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Chemical Compound Review

Caprylin     2,3-dioctanoyloxypropyl octanoate

Synonyms: Maceight, Axona, Tricaprilin, Tricaprylin, Trioctanoin, ...
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Disease relevance of Maceight


High impact information on Maceight


Chemical compound and disease context of Maceight


Biological context of Maceight


Anatomical context of Maceight

  • Extensive symplasma formation in the uterine epithelium of the tricaprylin-treated segments was observed on Days 2 and 3; this had degenerated by Day 4 and was absent by Day 6 [16].
  • Compared with the solvent control group (trioctanoin), both NNN and NNK induced significant numbers of tumors of the nasal cavity (P less than 0.01) at all three dose levels in both male and female rats [17].
  • Mice given 10-weekly injections (i.m.) of 20 mumol of isopropyl methanesulfonate (IPMS) in trioctanoin exhibited depressed hematopoiesis as manifested by reduced peripheral blood counts and by reduced thymic and bone marrow cellularities [18].
  • Racemic 7,t-8-dihydroxy-t-9,10-epoxy-7,8,9,10-tetrahydro-benzo[a]pyrene ((+/-)-anti-BPDE) modified DNA samples were produced in vitro, by reacting (+/-)-anti-BPDE with calf thymus DNA, and in vivo in Swiss female mice by single i.p. injection of benzo[a]pyrene (B[a]P) (200 mg/kg body weight dissolved in tricaprylin) [19].
  • Subcutaneous injections of Tricaprylin in rats over a period of 5 weeks caused a granulomatous reaction characterized by oil deposits surrounded by macrophages [20].

Associations of Maceight with other chemical compounds


Gene context of Maceight

  • Recombinant human HSL also hydrolyzes insoluble medium- and long-chain acylglycerols such as trioctanoylglycerol, dioleoylglycerol, and olive oil, and can therefore be classified as a true lipase [26].
  • Orally ingested glyceryl trioctanoate, a medium-chain triacylglyceride rich in milk lipids, significantly increased the level of n-octanoyl-modified ghrelin in murine stomach [27].
  • Line widths of trioctanoin surface peaks were half that of LCT, and relaxation times, T1, were also shorter for trioctanoin, showing greater mobility for MCT in phospholipid [28].
  • At all time points, chicks fed the diet containing LCT had significantly lower plasma CCK concentrations than those fed MCT, and chicks fed glyceryl tricaprate had higher concentrations than those fed glyceryl tricaprylate [29].
  • The mean +/- SD PDR of 13C from trioctanoin was 36.3 +/- 8.4% for FBM and 34.6 +/- 6.3% for HBM (NS) [30].

Analytical, diagnostic and therapeutic context of Maceight


  1. Cytotoxic carcinogeneic response to monocrotaline pyrrole. Hooson, J., Grasso, P. J. Pathol. (1976) [Pubmed]
  2. Dibenzo[a,l]pyrene-induced DNA adduction, tumorigenicity, and Ki-ras oncogene mutations in strain A/J mouse lung. Prahalad, A.K., Ross, J.A., Nelson, G.B., Roop, B.C., King, L.C., Nesnow, S., Mass, M.J. Carcinogenesis (1997) [Pubmed]
  3. Interstrain differences in susceptibility to liver carcinogenesis initiated by N-nitrosodiethylamine and its promotion by phenobarbital in C57BL/6NCr, C3H/HeNCrMTV- and DBA/2NCr mice. Diwan, B.A., Rice, J.M., Ohshima, M., Ward, J.M. Carcinogenesis (1986) [Pubmed]
  4. Comparative tumorigenicity of benzo[a]pyrene, 1-nitropyrene and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine administered by gavage to female CD rats. el-Bayoumy, K., Chae, Y.H., Upadhyaya, P., Rivenson, A., Kurtzke, C., Reddy, B., Hecht, S.S. Carcinogenesis (1995) [Pubmed]
  5. Transplacental teratogenic and carcinogenic effects in rabbits chronically treated with N-ethyl-N-nitrosourea. Fox, R.R., Meier, H., Pottathil, R., Bedigian, H.G. J. Natl. Cancer Inst. (1980) [Pubmed]
  6. Triolein breath test: a sensitive and specific test for fat malabsorption. Newcomer, A.D., Hofmann, A.F., DiMagno, E.P., Thomas, P.J., Carlson, G.L. Gastroenterology (1979) [Pubmed]
  7. Changes in the host lymphocyte subsets during chemical carcinogenesis. Brodt, P., Lala, P.K. Cancer Res. (1983) [Pubmed]
  8. Stereoselectivity of lipases. II. Stereoselective hydrolysis of triglycerides by gastric and pancreatic lipases. Rogalska, E., Ransac, S., Verger, R. J. Biol. Chem. (1990) [Pubmed]
  9. Coconut oil and beef tallow, but not tricaprylin, can replace menhaden oil in the diet of red drum (Sciaenops ocellatus) without adversely affecting growth or fatty acid composition. Craig, S.R., Gatlin, D.M. J. Nutr. (1995) [Pubmed]
  10. Review of the toxicologic properties of medium-chain triglycerides. Traul, K.A., Driedger, A., Ingle, D.L., Nakhasi, D. Food Chem. Toxicol. (2000) [Pubmed]
  11. Transplacental induction of primary renal tumors in rabbits treated with 1-ethyl-1-nitrosourea. Fox, R.R., Diwan, B.A., Meier, H. J. Natl. Cancer Inst. (1975) [Pubmed]
  12. Hydrolysis of mixed monomolecular films of triglyceride/lecithin by pancreatic lipase. Pieroni, G., Verger, R. J. Biol. Chem. (1979) [Pubmed]
  13. Biochemical events during initiation of rat hepatocarcinogenesis. Dragan, Y.P., Hully, J.R., Nakamura, J., Mass, M.J., Swenberg, J.A., Pitot, H.C. Carcinogenesis (1994) [Pubmed]
  14. Altered acyl chain length specificity of Rhizopus delemar lipase through mutagenesis and molecular modeling. Klein, R.R., King, G., Moreau, R.A., Haas, M.J. Lipids (1997) [Pubmed]
  15. Tricaprylin microemulsion for oral delivery of low molecular weight heparin conjugates. Kim, S.K., Lee, E.H., Vaishali, B., Lee, S., Lee, Y.K., Kim, C.Y., Moon, H.T., Byun, Y. Journal of controlled release : official journal of the Controlled Release Society. (2005) [Pubmed]
  16. Symplasma formation and decidualization in the pseudopregnant rabbit after intraluminal instillation of tricaprylin. Davies, J., Davenport, G.R. J. Reprod. Fertil. (1979) [Pubmed]
  17. Dose-response study of the carcinogenicity of tobacco-specific N-nitrosamines in F344 rats. Hoffmann, D., Rivenson, A., Amin, S., Hecht, S.S. J. Cancer Res. Clin. Oncol. (1984) [Pubmed]
  18. Isopropyl methanesulfonate is a potent red cell hematotoxicant. Snyder, C.A., Valle-Paul, C. Toxicol. Lett. (1987) [Pubmed]
  19. Identification of optimal conditions for the detection of benzo[a]pyrene-DNA adducts by enzyme-linked immunoadsorbent assays (ELISA). Bucci, F., Galati, R., Zito, R., Falasca, G., Federico, A., Verdina, A. Anticancer Res. (1998) [Pubmed]
  20. Final report on the safety assessment of trilaurin, triarachidin, tribehenin, tricaprin, tricaprylin, trierucin, triheptanoin, triheptylundecanoin, triisononanoin, triisopalmitin, triisostearin, trilinolein, trimyristin, trioctanoin, triolein, tripalmitin, tripalmitolein, triricinolein, tristearin, triundecanoin, glyceryl triacetyl hydroxystearate, glyceryl triacetyl ricinoleate, and glyceryl stearate diacetate. Johnson, W. International journal of toxicology. (2001) [Pubmed]
  21. Comparison of the effects of tamoxifen and toremifene on liver and kidney tumor promotion in female rats. Dragan, V.P., Vaughan, J., Jordan, V.C., Pitot, H.C. Carcinogenesis (1995) [Pubmed]
  22. Dietary fat-dependent changes in hepatic cholesterogenesis and the activity of 3-hydroxy-3-methylglutaryl-CoA reductase in fasted-refed rats. Ide, T., Tanaka, T., Sugano, M. J. Nutr. (1979) [Pubmed]
  23. Tricaproin, tricaprin and trilaurin are utilized more efficiently than tricaprylin by carp (Cyprinus carpio L.) larvae. Fontagné, S., Corraze, G., Bergot, P. J. Nutr. (2000) [Pubmed]
  24. Comparative tumorigenicity of the environmental pollutant 6-nitrochrysene and its metabolites in the rat mammary gland. El-Bayoumy, K., Desai, D., Boyiri, T., Rosa, J., Krzeminski, J., Sharma, A.K., Pittman, B., Amin, S. Chem. Res. Toxicol. (2002) [Pubmed]
  25. Skin permeation enhancement of tegafur by ethanol/panasate 800 or ethanol/water binary vehicle and combined effect of fatty acids and fatty alcohols. Lee, C.K., Uchida, T., Noguchi, E., Kim, N.S., Goto, S. Journal of pharmaceutical sciences. (1993) [Pubmed]
  26. Might the kinetic behavior of hormone-sensitive lipase reflect the absence of the lid domain? Ben Ali, Y., Chahinian, H., Petry, S., Muller, G., Carrière, F., Verger, R., Abousalham, A. Biochemistry (2004) [Pubmed]
  27. Developmental changes in the pattern of ghrelin's acyl modification and the levels of acyl-modified ghrelins in murine stomach. Nishi, Y., Hiejima, H., Mifune, H., Sato, T., Kangawa, K., Kojima, M. Endocrinology (2005) [Pubmed]
  28. Medium-chain versus long-chain triacylglycerol emulsion hydrolysis by lipoprotein lipase and hepatic lipase: implications for the mechanisms of lipase action. Deckelbaum, R.J., Hamilton, J.A., Moser, A., Bengtsson-Olivecrona, G., Butbul, E., Carpentier, Y.A., Gutman, A., Olivecrona, T. Biochemistry (1990) [Pubmed]
  29. Medium-chain triacylglycerols enhance release of cholecystokinin in chicks. Mabayo, R.T., Furuse, M., Yang, S.I., Okumura, J. J. Nutr. (1992) [Pubmed]
  30. Bile salt-stimulated lipase and digestion of non-breast milk fat. McClean, P., Harding, M., Coward, W.A., Prentice, A., Austin, S., Weaver, L.T. J. Pediatr. Gastroenterol. Nutr. (1998) [Pubmed]
  31. Tumor promotion by an anticonvulsant agent, phenytoin, in mouse liver: correlation with CYP2B induction. Diwan, B.A., Henneman, J.R., Nims, R.W., Rice, J.M. Carcinogenesis (1993) [Pubmed]
  32. In vitro inhibition of aryl hydrocarbon hydroxylase by heavy metals. Tsang, S., Furst, A. Oncology (1976) [Pubmed]
  33. 13C-labeled trioctanoin breath test for exocrine pancreatic function test in patients after pancreatoduodenectomy. Kato, H., Nakao, A., Kishimoto, W., Nonami, T., Harada, A., Hayakawa, T., Takagi, H. Am. J. Gastroenterol. (1993) [Pubmed]
  34. Synergistic stabilization of emulsions by a mixture of surface-active nanoparticles and surfactant. Binks, B.P., Desforges, A., Duff, D.G. Langmuir : the ACS journal of surfaces and colloids (2007) [Pubmed]
  35. Lung tumor induction in strain A mice with benzotrichloride. Stoner, G.D., You, M., Morgan, M.A., Superczynski, M.J. Cancer Lett. (1986) [Pubmed]
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