TETRADECYLTHIOACETIC ACID

Investigational

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

Structure Search

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)

HIDE SMILES / InChI

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15920037 | https://www.ncbi.nlm.nih.gov/pubmed/21338276 | https://www.ncbi.nlm.nih.gov/pubmed/23266898 | https://www.ncbi.nlm.nih.gov/pubmed/19267708

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

Targets

Primary Target	Pharmacology	Condition	Potency
Peroxisome proliferator-activated receptor alpha 62 Target ID: CHEMBL239 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19267708 \| https://www.ncbi.nlm.nih.gov/pubmed/15920037	Activator 1430
Peroxisome proliferator-activated receptor delta 29 Target ID: CHEMBL3979 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19267708	Activator 1430
Peroxisome proliferator-activated receptor gamma 111 Target ID: CHEMBL235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19267708	Activator 1430

Conditions

Condition	Modality	Highest Phase	Product
Dyslipidemia 30 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19267708	Primary	Phase II 1132	Unknown Approved Use Unknown
Heart failure 103 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23266898	Primary	Preclinical	Unknown Approved Use Unknown
Psoriasis 84 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21338276	Primary	Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
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
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
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
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
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

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P002Y6F	https://www.1pchem.com/search?query=1P002Y6F
A2B Chem	AB36807	http://a2bchem.com/prod/AB36807
AK Scientific	F573	https://aksci.com/item_detail.php?cat=F573
Achemo Scientific Limited	AC-20026	http://www.achemo.com/search/?Keyword=AC-20026
BOC Sciences	2921-20-2	http://www.bocsci.com/description.asp?cas=2921-20-2
Lab Network	LN01312544	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01312544
MolPort	MolPort-003-850-468	https://www.molport.com/shop/molecule-link/MolPort-003-850-468
Tetrahedron	TS57976	http://www.thsci.com/search.do?q=TS57976
Toronto Research Chemicals	T292625	https://www.trc-canada.com/product-detail/?CatNum=T292625
eMolecules	594697	https://orderbb.emolecules.com/search/#?query=594697
mcule	MCULE-6925387619	https://mcule.com/MCULE-6925387619/

PubMed

Title	Date	PubMed
Transient up-regulation of liver mitochondrial thymidine kinase activity in proliferating mitochondria.	2001 Feb	11463171
Tetradecylthioacetic acid reduces stenosis development after balloon angioplasty injury of rabbit iliac arteries.	2001 Oct	11583704
Metabolic effects of thia fatty acids.	2002 Jun	12045400
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 Aug 15	12756242
Evaluation of the therapeutic potential of PPARalpha agonists for X-linked adrenoleukodystrophy.	2003 Dec	14654352
Impact of mitochondrial beta-oxidation in fatty acid-mediated inhibition of glioma cell proliferation.	2003 Jan	12518030
Effect of 18:1n-9, 20:5n-3, and 22:6n-3 on lipid accumulation and secretion by Atlantic salmon hepatocytes.	2005 May	16094857
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 Aug	16731579
A bioactively modified fatty acid improves survival and impairs metastasis in preclinical models of acute leukemia.	2006 Jun 1	16740779
PPARalpha activators and fasting induce the expression of adipose differentiation-related protein in liver.	2006 May	16489205
Dose-dependent coronary artery intimal thickening after local delivery of the anti-oxidant tetradecylthioacetic acid from stents.	2007 Nov	17399716
Long term treatment with tetradecylthioacetic acid improves the antioxidant status in obese Zucker (fa/fa) rats.	2008 Apr	19356083
The absorption, distribution and biological effects of a modified fatty acid in its free form and as an ethyl ester in rats.	2009 May 15	18992229
Lipid-lowering effects of tetradecylthioacetic acid in antipsychotic-exposed, female rats: challenges with long-term treatment.	2012	23226405

Patents

Sample Use Guides

In Vivo Use Guide

1000mg capsules once daily for 28 days

Route of Administration: Oral

In Vitro Use Guide

In cultured human skeletal muscle cells (myotubes), 24-h preincubation with 100 uM of tetradecylthioacetic acid significantly enhanced production of [1-14C]CO2 from oxidation of [1-14C]oleic acid in a dose-responsive manner.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:57:06 GMT 2023` Edited by `admin` on `Fri Dec 15 17:57:06 GMT 2023`
Record UNII	7ZU5I25S2O
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TETRADECYLTHIOACETIC ACID

Systematic Name

English

TTA

Common Name

English

1-(CARBOXYMETHYLTHIO)TETRADECANE

Systematic Name

English

ACETIC ACID, 2-(TETRADECYLTHIO)-

Systematic Name

English

Code System Code Type Description

CAS

2921-20-2