Tricaprin

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Tricaprin
Skeletal formula of decanoic acid Tricaprin.png
Skeletal formula of decanoic acid
Names
Preferred IUPAC name
2,3-di(decanoyloxy)propyl decanoate
Other names
Tridecanoin; Glyceryl tricaprate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.009.730 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 210-702-0
PubChem CID
UNII
  • InChI=1S/C33H62O6/c1-4-7-10-13-16-19-22-25-31(34)37-28-30(39-33(36)27-24-21-18-15-12-9-6-3)29-38-32(35)26-23-20-17-14-11-8-5-2/h30H,4-29H2,1-3H3
    Key: LADGBHLMCUINGV-UHFFFAOYSA-N
  • CCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCC)OC(=O)CCCCCCCCC
Properties
C33H62O6
Molar mass 554.853 g·mol−1
AppearanceWhite (light yellow?) crystals [1]
Melting point 31 °C (88 °F; 304 K) [1]
Thermochemistry
1109 J/mol·K [2]
−1985.1 kJ/mol [2]
19861.4 ± 1.8 kJ/mol [2]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Not classified as a hazardous substance
Lethal dose or concentration (LD, LC):
>10 g/kg (mouse, intravenous) [3]
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tricaprin or tridecanoin is a triglyceride of capric acid [4] and a component of MCT oil. [5] Its formula is C33H62O6.

Occurrence

Tricaprin occurs naturally in the seeds of Umbellularia californica , a hardwood tree native to North America. [6]

Production

Tricaprin and other medium-chain triglycerides (MCTs) are either isolated from natural or genetically engineered sources in the production of MCT oils, [5] 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. [7]

Uses

Tricaprin is used as an additive to diesel fuel [8] and as part of current and speculative biodiesels. [9] [10]

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. [11] It, along with other medium-chain triglycerides, has been studied as a treatment option to prevent ruptures of abdominal aortic aneurysm, [12] and has been specifically studied as a regulator of membrane functions [13] and in the heart to facilitate lipolysis. [14]

See also

References

  1. 1 2 "Tricaprin". Sigma-Aldrich. June 18, 2023.
  2. 1 2 3 Decanoic acid, 1,2,3-propanetriyl ester in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD)
  3. ↑ Wretlind A (October 1957). "The toxicity of low-molecular triglycerides". Acta Physiologica Scandinavica. 40 (4): 338–343. doi:10.1111/j.1748-1716.1957.tb01502.x. PMID   13478501.
  4. ↑ Aimo L. "tricaprin (CHEBI:77388)". ChEBI. Retrieved April 12, 2024.
  5. 1 2 Nimbkar S, Leena MM, Moses JA, Anandharamakrishnan C (March 2022). "Medium chain triglycerides (MCT): State-of-the-art on chemistry, synthesis, health benefits and applications in food industry". Comprehensive Reviews in Food Science and Food Safety. 21 (2): 843–867. doi:10.1111/1541-4337.12926. ISSN   1541-4337. PMID   35181994.
  6. ↑ Reynolds T, Dring JV, Hughes C (December 1991). "Lauric acid-containing triglycerides in seeds of umbellularia californica nutt. (Lauraceae)". Journal of the American Oil Chemists' Society. 68 (12): 976–977. doi:10.1007/BF02657546. ISSN   0003-021X.
  7. ↑ Langone MA, Sant'Anna Jr GL (2002). "Process Development For Production Of Medium Chain Triglycerides Using Immobilized Lipase In A Solvent-Free System". Applied Biochemistry and Biotechnology. 98–100 (1–9): 997–1008. doi:10.1385/ABAB:98-100:1-9:997. ISSN   0273-2289. PMID   12018320.
  8. ↑ Eiteman MA, Goodrum JW (1993). "Rheology of the Triglycerides Tricaproin, Tricaprylin, and Tricaprin and of Diesel Fuel". Transactions of the ASAE. 36 (2): 503–507. doi:10.13031/2013.28366. ISSN   2151-0059.
  9. ↑ Goodrum JW, Eiteman MA (April 1996). "Physical properties of low molecular weight triglycerides for the development of bio-diesel fuel models". Bioresource Technology. 56 (1): 55–60. Bibcode:1996BiTec..56...55G. doi:10.1016/0960-8524(95)00167-0.
  10. ↑ Ferreira IM, de Ganzeli L, Rosset IG, Yoshioka SA, Porto AL (January 2017). "Ethylic Biodiesel Production Using Lipase Immobilized in Silk Fibroin-Alginate Spheres by Encapsulation". Catalysis Letters. 147 (1): 269–280. doi:10.1007/s10562-016-1917-0. ISSN   1011-372X.
  11. ↑ "Tricaprin (Code C153424)". NCI Thesaurus. Retrieved April 12, 2024.
  12. ↑ Kugo H, Sugiura Y, Fujishima R, Jo S, Mishima H, Sugamoto E, et al. (April 2023). "Tricaprin can prevent the development of AAA by attenuating aortic degeneration". Biomedicine & Pharmacotherapy. 160: 114299. doi: 10.1016/j.biopha.2023.114299 . PMID   36724640.
  13. ↑ Ro SY, Choi HM, Choi SH, Lee SW, Lim SJ (July 2023). "Tricaprin as a membrane permeability regulator: sustained small hydrophilic substance release from liposomes". Journal of Pharmaceutical Investigation. 53 (4): 539–548. doi:10.1007/s40005-023-00621-2. ISSN   2093-5552.
  14. ↑ Miyauchi H, Hirano KI, Nakano Y, Shimada K, Nishikawa M, Yamamoto H, et al. (2022). "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. doi:10.17996/anc.22-00167. PMC   9749752 . PMID   36540180.
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