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T6575

Sigma-Aldrich

TOFA

≥98% (HPLC)

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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

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

Related Categories

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.

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Acetyl-CoA carboxylase 1-dependent protein acetylation controls breast cancer metastasis and recurrence
Garcia MR, et al.
Cell Metabolism, 26(6), 842-855 (2017)
Extracellular matrix mechanical cues regulate lipid metabolism through Lipin-1 and SREBP
Romani P, et al.
Nature Cell Biology, 21(3), 338-338 (2019)
Effects of a novel dual lipid synthesis inhibitor and its potential utility in treating dyslipidemia and metabolic syndrome
Cramer CT, et al.
Journal of Lipid Research, 45(7), 1289-1301 (2004)
Fanconi anemia mesenchymal stromal cells-derived glycerophospholipids skew hematopoietic stem cell differentiation through toll-like receptor signaling
Amarachintha S, et al.
Stem Cells, 33(11), 3382-3396 (2015)
Inhibition of fatty acid synthesis induces apoptosis of human pancreatic cancer cells
Nishi K, et al.
Anticancer Research, 36(9), 4655-4660 (2016)
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