Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C16H32O2S |
| Molecular Weight | 288.489 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCCCCCCCCSCC(O)=O
InChI
InChIKey=IPBCWPPBAWQYOO-UHFFFAOYSA-N
InChI=1S/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)
| Molecular Formula | C16H32O2S |
| Molecular Weight | 288.489 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Tetradecylthioacetic acid (TTA) is a hypolipidemic antioxidant with immunomodulating properties involving activation of peroxisome proliferator-activated receptors (PPARs). TTA exerts both hypolipidemic and anti-inflammatory effects in psoriasis patients - TTA can be of therapeutic benefit for a subgroup of psoriatic patients. TTA may improve myocardial function in heart failure, potentially involving its ability to decrease the availability of free fatty acids in plasma and increase the myocardial proportion of n-3 polyunsaturated fatty acids. TTA attenuates dyslipidemia in patients with type 2 diabetes mellitus. These effects may occur through mechanisms involving PPAR-alpha and PPAR-delta activation, resulting in increased mitochondrial fatty acid oxidation.
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
9 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18427285 |
600 mg 1 times / day multiple, oral dose: 600 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TETRADECYLTHIOACETIC ACID serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
14 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18427285 |
1000 mg 1 times / day multiple, oral dose: 1000 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TETRADECYLTHIOACETIC ACID serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2.9 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18427285 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
TETRADECYLTHIOACETIC ACID serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
11.5 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18427285 |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
TETRADECYLTHIOACETIC ACID serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
4 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18427285 |
200 mg 1 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TETRADECYLTHIOACETIC ACID serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
11 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18427285 |
1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered: |
TETRADECYLTHIOACETIC ACID serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Lipid-lowering effects of tetradecylthioacetic acid in antipsychotic-exposed, female rats: challenges with long-term treatment. | 2012 |
|
| Dual acting and pan-PPAR activators as potential anti-diabetic therapies. | 2011 |
|
| Platelet activating factor stimulates arachidonic acid release in differentiated keratinocytes via arachidonyl non-selective phospholipase A2. | 2010-04 |
|
| Novel phospholipid analogues of pan-PPAR activator tetradecylthioacetic acid are more PPAR alpha selective. | 2010-02-01 |
|
| Protein kinase A activators and the pan-PPAR agonist tetradecylthioacetic acid elicit synergistic anti-leukaemic effects in AML through CREB. | 2010-01 |
|
| Dietary supplementation of tetradecylthioacetic acid increases feed intake but reduces body weight gain and adipose depot sizes in rats fed on high-fat diets. | 2009-11 |
|
| Increased survival by feeding tetradecylthioacetic acid during a natural outbreak of heart and skeletal muscle inflammation in S0 Atlantic salmon, Salmo salar L. | 2009-11 |
|
| A pan-PPAR ligand induces hepatic fatty acid oxidation in PPARalpha-/- mice possibly through PGC-1 mediated PPARdelta coactivation. | 2009-11 |
|
| Cardiac peroxisome proliferator-activated receptor-alpha activation causes increased fatty acid oxidation, reducing efficiency and post-ischaemic functional loss. | 2009-08-01 |
|
| The absorption, distribution and biological effects of a modified fatty acid in its free form and as an ethyl ester in rats. | 2009-05-15 |
|
| Tetradecylthioacetic acid attenuates dyslipidaemia in male patients with type 2 diabetes mellitus, possibly by dual PPAR-alpha/delta activation and increased mitochondrial fatty acid oxidation. | 2009-04 |
|
| Synthesis and analysis of novel glycerolipids for the treatment of metabolic syndrome. | 2009-02-26 |
|
| Tetradecylthioacetic acid downregulates cyclooxygenase 2 in the renal cortex of two-kidney, one-clip hypertensive rats. | 2008-12 |
|
| Long term treatment with tetradecylthioacetic acid improves the antioxidant status in obese Zucker (fa/fa) rats. | 2008-04 |
|
| Pharmacology and safety of tetradecylthioacetic acid (TTA): phase-1 study. | 2008-04 |
|
| Tetradecylthioacetic acid prevents the inflammatory response in two-kidney, one-clip hypertension. | 2008-02 |
|
| Effect of dietary tetradecylthioacetic acid on colon cancer growth studied by dynamic contrast enhanced MRI. | 2007-11 |
|
| Dose-dependent coronary artery intimal thickening after local delivery of the anti-oxidant tetradecylthioacetic acid from stents. | 2007-11 |
|
| Does the capacity for energy utilization affect the survival of post-smolt Atlantic salmon, Salmo salar L., during natural outbreaks of infectious pancreatic necrosis? | 2007-07 |
|
| Effects of 3-thia fatty acids on expression of some lipid related genes in Atlantic salmon (Salmo salar L.). | 2006-10 |
|
| Causes and prevention of tamoxifen-induced accumulation of triacylglycerol in rat liver. | 2006-10 |
|
| Phospholipid molecular species, beta-oxidation, desaturation and elongation of fatty acids in Atlantic salmon hepatocytes: effects of temperature and 3-thia fatty acids. | 2006-09 |
|
| Differential activation of nuclear receptors by perfluorinated fatty acid analogs and natural fatty acids: a comparison of human, mouse, and rat peroxisome proliferator-activated receptor-alpha, -beta, and -gamma, liver X receptor-beta, and retinoid X receptor-alpha. | 2006-08 |
|
| A bioactively modified fatty acid improves survival and impairs metastasis in preclinical models of acute leukemia. | 2006-06-01 |
|
| PPARalpha activators and fasting induce the expression of adipose differentiation-related protein in liver. | 2006-05 |
|
| The metabolic effects of thia fatty acids in rat liver depend on the position of the sulfur atom. | 2005-06-30 |
|
| Effect of 18:1n-9, 20:5n-3, and 22:6n-3 on lipid accumulation and secretion by Atlantic salmon hepatocytes. | 2005-05 |
|
| The metabolic syndrome and the hepatic fatty acid drainage hypothesis. | 2005-01 |
|
| Effects of 3-thia fatty acids on feed intake, growth, tissue fatty acid composition, beta-oxidation and Na+,K+-ATPase activity in Atlantic salmon. | 2004-12 |
|
| Lipid-lowering and anti-inflammatory effects of tetradecylthioacetic acid in HIV-infected patients on highly active antiretroviral therapy. | 2004-10 |
|
| Evaluation of the therapeutic potential of PPARalpha agonists for X-linked adrenoleukodystrophy. | 2003-12 |
|
| Changed energy state and increased mitochondrial beta-oxidation rate in liver of rats associated with lowered proton electrochemical potential and stimulated uncoupling protein 2 (UCP-2) expression: evidence for peroxisome proliferator-activated receptor-alpha independent induction of UCP-2 expression. | 2003-08-15 |
|
| Mitochondrial-targeted fatty acid analog induces apoptosis with selective loss of mitochondrial glutathione in promyelocytic leukemia cells. | 2003-07 |
|
| Immunomodulating effects of 3-thia fatty acids in activated peripheral blood mononuclear cells. | 2003-05 |
|
| Impact of mitochondrial beta-oxidation in fatty acid-mediated inhibition of glioma cell proliferation. | 2003-01 |
|
| Antiproliferative effects of a non-beta-oxidizable fatty acid, tetradecylthioacetic acid, in native human acute myelogenous leukemia blast cultures. | 2002-11 |
|
| Nuclear import of factors involved in signaling is inhibited in C3H/10T1/2 cells treated with tetradecylthioacetic acid. | 2002-10 |
|
| Metabolic effects of thia fatty acids. | 2002-06 |
|
| Tetradecylthioacetic acid prevents high fat diet induced adiposity and insulin resistance. | 2002-05 |
|
| Inhibition of rat lipoprotein oxidation after tetradecylthioacetic acid feeding. | 2002-03-15 |
|
| Tetradecylthioacetic acid inhibits growth of rat glioma cells ex vivo and in vivo via PPAR-dependent and PPAR-independent pathways. | 2001-11 |
|
| Sustained retention of tetradecylthioacetic acid after local delivery reduces angioplasty-induced coronary stenosis in the minipig. | 2001-11 |
|
| Tetradecylthioacetic acid reduces stenosis development after balloon angioplasty injury of rabbit iliac arteries. | 2001-10 |
|
| Modulation of keratinocyte gene expression and differentiation by PPAR-selective ligands and tetradecylthioacetic acid. | 2001-05 |
|
| Growth reduction in glioma cells after treatment with tetradecylthioacetic acid: changes in fatty acid metabolism and oxidative status. | 2001-03-15 |
|
| Long-term retention of a novel antioxidant sulphur-substituted fatty acid analogue after local delivery in porcine coronary arteries. | 2001-03 |
|
| Transient up-regulation of liver mitochondrial thymidine kinase activity in proliferating mitochondria. | 2001-02 |
|
| Negative regulation of the human apolipoprotein A-I promoter by fibrates can be attenuated by the interaction of the peroxisome proliferator-activated receptor with its response element. | 1994-12-09 |
Patents
Sample Use Guides
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:57:30 GMT 2025
by
admin
on
Mon Mar 31 18:57:30 GMT 2025
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| Record UNII |
7ZU5I25S2O
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| Record Status |
Validated (UNII)
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| Record Version |
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2921-20-2
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DTXSID0040759
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114924
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7ZU5I25S2O
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TETRADECYLTHIOACETIC ACID
Created by
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