Record Information |
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Version | 1.0 |
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Created at | 2020-03-18 23:22:56 UTC |
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Updated at | 2020-12-07 19:07:00 UTC |
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CannabisDB ID | CDB000050 |
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Secondary Accession Numbers | Not Available |
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Cannabis Compound Identification |
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Common Name | Arachidic acid |
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Description | Arachidic acid, also known as eicosanoic acid, is a saturated fatty acid with a 20-carbon chain. It 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. Arachidic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It is a white crystalline solid. Arachidic acid’s name derives from the Latin arachis—peanut. It can be formed by the hydrogenation of arachidonic acid. Arachidic acid is a minor constituent of cupuaçu butter (7%), perilla oil (0–1%), peanut oil (1.1–1.7%), corn oil (3%), Arabica coffee oil and cocoa butter (1%). It also constitutes 7.1% of the fats from the durian fruit. Arachidic acid is also found in cannabis (PMID:6991645 ). Arachidic acid occurs naturally in fish and vegetable oils. The salts and esters of arachidic acid are known as arachidates. Diets rich in saturated fats like arachidic acid are associated with increased levels of serum low density lipoproteins. In a study of arachidic acid on Arabica coffee oil (PMID: 29995918 ), the influence of high-temperature heating on composition and thermo-oxidative stability was studied. The investigated samples showed a stability to oxidation up to approx. 276.8 ̊C -278.3 ̊C and the heat treatment of the beans during the roasting process did not significantly affect the composition in fatty acids. Arabica coffee oil may be used in processes which require high-temperature heating, such as those employed by the food industry, or in the production of pastries. Arachidic acid is also used for the production of detergents, photographic materials and lubricants. Arachidic acid is also 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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Arachic acid | ChEBI | Arachidinic acid | ChEBI | Arachinsaeure | ChEBI | C20:0 | ChEBI | CH3-[CH2]18-COOH | ChEBI | Eicosanoic acid | ChEBI | N-Eicosanoic acid | ChEBI | Arachate | Generator | Arachidinate | Generator | Eicosanoate | Generator | N-Eicosanoate | Generator | Arachidate | Generator | Eicosoic acid | ChEBI, HMDB | Icosanoic acid | ChEBI, HMDB | Eicosoate | Generator, HMDB | Icosanoate | Generator, HMDB | Arachidic acid | HMDB | C 20 | HMDB | C20 fatty acid | HMDB | FA(20:0) | HMDB | Peanut acid | HMDB | n-Eicosanic acid | HMDB |
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Chemical Formula | C20H40O2 |
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Average Molecular Weight | 312.53 |
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Monoisotopic Molecular Weight | 312.3028 |
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IUPAC Name | icosanoic acid |
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Traditional Name | arachidic acid |
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CAS Registry Number | 506-30-9 |
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SMILES | CCCCCCCCCCCCCCCCCCCC(O)=O |
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InChI Identifier | InChI=1S/C20H40O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h2-19H2,1H3,(H,21,22) |
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InChI Key | VKOBVWXKNCXXDE-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 | Industrial application: Biological role: |
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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 | 75.4 °C | Not Available | Boiling Point | 328 °C | Wikipedia | Water Solubility | Not Available | Not Available | logP | 9.29 | 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) | splash10-0596-9100000000-091619221e36a7a177ff | 2014-09-20 | View Spectrum | GC-MS | Arachidic acid, non-derivatized, GC-MS Spectrum | splash10-0159-0900000000-cc7f30812c4ef45583b1 | Spectrum | GC-MS | Arachidic acid, 1 TMS, GC-MS Spectrum | splash10-0159-2901000000-7d146c5d993118307ce5 | Spectrum | GC-MS | Arachidic acid, non-derivatized, GC-MS Spectrum | splash10-0596-9100000000-53a544b7fbf2ee3b176a | Spectrum | GC-MS | Arachidic acid, non-derivatized, GC-MS Spectrum | splash10-0159-0900000000-cc7f30812c4ef45583b1 | Spectrum | GC-MS | Arachidic acid, non-derivatized, GC-MS Spectrum | splash10-0159-2901000000-7d146c5d993118307ce5 | Spectrum | GC-MS | Arachidic acid, non-derivatized, GC-MS Spectrum | splash10-014i-1900000000-33733dae76fd89dc7394 | Spectrum | Predicted GC-MS | Arachidic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0006-9450000000-ff95bd6be578f2c72ce9 | Spectrum | Predicted GC-MS | Arachidic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0109-9560000000-d2d19ad6d5ef54fdf90a | Spectrum | Predicted GC-MS | Arachidic acid, non-derivatized, 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, Positive (Annotated) | splash10-03di-0029000000-273e657da59fa67385c2 | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0a4i-9200000000-84b07a6d22109c441336 | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0a4i-9100000000-9d6e321e2bf8cd1f20e4 | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-03di-0009000000-d7e3408b3b2e854229b0 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-03di-0109000000-c0ed9d28e54855b40069 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-0a6r-0013493000-832a78a9cf97d74660ea | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-06vi-0012391000-e4dcf31aba99059fcf39 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0a4i-0193000000-031626259c4a17016165 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0a4i-0091000000-9389b44ea9cfe1afe40b | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-03di-0009000000-6bf31eaaa3592667dc53 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-03di-0009000000-32767cc1909515840261 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-03e9-3409000000-c86c0c5c2a80a4d1a6d6 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0009000000-545adcea3fffd230d8c7 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0092000000-c40a8544a31d253f26c6 | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0i01-2491000000-60bf2b9a6912f287f6f0 | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0zfu-8970000000-fd0569abd03da6142ee2 | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0092000000-c40a8544a31d253f26c6 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0i01-2491000000-60bf2b9a6912f287f6f0 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0zfu-8970000000-fd0569abd03da6142ee2 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0049000000-54fd1cf54bdd386d406e | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03xu-1095000000-2584a862e47ea0cb88f2 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052f-9140000000-2caaff4da05fbcb0fdf7 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0049000000-54fd1cf54bdd386d406e | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03xu-1095000000-2584a862e47ea0cb88f2 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052f-9140000000-2caaff4da05fbcb0fdf7 | 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 | 1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental) | | Spectrum |
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Pathways |
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Pathways | 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 | HMDB0002212 |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB002927 |
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KNApSAcK ID | C00001209 |
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Chemspider ID | 10035 |
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KEGG Compound ID | C06425 |
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BioCyc ID | ARACHIDIC_ACID |
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BiGG ID | 48230 |
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Wikipedia Link | Arachidic_acid |
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METLIN ID | 401 |
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PubChem Compound | 10467 |
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PDB ID | Not Available |
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ChEBI ID | 28822 |
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References |
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General References | - Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
- Raba DN, Chambre DR, Copolovici DM, Moldovan C, Copolovici LO: The influence of high-temperature heating on composition and thermo-oxidative stability of the oil extracted from Arabica coffee beans. PLoS One. 2018 Jul 11;13(7):e0200314. doi: 10.1371/journal.pone.0200314. eCollection 2018. [PubMed:29995918 ]
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