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Chemical Compound Review

Retinyl ester     (2E,4E,6E,8E)-3,7-dimethyl-9- (2,2,6...

Synonyms: AC1NUSW0, CHEMBL520689, HMDB03598, All-E-Retinoic Acid, 5,6-dihydroretinoic acid
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Disease relevance of retinyl esters


Psychiatry related information on retinyl esters

  • After adjusting for age, sex, race or ethnicity, education, smoking status, cotinine concentration, physical activity, fruit and vegetable intake, and vitamin or mineral use, participants with the metabolic syndrome had significantly lower concentrations of retinyl esters, vitamin C, and carotenoids, except lycopene [5].
  • A concomitant alteration in vitamin-hormone status is observed with progressive metabolic alterations: low T3, T4, and elevated retinyl esters in subjects with the hypercarotenemia associated with anorexia nervosa [6].

High impact information on retinyl esters


Chemical compound and disease context of retinyl esters


Biological context of retinyl esters


Anatomical context of retinyl esters


Associations of retinyl esters with other chemical compounds


Gene context of retinyl esters

  • We conclude that Lrat-/- mice may serve as an animal model with early onset severe retinal dystrophy and severe retinyl ester deprivation [26].
  • When retinyl esters were allowed to form prior to the addition of the LRAT inhibitors, a significant amount of isomerization product was generated [27].
  • Both transcription and translation were required, suggesting that signaling from the EGF receptor through the MAPK cascade controls the expression of modulators or inhibitors of the retinyl ester hydrolase(s) [28].
  • During vitamin A deficiency, the additional loss of Adh1 completely prevented the excessive loss of liver retinyl esters observed in Crbp1-/- mice for the first 5 weeks of deficiency and greatly minimized this loss for up to 13 weeks [29].
  • Lipoprotein lipase hydrolysis of retinyl ester. Possible implications for retinoid uptake by cells [30].

Analytical, diagnostic and therapeutic context of retinyl esters


  1. Spontaneous activity of opsin apoprotein is a cause of Leber congenital amaurosis. Woodruff, M.L., Wang, Z., Chung, H.Y., Redmond, T.M., Fain, G.L., Lem, J. Nat. Genet. (2003) [Pubmed]
  2. Increased risk for vitamin A toxicity in severe hypertriglyceridemia. Ellis, J.K., Russell, R.M., Makrauer, F.L., Schaefer, E.J. Ann. Intern. Med. (1986) [Pubmed]
  3. Reduced levels of retinyl esters and vitamin A in human renal cancers. Guo, X., Nanus, D.M., Ruiz, A., Rando, R.R., Bok, D., Gudas, L.J. Cancer Res. (2001) [Pubmed]
  4. The clearance rate of chylomicron retinyl ester from plasma can be used to distinguish rats with cirrhosis from those with portacaval shunt. Kasai, T., Moriwaki, H., Okuno, M., Numaguchi, S., Murakami, N., Seishima, M., Ohnishi, H., Shidoji, Y., Muto, Y. Hepatology (1993) [Pubmed]
  5. The metabolic syndrome and antioxidant concentrations: findings from the Third National Health and Nutrition Examination Survey. Ford, E.S., Mokdad, A.H., Giles, W.H., Brown, D.W. Diabetes (2003) [Pubmed]
  6. Alterations in vitamin A and thyroid hormone status in anorexia nervosa and associated disorders. Curran-Celentano, J., Erdman, J.W., Nelson, R.A., Grater, S.J. Am. J. Clin. Nutr. (1985) [Pubmed]
  7. The visual cycle operates via an isomerase acting on all-trans retinol in the pigment epithelium. Bridges, C.D., Alvarez, R.A. Science (1987) [Pubmed]
  8. Vitamin A contents of rat intestinal epithelium and jejunal mucinous adenocarcinoma. Sundaresan, P.R., De Luca, L.M. J. Natl. Cancer Inst. (1977) [Pubmed]
  9. Noninvasive two-photon imaging reveals retinyl ester storage structures in the eye. Imanishi, Y., Batten, M.L., Piston, D.W., Baehr, W., Palczewski, K. J. Cell Biol. (2004) [Pubmed]
  10. Retinol and retinyl esters in patients with alcoholic liver disease. Bell, H., Nilsson, A., Norum, K.R., Pedersen, L.B., Raknerud, N., Rasmussen, M. J. Hepatol. (1989) [Pubmed]
  11. Uptake and storage of retinol and retinyl esters in bone marrow of children with acute myeloid leukemia treated with high-dose retinyl palmitate. Skrede, B., Lie, S.O., Blomhoff, R., Norum, K.R. Eur. J. Haematol. (1994) [Pubmed]
  12. Oxidative damage of plasma proteins and lipids in epidemic dropsy patients: alterations in antioxidant status. Das, M., Babu, K., Reddy, N.P., Srivastava, L.M. Biochim. Biophys. Acta (2005) [Pubmed]
  13. Serum vitamin A, retinyl esters and vitamin E in nephrotic syndrome. Mydlík, M., Derzsiová, K., Brátová, M., Havris, S. International urology and nephrology. (1991) [Pubmed]
  14. Cellular metabolism and activation of retinoids: roles of cellular retinoid-binding proteins. Ross, A.C. FASEB J. (1993) [Pubmed]
  15. Lipases and carboxylesterases: possible roles in the hepatic metabolism of retinol. Harrison, E.H. Annu. Rev. Nutr. (1998) [Pubmed]
  16. Rpe65 is a retinyl ester binding protein that presents insoluble substrate to the isomerase in retinal pigment epithelial cells. Mata, N.L., Moghrabi, W.N., Lee, J.S., Bui, T.V., Radu, R.A., Horwitz, J., Travis, G.H. J. Biol. Chem. (2004) [Pubmed]
  17. Retinol bound to physiological carrier molecules regulates growth and differentiation of myeloid leukemic cells. Wathne, K.O., Norum, K.R., Smeland, E., Blomhoff, R. J. Biol. Chem. (1988) [Pubmed]
  18. RPE65 is the isomerohydrolase in the retinoid visual cycle. Moiseyev, G., Chen, Y., Takahashi, Y., Wu, B.X., Ma, J.X. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
  19. Metabolism of retinol and retinoic acid in N-methyl-N-nitrosourea-induced mammary carcinomas in rats. Bhat, P.V., Lacroix, A. Cancer Res. (1989) [Pubmed]
  20. Lecithin:retinol acyltransferase is responsible for amidation of retinylamine, a potent inhibitor of the retinoid cycle. Golczak, M., Imanishi, Y., Kuksa, V., Maeda, T., Kubota, R., Palczewski, K. J. Biol. Chem. (2005) [Pubmed]
  21. Esterification of retinol in rat liver. Possible participation by cellular retinol-binding protein and cellular retinol-binding protein II. Ong, D.E., MacDonald, P.N., Gubitosi, A.M. J. Biol. Chem. (1988) [Pubmed]
  22. Hydrolysis of retinyl palmitate by enzymes of rat pancreas and liver. Differentiation of bile salt-dependent and bile salt-independent, neutral retinyl ester hydrolases in rat liver. Harrison, E.H., Gad, M.Z. J. Biol. Chem. (1989) [Pubmed]
  23. Apolipoprotein E-containing lipoproteins and lipoprotein remnants in experimental canine diabetes. Wilson, D.E., Chan, I.F., Elstad, N.L., Peric-Golia, L., Hejazi, J., Albu, D.S., Cutfield, R. Diabetes (1986) [Pubmed]
  24. RPE65 is an iron(II)-dependent isomerohydrolase in the retinoid visual cycle. Moiseyev, G., Takahashi, Y., Chen, Y., Gentleman, S., Redmond, T.M., Crouch, R.K., Ma, J.X. J. Biol. Chem. (2006) [Pubmed]
  25. Retinoid processing in retinal pigment epithelium of toad (Bufo marinus). Okajima, T.I., Wiggert, B., Chader, G.J., Pepperberg, D.R. J. Biol. Chem. (1994) [Pubmed]
  26. Lecithin-retinol acyltransferase is essential for accumulation of all-trans-retinyl esters in the eye and in the liver. Batten, M.L., Imanishi, Y., Maeda, T., Tu, D.C., Moise, A.R., Bronson, D., Possin, D., Van Gelder, R.N., Baehr, W., Palczewski, K. J. Biol. Chem. (2004) [Pubmed]
  27. Retinyl esters are the substrate for isomerohydrolase. Moiseyev, G., Crouch, R.K., Goletz, P., Oatis, J., Redmond, T.M., Ma, J.X. Biochemistry (2003) [Pubmed]
  28. Epidermal growth factor signaling pathway influences retinoid metabolism by reduction of retinyl ester hydrolase activities in normal and malignant keratinocytes. Jurukovski, V., Simon, M. J. Cell. Physiol. (2000) [Pubmed]
  29. Opposing actions of cellular retinol-binding protein and alcohol dehydrogenase control the balance between retinol storage and degradation. Molotkov, A., Ghyselinck, N.B., Chambon, P., Duester, G. Biochem. J. (2004) [Pubmed]
  30. Lipoprotein lipase hydrolysis of retinyl ester. Possible implications for retinoid uptake by cells. Blaner, W.S., Obunike, J.C., Kurlandsky, S.B., al-Haideri, M., Piantedosi, R., Deckelbaum, R.J., Goldberg, I.J. J. Biol. Chem. (1994) [Pubmed]
  31. Retinyl ester hydrolysis and retinol efflux from BFC-1beta adipocytes. Wei, S., Lai, K., Patel, S., Piantedosi, R., Shen, H., Colantuoni, V., Kraemer, F.B., Blaner, W.S. J. Biol. Chem. (1997) [Pubmed]
  32. Solubilization and partial purification of retinyl ester synthetase and retinoid isomerase from bovine ocular pigment epithelium. Barry, R.J., Cañada, F.J., Rando, R.R. J. Biol. Chem. (1989) [Pubmed]
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