5-(Tetradecyloxy)-2-furoic acid

Base Information

• Chemical Name: 5-(Tetradecyloxy)-2-furoic acid
• CAS No.: 54857-86-2
• Molecular Formula: C19H32 O4
• Molecular Weight: 324.461
• Hs Code.: 2932190090
• UNII: BI12FRY055
• DSSTox Substance ID: DTXSID60203338
• Nikkaji Number: J395.152I
• Wikidata: Q27089005
• Pharos Ligand ID: L9S8252SN74P
• ChEMBL ID: CHEMBL1562779
• Mol file: 54857-86-2.mol

Synonyms:5-(tetradecyloxy)-2-furancarboxylic acid;5-(tetradecyloxy)-2-furoic acid;RMI 14514;RMI-14514;TOFA

Chemical Property of 5-(Tetradecyloxy)-2-furoic acid

Chemical Property:

• Vapor Pressure: 1.41E-08mmHg at 25°C
• Melting Point: 112-115 °C
• Boiling Point: 441.7°C at 760 mmHg
• Flash Point: 220.9°C
• PSA: 59.67000
• Density: 1.003g/cm³
• LogP: 6.05770
• Storage Temp.: −20°C
• Solubility.: DMSO: 2.5 mg/mL
• XLogP3: 7.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 15
• Exact Mass: 324.23005950
• Heavy Atom Count: 23
• Complexity: 293

Purity/Quality:

98%,99%, ^*data from raw suppliers

TOFA ≥98% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCOC1=CC=C(O1)C(=O)O
• 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).

Technology Process of 5-(Tetradecyloxy)-2-furoic acid

There total 5 articles about 5-(Tetradecyloxy)-2-furoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

1-Tetradecanol (112-72-1) + tetradecyl ester of 5-bromofuroic acid → 5-(tetradecyloxy)-2-furancarboxylic acid (54857-86-2)

Guidance literature:

1-Tetradecanol; tetradecyl ester of 5-bromofuroic acid; With potassium tert-butylate; In tetrahydrofuran; at 45 ℃;

With methanol; potassium hydroxide; at 30 - 35 ℃;

Reference yield: 76.0%

methyl 5-bromo-2-furoate (2527-99-3) + 1-Tetradecanol (112-72-1) → 5-(tetradecyloxy)-2-furancarboxylic acid (54857-86-2)

Guidance literature:

methyl 5-bromo-2-furoate; 1-Tetradecanol; With titanium(IV) isopropylate; In toluene; at 115 - 135 ℃; for 4h; Industrial scale;

With potassium tert-butylate; In tetrahydrofuran; toluene; at 40 - 55 ℃; Industrial scale;

With methanol; potassium hydroxide; In tetrahydrofuran; toluene; for 4h; Heating; Industrial scale;

Reference yield:

5-bromo-furan-2-carboxylic acid (585-70-6) + 1-Tetradecanol (112-72-1) → 5-(tetradecyloxy)-2-furancarboxylic acid (54857-86-2)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1.) toluene, reflux, 3 h, 2.) 60 deg C, 1 h; reflux, 16 h;

DOI:10.1002/jps.2600701002

upstream raw materials:

5-bromo-furan-2-carboxylic acid

1-Tetradecanol

2-furanoic acid

methyl 5-bromo-2-furoate

Downstream raw materials:

2-((2-ethoxy-2-oxoethyl)(methylamino)-2-oxoethyl 5-tetradecyloxy)furan-2-carboxylate

1-(benzyl(methyl)carbamoyloxy)ethyl 5-(tetradecyloxy)furan-2-carboxylate

2-(benzyl(methyl)amino)-2-oxoethyl 5-(tetradecyloxy)furan-2-carboxylate

2-(5-(tetradecyloxy)furan-2-carbonyloxy)benzoic acid

Refernces

• 1、 -. "DERMATOLOGICAL FORMULATIONS OF 2-(2-ETHOXY-2-OXOETHYL)(METHYL)AMINO-2-OXOETHYL 5-(TETRADECYLOXY)FURAN-2-CARBOXYLATE". Page/Page column 28-31. . Retrieved 2018/02/28.
• 2、 -. "Antiretroviral furan ketones". . . Retrieved 2008/06/13.