Tetradecylthioacetic acid
Names | |
---|---|
Preferred IUPAC name (Tetradecylsulfanyl)acetic acid | |
Other names 1-(Carboxymethylthio)tetradecane | |
Identifiers | |
CAS Number |
|
3D model (JSmol) |
|
Abbreviations | TTA; CMTD |
ChemSpider |
|
PubChem CID |
|
UNII |
|
CompTox Dashboard (EPA) |
|
InChI
| |
| |
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 |
Chemical compound
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.
- v
- t
- e
- Propionic (C3)
- Butyric (C4)
- Valeric (C5)
- Caproic (C6)
- Enanthic (C7)
- Caprylic (C8)
- Pelargonic (C9)
- Capric (C10)
- Undecylic (C11)
- Lauric (C12)
- Tridecylic (C13)
- Myristic (C14)
- Pentadecylic (C15)
- Palmitic (C16)
- Margaric (C17)
- Stearic (C18)
- Nonadecylic (C19)
- Arachidic (C20)
- Heneicosylic (C21)
- Behenic (C22)
- Tricosylic (C23)
- Lignoceric (C24)
- Pentacosylic (C25)
- Cerotic (C26)
- Carboceric (C27)
- Montanic (C28)
- Nonacosylic (C29)
- Melissic (C30)
- Hentriacontylic (C31)
- Lacceroic (C32)
- Psyllic (C33)
- Geddic (C34)
- Ceroplastic (C35)
- Hexatriacontylic (C36)
- Heptatriacontanoic (C37)
- Octatriacontanoic (C38)
- Nonatriacontanoic (C39)
- Tetracontanoic (C40)
- Octenoic (8:1)
- Decenoic (10:1)
- Decadienoic (10:2)
- Lauroleic (12:1)
- Laurolinoleic (12:2)
- Myristovaccenic (14:1)
- Myristolinoleic (14:2)
- Myristolinolenic (14:3)
- Palmitolinolenic (16:3)
- Palmitidonic (16:4)
- α-Linolenic (18:3)
- Stearidonic (18:4)
- α-Parinaric (18:4)
- Dihomo-α-linolenic (20:3)
- Eicosatetraenoic (20:4)
- Eicosapentaenoic (20:5)
- Clupanodonic (22:5)
- Docosahexaenoic (22:6)
- 9,12,15,18,21-Tetracosapentaenoic (24:5)
- 6,9,12,15,18,21-Tetracosahexaenoic (24:6)
- Myristoleic (14:1)
- Palmitovaccenic (16:1)
- α-Eleostearic (18:3)
- β-Eleostearic (trans-18:3)
- Punicic (18:3)
- 7,10,13-Octadecatrienoic (18:3)
- 9,12,15-Eicosatrienoic (20:3)
- β-Eicosatetraenoic (20:4)
- 8-Tetradecenoic (14:1)
- 12-Octadecenoic (18:1)
- Linoleic (18:2)
- Linolelaidic (trans-18:2)
- γ-Linolenic (18:3)
- Calendic (18:3)
- Pinolenic (18:3)
- Dihomo-linoleic (20:2)
- Dihomo-γ-linolenic (20:3)
- Sciadonic (20:3)
- Arachidonic (20:4)
- Adrenic (22:4)
- Osbond (22:5)
- Palmitoleic (16:1)
- Vaccenic (18:1)
- Rumenic (18:2)
- Paullinic (20:1)
- 7,10,13-Eicosatrienoic (20:3)
- Sapienic (16:1)
- Gadoleic (20:1)
- 4-Hexadecenoic (16:1)
- Petroselinic (18:1)
- 8-Eicosenoic (20:1)