Misplaced Pages

Tetradecylthioacetic acid

Names
Preferred IUPAC name (Tetradecylsulfanyl)acetic acid
Other names 1-(Carboxymethylthio)tetradecane
Identifiers
CAS Number	2921-20-2
3D model (JSmol)	Interactive image
Abbreviations	TTA; CMTD
ChemSpider	102869
PubChem CID	114924
UNII	7ZU5I25S2O
CompTox Dashboard (EPA)	DTXSID0040759
InChI 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)Key: IPBCWPPBAWQYOO-UHFFFAOYSA-N 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)Key: IPBCWPPBAWQYOO-UHFFFAOYAU
SMILES O=C(O)CSCCCCCCCCCCCCCC
Properties
Chemical formula	C16H32O2S
Molar mass	288.49 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Tetradecylthioacetic acid (TTA) is a synthetic fatty acid used as a nutritional supplement.

TTA acts as a peroxisome proliferator-activated receptor alpha (PPARα) agonist and increases mitochondrial fatty acid oxidation in vitro. In rodent studies, TTA has been reported to have other activities such as reducing inflammation and preventing high fat diet induced adiposity and insulin resistance.

In human clinical study, there have been mixed observations in preliminary studies. One Phase I study showed no significant changes in the blood lipids or free fatty acids and another showed that TTA attenuates dyslipidemia in patients with type 2 diabetes mellitus.

References

1. ^ Løvås, K; Røst, TH; Skorve, J; Ulvik, RJ; Gudbrandsen, OA; Bohov, P; Wensaas, AJ; Rustan, AC; et al. (2009). "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". Diabetes, Obesity & Metabolism. 11 (4): 304–14. doi:10.1111/j.1463-1326.2008.00958.x. PMID 19267708. S2CID 22883377.
2. Bjørndal, B; Grimstad, T; Cacabelos, D; Nylund, K; Aasprong, OG; Omdal, R; Portero-Otin, M; Pamplona, R; Lied, GA; Hausken, Trygve; Berge, Rolf K. (2012). "Tetradecylthioacetic Acid Attenuates Inflammation and Has Antioxidative Potential During Experimental Colitis in Rats". Digestive Diseases and Sciences. 58 (1): 97–106. doi:10.1007/s10620-012-2321-2. hdl:1956/6530. PMID 22855292. S2CID 1539648.
3. Madsen, L; Guerre-Millo, M; Flindt, EN; Berge, K; Tronstad, KJ; Bergene, E; Sebokova, E; Rustan, AC; et al. (2002). "Tetradecylthioacetic acid prevents high fat diet induced adiposity and insulin resistance". Journal of Lipid Research. 43 (5): 742–50. doi:10.1016/S0022-2275(20)30116-4. PMID 11971945.
4. Pettersen, RJ; Salem, M; Skorve, J; Ulvik, RJ; Berge, RK; Nordrehaug, JE (2008). "Pharmacology and safety of tetradecylthioacetic acid (TTA): Phase-1 study". Journal of Cardiovascular Pharmacology. 51 (4): 410–7. doi:10.1097/FJC.0b013e3181673be0. PMID 18427285. S2CID 13784863.

• Fatty acids
• Thioethers
• PPAR agonists