T6575

TOFA

≥98% (HPLC)

• Synonym(s): 5-(Tetradecyloxy)-2-furoic acid
• Empirical Formula (Hill Notation): C₁₉H₃₂O₄
• CAS Number: 54857-86-2
• Molecular Weight: 324.45
• MDL number: MFCD01726059
• UNSPSC Code: 12352200
• PubChem Substance ID: 329826849
• NACRES: NA.77

Properties

• Assay: ≥98% (HPLC)
• form: powder
• color: white to beige
• mp: 112-115 °C
• solubility: DMSO: 2 mg/mL, clear
• storage temp.: −20°C
• SMILES string: CCCCCCCCCCCCCCOc1ccc(o1)C(O)=O
• 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

Description

Application

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).

TOFA has been used as an ACC inhibitor to study its effect on insulin secretion in INS-1E cells.

Biochem/physiol Actions

5-(Tetradecyloxy)-2-furoic acid (TOFA) elicits hypolipidemic functionality by favoring fatty acid breakdown and at the same time preventing biosynthesis. It induces apoptosis in pancreatic cancer cells and favors tumor suppression.

Studies have reported that TOFA can inhibit the anorectic effect of subcutaneous tamoxifen (TMX) on food intake during refeeding experiments in rats.

TOFA is a cell-permeable, potent, reversible, and competitive inhibitor of acetyl-CoA carboxylase (ACC). TOFA is a key enzyme involved in fatty acid biosynthesis. TOFA inhibits cellular fatty acid synthesis in a dose-dependent manner (IC₅₀ = 4 μM in human breast cancer cell line MCF7).

Preparation Note

TOFA is soluble in DMSO at a concentration that is greater than 2 mg/ml.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 2
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves