Record Information |
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Version | 1.0 |
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Created at | 2006-05-22 14:17:31 UTC |
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Updated at | 2021-08-19 20:22:30 UTC |
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NP-MRD ID | NP0000041 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Tetracosanoic acid |
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Description | Tetracosanoic acid is a C24 straight-chain saturated fatty acid. It has a role as a volatile oil component, a plant metabolite, a human metabolite and a Daphnia tenebrosa metabolite. It is a very long-chain fatty acid and a straight-chain saturated fatty acid. It is a conjugate acid of a tetracosanoate. Tetracosanoic acid, also known as N-tetracosanoate or lignoceric acid, belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Tetracosanoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Tetracosanoic acid is a potentially toxic compound. |
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Structure | CCCCCCCCCCCCCCCCCCCCCCCC(O)=O InChI=1S/C24H48O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24(25)26/h2-23H2,1H3,(H,25,26) |
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Synonyms | Value | Source |
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CH3-[CH2]22-COOH | ChEBI | Lignoceric acid | ChEBI | Lignozerinsaeure | ChEBI | N-Tetracosanoic acid | ChEBI | Tetracosanic acid | ChEBI | Tetracosansaeure | ChEBI | Tetracosoic acid | ChEBI | Tetraeicosanoic acid | ChEBI | Tetraicosanoic acid | ChEBI | Lignocerate | Generator | N-Tetracosanoate | Generator | Tetracosanate | Generator | Tetracosoate | Generator | Tetraeicosanoate | Generator | Tetraicosanoate | Generator | Tetracosanoate | Generator | Lignoceric acid, silver (1+) salt | HMDB | Lignoceric acid, sodium salt | HMDB | Lignoceric acid, potassium salt | HMDB | Tetracosanoic acid, potassium salt (1:1) | HMDB | Potassium tetracosanoate | HMDB | FA(24:0) | HMDB | Tetracosanoic acid | MeSH |
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Chemical Formula | C24H48O2 |
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Average Mass | 368.6367 Da |
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Monoisotopic Mass | 368.36543 Da |
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IUPAC Name | tetracosanoic acid |
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Traditional Name | lignoceric acid |
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CAS Registry Number | 557-59-5 |
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SMILES | CCCCCCCCCCCCCCCCCCCCCCCC(O)=O |
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InChI Identifier | InChI=1S/C24H48O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24(25)26/h2-23H2,1H3,(H,25,26) |
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InChI Key | QZZGJDVWLFXDLK-UHFFFAOYSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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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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| Not Available | Chemical Shift Submissions |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated) | V.dorna83 | | | 2021-08-13 | 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 very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 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 | Very long-chain fatty acids |
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Alternative Parents | |
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Substituents | - Very 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 | |
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Predicted Properties | |
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General References | - Galloway JH, Cartwright IJ, Bennett MJ: Abnormal myocardial lipid composition in an infant with type II glutaric aciduria. J Lipid Res. 1987 Mar;28(3):279-84. [PubMed:3572253 ]
- Dhaunsi GS, Kaur J, Alsaeid K, Turner RB, Bitar MS: Very long chain fatty acids activate NADPH oxidase in human dermal fibroblasts. Cell Biochem Funct. 2005 Jan-Feb;23(1):65-8. [PubMed:15565636 ]
- Petroni A, Blasevich M, Uziel G: Effects of the testosterone metabolite dihydrotestosterone and 5 alpha-androstan-3 alpha,17 beta-diol on very long chain fatty acid metabolism in X-adrenoleukodystrophic fibroblasts. Life Sci. 2003 Aug 8;73(12):1567-75. [PubMed:12865096 ]
- Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
- Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
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