Tetradecylthioacetic acid

Base Information

• Chemical Name: Tetradecylthioacetic acid
• CAS No.: 2921-20-2
• Molecular Formula: C16H32O2S
• Molecular Weight: 288.495
• Hs Code.: 2930909090
• European Community (EC) Number: 428-470-6,835-795-0
• UNII: 7ZU5I25S2O
• DSSTox Substance ID: DTXSID0040759
• Nikkaji Number: J457.039A
• Wikipedia: Tetradecylthioacetic_acid
• Wikidata: Q7706312
• ChEMBL ID: CHEMBL187734
• Mol file: 2921-20-2.mol

Synonyms:1-(carboxymethylthio)tetradecane;1-mono(carboxymethylthio)tetradecane;CMTD;tetradecylthioacetic acid

Chemical Property of Tetradecylthioacetic acid

Chemical Property:

• Appearance/Colour: white cyrstalline solid
• Vapor Pressure: 1.32E-07mmHg at 25°C
• Melting Point: 65-73 °C
• Refractive Index: 1.481
• Boiling Point: 402.6 °C at 760 mmHg
• PKA: 3.85±0.10(Predicted)
• Flash Point: 197.3 °C
• PSA: 62.60000
• Density: 0.957 g/cm³
• LogP: 5.50530
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO: ≥22 mg/mL, soluble
• XLogP3: 7.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 15
• Exact Mass: 288.21230143
• Heavy Atom Count: 19
• Complexity: 195

Purity/Quality:

99% ^*data from raw suppliers

Tetradecylthioacetic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCSCC(=O)O
• Recent ClinicalTrials: TTA in Treatment of Diabetes and Dyslipidemia
• Description: Tetradecylthioacetic acid (TTA), a representative member of the 3-thia family, has the chemical structure of palmitic acid (C16) in which a sulfur atom is located between the 2 and 3-carbon atoms (COOH-CH2-S-(CH2)13-CH3). TTA is a novel hypolipidemic drug which has been shown to combine several effects of w-3 PUFAs, such as EPA, and structurally unrelated peroxisome proliferators, such as phenylacetate and fibrates. From this perspective we wanted to investigate if TTA shares the antitumor activity found for these functionally related compounds, and furthermore to study the metabolic effects of TTA in cancer cells in relation to the effects found in hepatocytes.
• Uses: TTA is a novel thio-fatty acid which cannot undergo beta-oxidation. It induces apoptosis in IPC-81 leukemia cells via depolarization of mitochondrial membrane potential and inhibits glioma cell proliferation. TTA completely prevents high fat diet-induce TTA is a novel thio-fatty acid which cannot undergo beta-oxidation. It induces apoptosis in IPC-81 leukemia cells via depolarization of mitochondrial membrane potential and inhibits glioma cell proliferation. TTA completely prevents high fat diet-induced insulin resistance and adiposity in Wistar rats. Activates rodent PPAR’s with rank order PPARα>PPARδ>PPARγ.

Technology Process of Tetradecylthioacetic acid

There total 7 articles about Tetradecylthioacetic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

methyl 2-(tetradecylthio)acetate → tetradecylthioacetic Acid (2921-20-2)

Guidance literature:

With lithium hydroxide; In ethanol; at 20 ℃; for 48h;

DOI:10.1016/j.tet.2014.03.050

Reference yield: 95.0%

1-tetradecanethiol (2079-95-0) + chloroacetic acid (79-11-8) → tetradecylthioacetic Acid (2921-20-2)

Guidance literature:

1-tetradecanethiol; With sodium hydroxide; In ethanol; at 20 ℃; for 0.5h;

chloroacetic acid; With sodium hydrogencarbonate; In ethanol; water; for 2h;

Reference yield: 94.0%

1-Bromotetradecane (112-71-0) + mercaptoacetic acid (68-11-1) → tetradecylthioacetic Acid (2921-20-2)

Guidance literature:

1-Bromotetradecane; mercaptoacetic acid; With methanol; potassium hydroxide; at 20 ℃;

With hydrogenchloride; In water;

upstream raw materials:

1-tetradecene

mercaptoacetic acid

1-Bromotetradecane

1-tetradecanethiol

Downstream raw materials:

1,3-di(tert-butyloxycarbonylamino)-2-[(tetradecylthio)acetyloxy]-propane

1,3-Dicyclohexylurea

2-(tetradecylthio)ethanol