2921-20-2

Usage

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

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

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 
• 733010-31-6 3-{[(tetradecylthio)acetyl]amino}-propane-1,2-diol 
• 733010-52-1 1,3-di(tert-butyloxycarbonylamino)-2-[(tetradecylthio)acetyloxy]-propane 
• 731850-66-1 S-triphenylmethyl 2-(tetradecylthio)thioacetate 

Relevant academic research and scientific papers

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.

The molecular structure of thio-ether fatty acids influences PPAR-dependent regulation of lipid metabolism

Thio-ether fatty acids (THEFAs), including the parent 2-(tetradecylthio)acetic acid (TTA), are modified fatty acids (FAs) that have profound effects on lipid metabolism given that they are blocked for β-oxidation, and able to act as peroxisome proliferator-activated receptor (PPAR) agonists. Therefore, TTA in particular has been tested clinically for its therapeutic potential against metabolic syndrome related disorders. Here, we describe the preparation of THEFAs based on the TTA scaffold with either a double or a triple bond. These are tested in cultured human skeletal muscle cells (myotubes), either as free acid or following esterification as phospholipids, lysophospholipids or monoacylglycerols. Metabolic effects are assessed in terms of cellular bioavailabilities in myotubes, by FA substrate uptake and oxidation studies, and gene regulation studies with selected PPAR-regulated genes. We note that the inclusion of a triple bond promotes THEFA-mediated FA oxidation. Furthermore, esterification of THEFAs as lysophospholipids also promotes FA oxidation effects. Given that the apparent clinical benefits of TTA administration were offset by dose limitation and poor bioavailability, we discuss the possibility that a selection of our latest THEFAs and THEFA-containing lipids might be able to fulfill the therapeutic potential of the parent TTA while minimizing required doses for efficacy, side-effects and adverse reactions.

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.

Sulfur makes the difference: Synthesis and mesomorphic properties of novel thioether-functionalized imidazolium ionic liquid crystals

Novel thioether-linked imidazolium ionic liquid crystals were synthesized starting from methyl 2-mercaptoacetate. The mesomorphic properties were determined by differential scanning calorimetry (DSC), polarizing optical microscopy (POM), and X-ray diffraction. All mesogens displayed smectic A mesophase geometries with strongly interdigitated bilayer structures. Comparison of the thioether-linked imidazolium salts with the corresponding amine- and amide-linked imidazolium salts as well as simple N-alkyl-imidazolium salts showed that both mesophase width and stability increased with increasing softness of the linking unit, thus indicating the beneficial effect of sulfur. Additionally, an increase of the length of the linking unit decreased the interdigitation of the alkyl chains.

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.

Synthesis and analysis of novel glycerolipids for the treatment of metabolic syndrome

Tetradecylthioacetic acid (TTA) 1 is a peroxisome proliferator-activated receptor (PPAR) agonist found to improve insulin sensitivity, lower blood lipid levels, enhance fatty acid oxidation, and promote anti-inflammation in vivo. In an attempt to enhance these properties, two key thioether fatty acid (Thefa) lipids, ditetradecylthioacetyl phosphatidylcholine 2 and tritetradecylthioacetyl glycerol 3, are synthesized and administered po to male Wistar rats at two different doses to study and compare metabolic outcomes relative to the administration of 1 alone after 6 days. Liposomal formulations of 1 and 2 are also prepared to evaluate acute metabolic responses (at 3 h) post iv injection. Across all metrics measured, 1-induced responses post po administration are in line with previous data. Responses induced from 3 are mostly equivalent to 1-induced responses. By contrast, 2-induced responses almost always outperform those of 1 and 3. Therefore, 2 may represent a new lead for the treatment of metabolic syndrome.

Acylated aminopropanediols and analogues and therapeutic uses thereof

The invention relates to novel acylated aminopropanediols and the nitrogen and sulfur analogues thereof, pharmaceutical compositions comprising same, therapeutic uses thereof, in particular for the treatment of cerebral ischemia. The invention also provides a method of preparing said derivatives.

Therapeutic use of acyl glycerols and the nitrogen- and sulphur- containing analogues thereof

The invention relates to the use of acyl glycerols and the nitrogen- and sulfur-containing analogues thereof in the therapeutic field, particularly in human health. The inventive compounds have advantageous pharmacological properties and are particularly of use for the prevention or treatment of neurodegenerative diseases.

Uses of acylated aminopropanediols and sulphur and nitrogen analogues of same f

The invention relates to the use of molecules, particularly in the fields of human and veterinary health and cosmetics. The inventive compounds are acylated aminopropanediols and the nitrogen- and sulfur-containing analogues thereof and have advantageous pharmacological and cosmetic properties. In particular, the inventive compounds can be used to prevent and/or treat dyslipidemias, cardiovascular diseases, syndrome X, restenosis, diabetes, obesity, hypertension, some cancers, dermatological diseases, and, in the field of cosmetics, to combat skin ageing and the effects of same, in particular the development of wrinkles and the like.

Therapeutic use of of acyglycerols and the nitrogen-and sulphur-containing analogues thereof

The invention relates to the use of acylglycerols and the nitrogen- and sulfur-containing analogues thereof in therapy, particularly for the treatment of cerebral ischemia. The invention further relates to methods for preparing said derivatives, novel compounds, in particular acylglycerols, the nitrogen- and sulfur-containing analogues thereof and methods for preparing same.