Record Information |
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Version | 2.0 |
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Creation Date | 2012-08-09 09:16:12 -0600 |
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Update Date | 2015-09-13 15:15:33 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | Myristic acid |
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Description | Myristic acid ia a saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. It is used to synthesize flavor and as an ingredient in soaps and cosmetics. (From Dorland, 28th ed) Myristic acid is also commonly added to a penultimate nitrogen terminus glycine in receptor-associated kinases to confer the membrane localisation of the enzyme. |
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Structure | |
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Synonyms: | - 1-Tridecanecarboxylate
- 1-Tridecanecarboxylic acid
- Crodacid
- Myristate
- Myristate pure
- Myristic acid pure
- Myristoate
- Myristoic acid
- N-Tetradecan-1-oate
- N-Tetradecan-1-oic acid
- N-Tetradecanoate
- N-Tetradecanoic acid
- Tetradecanoate
- Tetradecanoic (Myristic) acid
- Tetradecanoic acid
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Chemical Formula: | C14H28O2 |
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Weight: | Average: 228.3709 Monoisotopic: 228.20893014 |
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InChI Key: | TUNFSRHWOTWDNC-UHFFFAOYSA-N |
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InChI: | InChI=1S/C14H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h2-13H2,1H3,(H,15,16) |
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CAS number: | 544-63-8 |
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IUPAC Name: | tetradecanoic acid |
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Traditional IUPAC Name: | myristic acid |
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SMILES: | CCCCCCCCCCCCCC(O)=O |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Fatty acids and conjugates |
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Direct Parent | Long-chain fatty acids |
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Alternative Parents | |
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Substituents | - Long-chain fatty acid
- Straight chain fatty acid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Physical Properties |
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State: | Solid |
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Charge: | -1 |
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Melting point: | 53.9 °C |
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Experimental Properties: | Property | Value | Source |
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Water Solubility: | 0.00107 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)] | PhysProp | LogP: | 6.11 [SANGSTER (1993)] | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations: | Membrane |
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Reactions: | |
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SMPDB Pathways: | fatty acid oxidation (myristate) | PW001021 |    |
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KEGG Pathways: | Not Available |
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EcoCyc Pathways: | Not Available |
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Concentrations |
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| Not Available |
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Spectra |
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Spectra: | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-MS (1 TMS) | splash10-017i-2910000000-66b35fb8449ba9de9cd6 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-017i-2910000000-66b35fb8449ba9de9cd6 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0159-0910000000-f45703c464ca75f98f26 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9700000000-ec8d81e37bc3b8531c99 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-0079-9330000000-5ec01705dfacc992be28 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-004i-0090000000-73ac1cfb8731e6318cc5 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-004i-1090000000-3aa768974da0ea81c1c9 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-004i-0090000000-22cd107a87b9acf058c5 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-004i-0090000000-2f7bb32e4b42206d851d | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-004i-2090000000-d45cffc15e2efbd45cd6 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-001i-9200000000-dbca68238dfebab35251 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-004r-9000000000-26827be8f8c2a4fbfd75 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-0006-0090000000-110165b889d231d09d59 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-0006-0090000000-110165b889d231d09d59 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-0006-0090000000-110165b889d231d09d59 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-0006-0090000000-110165b889d231d09d59 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-004i-0090000000-91f4f874b25705464fb0 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-004i-0090000000-15225a799e0a0bcff7c7 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0290000000-b88426a2003ceec57e30 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01q9-5940000000-6c73dc0032502abe4fc4 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052f-9300000000-bde9bfcd2889066fc853 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0290000000-b88426a2003ceec57e30 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01q9-5940000000-6c73dc0032502abe4fc4 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052f-9300000000-bde9bfcd2889066fc853 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0190000000-a32f141c7b5af0bc4de1 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-057i-1490000000-14bfb0d0344d7cf63443 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9400000000-512abb1322963024336f | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0190000000-a32f141c7b5af0bc4de1 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-057i-1490000000-14bfb0d0344d7cf63443 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9400000000-512abb1322963024336f | View in MoNA |
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MS | Mass Spectrum (Electron Ionization) | splash10-06xx-9200000000-4fdd41f0461ff5186901 | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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References |
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- Brod SA, Malone M, Darcan S, Papolla M, Nelson L: Ingested interferon alpha suppresses type I diabetes in non-obese diabetic mice. Diabetologia. 1998 Oct;41(10):1227-32. Pubmed: 9794112
- Cater NB, Denke MA: Behenic acid is a cholesterol-raising saturated fatty acid in humans. Am J Clin Nutr. 2001 Jan;73(1):41-4. Pubmed: 11124748
- Curry S, Brick P, Franks NP: Fatty acid binding to human serum albumin: new insights from crystallographic studies. Biochim Biophys Acta. 1999 Nov 23;1441(2-3):131-40. Pubmed: 10570241
- Dabadie H, Peuchant E, Bernard M, LeRuyet P, Mendy F: Moderate intake of myristic acid in sn-2 position has beneficial lipidic effects and enhances DHA of cholesteryl esters in an interventional study. J Nutr Biochem. 2005 Jun;16(6):375-82. Pubmed: 15936650
- Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. Pubmed: 8412012
- Kageura M, Hara K, Hieda Y, Takamoto M, Fujiwara Y, Fukuma Y, Kashimura S: [Screening of drugs and chemicals by wide-bore capillary gas chromatography with flame ionization and nitrogen phosphorus detectors] Nihon Hoigaku Zasshi. 1989 Apr;43(2):161-5. Pubmed: 2810891
- Kaminskas A, Zieden B, Elving B, Kristenson M, Abaravicius A, Bergdahl B, Olsson AG, Kucinskiene Z: Adipose tissue fatty acids in men from two populations with different cardiovascular risk: the LiVicordia study. Scand J Clin Lab Invest. 1999 May;59(3):227-32. Pubmed: 10400167
- Majeti BK, Karmali PP, Madhavendra SS, Chaudhuri A: Example of fatty acid-loaded lipoplex in enhancing in vitro gene transfer efficacies of cationic amphiphile. Bioconjug Chem. 2005 May-Jun;16(3):676-84. Pubmed: 15898737
- Matsubara M: [Structures and molecular recognition of MARCKS family proteins] Seikagaku. 2005 Jan;77(1):50-5. Pubmed: 15770953
- Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. Pubmed: 12829005
- Pieterse Z, Jerling JC, Oosthuizen W, Kruger HS, Hanekom SM, Smuts CM, Schutte AE: Substitution of high monounsaturated fatty acid avocado for mixed dietary fats during an energy-restricted diet: effects on weight loss, serum lipids, fibrinogen, and vascular function. Nutrition. 2005 Jan;21(1):67-75. Pubmed: 15661480
- Schewe T, Hiebsch C: [Action of respiratory inhibitors on the electron transport system of Escherichia coli] Acta Biol Med Ger. 1977;36(7-8):961-6. Pubmed: 347849
- Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
- van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
- Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
- Zhu W, Smart EJ: Myristic acid stimulates endothelial nitric-oxide synthase in a CD36- and an AMP kinase-dependent manner. J Biol Chem. 2005 Aug 19;280(33):29543-50. Epub 2005 Jun 21. Pubmed: 15970594
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Synthesis Reference: | Greaves, W. S.; Linstead, R. P.; Shephard, B. R.; Thomas, S. L. S.; Weedon, B. C. L. Anodic syntheses. I. New syntheses of stearic, myristic, and other acids. Journal of the Chemical Society (1950), 3326-30. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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Links |
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External Links: | |
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