Tetradecylthioacetic acid

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−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 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.^[1] In rodent studies, TTA has been reported to have other activities such as reducing inflammation^[2] and preventing high fat diet induced adiposity and insulin resistance.^[3]

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^[4] and another showed that TTA attenuates dyslipidemia in patients with type 2 diabetes mellitus.^[1]

References

^ ^a ^b 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.
^ 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.
^ 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.
^ 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.

[Pmid-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.

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