Summary: Salts and esters of the 14-carbon saturated monocarboxylic acid--myristic acid.

Top Publications

  1. Jantharaprapap R, Stagni G. Effects of penetration enhancers on in vitro permeability of meloxicam gels. Int J Pharm. 2007;343:26-33 pubmed
    ..These findings show that the 0.3% MLX gel formulation containing 5% menthol can possibly deliver therapeutically relevant doses of MLX. ..
  2. Wang Y, Luo Z, Shi X, Wang H, Nie L, Huang M. A fluorescent fatty acid probe, DAUDA, selectively displaces two myristates bound in human serum albumin. Protein Sci. 2011;20:2095-101 pubmed publisher
    ..This result also show that DAUDA is an appropriate probe for FA site 6 and 7 on HSA as previous studied, but not a good probe of FA binding site 1 that is likely bilirubin binding site on HSA. ..
  3. Zhang Y, Gao J, Zheng H, Zhang R, Han Y. The preparation of 3,5-dihydroxy-4-isopropylstilbene nanoemulsion and in vitro release. Int J Nanomedicine. 2011;6:649-57 pubmed publisher
    ..The nanoemulsion dramatically improved the transdermal release of DHPS (from 8.02 ?g · cm(-2) to 273.15 ?g · cm(-2)) and could become a favorable new dosage form for DHPS. ..
  4. Hartwig S, Auwärter V, Pragst F. Effect of hair care and hair cosmetics on the concentrations of fatty acid ethyl esters in hair as markers of chronically elevated alcohol consumption. Forensic Sci Int. 2003;131:90-7 pubmed
    ..5% ethanol, with a deodorant and with a hair spray. As an explanation, it is assumed that FAEE are formed in the sebum glands also after regular topical application of products with a higher ethanol content. ..
  5. Provitera P, El Maghrabi R, Scarlata S. The effect of HIV-1 Gag myristoylation on membrane binding. Biophys Chem. 2006;119:23-32 pubmed
    ..We found that myristoylated Gag shows a greater than twofold increase in binding affinity to model rafts. A structural model to explain these results is presented. ..
  6. Rozman B, Gasperlin M. Stability of vitamins C and E in topical microemulsions for combined antioxidant therapy. Drug Deliv. 2007;14:235-45 pubmed
  7. Hartwig S, Auwärter V, Pragst F. Fatty Acid ethyl esters in scalp, pubic, axillary, beard and body hair as markers for alcohol misuse. Alcohol Alcohol. 2003;38:163-7 pubmed
    ..0 ng/mg in almost all samples. FAEE concentrations in hair other than scalp hair can be used as markers of chronic alcohol misuse. ..
  8. Lieb R, Bronisch T, Hofler M, Schreier A, Wittchen H. Maternal suicidality and risk of suicidality in offspring: findings from a community study. Am J Psychiatry. 2005;162:1665-71 pubmed
    ..Suicidality seems to run in families, independent of depression and other psychopathology. ..
  9. Olzyńska A, Jurkiewicz P, Hof M. Properties of mixed cationic membranes studied by fluorescence solvent relaxation. J Fluoresc. 2008;18:925-8 pubmed publisher
    ..Langmuir 22:8741-8749, 2006), for DMPC/DMTAP system it was found at 45 mol% of DMTAP, which agrees with the literature. Both membranes increased their hydration upon increased cationic lipid content. ..

More Information


  1. Vorum H, Madsen P, Svendsen I, Cells J, Honore B. Expression of recombinant psoriasis-associated fatty acid binding protein in Escherichia coli: gel electrophoretic characterization, analysis of binding properties and comparison with human serum albumin. Electrophoresis. 1998;19:1793-802 pubmed
  2. Kamal M, Iimura N, Nabekura T, Kitagawa S. Enhanced skin permeation of diclofenac by ion-pair formation and further enhancement by microemulsion. Chem Pharm Bull (Tokyo). 2007;55:368-71 pubmed
    ..The present findings suggest the usefulness of combined use of ion-pairs with microemulsions for enhancement of skin permeation of ionic drugs. ..
  3. Duronio R, Reed S, Gordon J. Mutations of human myristoyl-CoA:protein N-myristoyltransferase cause temperature-sensitive myristic acid auxotrophy in Saccharomyces cerevisiae. Proc Natl Acad Sci U S A. 1992;89:4129-33 pubmed
    ..cerevisiae. These results indicate highly conserved structure-function relationships in vivo and underscore the usefulness of these functional assays for identifying factors that regulate protein N-myristoylation in mammalian systems. ..
  4. El Setouhy D, El Ashmony S. Ketorolac trometamol topical formulations: release behaviour, physical characterization, skin permeation, efficacy and gastric safety. J Pharm Pharmacol. 2010;62:25-34 pubmed publisher
    ..The developed ketorolac trometamol E7 emulgel appeared promising for dermal and transdermal delivery of ketorolac trometamol, which would circumvent most of the problems associated with drug therapy. ..
  5. Prchal J, Srb P, Hunter E, Ruml T, Hrabal R. The structure of myristoylated Mason-Pfizer monkey virus matrix protein and the role of phosphatidylinositol-(4,5)-bisphosphate in its membrane binding. J Mol Biol. 2012;423:427-38 pubmed publisher
    ..PI(4,5)P(2) binding was not strong enough for triggering of the myristoyl-switch. The structural changes of the myristoylated matrix protein were also found to result in a drop in the oligomerization capacity of the protein...
  6. Seumois G, Fillet M, Gillet L, Faccinetto C, Desmet C, Francois C, et al. De novo C16- and C24-ceramide generation contributes to spontaneous neutrophil apoptosis. J Leukoc Biol. 2007;81:1477-86 pubmed
  7. Kupchak B, Garitaonandia I, Villa N, Smith J, Lyons T. Antagonism of human adiponectin receptors and their membrane progesterone receptor paralogs by TNFalpha and a ceramidase inhibitor. Biochemistry. 2009;48:5504-6 pubmed publisher
  8. Wu Z, Alexandratos J, Ericksen B, Lubkowski J, Gallo R, Lu W. Total chemical synthesis of N-myristoylated HIV-1 matrix protein p17: structural and mechanistic implications of p17 myristoylation. Proc Natl Acad Sci U S A. 2004;101:11587-92 pubmed
  9. Bharati A, King C. Allergic contact dermatitis from isohexadecane and isopropyl myristate. Contact Dermatitis. 2004;50:256-7 pubmed
  10. Sterer N, Slutzky H, Kohavi D, Matalon S. In vitro CPC retention and VSC adsorption by IPM oil droplets: possible mechanisms of action of a two phase mouthwash. J Breath Res. 2013;7:031001 pubmed publisher
    ..These results taken together, suggests that VSC adsorption and CPC retention by IPM oil droplets may be two additional mechanisms in the activity of the two phase mouthwash formulation. ..
  11. Ding M, Vitale N, Tsai S, Adamik R, Moss J, Vaughan M. Characterization of a GTPase-activating protein that stimulates GTP hydrolysis by both ADP-ribosylation factor (ARF) and ARF-like proteins. Comparison to the ARD1 gap domain. J Biol Chem. 1996;271:24005-9 pubmed
    ..The non-ARF1 domain of ARD1 enhanced the GTPase activity of the ARF domain, but not that of the ARF proteins and Delta13ARF1, i.e. it lacks the relatively broad substrate specificity exhibited by ARF GAP. ..
  12. D SOUZA SCHOREY C, Stahl P. Myristoylation is required for the intracellular localization and endocytic function of ARF6. Exp Cell Res. 1995;221:153-9 pubmed
    ..Thus, although prenylation can replace myristoylation for membrane association, the latter appears to be critical for the proper targeting and biological activity of ARF6. ..
  13. Gloor M, Haus G, Keipert S. Keratolytic activity of microemulsions. Skin Pharmacol Appl Skin Physiol. 2003;16:151-5 pubmed
    ..Both MEs therefore appear suitable for the elimination or prevention of plantar desquamative and hyperkeratotic skin changes. ..
  14. Sréter T, Széll Z, Marucci G, Pozio E, Varga I. Extraintestinal nematode infections of red foxes (Vulpes vulpes) in Hungary. Vet Parasitol. 2003;115:329-34 pubmed
    ..britovi from the sylvatic cycle to the domestic cycle, enhancing the risk of infections in humans...
  15. Cafaggi S, Russo E, Caviglioli G, Parodi B, Stefani R, Sillo G, et al. Poloxamer 407 as a solubilising agent for tolfenamic acid and as a base for a gel formulation. Eur J Pharm Sci. 2008;35:19-29 pubmed publisher
    ..Results point out the possibility of both the systemic and topical administration of tolfenamic acid by means of aqueous solutions or gels containing P407 at an adequate concentration...
  16. Markovic B, Vladimirov S, Cudina O, Odovic J, Karljikovic Rajic K. A PAMPA assay as fast predictive model of passive human skin permeability of new synthesized corticosteroid C-21 esters. Molecules. 2012;17:480-91 pubmed publisher
    ..According to the PAMPA results the new synthesized esters could be considered as potential new prodrugs with useful benefit/risk ratio. ..
  17. Stasiuk M, Bartosiewicz D, Gubernator J, Cieslik Boczula K, Hof M, Kozubek A. A semisynthetic 5-n-alkylresorcinol derivative and its effect upon biomembrane properties. Z Naturforsch C. 2007;62:881-8 pubmed
  18. Engelbrecht T, Deme B, Dobner B, Neubert R. Study of the influence of the penetration enhancer isopropyl myristate on the nanostructure of stratum corneum lipid model membranes using neutron diffraction and deuterium labelling. Skin Pharmacol Physiol. 2012;25:200-7 pubmed publisher
    ..We conclude that IPM's mode of action as penetration promoter is presumably based on incorporation into the SC lipid matrix, extraction of certain SC lipids into a separate phase and perturbation of the multilamellar lipid assembly. ..
  19. Woolfson A, Malcolm R, Morrow R, Toner C, McCullagh S. Intravaginal ring delivery of the reverse transcriptase inhibitor TMC 120 as an HIV microbicide. Int J Pharm. 2006;325:82-9 pubmed
    ..TMC 120 release profiles and the mechanical properties of rings could be modified by the physicochemical nature of hydrophobic and hydrophilic excipients incorporated into the IVRs. ..
  20. Liu H, Li S, Wang Y, Han F, Dong Y. Bicontinuous water-AOT/Tween85-isopropyl myristate microemulsion: a new vehicle for transdermal delivery of cyclosporin A. Drug Dev Ind Pharm. 2006;32:549-57 pubmed
    ..The increased transdermal delivery was found to be due mainly to water concentration and appeared to be dependent on the structure of the microemulsions. ..
  21. Martínez Sancho C, Herrero Vanrell R, Negro S. Poly (D,L-lactide-co-glycolide) microspheres for long-term intravitreal delivery of aciclovir: influence of fatty and non-fatty additives. J Microencapsul. 2003;20:799-810 pubmed
    ..13 microg/day/mg microspheres. A dose of 0.74 mg microspheres would be therapeutic for the herpes simplex and Epstein-Barr viruses (MIC 0.1 microg/ml) and 7.4 mg for varicella zoster virus (MIC 1 microg/ml) treatment in an animal model. ..
  22. Liu P, Cettina M, Wong J. Effects of isopropanol-isopropyl myristate binary enhancers on in vitro transport of estradiol in human epidermis: a mechanistic evaluation. J Pharm Sci. 2009;98:565-72 pubmed publisher
    ..IPA uptake correlated well to E2 solubility in stratum corneum; both linearly increased with increasing IPA. IPM uptake appeared to correlate to E2 diffusivity in stratum corneum; both maximized around 50% IPA. ..
  23. Ramirez de Molina A, de la Cueva A, Machado Pinilla R, Rodriguez Fanjul V, Gomez del Pulgar T, Cebrian A, et al. Acid ceramidase as a chemotherapeutic target to overcome resistance to the antitumoral effect of choline kinase ? inhibition. Curr Cancer Drug Targets. 2012;12:617-24 pubmed
  24. Nesamony J, Kolling W. IPM/DOSS/water microemulsions as reactors for silver sulfadiazine nanocrystal synthesis. J Pharm Sci. 2005;94:1310-20 pubmed
    ..The DLS results are consistent with the successful formation of submicron AgSD crystals. ..
  25. Mesleh M, Valentine K, Opella S, Louis J, Gronenborn A. Myristoylation as a general method for immobilization and alignment of soluble proteins for solid-state NMR structural studies. J Biomol NMR. 2003;25:55-61 pubmed
    ..The protein is oriented such that its charged sides face the phosphatidylcholine headgroups of the lipids with the single amphiphilic helix running parallel to the bilayer surface. ..
  26. Song J, Hirschman J, Gunn K, Dohlman H. Regulation of membrane and subunit interactions by N-myristoylation of a G protein alpha subunit in yeast. J Biol Chem. 1996;271:20273-83 pubmed
    ..These data suggest that myristoylation is required for specific targeting of Gpa1p to the plasma membrane, where it is needed to interact with the receptor and to regulate the release of Gbetagamma. ..
  27. Wang Q, Pan D, Jiang S, Ji X, An L, Jiang B. A new two-phase route to high-quality CdS nanocrystals. Chemistry. 2005;11:3843-8 pubmed
  28. Hoeller S, Klang V, Valenta C. Skin-compatible lecithin drug delivery systems for fluconazole: effect of phosphatidylethanolamine and oleic acid on skin permeation. J Pharm Pharmacol. 2008;60:587-91 pubmed publisher
    ..The influence of oleic acid and isopropylmyristate as the oil component was compared and a greater penetration enhancing effect was found for the microemulsion containing oleic acid. ..
  29. Pepe D, Phelps J, Lewis K, Dujack J, Scarlett K, Jahan S, et al. Decylglucoside-based microemulsions for cutaneous localization of lycopene and ascorbic acid. Int J Pharm. 2012;434:420-8 pubmed publisher
    ..Skin treatment with ME-MC containing both antioxidants increased the tissue antioxidant activity by 10.2-fold, but no synergism between the antioxidants was observed. ..
  30. Wills J, Craven R, Weldon R, Nelle T, Erdie C. Suppression of retroviral MA deletions by the amino-terminal membrane-binding domain of p60src. J Virol. 1991;65:3804-12 pubmed
    ..We hypothesize that the amino terminus of p60src suppresses the effects of MA deletions by diverting the Rous sarcoma virus Gag protein from its normal site of assembly to the Src receptor for particle formation. ..
  31. Matsui R, Hasegawa M, Ishida M, Ebata T, Namiki N, Sugibayashi K. Skin permeation of lidocaine from crystal suspended oily formulations. Drug Dev Ind Pharm. 2005;31:729-38 pubmed
    ..Finally, mathematical analysis was done to evaluate the effect of BO-2, and it was shown that BO-2 improved the LID solubility in stratum corneum lipids to efficiently enhance the LID permeation through skin. ..
  32. Zoukhri D, Hodges R, Sergheraert C, Toker A, Dartt D. Lacrimal gland PKC isoforms are differentially involved in agonist-induced protein secretion. Am J Physiol. 1997;272:C263-9 pubmed
    ..We concluded that phorbol ester- and receptor-induced protein secretion involve different PKC isoforms in lacrimal gland. ..
  33. Gao T, Pereira A, Obukowho P. A new multifunctional, shine-enhancing emollient: PPG-3 benzyl ether myristate. J Cosmet Sci. 2004;55 Suppl:S143-50 pubmed
    ..The substantivity of Crodamol STS on hair surface, which was delivered from a rinse-off cream, was also determined by a solvent extraction method. ..
  34. Lee J, Park T, Lee Y, Shin S, Choi H. Effect of adding non-volatile oil as a core material for the floating microspheres prepared by emulsion solvent diffusion method. J Microencapsul. 2001;18:65-75 pubmed
    ..The internal morphology of the microspheres was slightly different depending on the entrapped oil phase used. Tiny spherical objects were present at the inner surface of microspheres and the inside of the shell. ..
  35. Giatrellis S, Nikolopoulos G, Sideratou Z, Nounesis G. Calorimetric study of the interaction of binary DMTAP/DOTAP cationic liposomes with plasmid DNA. J Liposome Res. 2009;19:220-30 pubmed publisher
    ..DNA-mediated aggregation effects are detected at high [ammonium]/[phosphate] molar ratios in the case of lipid-added-to-pDNA interactions and at relatively low [phosphate]/[ammonium] molar ratios in the case of pDNA-added-to-lipid. ..
  36. Ballesteros Gómez A, Rubio S. Hemimicelles of alkyl carboxylates chemisorbed onto magnetic nanoparticles: study and application to the extraction of carcinogenic polycyclic aromatic hydrocarbons in environmental water samples. Anal Chem. 2009;81:9012-20 pubmed publisher
    ..CPAHs were only present in the sample from the Navallana reservoir, at concentrations over the range 0.42-0.96 ng L(-1). ..
  37. Furuishi T, Fukami T, Suzuki T, Takayama K, Tomono K. Synergistic effect of isopropyl myristate and glyceryl monocaprylate on the skin permeation of pentazocine. Biol Pharm Bull. 2010;33:294-300 pubmed
    ..These results indicate that the synergistic effects of IPM and GEFA-C(8) enhance transdermal permeation of PTZ by disrupting SC lipids. ..
  38. Fries R, Reddy P, Mikhaylova M, Haverkamp S, Wei T, Muller M, et al. Dynamic cellular translocation of caldendrin is facilitated by the Ca2+-myristoyl switch of recoverin. J Neurochem. 2010;113:1150-62 pubmed publisher
    ..Apparently, the increase of intracellular Ca(2+) facilitates the translocation of caldendrin to intracellular membranes, which is under control of complex formation with recoverin. ..
  39. Knoll L, Johnson D, Gordon J. Biochemical studies of three Saccharomyces cerevisiae acyl-CoA synthetases, Faa1p, Faa2p, and Faa3p. J Biol Chem. 1994;269:16348-56 pubmed
    ..coli during exponential growth at 24 or 37 degrees C and (ii) measurement of the incorporation of [3H]myristate into a yeast N-myristoylprotein coexpressed with Nmt1p and Faa1p, Faa2p, or Faa3p in the fadD- strain. ..
  40. Macarthur I, Jones J, Goodlett D, Ernst R, Preston A. Role of pagL and lpxO in Bordetella bronchiseptica lipid A biosynthesis. J Bacteriol. 2011;193:4726-35 pubmed publisher
    ..These data refine the structure of B. bronchiseptica lipid A and demonstrate that pagL and lpxO are involved in its biosynthesis. ..
  41. Thompson G, Okuyama H. Lipid-linked proteins of plants. Prog Lipid Res. 2000;39:19-39 pubmed
    ..This report summarizes recent findings regarding the structure, metabolism and physiological functions of these important protein-linked lipids. ..
  42. Garzon J, Sánchez Blázquez P. Administration of myr(+)-G(i2)alpha subunits prevents acute tolerance (tachyphylaxis) to mu-opioid effects in mice. Neuropharmacology. 2001;40:560-9 pubmed
    ..Exogenous administration of myr(+)-G alpha subunits may be of therapeutic potential in improving agonist activity and accelerating the recovery of post-dependent receptors. ..
  43. Petro E, Balogh A, Blazso G, Eros I, Csoka I. In vitro and in vivo evaluation of drug release from semisolid dosage forms. Pharmazie. 2011;66:936-41 pubmed
    ..Significant differences were found among the developed products both in vitro and in vivo. Correlation between the in vitro penetration studies and in vivo results were found in the case of o/w creams, organogels and hydrogels. ..
  44. Levy R, Van Tilburg M. Functional abdominal pain in childhood: background studies and recent research trends. Pain Res Manag. 2012;17:413-7 pubmed
    ..The present article concludes with recommendations for clinical practice and research. ..
  45. Ramakrishnan M, Kenoth R, Kamlekar R, Chandra M, Radhakrishnan T, Swamy M. N-Myristoylethanolamine-cholesterol (1:1) complex: first evidence from differential scanning calorimetry, fast-atom-bombardment mass spectrometry and computational modelling. FEBS Lett. 2002;531:343-7 pubmed
  46. Raza K, Negi P, Takyar S, Shukla A, Amarji B, Katare O. Novel dithranol phospholipid microemulsion for topical application: development, characterization and percutaneous absorption studies. J Microencapsul. 2011;28:190-9 pubmed publisher
    ..31%) vis-à-vis systems containing TA and T20. The results suggest that the developed novel lecithinized microemulsion systems have a promising potential for the improved topical delivery of dithranol. ..
  47. Voronova A, Sefton B. Expression of a new tyrosine protein kinase is stimulated by retrovirus promoter insertion. Nature. 1986;319:682-5 pubmed
    ..The three- to ninefold transcriptional activation of the gene therefore results from retroviral promoter insertion. ..
  48. Xiao Y, Liu F, Chen Z, Ping Q. [Microemulsion-based gel of fluorouracil for transdermal delivery]. Yao Xue Xue Bao. 2010;45:1440-6 pubmed
    ..Microemulsion-based gel exhibited some irritation, but could be subsided after drug withdrawal. Microemulsion-based gel may be a promising vehicle for transdermal delivery of 5-Fu and other hydrophilic drug. ..
  49. Bukrinskaya A, Ghorpade A, Heinzinger N, Smithgall T, Lewis R, Stevenson M. Phosphorylation-dependent human immunodeficiency virus type 1 infection and nuclear targeting of viral DNA. Proc Natl Acad Sci U S A. 1996;93:367-71 pubmed
    ..These results reveal a novel level of regulation of primate lentivirus infectivity. ..
  50. Fortunelli A, Monti S. Simulations of lipid adsorption on TiO2 surfaces in solution. Langmuir. 2008;24:10145-54 pubmed publisher
    ..occurring at the lipid/oxide interface are analyzed in detail, putting on a roughly quantitative basis time scales and energy barriers of the latter processes. ..
  51. Ascenzi P, Fasano M. Pseudo-enzymatic hydrolysis of 4-nitrophenyl myristate by human serum albumin. Biochem Biophys Res Commun. 2012;422:219-23 pubmed publisher
    ..9 ± 0.2 in NphOMy-free HSA to 6.8 ± 0.3 in the HSA:NphOMy adduct. The HSA-catalyzed hydrolysis of NphOMy is inhibited competitively by diazepam, indicating that Tyr411 is the active-site nucleophile. ..
  52. Bonacucina G, Cespi M, Mencarelli G, Casettari L, Palmieri G. The use of acoustic spectroscopy in the characterisation of ternary phase diagrams. Int J Pharm. 2013;441:603-10 pubmed publisher
    ..In fact, it is possible to analyse samples without dilution and despite their degree of turbidity, allowing complete characterisation of both properties and structure. ..
  53. Casas J, Espina M, Haro M, Royo F, Alsina M, Haro I, et al. Interfacial properties of a synthetic peptide derived from hepatitis G virus E2 protein: interaction with lipid monolayers. Langmuir. 2006;22:246-54 pubmed
    ..In these effects electrostatic interactions seem to have some participation. ..