T6575
TOFA
≥98% (HPLC)
Synonym(s):
5-(Tetradecyloxy)-2-furoic acid
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About This Item
Empirical Formula (Hill Notation):
C19H32O4
CAS Number:
Molecular Weight:
324.45
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
Quality Level
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
Application
TOFA has been used as an ACC inhibitor to study its effect on insulin secretion in INS-1E cells.
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).
Biochem/physiol Actions
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 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).
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.
Preparation Note
TOFA is soluble in DMSO at a concentration that is greater than 2 mg/ml.
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Storage Class
11 - Combustible Solids
wgk
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Extracellular matrix mechanical cues regulate lipid metabolism through Lipin-1 and SREBP
Romani P, et al.
Nature Cell Biology, 21(3), 338-338 (2019)
Acetyl-CoA carboxylase 1-dependent protein acetylation controls breast cancer metastasis and recurrence
Garcia MR, et al.
Cell Metabolism, 26(6), 842-855 (2017)
Modulation of lipolysis and glycolysis pathways in cancer stem cells changed multipotentiality and differentiation capacity toward endothelial lineage
Pouyafar A, et al.
Cell & Bioscience, 9(1), 30-30 (2019)