Medium-chain triglyceride

Medium-chain triglycerides (MCTs) are triglycerides with two or three fatty acids having an aliphatic tail of 6–12 carbon atoms, i.e., medium-chain fatty acids (MCFAs). Rich food sources for commercial extraction of MCTs include palm kernel oil and coconut oil.

Typical example of a medium-chain triglyceride, containing three medium chain fatty acids (Caprylic acid in blue and Capric acid in red)

Sources of MCTs

MCTs are found in palm kernel oil and coconut oil and can be separated by fractionation. They can also be produced by interesterification.[1]

List of MCFAs
Lipid number Name Salt/ester name Formula Mass
(g/mol)		 Appearance Chemical structure
Common Systematic Common Systematic Molecular Structural
C6:0 Caproic acid Hexanoic acid Caproate Hexanoate C6H12O2 CH3(CH2)4COOH 116.16 Oily liquid
C8:0 Caprylic acid Octanoic acid Caprylate Octanoate C8H16O2 CH3(CH2)6COOH 144.21 Oily liquid
C10:0 Capric acid Decanoic acid Caprate Decanoate C10H20O2 CH3(CH2)8COOH 172.26 White crystals
C12:0 Lauric acid Dodecanoic acid Laurate Dodecanoate C12H24O2 CH3(CH2)10COOH 200.32 White powder

With regard to MCFAs, apart from the above listed straight chain (unbranched chain) fatty acids, side chain (branched chain) fatty acids also exist.[2]

Applications

Dietary relevance

Molecular weight analysis[3] of milk from different species showed that while milk fats from all studied species were primarily composed of long-chain fatty acids (16 and 18 carbons long), approximately 10–20% of the fatty acids in milk from horses, cows, sheep, and goats were medium-chain fatty acids.

Some studies have shown that MCTs can help in the process of excess calorie burning, thus weight loss.[4][5][6] MCTs are also seen as promoting fat oxidation and reduced food intake.[7] MCTs have been recommended by some endurance athletes and the bodybuilding community.[8] While health benefits from MCTs seem to occur, a link to improved exercise performance is inconclusive.[7] A number of studies back the use of MCT oil as a weight loss supplement, but these claims are not without conflict, as about an equal number found inconclusive results.[9]

Medical relevance

MCTs passively diffuse from the GI tract to the portal system (longer fatty acids are absorbed into the lymphatic system) without requirement for modification like long-chain fatty acids or very-long-chain fatty acids. In addition, MCTs do not require bile salts for digestion. Patients who have malnutrition, malabsorption or particular fatty-acid metabolism disorders are treated with MCTs because MCTs do not require energy for absorption, use, or storage.

Medium-chain triglycerides are generally considered a good biologically inert source of energy that the human body finds reasonably easy to metabolize. They have potentially beneficial attributes in protein metabolism, but may be contraindicated in some situations due to a reported tendency to induce ketogenesis and metabolic acidosis.[10] However, there is other evidence demonstrating no risk of ketoacidosis or ketonemia with MCTs at levels associated with normal consumption,[5] and that the moderately elevated blood ketones can be an effective treatment for epilepsy.[11]

Due to their ability to be absorbed rapidly by the body, medium-chain triglycerides have found use in the treatment of a variety of malabsorption ailments. MCT supplementation with a low-fat diet has been described as the cornerstone of treatment for Waldmann disease.[12] MCTs are an ingredient in some specialised parenteral nutritional emulsions in some countries.[13][14] Studies have also shown promising results for epilepsy through the use of ketogenic dieting.[11][15][16]

Technical uses

MCTs are bland compared to other fats and do not generate off-notes (dissonant tastes) as quickly as LCTs. They are also more polar than LCTs. Because of these attributes, they are widely used as solvents for flavours and oral medicines and vitamins.[17]

gollark: I wonder how many dark gods I'll end up invoking if I try and patch this *myself*.
gollark: Firefox actually supports HTTP/3 if you enable seeecret config options.
gollark: Due to current limitations of the highly experimental nginx build I use, I can't offer HTTP/3 on any osmarks.net subdomains.
gollark: Yes.
gollark: It's *basically* just HTTP/2 over QUIC.

See also

References
  1. Mensink, Ronald P.; Sanders, Thomas A.; Baer, David J.; Hayes, K. C.; Howles, Philip N.; Marangoni, Alejandro (2016-07-01). "The Increasing Use of Interesterified Lipids in the Food Supply and Their Effects on Health Parameters". Advances in Nutrition. 7 (4): 719–729. doi:10.3945/an.115.009662. ISSN 2161-8313. PMC 4942855. PMID 27422506.
  2. Chang, P.; Terbach, N.; Plant, N.; Chen, P. E.; Walker, M. C.; Williams, R. S. (2013). "Seizure control by ketogenic diet-associated medium chain fatty acids". Neuropharmacology. 69: 105–114. doi:10.1016/j.neuropharm.2012.11.004. PMC 3625124. PMID 23177536.
  3. Breckenridge, W. C.; Kuksis, A. (September 1967). "Molecular weight distributions of milk fat triglycerides from seven species". Journal of Lipid Research. 8 (5): 473–8. PMID 6049672.
  4. M-P. St-Onge; P.J.H. Jones (2003). "Greater rise in fat oxidation with medium-chain triglyceride consumption relative to long-chain triglyceride is associated with lower initial body weight and greater loss of subcutaneous adipose tissue". International Journal of Obesity. 27 (12): 1565–1571. doi:10.1038/sj.ijo.0802467. PMID 12975635. S2CID 21935201.
  5. B. Martena; M. Pfeuffer; J. Schrezenmeir (2006). "Medium-chain triglycerides". International Dairy Journal. 16 (11): 1374–1382. doi:10.1016/j.idairyj.2006.06.015. PMC 2020023.
  6. St-Onge, MP; Jones, PJ (2002). "Physiological effects of medium-chain triglycerides: potential agents in the prevention of obesity". The Journal of Nutrition. 132 (3): 329–332. doi:10.1093/jn/132.3.329. PMID 11880549.
  7. Clegg, ME (2010). "Medium-chain triglycerides are advantageous in promoting weight loss although not beneficial to exercise performance". International Journal of Food Sciences and Nutrition. 61 (7): 653–679. doi:10.3109/09637481003702114. PMID 20367215. S2CID 6128370.
  8. Talbott, Shawn M. and Kerry Hughes. (2006). The Health Professional's Guide to Dietary Supplements. Lippincott Williams & Wilkins. pp. 60–63. ISBN 978-0-7817-4672-4.
  9. Rego Costa, AC; Rosado, EL; Soares-Mota, M (2012). "Influence of the dietary intake of medium chain triglycerides on body composition, energy expenditure and satiety: a systematic review". Nutr Hosp. 27 (1): 103–138. doi:10.3305/nh.2012.27.1.5369. PMID 22566308.
  10. Wanten, GJ; Naber, AH (2004). "Cellular and physiological effects of medium-chain triglycerides". Mini Reviews in Medicinal Chemistry. 4 (8): 847–57. doi:10.2174/1389557043403503. PMID 15544546.
  11. Chang P, Terbach N, Plant N, Chen PE, Walker MC, Williams RS (2013). "Seizure control by ketogenic diet-associated medium chain fatty acids". Neuropharmacology. 69: 105–114. doi:10.1016/j.neuropharm.2012.11.004. PMC 3625124. PMID 23177536.
  12. Vignes, S.; Bellanger, J. (Feb 2008). "Primary intestinal lymphangiectasia (Waldmann's disease)". Orphanet Journal of Rare Diseases (Free full text). 3: 5. doi:10.1186/1750-1172-3-5. PMC 2288596. PMID 18294365.
  13. Waitzberg, D. L.; Torrinhas, R. S.; Jacintho, T. M. (July–August 2006). "New parenteral lipid emulsions for clinical use". Journal of Parenteral and Enteral Nutrition. 30 (4): 351–367. doi:10.1177/0148607106030004351. PMID 16804134. S2CID 24109426.
  14. Krohn, K.; Koletzko, B. (2006). "Parenteral lipid emulsions in paediatrics". Current Opinion in Clinical Nutrition and Metabolic Care. 9 (3): 319–323. doi:10.1097/01.mco.0000222118.76536.ad. PMID 16607135. S2CID 27961868.
  15. Neal, E. G.; Cross, J. H. (2010). "Efficacy of dietary treatments for epilepsy". Journal of Human Nutrition and Dietetics. 23 (2): 113–119. doi:10.1111/j.1365-277X.2010.01043.x. PMID 20487176.
  16. Liu, Y. M. C. (2008). "Medium-chain triglyceride (MCT) ketogenic therapy". Epilepsia. 49: 33–36. doi:10.1111/j.1528-1167.2008.01830.x. PMID 19049583.
  17. Akoh, Casimir C. (2006). Handbook of Functional Lipids. Washington, DC: Taylor & Francis. ISBN 978-0-8493-2162-7.

Further reading
  • Nagao, K.; Yanagita, T. (2010). "Medium-chain fatty acids: Functional lipids for the prevention and treatment of the metabolic syndrome". Pharmacological Research. 61 (3): 208–212. doi:10.1016/j.phrs.2009.11.007. PMID 19931617.
  • Aoyama, T; Nosaka, N; Kasai, M (2007). "Research on the nutritional characteristics of medium-chain fatty acids". The Journal of Medical Investigation. 54 (3–4): 385–8. doi:10.2152/jmi.54.385. PMID 17878693. S2CID 905470.
  • Bach André C.; Babayan Vigen K (1982). "Medium-chain triglycerides: an update". The American Journal of Clinical Nutrition. 36 (5): 950–962. doi:10.1093/ajcn/36.5.950. PMID 6814231.
  • Babayan, VK (1987). "Medium chain triglycerides and structured lipids". Lipids. 22 (6): 417–20. doi:10.1007/BF02537271. PMID 3112486. S2CID 3942399.
  • Heydinger, Jenifer A., Dilip K. Nakhasi (1996). "Medium Chain Triacylglycerols". Journal of Food Lipids. 3 (4): 251–257. doi:10.1111/j.1745-4522.1996.tb00072.x.
  • Kaunitz, H. (1986). "Medium chain triglycerides (MCT) in aging and arteriosclerosis". Journal of Environmental Pathology, Toxicology and Oncology. 6 (3–4): 115–121. PMID 3519928.
  • Labarthe, F. O.; Gélinas, R.; Des Rosiers, C. (2008). "Medium-chain Fatty Acids as Metabolic Therapy in Cardiac Disease". Cardiovascular Drugs and Therapy. 22 (2): 97–106. doi:10.1007/s10557-008-6084-0. PMID 18253821. S2CID 25297875.
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