Chemistry:Tricaprin

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Tricaprin or tridecanoin is a triglyceride of capric acid[1] and a component of MCT oil.[2] Its formula is C
33H
62O
6.

Occurrence

Tricaprin occurs naturally in the seeds of Umbellularia californica, a hardwood tree native to North America.[3]

Production

Tricaprin and other medium-chain triglycerides (MCTs) are either isolated from natural or genetically engineered sources in the production of MCT oils,[2] or are synthesized on a large scale through the esterification of medium-chain fatty acids with glycerol, specifically capric acid in the case of tricaprin. These esterification reactions have been investigated with a focus on enzyme catalysis as an alternative to traditional manufacturing processes that take place at high temperature and pressure, which result in poorer quality product at low yield. Compared to similar reactions used in the synthesis of other MCTs, tricaprin has a slow conversion rate from capric acid in the presence of lipozyme.[4]

Uses

Tricaprin is used as an additive to diesel fuel[5] and as part of current and speculative biodiesels.[6][7]

Pharmacological

Tricaprin has been indicated as a possible drug to increase the production of insulin and decrease the production of androgen in the body when taken orally.[8] It, along with other medium-chain triglycerides, has been studied as a treatment option to prevent ruptures of abdominal aortic aneurysm,[9] and has been specifically studied as a regulator of membrane functions[10] and in the heart to facilitate lipolysis.[11]

See also

  • Tributyrin
  • Tricaprylin

References

  1. ↑ "tricaprin (CHEBI:77388)". https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:77388. 
  2. ↑ 2.0 2.1 Nimbkar, Shubham; Leena, M. Maria; Moses, J. A.; Anandharamakrishnan, C. (March 2022). "Medium chain triglycerides (MCT): State-of-the-art on chemistry, synthesis, health benefits and applications in food industry" (in en). Comprehensive Reviews in Food Science and Food Safety 21 (2): 843–867. doi:10.1111/1541-4337.12926. ISSN 1541-4337. PMID 35181994. https://ift.onlinelibrary.wiley.com/doi/10.1111/1541-4337.12926. 
  3. ↑ "Lauric acid-containing triglycerides in seeds of umbellularia californica nutt. (Lauraceae)" (in en). Journal of the American Oil Chemists' Society 68 (12): 976–977. December 1991. doi:10.1007/BF02657546. ISSN 0003-021X. https://aocs.onlinelibrary.wiley.com/doi/10.1007/BF02657546. 
  4. ↑ Langone, Marta A. P.; Sant'Anna Jr., Geraldo L (2002). "Process Development For Production Of Medium Chain Triglycerides Using Immobilized Lipase In A Solvent-Free System" (in en). Applied Biochemistry and Biotechnology 98-100 (1–9): 997–1008. doi:10.1385/ABAB:98-100:1-9:997. ISSN 0273-2289. PMID 12018320. http://link.springer.com/10.1385/ABAB:98-100:1-9:997. 
  5. ↑ "Rheology of the Triglycerides Tricaproin, Tricaprylin, and Tricaprin and of Diesel Fuel" (in en). Transactions of the ASAE 36 (2): 503–507. 1993. doi:10.13031/2013.28366. ISSN 2151-0059. http://elibrary.asabe.org/abstract.asp??JID=3&AID=28366&CID=t1993&v=36&i=2&T=1. 
  6. ↑ "Physical properties of low molecular weight triglycerides for the development of bio-diesel fuel models" (in en). Bioresource Technology 56 (1): 55–60. April 1996. doi:10.1016/0960-8524(95)00167-0. Bibcode: 1996BiTec..56...55G. 
  7. ↑ "Ethylic Biodiesel Production Using Lipase Immobilized in Silk Fibroin-Alginate Spheres by Encapsulation" (in en). Catalysis Letters 147 (1): 269–280. January 2017. doi:10.1007/s10562-016-1917-0. ISSN 1011-372X. 
  8. ↑ "Tricaprin (Code C153424)". https://evsexplore.semantics.cancer.gov/evsexplore/concept/ncit/C153424. 
  9. ↑ "Tricaprin can prevent the development of AAA by attenuating aortic degeneration". Biomedicine & Pharmacotherapy 160. April 2023. doi:10.1016/j.biopha.2023.114299. PMID 36724640. 
  10. ↑ "Tricaprin as a membrane permeability regulator: sustained small hydrophilic substance release from liposomes" (in en). Journal of Pharmaceutical Investigation 53 (4): 539–548. July 2023. doi:10.1007/s40005-023-00621-2. ISSN 2093-5552. 
  11. ↑ "123I-BMIPP Scintigraphy Shows That CNT-01 (Tricaprin) Improves Myocardial Lipolysis in Patients with Idiopathic Triglyceride Deposit Cardiomyovasculopathy: First Randomized Controlled, Exploratory Trial for TGCV". Annals of Nuclear Cardiology 8 (1): 67–75. 2022. doi:10.17996/anc.22-00167. PMID 36540180. 



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