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Medium-chain triglyceride
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<h2 id="sources-of-mcts">Sources of MCTs</h2> <p>MCTs are found in <a href="/facts/Palm_kernel_oil/sCaLNndQ">palm kernel oil</a> and <a href="/facts/Coconut_oil/mULGkRTS">coconut oil</a> and can be separated by <a href="/facts/Fractionation/85wUlYTN">fractionation</a>.<a class="footnote-ref" id="fnref:1" href="#fn:1"><sup>1</sup></a><a class="footnote-ref" id="fnref:2" href="#fn:2"><sup>2</sup></a> They can also be produced by <a href="/facts/Interesterified_fat/L02ADdq2">interesterification</a>.<a class="footnote-ref" id="fnref:3" href="#fn:3"><sup>3</sup></a> Retail MCT powder is MCT oil embedded in starch and thus contains carbohydrates in addition to fats. It is manufactured by spray drying. </p> <h2 id="list-of-mcfas">List of MCFAs</h2> <table><tbody><tr><th rowspan="2">Lipidnumber</th><th colspan="2">Name</th><th colspan="2">Salt/ester name</th><th colspan="2">Formula</th><th rowspan="2">Mass(g/mol)</th><th rowspan="2">Appearance</th><th rowspan="2">Chemicalstructure</th></tr><tr><th>Common</th><th>Systematic</th><th>Common</th><th>Systematic</th><th>Molecular</th><th>Structural</th></tr><tr><td>C6:0</td><td><a href="/facts/Hexanoic_acid/6oz3f3wK">Caproic acid</a></td><td>Hexanoic acid</td><td>Caproate</td><td>Hexanoate</td><td><a href="/facts/Carbon/ukrgQexo">C</a>6<a href="/facts/Hydrogen/BoYHjl0J">H</a>12<a href="/facts/Oxygen/acyn6o8r">O</a>2</td><td>CH3(CH2)4COOH</td><td>116.16</td><td>Oily liquid</td><td></td></tr><tr><td>C8:0</td><td><a href="/facts/Caprylic_acid/b2VuaggT">Caprylic acid</a></td><td>Octanoic acid</td><td>Caprylate</td><td>Octanoate</td><td>C8H16O2</td><td>CH3(CH2)6COOH</td><td>144.21</td><td>Oily liquid</td><td></td></tr><tr><td>C10:0</td><td><a href="/facts/Decanoic_acid/5R0c0EDl">Capric acid</a></td><td>Decanoic acid</td><td>Caprate</td><td>Decanoate</td><td>C10H20O2</td><td>CH3(CH2)8COOH</td><td>172.26</td><td>White crystals</td><td></td></tr><tr><td>C12:0</td><td><a href="/facts/Lauric_acid/ejIJQaMc">Lauric acid</a></td><td>Dodecanoic acid</td><td>Laurate</td><td>Dodecanoate</td><td>C12H24O2</td><td>CH3(CH2)10COOH</td><td>200.32</td><td>White powder</td><td></td></tr></tbody></table> <p>With regard to MCFAs, apart from the above listed straight chain (unbranched chain) fatty acids, side chain (branched chain) fatty acids also exist.<a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a> </p> <h2 id="applications">Applications</h2> <h3>Calorie restriction</h3> <p>A 2020 <a href="/facts/Systematic_review/dGvq3BGx">systematic review</a> and <a href="/facts/Meta-analysis/IcfChd8z">meta-analysis</a> by <i><a href="/facts/Critical_Reviews_in_Food_Science_and_Nutrition/y0IVjwjV">Critical Reviews in Food Science and Nutrition</a></i> supported evidence that MCT decreases subsequent energy intake compared to Long-Chain Triglycerides (LCTs). Despite this, it does not appear to affect appetite, and thus the authors stated that further research is required to elucidate the mechanism by which this occurs.<a class="footnote-ref" id="fnref:5" href="#fn:5"><sup>5</sup></a> </p> <h3>Dietary relevance</h3> <p>Molecular weight analysis<a class="footnote-ref" id="fnref:6" href="#fn:6"><sup>6</sup></a> of milk from different species showed that while milk fats from all studied species were <i>primarily</i> composed of long-chain fatty acids (16 and 18 carbons long), approximately 10–20% of the fatty acids in milk from <a href="/facts/Horse/uQ3FA0Ak">horses</a>, <a href="/facts/Cow/44qV9B6S">cows</a>, <a href="/facts/Sheep/cjkJyI4f">sheep</a>, and <a href="/facts/Goat/BrsPJmdX">goats</a> were medium-chain fatty acids. </p><p>Some studies have shown that MCTs can help in the process of excess calorie burning, thus weight loss.<a class="footnote-ref" id="fnref:7" href="#fn:7"><sup>7</sup></a><a class="footnote-ref" id="fnref:8" href="#fn:8"><sup>8</sup></a><a class="footnote-ref" id="fnref:9" href="#fn:9"><sup>9</sup></a> MCTs are also seen as promoting fat oxidation and reduced food intake.<a class="footnote-ref" id="fnref:10" href="#fn:10"><sup>10</sup></a> MCTs have been recommended by some endurance athletes and the <a href="/facts/Bodybuilding/Ggt22bNA">bodybuilding</a> community.<a class="footnote-ref" id="fnref:11" href="#fn:11"><sup>11</sup></a> While health benefits from MCTs seem to occur, a link to improved exercise performance is inconclusive.<a class="footnote-ref" id="fnref:12" href="#fn:12"><sup>12</sup></a> 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.<a class="footnote-ref" id="fnref:13" href="#fn:13"><sup>13</sup></a> </p> <h3>Pharmaceutical relevance</h3> <p>MCTs can be used in solutions, liquid suspensions and lipid-based drug delivery systems for emulsions, self-emulsifying drug delivery systems,<a class="footnote-ref" id="fnref:14" href="#fn:14"><sup>14</sup></a> creams, ointments, gels and foams as well as suppositories. MCTs are also suitable for use as solvent and liquid oily lubricant in soft gels. Brand names of pharma-grade MCT include Kollisolv MCT 70.<a class="footnote-ref" id="fnref:15" href="#fn:15"><sup>15</sup></a> </p> <h3>Medical relevance</h3> <p>MCTs passively diffuse from the <a href="/facts/GI_tract/nK2zwqBS">GI tract</a> to the <a href="/facts/Hepatic_portal_system/huzplAIs">hepatic portal system</a> (longer fatty acids are absorbed into the <a href="/facts/Lymphatic_system/yw5QLgMT">lymphatic system</a>) without requirement for modification like <a href="/facts/Long-chain_fatty_acids/JGg3erIu">long-chain fatty acids</a> or very-long-chain fatty acids. In addition, MCTs do not require <a href="/facts/Bile_salt/ojTJzf0c">bile salts</a> for absorption. Patients who have <a href="/facts/Malnutrition/KasQy5MR">malnutrition</a>, <a href="/facts/Malabsorption/hWRQd4c5">malabsorption</a> or particular <a href="/facts/Fatty-acid_metabolism_disorder/cNfAguCH">fatty-acid metabolism disorders</a> are treated with MCTs because MCTs do not require energy for absorption, use, or storage. </p><p>Medium-chain triglycerides are generally considered a good biologically inert source of energy that the <a href="/facts/Human_body/WP1QbDTn">human body</a> 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 <a href="/facts/Ketogenesis/F7uK4uxE">ketogenesis</a> and <a href="/facts/Metabolic_acidosis/sSKCKBHA">metabolic acidosis</a>.<a class="footnote-ref" id="fnref:16" href="#fn:16"><sup>16</sup></a> However, there is other evidence demonstrating no risk of ketoacidosis or ketonemia with MCTs at levels associated with normal consumption,<a class="footnote-ref" id="fnref:17" href="#fn:17"><sup>17</sup></a> and that the moderately elevated blood ketones can be an effective treatment for <a href="/facts/Epilepsy/wawyp56a">epilepsy</a>.<a class="footnote-ref" id="fnref:18" href="#fn:18"><sup>18</sup></a> </p><p>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 <a href="/facts/Low-fat_diet/sFW354vD">low-fat diet</a> has been described as the cornerstone of treatment for <a href="/facts/Waldmann_disease/r6v9RlaV">Waldmann disease</a>.<a class="footnote-ref" id="fnref:19" href="#fn:19"><sup>19</sup></a> MCTs are an ingredient in some specialised <a href="/facts/Parenteral_nutrition/a27wA3AH">parenteral nutritional</a> emulsions in some countries.<a class="footnote-ref" id="fnref:20" href="#fn:20"><sup>20</sup></a><a class="footnote-ref" id="fnref:21" href="#fn:21"><sup>21</sup></a> Studies have also shown promising results for epilepsy through the use of <a href="/facts/Ketogenic_diet/npP2Hl1o">ketogenic dieting</a>.<a class="footnote-ref" id="fnref:22" href="#fn:22"><sup>22</sup></a><a class="footnote-ref" id="fnref:23" href="#fn:23"><sup>23</sup></a><a class="footnote-ref" id="fnref:24" href="#fn:24"><sup>24</sup></a> </p><p>Orally ingested medium chain triglycerides would be very rapidly degraded by first-pass metabolism by being taken up in the liver via the <a href="/facts/Portal_vein/pfyB986q">portal vein</a>, and are quickly metabolized via <a href="/facts/Coenzyme_A/loAfeGpx">coenzyme A</a> intermediates through <a href="/facts/%CE%92-oxidation/mbwIMN7D">β-oxidation</a> and the <a href="/facts/Citric_acid_cycle/EGJL9NXP">citric acid cycle</a> to produce <a href="/facts/Carbon_dioxide/xGzpppEp">carbon dioxide</a>, <a href="/facts/Acetate/U90VVczy">acetate</a> and <a href="/facts/Ketone_bodies/hj1EPGmS">ketone bodies</a>.<a class="footnote-ref" id="fnref:25" href="#fn:25"><sup>25</sup></a> Whether the ketones β-hydroxybutyrate and <a href="/facts/Acetone/cVyJxKqw">acetone</a> have direct antiseizure activity is unclear.<a class="footnote-ref" id="fnref:26" href="#fn:26"><sup>26</sup></a><a class="footnote-ref" id="fnref:27" href="#fn:27"><sup>27</sup></a><a class="footnote-ref" id="fnref:28" href="#fn:28"><sup>28</sup></a><a class="footnote-ref" id="fnref:29" href="#fn:29"><sup>29</sup></a> </p> <h3>Technical uses</h3> <p>MCTs are bland compared to other fats and do not generate off-notes (dissonant tastes) as quickly as LCTs. They are also more <a href="/facts/Chemical_polarity/KlIJ0zjB">polar</a> than LCTs. Because of these attributes, they are widely used as carrier oils or solvents for flavours and oral medicines and vitamins.<a class="footnote-ref" id="fnref:30" href="#fn:30"><sup>30</sup></a> </p> <h2 id="see-also">See also</h2> <ul> <li>Food portal</li><li>Chemistry portal</li></ul> <ul><li><a href="/facts/List_of_carboxylic_acids/aWQBgn3M">List of carboxylic acids</a></li> <li><a href="/facts/Ketogenic_diet/npP2Hl1o">Ketogenic diet</a></li> <li><a href="/facts/List_of_saturated_fatty_acids/qVcDrPvg">List of saturated fatty acids</a></li></ul> <h2 id="further-reading">Further reading</h2> <ul><li>Aoyama T, Nosaka N, Kasai M (August 2007). <a href="https://doi.org/10.2152%2Fjmi.54.385">"Research on the nutritional characteristics of medium-chain fatty acids"</a>. <i>The Journal of Medical Investigation</i>. 54 (3–4): 385–388. <a href="/facts/Doi_(identifier)/muM9Etpq">doi</a>:<a href="https://doi.org/10.2152%2Fjmi.54.385">10.2152/jmi.54.385</a>. <a href="/facts/PMID_(identifier)/JlHAvMHt">PMID</a> <a href="https://pubmed.ncbi.nlm.nih.gov/17878693">17878693</a>. <a href="/facts/S2CID_(identifier)/ldJsHa2Y">S2CID</a> <a href="https://api.semanticscholar.org/CorpusID:905470">905470</a>.</li> <li>Babayan VK (June 1987). "Medium chain triglycerides and structured lipids". <i>Lipids</i>. 22 (6): 417–420. <a href="/facts/Doi_(identifier)/muM9Etpq">doi</a>:<a href="https://doi.org/10.1007%2FBF02537271">10.1007/BF02537271</a>. <a href="/facts/PMID_(identifier)/JlHAvMHt">PMID</a> <a href="https://pubmed.ncbi.nlm.nih.gov/3112486">3112486</a>. <a href="/facts/S2CID_(identifier)/ldJsHa2Y">S2CID</a> <a href="https://api.semanticscholar.org/CorpusID:3942399">3942399</a>.</li> <li>Bach AC, Babayan VK (November 1982). "Medium-chain triglycerides: an update". <i>The American Journal of Clinical Nutrition</i>. 36 (5): 950–962. <a href="/facts/Doi_(identifier)/muM9Etpq">doi</a>:<a href="https://doi.org/10.1093%2Fajcn%2F36.5.950">10.1093/ajcn/36.5.950</a>. <a href="/facts/PMID_(identifier)/JlHAvMHt">PMID</a> <a href="https://pubmed.ncbi.nlm.nih.gov/6814231">6814231</a>.</li> <li>Hayasaka K, Numakura C, Toyota K, Kakizaki S, Watanabe H, Haga H, et al. (2014). <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5121258">"Medium-chain triglyceride supplementation under a low-carbohydrate formula is a promising therapy for adult-onset type II citrullinemia"</a>. <i>Molecular Genetics and Metabolism Reports</i>. 1: 42–50. <a href="/facts/Doi_(identifier)/muM9Etpq">doi</a>:<a href="https://doi.org/10.1016%2Fj.ymgmr.2013.12.002">10.1016/j.ymgmr.2013.12.002</a>. <a href="/facts/PMC_(identifier)/dX1zMt71">PMC</a> <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5121258">5121258</a>. <a href="/facts/PMID_(identifier)/JlHAvMHt">PMID</a> <a href="https://pubmed.ncbi.nlm.nih.gov/27896073">27896073</a>.</li> <li>Heydinger JA, Nakhasi DK (1996). "Medium Chain Triacylglycerols". <i>Journal of Food Lipids</i>. 3 (4): 251–257. <a href="/facts/Doi_(identifier)/muM9Etpq">doi</a>:<a href="https://doi.org/10.1111%2Fj.1745-4522.1996.tb00072.x">10.1111/j.1745-4522.1996.tb00072.x</a>.</li> <li>Kaunitz H (1986). "Medium chain triglycerides (MCT) in aging and arteriosclerosis". <i>Journal of Environmental Pathology, Toxicology and Oncology</i>. 6 (3–4): 115–121. <a href="/facts/PMID_(identifier)/JlHAvMHt">PMID</a> <a href="https://pubmed.ncbi.nlm.nih.gov/3519928">3519928</a>.</li> <li>Labarthe F, Gélinas R, Des Rosiers C (April 2008). "Medium-chain fatty acids as metabolic therapy in cardiac disease". <i>Cardiovascular Drugs and Therapy</i>. 22 (2): 97–106. <a href="/facts/Doi_(identifier)/muM9Etpq">doi</a>:<a href="https://doi.org/10.1007%2Fs10557-008-6084-0">10.1007/s10557-008-6084-0</a>. <a href="/facts/PMID_(identifier)/JlHAvMHt">PMID</a> <a href="https://pubmed.ncbi.nlm.nih.gov/18253821">18253821</a>. <a href="/facts/S2CID_(identifier)/ldJsHa2Y">S2CID</a> <a href="https://api.semanticscholar.org/CorpusID:25297875">25297875</a>.</li> <li>Nagao K, Yanagita T (March 2010). "Medium-chain fatty acids: functional lipids for the prevention and treatment of the metabolic syndrome". <i>Pharmacological Research</i>. 61 (3): 208–212. <a href="/facts/Doi_(identifier)/muM9Etpq">doi</a>:<a href="https://doi.org/10.1016%2Fj.phrs.2009.11.007">10.1016/j.phrs.2009.11.007</a>. <a href="/facts/PMID_(identifier)/JlHAvMHt">PMID</a> <a href="https://pubmed.ncbi.nlm.nih.gov/19931617">19931617</a>.</li></ul> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>Gervajio GC (2005). "Fatty Acids and Derivatives from Coconut Oil". Bailey's Industrial Oil and Fat Products. doi:10.1002/047167849X.bio039. ISBN 978-0471678496. S2CID 98315975. <a href="978-0471678496" target="_blank">978-0471678496</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>Raymond ER, Kent JA (2003). "Soap, Fatty Acids, and Synthetic Detergents". Riegel's Handbook of Industrial Chemistry (10th ed.). Springer. pp. 1100–1117. doi:10.1007/0-387-23816-6_27. ISBN 978-0-387-23816-6. Retrieved 2012-10-20. <a href="978-0-387-23816-6" target="_blank">978-0-387-23816-6</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>Mensink RP, Sanders TA, Baer DJ, Hayes KC, Howles PN, Marangoni A (July 2016). "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. PMC 4942855. PMID 27422506. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4942855" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4942855</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>Chang P, Terbach N, Plant N, Chen PE, Walker MC, Williams RS (June 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. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3625124" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3625124</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>Maher T, Clegg ME (2021). "A systematic review and meta-analysis of medium-chain triglycerides effects on acute satiety and food intake" (PDF). Critical Reviews in Food Science and Nutrition. 61 (4): 636–648. doi:10.1080/10408398.2020.1742654. PMID 32212947. S2CID 214683227. Archived (PDF) from the original on 2021-07-15. Retrieved 2021-06-24. <a href="http://centaur.reading.ac.uk/89667/5/CRIFSAN.%20MCT%20and%20satiety%20-%20A%20systematic%20review%2010.3.20.pdf" target="_blank">http://centaur.reading.ac.uk/89667/5/CRIFSAN.%20MCT%20and%20satiety%20-%20A%20systematic%20review%2010.3.20.pdf</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><p>Breckenridge WC, Kuksis A (September 1967). "Molecular weight distributions of milk fat triglycerides from seven species". Journal of Lipid Research. 8 (5): 473–478. doi:10.1016/S0022-2275(20)38904-5. PMID 6049672. <a href="https://doi.org/10.1016%2FS0022-2275%2820%2938904-5" target="_blank">https://doi.org/10.1016%2FS0022-2275%2820%2938904-5</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> <li id="fn:7"><p>St-Onge MP, Jones PJ (December 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 and Related Metabolic Disorders. 27 (12): 1565–1571. doi:10.1038/sj.ijo.0802467. PMID 12975635. S2CID 21935201. <a href="https://doi.org/10.1038%2Fsj.ijo.0802467" target="_blank">https://doi.org/10.1038%2Fsj.ijo.0802467</a> <a href="#fnref:7" class="footnote-back-ref">↩</a></p></li> <li id="fn:8"><p>Marten B, Pfeuffer M, Schrezenmeir J (2006). "Medium-chain triglycerides". International Dairy Journal. 16 (11): 1374–1382. doi:10.1016/j.idairyj.2006.06.015. PMC 2020023. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2020023" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2020023</a> <a href="#fnref:8" class="footnote-back-ref">↩</a></p></li> <li id="fn:9"><p>St-Onge MP, Jones PJ (March 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. <a href="https://doi.org/10.1093%2Fjn%2F132.3.329" target="_blank">https://doi.org/10.1093%2Fjn%2F132.3.329</a> <a href="#fnref:9" class="footnote-back-ref">↩</a></p></li> <li id="fn:10"><p>Clegg ME (November 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. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:10" class="footnote-back-ref">↩</a></p></li> <li id="fn:11"><p>Talbott, Shawn M., Hughes, Kerry (2006). The Health Professional's Guide to Dietary Supplements. Lippincott Williams & Wilkins. pp. 60–63. ISBN 978-0781746724. <a href="978-0781746724" target="_blank">978-0781746724</a> <a href="#fnref:11" class="footnote-back-ref">↩</a></p></li> <li id="fn:12"><p>Clegg ME (November 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. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:12" class="footnote-back-ref">↩</a></p></li> <li id="fn:13"><p>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". Nutricion Hospitalaria. 27 (1): 103–108. doi:10.3305/nh.2012.27.1.5369. PMID 22566308. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:13" class="footnote-back-ref">↩</a></p></li> <li id="fn:14"><p>Banov D, Liu Y, Ip K, Shan A, Vu C, Zdoryk O, et al. (November 2023). 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