Record Information |
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Version | 2.0 |
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Created at | 2005-11-16 15:48:42 UTC |
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Updated at | 2024-09-03 04:16:39 UTC |
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NP-MRD ID | NP0000315 |
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Natural Product DOI | https://doi.org/10.57994/0751 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Myristic acid |
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Description | Myristic acid, also known as tetradecanoic acid or C14:0, 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. Myristic acid (its ester is called myristate) is a saturated fatty acid that has 14 carbons; as such, it is a very hydrophobic molecule that is practically insoluble in water. It exists as an oily white crystalline solid. Myristic acid is found in all living organisms ranging from bacteria to plants to animals, and is found in most animal and vegetable fats, particularly butterfat, as well as coconut, palm, and nutmeg oils. Industrially, myristic acid is used to synthesize a variety of flavour compounds and as an ingredient in soaps and cosmetics (Dorland, 28th ed). Within eukaryotic cells, myristic acid is also commonly conjugated to a penultimate N-terminal glycine residue in receptor-associated kinases to confer membrane localization of these enzymes (a post-translational modification called myristoylation via the enzyme N-myristoyltransferase). Myristic acid has a high enough hydrophobicity to allow the myristoylated protein to become incorporated into the fatty acyl core of the phospholipid bilayer of the plasma membrane of eukaryotic cells. Also, this fatty acid is known because it accumulates as fat in the body; however, its consumption also impacts positively on cardiovascular health (see, for example, PMID: 15936650 ). Myristic acid is named after the scientific name for nutmeg, Myristica fragrans, from which it was first isolated in 1841 by Lyon Playfair. |
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Structure | 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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Synonyms | Value | Source |
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1-Tetradecanecarboxylic acid | ChEBI | 14 | ChEBI | 14:0 | ChEBI | 14:00 | ChEBI | Acide tetradecanoique | ChEBI | C14 | ChEBI | CH3-[CH2]12-COOH | ChEBI | Myristinsaeure | ChEBI | N-Tetradecan-1-Oic acid | ChEBI | N-Tetradecanoic acid | ChEBI | N-Tetradecoic acid | ChEBI | Tetradecoic acid | ChEBI | Tetradecanoate | Kegg | 1-Tetradecanecarboxylate | Generator | N-Tetradecan-1-Oate | Generator | N-Tetradecanoate | Generator | N-Tetradecoate | Generator | Tetradecoate | Generator | Tetradecanoic acid | Generator | Myristate | Generator | 1-Tridecanecarboxylate | HMDB | 1-Tridecanecarboxylic acid | HMDB | Crodacid | HMDB | Myristic acid pure | HMDB | Myristoate | HMDB | Myristoic acid | HMDB | Tetradecanoic (myristic) acid | HMDB | Acid, tetradecanoic | HMDB | Acid, myristic | HMDB | FA(14:0) | HMDB |
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Chemical Formula | C14H28O2 |
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Average Mass | 228.3709 Da |
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Monoisotopic Mass | 228.20893 Da |
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IUPAC Name | tetradecanoic acid |
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Traditional Name | myristic acid |
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CAS Registry Number | 544-63-8 |
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SMILES | CCCCCCCCCCCCCC(O)=O |
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InChI Identifier | 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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InChI Key | TUNFSRHWOTWDNC-UHFFFAOYSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental) | bgnzk@missouri.edu | Not Available | Not Available | 2023-07-24 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental) | bgnzk@missouri.edu | Not Available | Not Available | 2023-07-24 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| Chemical Shift Submissions |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 600.133705802, CDCl3, simulated) | bgnzk@missouri.edu | Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-05-14 | View Spectrum |
| Species |
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Species of Origin | |
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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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Experimental Properties | Property | Value | Reference |
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Melting Point | 53.9 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.0011 mg/mL | Not Available | LogP | 6.11 | Sangster, J. (1993). LOGKOW- a Databank of Evaluated Octanol-Water Partition Coefficients. Sangster Research Laboratories, Montreal. |
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Predicted Properties | |
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General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- Bhattacharya A, Ghosal SK: Permeation kinetics of ketotifen fumarate alone and in combination with hydrophobic permeation enhancers through human cadaver epidermis. Boll Chim Farm. 2000 Jul-Aug;139(4):177-81. [PubMed:11059101 ]
- 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 ]
- 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 ]
- 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 ]
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