Point | 220.9°C |
Solubility | DMSO: 2.5mg/mL |
Vapor Presure | 1.41E-08mmHg at 25°C |
Appearance | solid |
Color | white to beige |
Storage Condition | -20°C |
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. |
Refractive Index | 1.483 |
In vitro study | TOFA (5-tetradecyloxy-2-furoic acid) is cytotoxic to lung cancer cells NCI-H460 and colon carcinoma cells HCT-8 and HCT-15, with an IC 50 at approximately 5.0, 5.0, and 4.5 μg/mL, respectively. TOFA at 1.0–20.0 μg/mL effectively blocks fatty acid synthesis and induces cell death in a dose-dependent manner. TOFA is found to be cytotoxic to COC1 and COC1/DDP cells with IC 50 values of ~26.1 and 11.6 µg/mL, respectively. TOFA inhibits the proliferation of the cancer cells examined in a time and dose dependent manner, arrests the cells in the G0/G1 cell cycle phase and induces apoptosis. Acetyl-CoA-carboxylase-α (ACCA) is a key enzyme in the regulation of fatty acids synthesis. Inhibition of ACCA by TOFA decreases fatty acid synthesis and induces caspase activation and cell death in most PCa cell lines. |
In vivo study | 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 mm 3 . 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. |
WGK Germany | 2 |
RTECS | LU0288000 |
HS Code | 29321900 |
1mg | 5mg | 10mg | |
---|---|---|---|
1 mM | 3.082 ml | 15.411 ml | 30.821 ml |
5 mM | 0.616 ml | 3.082 ml | 6.164 ml |
10 mM | 0.308 ml | 1.541 ml | 3.082 ml |
5 mM | 0.062 ml | 0.308 ml | 0.616 ml |
application | 5-(decyloxy)-2-furoic acid can be used as an intermediate in organic synthesis and a pharmaceutical intermediate, and can be used in laboratory research and development processes and chemical and pharmaceutical production processes. |
Biological activity | TOFA (5-(Tetradecyloxy)-2-furoic acid, Tyrphostin 46,Tyrphostin A46,Tyrphostin B40) is an allosteric inhibitor acetyl-CoA carboxylase-α (ACCA). TOFA is transformed into TOFyl-CoA (5-tetradecyloxy-2-furoyl-CoA) in cells, which has allosteric inhibitory effect on ACCA. TOFA blocks fatty acid synthesis and induces cell death in a dose-dependent manner. |
Target | Value |