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Merck

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:
54857-86-2
Molecular Weight:
324.45
NACRES:
NA.77
PubChem Substance ID:
329826849
UNSPSC Code:
12352200
MDL number:
MFCD01726059

Product Name

TOFA, ≥98% (HPLC)

InChI key

CZRCFAOMWRAFIC-UHFFFAOYSA-N

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)

assay

≥98% (HPLC)

form

powder

color

white to beige

mp

112-115 °C

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

Quality Level

200

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 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.

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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Certificates of Analysis (COA)

Lot/Batch Number
0000417049
0000417049
0000247182
0000247181
0000247182

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Weibo Zhou et al.
Cancer research, 63(21), 7330-7337 (2003-11-13)
C75, an inhibitor of fatty acid synthase (FAS), induces apoptosis in cultured human cancer cells. Its proposed mechanism of action linked high levels of malonyl-CoA after FAS inhibition to potential downstream effects including inhibition of carnitine palmitoyltransferase-1 (CPT-1) with resultant
Inhibition of fatty acid synthesis induces apoptosis of human pancreatic cancer cells
Nishi K, et al.
Anticancer Research, 36(9), 4655-4660 (2016)
P T Lange et al.
mBio, 9(4) (2018-07-19)
Gammaherpesviruses are oncogenic pathogens that persist in ~95% of the adult population. Cellular metabolic pathways have emerged as important regulators of many viral infections, including infections by gammaherpesviruses that require several lipid synthetic pathways for optimal replication. Liver X receptors
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)
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Articles

Fatty Acid Synthesis in Cancer Cells

Fatty acid synthesis supports cancer cell proliferation, essential for membrane generation, protein modification, and bioenergetics.

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