Medium-chain triglyceride

Medium-chain triglycerides (MCTs) are triglycerides whose fatty acids have an aliphatic tail of 6–12 carbon atoms.[1]

The fatty acids found in MCTs are called medium-chain fatty acids (MCFAs). Like all triglycerides, MCTs are composed of a glycerol backbone and three fatty acids. In the case of MCTs, 2 or 3 of the fatty acid chains attached to glycerol are medium-chain in length.

Rich sources for commercial extraction of beneficial MCTs include palm kernel oil and coconut oil.

List of MCFAs

Lipid number Name Salt/Ester Name Formula Mass
(g/mol)		 Appearance Diagram
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, e.g. nonanoic acid, 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 acid (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][7][8] MCTs are also seen as promoting fat oxidation and reduced food intake.[9] Interest in MCTs has been expressed by endurance athletes and the bodybuilding community.[10] While health benefits from MCTs seem to occur, a link to improved exercise performance is weak.[9] 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.[11]

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.[12] However, there is other authority reporting no risk of ketoacidosis or ketonemia with MCTs at levels associated with normal consumption.[13]

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.[14] MCTs are an ingredient in some specialised parenteral nutritional emulsions in some countries (not USA).[15][16] Studies have also shown promising results for epilepsy through the use of ketogenic dieting.[17][18] Select studies have shown promising results for neurodegenerative disorders (e.g. Alzheimer's and Parkinson's diseases)[19] but clinical effectiveness is not yet established.

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.[20]

See also

References

  1. ↑ "Medium chain triglyceride oil consumption as part of a weight loss diet does not lead to an adverse metabolic profile when compared to olive oil". J Am Coll Nutr 27: 547–52. 2008. doi:10.1080/07315724.2008.10719737. PMC 2874191. PMID 18845704.
  2. ↑ "Seizure control by ketogenic diet-associated medium chain fatty acids". 2013. Retrieved 2015-11-25.
  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.
  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.
  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.
  6. ↑ Takeuchi, H; Sekine, S; Kojima, K; Aoyama, T (2008). "The application of medium-chain fatty acids: edible oil with a suppressing effect on body fat accumulation". Asia Pacific journal of clinical nutrition. 17 Suppl 1: 320–3. PMID 18296368.
  7. ↑ 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): 329–32. PMID 11880549.
  8. ↑ Papamandjaris, AA; MacDougall, DE; Jones, PJ (1998). "Medium chain fatty acid metabolism and energy expenditure: obesity treatment implications". Life Sciences 62 (14): 1203–15. doi:10.1016/S0024-3205(97)01143-0. PMID 9570335.
  9. 1 2 Clegg, M. E. (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.
  10. ↑ 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.
  11. ↑ "Influence of the dietary intake of medium chain triglycerides on body composition, energy expenditure and satiety: a systematic review". Nutr Hosp 27: 103–8. 2012. doi:10.1590/S0212-16112012000100011. PMID 22566308.
  12. ↑ 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.
  13. ↑ "Medium-chain triglycerides. Int Dairy J". ResearchGate. Retrieved 2015-10-04.
  14. ↑ 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.
  15. ↑ 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.
  16. ↑ 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.
  17. ↑ 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.
  18. ↑ 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.
  19. ↑ Stafstrom CE, Rho JM (2012). "The ketogenic diet as a treatment paradigm for diverse neurological disorders". Frontiers in Pharmacology 3: Article 59. doi:10.3389/fphar.2012.00059. PMC 3321471. PMID 22509165.
  20. ↑ Akoh, Casimir C. (2006). Handbook of Functional Lipids. Washington, DC: Taylor & Francis. ISBN 0-8493-2162-X.

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 : JMI 54 (3-4): 385–8. PMID 17878693. 
  • Bach André C., Babayan Vigen K (1982). "Medium-chain triglycerides: an update" (PDF). The American Journal of Clinical Nutrition 36 (5): 950–962. PMID 6814231. 
  • Babayan, VK (1987). "Medium chain triglycerides and structured lipids". Lipids 22 (6): 417–20. doi:10.1007/BF02537271. PMID 3112486. 
  • 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. 
  • Medium chain triglycerides - Monograph. "Medium chain triglycerides. Monograph". Alternative Medicine Review 7 (5): 418–20. 2002. PMID 12410626. 
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