CAS Number54857-86-2
Synonyms5-Tetradecyloxy-2-furonic acid; TOFA; 5-tetradecoxyfuran-2-carboxylic acid; 5-(Tetradecyloxy)-2-furoic acid; MFCD01726059
Molecular FormulaC19H32O4
Molecular Weight324.455
Density1.0±0.1 g/cm3
Boiling Point441.7±25.0 °C at 760 mmHg
Melting Point112-115ºC
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 54857-86-2 |
| Catalog No. | 2A-1167428 |
| Chinese Name | 5-(十四烷基氧)-2-糠酸 |
| Synonyms | 5-Tetradecyloxy-2-furonic acid; TOFA; 5-tetradecoxyfuran-2-carboxylic acid; 5-(Tetradecyloxy)-2-furoic acid; MFCD01726059 |
| Molecular Formula | C19H32O4 |
| Molecular Weight | 324.455 |
| Density | 1.0±0.1 g/cm3 |
| Boiling Point | 441.7±25.0 °C at 760 mmHg |
| Melting Point | 112-115ºC |
| Storage Condition | Sealed in a cool, dry environment at -20ºC |
| Application | TOFA (RMI14514; MDL14514) is an allosteric inhibitor of acetyl-CoA carboxylase-alpha (ACCA). |
| HTC | 2932190090 |
| PubChem ID | 10236666 |
| SMILES | CCCCCCCCCCCCCCOc1ccc(C(=O)O)o1 |
| InChI | 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) |
| InChI Key | CZRCFAOMWRAFIC-UHFFFAOYSA-N |
| Hazard Symbols | transportation |
| MSDS | msds/167455_2_54857_86_2.pdf |
| Bioactivity | TOFA (RMI14514;MDL14514) is an allosteric inhibitor of acetyl-CoA carboxylase-α (ACCA ). Related Catalog Signaling Pathways >> Metabolic Enzyme/Protease >> Acetyl-CoA Carboxylase Research Areas >> Cancer In Vitro 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 IC50 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[1]. TOFA is found to be cytotoxic to COC1 and COC1/DDP cells with IC50 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[2]. 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[3]. 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]. Cell Assay NCI-H460, human lung cancer cells, and HCT-8 and HCT-15 cells (5,000/well) are seeded in 96-well plates overnight and then exposed to TOFA at indicated concentrations (0, 1, 5, 10, 20, 50 µg/mL) for 72 hours. Viable cells are detected using MTT assay[1]. Animal Admin Mice: Mice are treated with 50 μL DMSO (control group) or treated with TOFA (50 mg/kg). The drugs are injected intraperitoneally daily for two weeks. Tumor volumes are recorded every two days by measuring dimensions (length and width) with Vernier calipers. The mice are sacrificed four weeks after the final treatment. Tumor weights are measured by a scale[2]. References [1]. Wang C, et al. Acetyl-CoA carboxylase-alpha inhibitor TOFA induces human cancer cell apoptosis. Biochem Biophys Res Commun. 2009 Jul 31;385(3):302-6. [2]. Li S, et al. TOFA suppresses ovarian cancer cell growth in vitro and in vivo. Mol Med Rep. 2013 Aug;8(2):373-8. [3]. Guseva NV, et al. 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. 2011 Jul 1;12(1):80-5. Chemical & Physical Properties Density 1.0±0.1 g/cm3 Boiling Point 441.7±25.0 °C at 760 mmHg Melting Point 112-115ºC Molecular Formula C19H32O4 Molecular Weight 324.455 Flash Point 220.9±23.2 °C Exact Mass 324.230072 PSA 59.67000 LogP 7.82 Vapour Pressure 0.0±1.1 mmHg at 25°C Index of Refraction 1.483 InChIKey CZRCFAOMWRAFIC-UHFFFAOYSA-N SMILES CCCCCCCCCCCCCCOc1ccc(C(=O)O)o1 Storage condition 2-8℃ |
| Use of | TOFA (RMI14514;MDL14514) is an allosteric inhibitor of acetyl-CoA carboxylase-α (ACCA ). Properties Articles40 Name 5-(tetradecyloxy)-2-furoic acid Synonym More Synonyms TOFA Biological Activity Description TOFA (RMI14514;MDL14514) is an allosteric inhibitor of acetyl-CoA carboxylase-α (ACCA ). Related Catalog Signaling Pathways >> Metabolic Enzyme/Protease >> Acetyl-CoA Carboxylase Research Areas >> Cancer References [1]. Wang C, et al. Acetyl-CoA carboxylase-alpha inhibitor TOFA induces human cancer cell apoptosis. Biochem Biophys Res Commun. 2009 Jul 31;385(3):302-6. [2]. Li S, et al. TOFA suppresses ovarian cancer cell growth in vitro and in vivo. Mol Med Rep. 2013 Aug;8(2):373-8. [3]. Guseva NV, et al. 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. 2011 Jul 1;12(1):80-5. Chemical & Physical Properties Molecular Formula C19H32O4 Exact Mass 324.230072 PSA 59.67000 Index of Refraction 1.483 InChIKey CZRCFAOMWRAFIC-UHFFFAOYSA-N Storage condition 2-8℃ |
| Tax Rebate | 9.0% |
| Supervision | None MFN tariff: 6.5% Ordinary tariff: 20.0% |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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