DC Chemicals Limited
China
Product Name: TOFA
Price: $250.0/100mg $500.0/250mg $1000.0/1g
Purity: 98.0%
Stocking Period: 3 Day
Contact: Tony Cao

Dayang Chem (Hangzhou) Co., Ltd.
China
Product Name: 5-(TETRADECYLOXY)-2-FUROIC ACID
Price: $Inquiry/100g $Inquiry/1kg $Inquiry/100kg $Inquiry/1000kg
Purity: 98.0%
Stocking Period: Inquiry
Contact: Ms Wang

54857-86-2

54857-86-2 structure

54857-86-2 structure

Name: TOFA
Chemical Name: 5-(tetradecyloxy)-2-furoic acid
CAS Number: 54857-86-2
Molecular Formula: C₁₉H₃₂O₄
Molecular Weight: 324.455
Catalog: Signaling Pathways Metabolic Enzyme/Protease Acetyl-CoA Carboxylase
Create Date: 2018-09-18 22:56:44
Modify Date: 2024-01-02 13:23:53
TOFA (RMI14514;MDL14514) is an allosteric inhibitor of acetyl-CoA carboxylase-α (ACCA ).

Name	5-(tetradecyloxy)-2-furoic acid
Synonyms	5-Tetradecyloxy-2-furonic acid TOFA 2-Furancarboxylic acid, 5-(tetradecyloxy)- 5-tetradecoxyfuran-2-carboxylic acid 5-(Tetradecyloxy)-2-furoic acid MFCD01726059

Description	TOFA (RMI14514;MDL14514) is an allosteric inhibitor of acetyl-CoA carboxylase-α (ACCA ).
Related Catalog	Signaling Pathways >> Metabolic Enzyme/Protease >> Acetyl-CoA Carboxylase Research Areas >> Cancer
In Vitro	TOFA (5-tetradecyloxy-2-furoic acid) is cytotoxic to lung cancer cells NCI-H460 and colon carcinoma cells HCT-8 and HCT-15, with an IC50 at approximately 5.0, 5.0, and 4.5 μg/mL, respectively. TOFA at 1.0–20.0 μg/mL effectively blocks fatty acid synthesis and induces cell death in a dose-dependent manner[1]. TOFA is found to be cytotoxic to COC1 and COC1/DDP cells with IC50 values of ~26.1 and 11.6 µg/mL, respectively. TOFA inhibits the proliferation of the cancer cells examined in a time and dose dependent manner, arrests the cells in the G0/G1 cell cycle phase and induces apoptosis[2]. Acetyl-CoA-carboxylase-α (ACCA) is a key enzyme in the regulation of fatty acids synthesis. Inhibition of ACCA by TOFA decreases fatty acid synthesis and induces caspase activation and cell death in most PCa cell lines[3].
In Vivo	TOFA inhibits COC1/DDP cell growth in ovarian tumor mouse xenografts. The tumor growth rate is signifi¬cantly inhibited by TOFA compared with the DMSO treated control mice (1649±356.3 vs. 5128±390.4 mm3. No toxicity is observed in the heart, liver, spleen, lung, kidney and intestinal tissues. By inhibiting ACC, TOFA may be a promising small molecule agent for ovarian cancer therapy[2].
Cell Assay	NCI-H460, human lung cancer cells, and HCT-8 and HCT-15 cells (5,000/well) are seeded in 96-well plates overnight and then exposed to TOFA at indicated concentrations (0, 1, 5, 10, 20, 50 µg/mL) for 72 hours. Viable cells are detected using MTT assay[1].
Animal Admin	Mice: Mice are treated with 50 μL DMSO (control group) or treated with TOFA (50 mg/kg). The drugs are injected intraperitoneally daily for two weeks. Tumor volumes are recorded every two days by measuring dimensions (length and width) with Vernier calipers. The mice are sacrificed four weeks after the final treatment. Tumor weights are measured by a scale[2].
References	[1]. Wang C, et al. Acetyl-CoA carboxylase-alpha inhibitor TOFA induces human cancer cell apoptosis. Biochem Biophys Res Commun. 2009 Jul 31;385(3):302-6. [2]. Li S, et al. TOFA suppresses ovarian cancer cell growth in vitro and in vivo. Mol Med Rep. 2013 Aug;8(2):373-8. [3]. Guseva NV, et al. TOFA (5-tetradecyl-oxy-2-furoic acid) reduces fatty acid synthesis, inhibits expression of AR, neuropilin-1 and Mcl-1 and kills prostate cancer cells independent of p53 status. Cancer Biol Ther. 2011 Jul 1;12(1):80-5.

Density	1.0±0.1 g/cm3
Boiling Point	441.7±25.0 °C at 760 mmHg
Melting Point	112-115ºC
Molecular Formula	C₁₉H₃₂O₄
Molecular Weight	324.455
Flash Point	220.9±23.2 °C
Exact Mass	324.230072
PSA	59.67000
LogP	7.82
Vapour Pressure	0.0±1.1 mmHg at 25°C
Index of Refraction	1.483
Storage condition	2-8℃

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LU0288000

CHEMICAL NAME :: 2-Furancarboxylic acid, 5-(tetradecyloxy)-

CAS REGISTRY NUMBER :: 54857-86-2

LAST UPDATED :: 199612

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C19-H32-O4

MOLECULAR WEIGHT :: 324.51

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Gastrointestinal - hypermotility, diarrhea

REFERENCE :: FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 1,19,1981

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >1 gm/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Olfaction) - effect, not otherwise specified Behavioral - somnolence (general depressed activity)

REFERENCE :: FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 1,19,1981 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 18200 mg/kg/26W-C

TOXIC EFFECTS :: Liver - changes in liver weight

REFERENCE :: FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 1,19,1981

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 9100 mg/kg/13W-C

TOXIC EFFECTS :: Liver - changes in liver weight

REFERENCE :: FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 1,19,1981

Personal Protective Equipment	Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
RIDADR	NONH for all modes of transport
HS Code	2932190090

585-70-6 structure

585-70-6

112-72-1 structure

112-72-1

~%

54857-86-2 structure

54857-86-2

Literature: Journal of Pharmaceutical Sciences, , vol. 70, # 10 p. 1095 - 1100

88-14-2 structure

88-14-2

~%

54857-86-2 structure

54857-86-2

Literature: Journal of Pharmaceutical Sciences, , vol. 70, # 10 p. 1095 - 1100

Precursor 3
585-70-6 112-72-1 88-14-2
DownStream 1
62443-38-3

HS Code	2932190090
Summary	2932190090 other compounds containing an unfused furan ring (whether or not hydrogenated) in the structure VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:20.0%