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T6575

Sigma-Aldrich

TOFA

≥98% (HPLC)

Sinónimos:

5-(Tetradecyloxy)-2-furoic acid

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About This Item

Fórmula empírica (notación de Hill):
C19H32O4
Número de CAS:
54857-86-2
Peso molecular:
324.45
Número MDL:
MFCD01726059
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
329826849
NACRES:
NA.77

Ensayo

≥98% (HPLC)

Formulario

powder

color

white to beige

mp

112-115 °C

solubilidad

DMSO: 2 mg/mL, clear

temp. de almacenamiento

−20°C

cadena SMILES

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)

Clave InChI

CZRCFAOMWRAFIC-UHFFFAOYSA-N

Aplicación

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.

Acciones bioquímicas o fisiológicas

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).

Nota de preparación

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

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 2

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (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
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
Inhibition of fatty acid synthesis induces apoptosis of human pancreatic cancer cells
Nishi K, et al.
Anticancer Research, 36(9), 4655-4660 (2016)
Weibo Zhou et al.
Cancer research, 67(7), 2964-2971 (2007-04-06)
Fatty acid synthase (FAS), the enzyme responsible for the de novo synthesis of fatty acids, is highly expressed in ovarian cancers and most common human carcinomas. Inhibition of FAS and activation of AMP-activated protein kinase (AMPK) have been shown to
Extracellular matrix mechanical cues regulate lipid metabolism through Lipin-1 and SREBP
Romani P, et al.
Nature Cell Biology, 21(3), 338-338 (2019)
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