2921-20-2

Basic information

• Product Name: Tetradecylthioacetic acid
• Synonyms: TETRADECYLTHIOACETIC ACID;TETRADECYLMERCAPTO ACETIC ACID;TTA;THTRADECYLMERCAPTO ACETIC ACID;Tetradcylthioacetic Acid;1-(carboxymethylthio)tetradecane;1-MONO(CARBOXYMETHYLTHIO)TETRADECANE;Tetradecylthioacetic acid (TTA)
• CAS NO: 2921-20-2
• Molecular Formula: C₁₆H₃₂O₂S
• Molecular Weight: 288.49
• EINECS: 1308068-626-2
• Product Categories: Apoptosis;Fatty Acid Derivatives & Lipids;Glycerols;Inhibitors;Sulfur & Selenium Compounds
• Mol File: 2921-20-2.mol
• Article Data: 17

Chemical Properties

• Melting Point: 65-73°C
• Boiling Point: 402.6 °C at 760 mmHg
• Flash Point: 197.3 °C
• Appearance: white/
• Density: 0.957 g/cm³
• Vapor Pressure: 1.32E-07mmHg at 25°C
• Refractive Index: 1.481
• Storage Temp.: -20°C Freezer
• Solubility: DMSO: ≥22 mg/mL, soluble
• PKA: 3.85±0.10(Predicted)
• CAS DataBase Reference: Tetradecylthioacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Tetradecylthioacetic acid(2921-20-2)
• EPA Substance Registry System: Tetradecylthioacetic acid(2921-20-2)

Safety Data

• WGK Germany: 3
• RTECS: AJ5087000
• Hazardous Substances Data: 2921-20-2(Hazardous Substances Data)

Usage

Description

Tetradecylthioacetic acid (TTA), a member of the 3-thia family, is a novel hypolipidemic drug with a chemical structure similar to palmitic acid (C16), featuring a sulfur atom between the 2nd and 3rd carbon atoms. It is a white crystalline solid and has been shown to combine the effects of omega-3 polyunsaturated fatty acids (PUFAs), such as eicosapentaenoic acid (EPA), and structurally unrelated peroxisome proliferators like phenylacetate and fibrates.

Uses

Used in Pharmaceutical Industry:
Tetradecylthioacetic acid is used as an anti-cancer agent for its ability to induce apoptosis in IPC-81 leukemia cells through the depolarization of mitochondrial membrane potential and inhibiting glioma cell proliferation.
Used in Obesity and Metabolic Syndrome Treatment:
Tetradecylthioacetic acid is used as a treatment for obesity and insulin resistance, as it has been shown to completely prevent high-fat diet-induced insulin resistance and adiposity in Wistar rats.
Used in Drug Development:
Tetradecylthioacetic acid is used as a novel thio-fatty acid that cannot undergo beta-oxidation, making it a potential candidate for the development of new drugs targeting various diseases.
Used in Activation of Rodent PPARs:
Tetradecylthioacetic acid is used as an activator for rodent peroxisome proliferator-activated receptors (PPARs) with a rank order of PPARα > PPARδ > PPARγ, which may have implications in the treatment of various metabolic disorders.

InChI:InChI=1/C16H32O2S/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-19-15-16(17)18/h2-15H2,1H3,(H,17,18)

Upstream product

• 1120-36-1 1-tetradecene 
• 68-11-1 mercaptoacetic acid 
• 112-71-0 1-Bromotetradecane 
• 2079-95-0 1-tetradecanethiol 
• 79-11-8 chloroacetic acid 

Downstream Products

• 497263-42-0 2-tetradecylthioacetamidopropane-1,3-diol 
• 731850-58-1 1-O-tetradecylthioacetyl-2,3-di-O-isopropylideneglycerol 
• 13887-96-2 (tetradecane-1-sulfonyl)-acetic acid 
• 731850-59-2 2-O-tetradecylthioacetyl-1,3-di-O-benzylideneglycerol 
• 733010-52-1 1,3-di(tert-butyloxycarbonylamino)-2-[(tetradecylthio)acetyloxy]-propane 
• 2387-23-7 1,3-Dicyclohexylurea 
• 733010-31-6 3-{[(tetradecylthio)acetyl]amino}-propane-1,2-diol 

Relevant articles and documents

Metal extracting agent containing sulfoxide group and preparation method thereof

The invention discloses a metal extracting agent containing a sulfoxide group and a preparation method thereof. The metal extracting agent containing the sulfoxide group is 2-(alkylsulfinyl)-N-((tetrahydrofuran-2-yl)methyl)acetamide. According to the preparation method, thioalcohol is used as a raw material, reacts with chloroacetic acid in an alkaline condition to generate corresponding thioether; afterwards, the corresponding thioether is oxidized through hydrogen peroxide in an organic-acid environment to obtain sulfoxide; the sulfoxide reacts with 2-tetrahydrofurfuryl amine in highly-acidic and high-temperature conditions, so as to generate corresponding amide. The metal extracting agent containing the sulfoxide group, which is provided by the invention, is high in the safety to an environment and an organism, is low-toxicity, is good in wettability, high in foaming capacity and liable in biodegradation, and has quite good extraction effects on rare earth metals thulium, ytterbium and lutetium in a weakly acidic condition.

NATURAL LIPIDS CONTAINING NON-OXIDIZABLE FATTY ACIDS

Provided herein is technology relating to natural lipids containing non-β-oxidizable fatty acids and particularly, but not exclusively, to compositions and methods related to the production and use of natural lipids containing non-β-oxidizable fatty acids.

Synthesis and characterization of some novel higher C,N-diphenyl nitrones, isoxazolines, and mercaptobenzimidazoles as oleochemicals

Some novel long-chain nitrones, isoxazolines, and (1H-benzo[d]-imidazol-2- ylthio) derivatives were synthesized. Nitrones, N-{4-[2-(tetradecylthio)acetoxy] benzylidene}aniline oxide, and N-[4-(12-oxo-2,5,8,11-tetraoxadocosan-22-yloxy) benzylidene]aniline oxide were prepared via the reaction of -phenylhydroxylamine with the corresponding aromatic aldehydes. The isoxazolines were prepared from undec-10-en-1-ol and benzonitrile-N-oxide which was generated in situ. The 1H-benzo[d]-imidazol-2-ylthio derivatives were synthesized via the replacement reaction of -bromo esters and 2-mercaptobenzimidazole.