Trilaurin

Trilaurin (CAS No. 538-24-9) is a long-chain triacylglycerol (fatty acid side-chain carbon number C12), with core biological functions spanning multiple application areas: as a cosmetic ingredient, it provides skin conditioning and thickening effects; as a substrate for biocatalytic synthesis, it is used to prepare fatty amine compounds such as laurylamine; as a lipid excipient for solid lipid microparticles (SLM), it is used for oral delivery of peptide/protein drugs (e.g., desmopressin) by modulating drug release rate and protecting the drug from α-chymotrypsin-mediated degradation, thereby improving bioavailability; it can also serve as a component of lipid nanoparticles (LNP), contributing to the construction of an oral targeted drug delivery system for colorectal cancer, carrying cisplatin and superparamagnetic iron oxide nanoparticles (SPIONs) to achieve combined chemotherapy and magnetic hyperthermia therapy.

In animal modeling, it has both supportive research and model-treatment applications: in a mouse fluorescein isothiocyanate (FITC)-induced contact hypersensitivity (CHS) model, it is used as a control component (2% concentration, administered transdermally) and does not enhance skin sensitization responses; in a CT26 orthotopic colorectal cancer mouse model, it serves as an LNP carrier component involved in tumor-targeted therapy.

Common applications and concentrations: 0.2%-46% in cosmetics; in biocatalytic synthesis, an in vitro reaction concentration of 2 mM (with enzyme preparations such as lipase, reacted at 30℃ for 20 hours); in drug delivery systems, during SLM preparation it can be mixed with other triglycerides (e.g., TG16) at different ratios (20:80 to 80:20), and in LNP preparation the amount used is 18 mg / batch; in animal experiments, in the colorectal cancer model it is administered orally via a microgel formulation containing this component (drug loading corresponding to cisplatin 5 mg/kg/ day); clinically, there is no clearly defined application concentration, and in nutritional management for patients with chyle leakage it may be used as an adjunct component of a low-fat diet (no specific concentration standard).

Concentrations related to effective effects: in biocatalytic synthesis, a 2 mM concentration can achieve an 89% analytical yield for laurylamine preparation; in drug delivery, SLM mixed with TG16 can improve desmopressin bioavailability, and in colorectal cancer treatment, an LNP microgel formulation containing this component, after oral administration, releases the drug in the colon via dextranase degradation, significantly inhibiting tumor growth and peritoneal metastasis.

References:

[1] Christophersen PC, Zhang L, Müllertz A, Nielsen HM, Yang M, Mu H. Solid lipid particles for oral delivery of peptide and protein drugs II--the digestion of trilaurin protects desmopressin from proteolytic degradation. Pharm Res. 2014 Sep;31(9):2420-8. doi: 10.1007/s11095-014-1337-z. Epub 2014 Mar 13. PMID: 24623481.

[2] Steven BR, Carey S. Nutritional management in patients with chyle leakage: a systematic review. Eur J Clin Nutr. 2015 Jul;69(7):776-80. doi: 10.1038/ejcn.2015.48. Epub 2015 Apr 29. PMID: 25920423.

[3] Citoler J, Finnigan W, Bevinakatti H, Turner NJ. Direct Enzymatic Synthesis of Fatty Amines from Renewable Triglycerides and Oils. Chembiochem. 2022 Jan 19;23(2):e202100578. doi: 10.1002/cbic.202100578. Epub 2021 Nov 23. PMID: 34726829.

[4] Lu IL, Yu TW, Liu TI, Chen HH, Yang YC, Lo CL, Wang CY, Chiu HC. Microfluidized Dextran Microgels Loaded with Cisplatin/SPION Lipid Nanotherapeutics for Local Colon Cancer Treatment via Oral Administration. Adv Healthc Mater. 2022 Oct;11(20):e2201140. doi: 10.1002/adhm.202201140. Epub 2022 Aug 15. PMID: 35881562.

[5] Orii A, Kurohane K, Sekiguchi K, Tsutsumi M, Imai Y. Comparison of adjuvant mechanisms of medium-chain triacylglycerol in a mouse FITC-induced contact hypersensitivity model. Toxicology. 2023 Apr;488:153482. doi: 10.1016/j.tox.2023.153482. Epub 2023 Mar 2. PMID: 36870414.