Record Information |
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Version | 1.0 |
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Created at | 2020-03-18 23:22:32 UTC |
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Updated at | 2020-12-07 19:06:59 UTC |
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CannabisDB ID | CDB006174 |
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Secondary Accession Numbers | Not Available |
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Cannabis Compound 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 is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It has a waxy, fatty or soapy odor and a fatty, creamy or cheesy taste. Myristic acid exists in all living species, ranging from bacteria to humans. Myristic acid is a naturally occurring saturated fatty acid found in most animal and vegetable fats. Some of the highest levels of myristic acid are found in nutmeg. In particular, nutmeg butter has 75% trimyristin, the triglyceride of myristic acid. Besides nutmeg, myristic acid is also found in palm kernel oil, coconut oil, butterfat, 8–14% of bovine milk, and 8.6% of breast milk as well as being a minor component of many other animal fats. It also comprises 14.49% of the fats from the fruit of the Durian species. Industrially myristic acid is used as an ingredient in soaps and cosmetics (From Dorland, 28th ed). In many eukaryotes (including humans), myristic acid is commonly added to the N-terminal glycine residue in receptor-associated kinases to confer membrane localization of the enzyme. This is achieved by the myristic acid having a high enough hydrophobicity to become incorporated into the fatty acyl core of the phospholipid bilayer of the plasma membrane of the eukaryotic cell (Wikipedia ). Some research has pointed to myristic acid's positive effects on regulating HDL cholesterol and hence improving the HDL (good cholesterol) to total cholesterol ratio (PMID: 7644455 ). Myristic acid is a constituent of cannabis plant and cannabis smoke. It is volatilized during the combustion of cannabis ( Ref:DOI ). |
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Structure | |
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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 Molecular Weight | 228.37 |
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Monoisotopic Molecular Weight | 228.2089 |
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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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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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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Biological role: Industrial application: |
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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 | 326.2 °C at 760 mmHg | Wikipedia | Water Solubility | 0.0011 mg/mL | Not Available | logP | 6.11 | SANGSTER (1993) |
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Predicted Properties | [] |
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Spectra |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-06xx-9200000000-4fdd41f0461ff5186901 | 2014-09-20 | View Spectrum | GC-MS | Myristic acid, 1 TMS, GC-MS Spectrum | splash10-017i-2910000000-66b35fb8449ba9de9cd6 | Spectrum | GC-MS | Myristic acid, non-derivatized, GC-MS Spectrum | splash10-017i-2910000000-66b35fb8449ba9de9cd6 | Spectrum | GC-MS | Myristic acid, non-derivatized, GC-MS Spectrum | splash10-0159-0910000000-f45703c464ca75f98f26 | Spectrum | Predicted GC-MS | Myristic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0006-9700000000-ec8d81e37bc3b8531c99 | Spectrum | Predicted GC-MS | Myristic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0079-9330000000-5ec01705dfacc992be28 | Spectrum | Predicted GC-MS | Myristic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Myristic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-004i-0090000000-73ac1cfb8731e6318cc5 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-004i-1090000000-3aa768974da0ea81c1c9 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-004i-0090000000-22cd107a87b9acf058c5 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-004i-0090000000-2f7bb32e4b42206d851d | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-004i-2090000000-d45cffc15e2efbd45cd6 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-001i-9200000000-dbca68238dfebab35251 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-004r-9000000000-26827be8f8c2a4fbfd75 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-0006-0090000000-110165b889d231d09d59 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-0006-0090000000-110165b889d231d09d59 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-0006-0090000000-110165b889d231d09d59 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-0006-0090000000-110165b889d231d09d59 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-004i-0090000000-91f4f874b25705464fb0 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-004i-0090000000-15225a799e0a0bcff7c7 | 2017-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0290000000-b88426a2003ceec57e30 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01q9-5940000000-6c73dc0032502abe4fc4 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052f-9300000000-bde9bfcd2889066fc853 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0290000000-b88426a2003ceec57e30 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01q9-5940000000-6c73dc0032502abe4fc4 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052f-9300000000-bde9bfcd2889066fc853 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0190000000-a32f141c7b5af0bc4de1 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-057i-1490000000-14bfb0d0344d7cf63443 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9400000000-512abb1322963024336f | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0190000000-a32f141c7b5af0bc4de1 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-057i-1490000000-14bfb0d0344d7cf63443 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9400000000-512abb1322963024336f | 2015-05-27 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, CDCl3, experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | | Spectrum |
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Pathways |
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Pathways | Name | SMPDB/Pathwhiz | KEGG | Fatty Acid Biosynthesis | | Not Available |
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Protein Targets |
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Enzymes | |
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Transporters | |
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Metal Bindings | |
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Receptors | |
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Transcriptional Factors | |
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Concentrations Data |
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| Not Available |
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External Links |
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HMDB ID | HMDB0000806 |
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DrugBank ID | DB08231 |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB031009 |
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KNApSAcK ID | C00001228 |
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Chemspider ID | 10539 |
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KEGG Compound ID | C06424 |
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BioCyc ID | CPD-7836 |
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BiGG ID | 215851 |
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Wikipedia Link | Myristic_acid |
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METLIN ID | 196 |
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PubChem Compound | 11005 |
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PDB ID | Not Available |
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ChEBI ID | 28875 |
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References |
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General References | - Kromhout D, Menotti A, Bloemberg B, Aravanis C, Blackburn H, Buzina R, Dontas AS, Fidanza F, Giampaoli S, Jansen A, et al.: Dietary saturated and trans fatty acids and cholesterol and 25-year mortality from coronary heart disease: the Seven Countries Study. Prev Med. 1995 May;24(3):308-15. doi: 10.1006/pmed.1995.1049. [PubMed:7644455 ]
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