Safety assessment of myristic acid as a food ingredient

Food and Chemical Toxicology

Volumn 45, Issue 4, 2007, Pages 517-529

  Burdock, George A ^a   Carabin, Ioana G ^b  

^a Burdock Group   (United States)

^b Women in Science   (United States)

Author keywords

Burdock; Food additive; GRAS; Myristic acid; Toxicity

Indexed keywords

LAURIC ACID; MYRISTIC ACID; PALMITIC ACID;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; CONTROLLED STUDY; EYE TOXICITY; FLAVOR; FOOD COMPOSITION; FOOD INDUSTRY; FOOD SAFETY; IN VITRO STUDY; MALE; MUTAGENESIS; NONHUMAN; NUTMEG; RAT; REVIEW; RISK ASSESSMENT; SENSITIZATION; SKIN TOXICITY;

ABSORPTION; ANIMALS; FLAVORING AGENTS; HUMANS; MYRISTIC ACID; RISK ASSESSMENT; SAFETY;

ANIMALIA; ARCTIUM; BACTERIA (MICROORGANISMS); MAMMALIA; MYRISTICA FRAGRANS; RATTUS; RODENTIA;

EID: 33846818574     PISSN: 02786915     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.fct.2006.10.009     Document Type: Review

References (76)

1. Adas F., Berthou F., Salauen J.P., Dreano Y., and Amet Y. Interspecies variations in fatty acid hydroxylations involving cytochromes P450 2E1 and 4A. Toxicology Letters 110 (1999) 43-55
2. Aderem, A.A., Keum, M.M., Pure, E., Cohn, Z.A. 1986. Bacterial lipopolysaccharides, phorbol myristate acetate, and zymosan induce the myristoylation of specific macrophage proteins. In: Proceedings of the National Academy of Sciences of the United States of America, vol. 83, pp. 5817-5821.
3. Aderem A.A., Albert K.A., Keum M.M., Wang J.K., Greengard P., and Cohn Z.A. Stimulus-dependent myristoylation of a major substrate for protein kinase C. Nature 332 (1988) 362-364
4. fyn affects subcellular localization. Journal of Biological Chemistry 269 (1994) 16701-16705
5. Anon. Final report on the safety assessment of oleic acid, lauric acid, palmitic acid, myristic acid, and stearic acid. Journal of the American College of Toxicology 6 (1987) 321-401
6. Anon. Final report on the safety assessment of butyl myristate. Journal of the American College of Toxicology 9 (1990) 247-258
7. Arctander S. 2288: myristic acid. Perfume and Flavor Chemicals (1994), Allured Publishing, Carol Stream, IL
8. Arnold D.L., McGuire P.F., Miller D., Malcolm S., Hayward S., and Paquet A. The ability of the rat to metabolize myristoyl-methionine: an acylamino acid with potentially useful antibacterial properties. Food and Chemical Toxicology 36 (1998) 771-779
9. Ash M., and Ash I. Mytristic acid. Handbook of Food Additives (1995), Publication, Brookfield, VT 606
10. BACIS, 1999. Tetradecanoic acid. Database of Volatile Compounds in Food. TNO Nutrition and Food Research, Boelens Aroma Chemical Information Service, The Netherlands. CD-ROM.
11. Bellizzi M.C., Franklin M.F., Duthie G.G., and James W.P.T. Vitamin E and coronary heart disease: the European paradox. European Journal of Clinical Nutrition 48 (1994) 822-831
12. Bradley, S.G. 1976. Endotoxic activity of complexes of myristic acid and proteins. In: Proceedings of the Society for Experimental Biology and Medicine, vol. 151, pp. 267-270.
13. Brand S.H., Holtzman E.J., Scher D.A., Ausiello D.A., and Stow J.L. Role of myristoylation in membrane attachment and function of G-alphai-3 on golgi membranes. American Journal of Physiology 270 (1996) C1362-C1369
14. Bryant, M.L., Heuckeroth, R.O., Kimata, J.T., Ratner, L. Gordon, J.I., 1989. Replication of human immunodeficiency virus 1 and Moloney murine leukemia virus is inhibited by different heteroatom-containing analogs of myristic acid. In: Proceedings of the National Academy of Sciences of the United States of America, vol. 86, pp. 8655-8659.
15. Burdock G.A. Myristic acid. Encyclopedia of Food and Color Additives (1997), CRC Press, Boca Raton, FL 1925-1927
16. Burdock G.A. Myristic acid. Fenaroli's Handbook of Flavor Ingredients. fourth ed. (2002), CRC Press, Boca Raton, FL 1273-1274
17. Burdock G.A. Regulation of flavor ingredients. In: Kotsonis F.N., and Mackey M. (Eds). Nutritional Toxicology. second ed. (2002), Taylor and Francis, New York, NY 316-339
18. Busconi L., and Michel T. Endothelial nitric oxide synthase. N-Terminal myristoylation determines subcellular localization. Journal of Biological Chemistry 268 (1993) 8410-8413
19. v-ras. Molecular and Cellular Biology 8 (1988) 3960-3963
20. Clegg C.H., Ran W., Uhler M.D., and McKnight G.S. A mutation in the catalytic subunit of protein kinase A prevents myristylation but does not inhibit biological activity. Journal of Biological Chemistry 264 (1989) 20140-20146
21. Clydesdale F.M. Myristic acid. Food Additives: Toxicology, Regulation and Properties (1997), CRC Press, Boca Raton, FL CD-ROM
22. Cohen L.A., Thompson D.O., Maeura Y., Choi K., Blank M.E., and Rose D.P. Dietary fat and mammary cancer I. Promoting effects of different dietary fats on N-nitrosomethylurea-induced rat mammary tumorigenesis. Journal of the National Cancer Institute 77 (1986) 33-42
23. CSFII 1994-96, 2000. Continuing Survey of Food Intakes by Individuals (CSFII) 1994-96, 98. Agricultural Research Service, US Department of Agriculture, Washington, DC. CD-ROM.
24. De Albuquerque K.T., Do Carmo M.D.G.T., and Herrera E. Ethanol consumption by lactating rats induces changes in pup's fatty acid profiles. Nutritional Neuroscience 3 (2000) 331-337
25. DeGrella R.F., and Light R.J. Uptake and metabolism of fatty acids by dispersed adult rat heart myocytes. I. Kinetics of homologous fatty acids. Journal of Biological Chemistry 255 (1980) 9731-9738
26. Devadas B., Lu T.B., Katoh A., Kishore N.S., Wade A.C., Mehta P.P., Rudnick D.A., Bryant M.L., Adams S.P., Li Q., Gokel G.W., and Gordon J.I. Substrate-specificity of Saccharomyces cerevisiae myristoyl-CoA: protein N-myristoyltransferase. Journal of Biological Chemistry 267 (1992) 7224-7239
27. Doering T.L., Raper J., Buxbaum L.U., Adams S.P., Gordon J.I., Hart G.W., and Englund P.T. An analog of myristic acid with selective toxicity for African trypanosomes. Science 252 (1991) 1851-1854
28. EC, 2002. Commission Decision of 23 January 2002. Myristic acid. Official Journal of the European Communities L49, 52-53.
29. Eid A., and Berry E.M. The relationship between dietary fat adipose tissue composition and neoplasms of the breast. Nutrition and Cancer 11 (1988) 173-178
30. FCC. Myristic acid. Food Chemicals Codex. fourth ed. (2003), National Academy Press, Washington, DC 297
31. FDA, 1996. Inactive ingredient guide. Myristic acid. Food and Drug Administration; Center for Drug Evaluation and Research; Office of Management, Rockville, MD. p. 84.
32. FSA, 2002. A list of additives currently permitted in food in the European Union and their E numbers. Fatty acids. Food Standards Agency (FSA). http://www.food.gov.uk/safereating/chemsafe/additivesbranch/enumberlist (site visited on November 13, 2006).
33. Hall R.L., and Oser B.L. Recent progress in the consideration of flavoring ingredients under the food additives ammendment III. GRAS substances. Myristic acid. Food Technology 19 (1965) 285
34. Hubbard N.E., Socolich R.J., and Erickson K.L. Dietary myristic acid alters acylated proteins in activated murine macrophages. The Journal of Nutrition 126 (1996) 1563-1570
35. Imamura Y., Migita T., Anraku M., and Otagiri M. Inhibition of rabbit heart carbonyl reductase by fatty acids. Biological and Pharmaceutical Bulletin 22 (1999) 731-733
36. James G., and Olson E.N. Identification of a novel fatty acylated protein that partitions between the plasma membrane and cytosol and is deacylated in response to serum and growth factor stimulation. Journal of Biological Chemistry 264 (1989) 20998-21006
37. James G., and Olson E.N. Myristoylation, phosphorylation, and subcellular distribution of the 80-kDa protein kinase C substrate in BC3H1 myocytes. Journal of Biological Chemistry 264 (1989) 20928-20933
38. JECFA 1997. Summary of evaluations performed by the Joint FAO/WHO Expert Committee on Food Additives (JECFA). Myristic acid. Joint FAO/WHO Expert Committee on Food Additives. <>. (Site visited on June 4, 2003).
39. JECFA. Saturated aliphatic acyclic linear primary alcohols, aldehydes, and acids (1998), World Health Organization, Geneva, Switzerland
40. JECFA, 2003. Compendium of Food Additive Specifications-Flavouring Agents Database.Myristic acid. <>. (Site visited on June 16, 2003).
41. Kageyama K., Nagasawa T., Kimura S., Kobayashi T., and Kinoshita Y. Cytotoxic activity of unsaturated fatty acids to lymphocytes. Canadian Journal of Biochemistry 58 (1980) 504-508
42. Kamata N., Jotte R.M., and Holt J.T. Myristylation alters DNA-binding activity and transactivation of FBR (gag-fos) protein. Molecular and Cellular Biology 11 (1991) 765-772
43. Kinderlerer J.L., Matthias H.E., and Finner P. Effect of medium-chain fatty acids in mould ripened cheese on the growth of Listeria monocytogenes. Journal of Dairy Research 63 (1996) 593-606
44. Knoll L.J., Johnson D.R., Bryant M.L., and Gordon J.I. Functional significance of myristoyl moiety in N-myristoyl proteins. Methods in Enzymology 250 (1995) 405-435
45. Lucas C.D., Putnam J.M., and Hallagan J.B. Myristic acid. 1995 Poundage and Technical Effects Update Survey (1999), Flavor and Extract Manufacturers' Association of the United States, Washington, DC
46. MRCA. Market Research Corporation of America (MRCA), in conjunction with the Food intake and nutritive value of the diets of men, women and children in United States, Spring 1965 (1965), United States Department of Agriculture, Washington, DC
47. Mumby S.M., and Linder M.E. Myristoylation of G-protein alpha subunits. Methods in Enzymology 237 (1994) 254-268
48. Mumby, S.M., Heukeroth, R.O., Gordon, J.I. Gilman, A.G. 1990. G-protein alpha-subunit expression, myristoylation, and membrane association in COS cells. In: Proceedings of the National Academy of Sciences of the United States of America, vol. 87, pp. 728-732.
49. NACGM, 1977. Myristic acid. National Association of Chewing Gum Manufacturers, personal communication.
50. NAS. Myristic acid. 1987 Poundage and Technical Effects Update of Substances Added to Food (1989), National Research Council, National Academy of Sciences, Washington, DC 410
51. 2+signals in Jurkat T-cells by myristic acid. Cell Calcium 12 (1991) 449-455
52. Ogiso T., and Shintani M. Mechanism for the enhancement effect of fatty acids on the percutaneous absorption of propranolol. Journal of Pharmaceutical Sciences 79 (1990) 1065-1071
53. Ouattara B., Simard R.E., Holley R.A., Piette G., and Begin A. Antibacterial activity of selected fatty acids and essential oils against six meat spoilage organisms. International Journal of Food Microbiology 37 (1997) 155-162
54. Pownall H.J. Dietary ethanol is associated with reduced lipolysis of intestinally derived lipoproteins. Journal of Lipid Research 35 (1994) 2105-2113
55. Raju R.V., and Sharma R.K. Coenzyme A dependent myristoylation and demyristoylation in the regulation of bovine spleen N-myristoyltransferase. Molecular and Cellular Biochemistry 158 (1996) 107-113
56. Resh M.D. Fatty acylation of proteins: new insights into membrane targeting of myristoylated and palmitoylated proteins. Biochimica et Biophysica Acta 1451 (1999) 1-16
57. Richieri G.V., Low P.J., Ogata R.T., and Kleinfeld A.M. Binding kinetics of engineered mutants provide insight about the pathway for entering and exiting the intestinal fatty acid binding protein. Biochemistry 38 (1999) 5888-5895
58. Sax N.I., and Lewis R.J. Myristic acid. Hawley's Condensed Chemical Dictionary. 11th ed. (1987), Van Nostrand Reinhold Company, Inc., New York, NY 803
59. Simon J.A., Fong J., Bernert J.T.J., and Browner W.S. Relation of smoking and alcohol consumption to serum fatty acids. American Journal of Epidemiology 144 (1996) 325-334
60. Solski P.A., Quilliam L.A., Coats S.G., Der C.J., and Buss J.E. Targeting proteins to membranes using signal sequences for lipid modification. Methods in Enzymology 250 (1995) 435-454
61. Stecher P.G., Windholz M., Leahy D.S., Bolton D.M., and Eaton L.G. Myristic acid. The Merck Index. An Encyclopedia of Chemicals and Drugs (1968), Merck and Company, Rahway, NJ 709
62. Stofberg J., and Grundschober F. Consumption ratio and food predominance of flavoring materials. Methyl sulfide. Perfumer and Flavorist 12 (1987) 27
63. Stryer L. Fatty acid metabolism. Biochemistry. third ed. (1988), W.H. Freeman and Company, New York 469-493
64. Tatara T., Kamaya H., and Ueda I. Myristate, a 14-carbon fatty acid, effectively reverses anesthesia. Anesthesiology 97 (2002) 518-520
65. Thams P., and Capito K. Differential mechanisms of glucose and palmitate in augmentation of insulin secretion in mouse pancreatic islets. Diabetologia 44 (2001) 738-746
66. Thelen M., Rosen A., Nairn A.C., and Aderem A. Regulation by phosphorylation of reversible association of a myristoylated protein kinase C substrate with the plasma membrane. Nature 351 (1991) 320-322
67. Tinsley I.J., Schmitz J.A., and Pierce D.A. Influence of dietary fatty acids on the incidence of mammary tumors in the C3H mouse. Cancer Research 41 (1981) 1460-1465
68. Towler D.A., Gordon J.I., Adams S.P., and Glaser L. The biology and enzymology of eukaryotic protein acylation. Annual Review of Biochemistry 57 (1988) 69-99
69. Warnotte C., Nenquin M., and Henquin J.C. Unbound rather than total concentration and saturation rather than unsaturation determine the potency of fatty acids on insulin secretion. Molecular and Cellular Endocrinology 153 (1999) 147-153
70. Wenzel D.G., and Hale T.W. Toxicity of free fatty acids upon cultured rat heart muscle and endothelial cells. Toxicology and Applied Pharmacology 41 (1977) 170-171
71. Wenzel D.G., and Hale T.W. Toxicity of free fatty acids for cultured rat heart muscle and endothelioid cells. I. Saturated longchain fatty acids. Toxicology 11 (1978) 109-117
72. Whittle E., Barratt M.D., Carter J.A., Basketter D.A., and Chamberlain M. Skin corrosivity potential of fatty acids: in vitro rat and human skin testing and OSAR studies. Toxicology in Vitro 10 (1996) 95-100
73. Winocour P.D., Kinlough-Rathbone R.L., Morazain R., and Mustard J.F. Effect of the amount and type of dietary fat on platelet function, platelet survival and response to continuous aortic injury in rats. Atherosclerosis 68 (1987) 221-230
74. Wolters H., Kelholt D., and Konings A.W.T. Effect of membrane fatty acid substitution and temperature on repair of sublethal damage in mammalian cells. Radiation Research 102 (1985) 206-212
75. Zeiger E., Anderson B., Haworth S., Lawlor T., and Mortelmans K. Salmonella mutagenicity tests. IV. Results from the testing of 300 chemicals. Environmental and Molecular Mutagenesis 11 (1988) 1-158
76. Zhu W., and Smart E.J. Myristic acid stimulates endothelial nitric-oxide synthase in a CD36- and an AMP kinase-dependent manner. Journal of Biological Chemistry 280 (2005) 29543-29550