Tetradecylthioacetic acid

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

Tetradecylthioacetic acid
Names
Preferred IUPAC name
(Tetradecylsulfanyl)acetic acid
Other names
1-(Carboxymethylthio)tetradecane
Identifiers
3D model (JSmol)
Abbreviations TTA; CMTD
ChemSpider
UNII
  • 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
  • O=C(O)CSCCCCCCCCCCCCCC
Properties
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).

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

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  1. ^ 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.
  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.