Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C24H48O2 |
| Molecular Weight | 368.6367 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCCCCCCCCCCCCCCCCCC(O)=O
InChI
InChIKey=QZZGJDVWLFXDLK-UHFFFAOYSA-N
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)
| Molecular Formula | C24H48O2 |
| Molecular Weight | 368.6367 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/25702090 | https://www.ncbi.nlm.nih.gov/pubmed/15653672 | https://www.ncbi.nlm.nih.gov/pubmed/1194916 | https://www.ncbi.nlm.nih.gov/pubmed/18998246
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/25702090 | https://www.ncbi.nlm.nih.gov/pubmed/15653672 | https://www.ncbi.nlm.nih.gov/pubmed/1194916 | https://www.ncbi.nlm.nih.gov/pubmed/18998246
Lignoceric Acid (tetracosanoic acid) is a saturated fatty acid with a 24-carbon backbone, that occurs naturally in wood tar, various cerebrosides, and in small amount in most natural fats. In mammals, it is found in cerebrosides and is synthesized during brain development. The deficient peroxisomal oxidation of very-long-chain fatty acids, including lignoceric acid, contributes to certain syndromes, including Zellweger cerebro-hepato-renal syndrome and X chromosome-linked adrenoleukodystrophy. Lignoceric acid is also a product of lignin production.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Chemical and enzymatic transacylation of amide-linked FA of buttermilk gangliosides. | 2003 Aug |
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| Expression of the Arabidopsis ADS1 gene in Brassica juncea results in a decreased level of total saturated fatty acids. | 2003 May |
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| Characterization of the cuticular surface wax pores and the waxy particles of the dustywing, Semidalis flinti (Neuroptera: Coniopterygidae). | 2003 Oct |
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| Characterization of the Acyl-CoA synthetase activity of purified murine fatty acid transport protein 1. | 2003 Oct 31 |
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| Synthetic glycolipid OCH prevents insulitis and diabetes in NOD mice. | 2004 Dec |
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| Alterations of fatty acid metabolism and membrane fluidity in peroxisome-defective mutant ZP102 cells. | 2004 Jan |
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| Evidence that oxidative stress is increased in patients with X-linked adrenoleukodystrophy. | 2004 Jan 20 |
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| Structural elucidation of fritillahupehin from bulbs of Fritillaria hupehensis Hsiao et K.C. Hsia. | 2004 Mar |
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| Very long chain fatty acid synthesis in sunflower kernels. | 2005 Apr 6 |
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| sn-position determination of phospholipid-linked fatty acids derived from erythrocytes by liquid chromatography electrospray ionization ion-trap mass spectrometry. | 2005 Feb |
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| Very long chain fatty acids activate NADPH oxidase in human dermal fibroblasts. | 2005 Jan-Feb |
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| Enzymatic properties of purified murine fatty acid transport protein 4 and analysis of acyl-CoA synthetase activities in tissues from FATP4 null mice. | 2005 Mar 25 |
|
| [Synthetic glycolipid ligands as novel therapeutics for multiple sclerosis]. | 2005 Nov |
|
| Fat intake and composition of fatty acids in serum phospholipids in a randomized, controlled, Mediterranean dietary intervention study on patients with rheumatoid arthritis. | 2005 Oct 10 |
|
| [Studies on chemical constituents from roots of Peucedanum praeruptorum II]. | 2006 Aug |
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| High-fat feeding reduces endothelium-dependent vasodilation in rats: differential mechanisms for saturated and unsaturated fatty acids? | 2006 Aug |
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| Analysis of fatty acids in lung tissues using gas chromatography-mass spectrometry preceded by derivatization-solid-phase microextraction with a novel fiber. | 2006 Jul 14 |
|
| Uptake of the glycosphingolipid sulfatide in the gastrointestinal tract and pancreas in vivo and in isolated islets of Langerhans. | 2006 Oct 17 |
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| Bafoudiosbulbins A, and B, two anti-salmonellal clerodane diterpenoids from Dioscorea bulbifera L. var sativa. | 2006 Sep |
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| The effect of Lorenzo's oil on oxidative stress in X-linked adrenoleukodystrophy. | 2006 Sep 25 |
|
| [Immunomodulation by modified glycolipid ligand-stimulated invariant natural killer T (iNKT) cells]. | 2007 Apr |
|
| Relationship between serum concentrations of saturated fatty acids and unsaturated fatty acids and the homeostasis model insulin resistance index in Japanese patients with type 2 diabetes mellitus. | 2007 Aug |
|
| Comparison between different hydrolysis processes of vine-trimming waste to obtain hemicellulosic sugars for further lactic acid conversion. | 2007 Dec |
|
| Novel free ceramides as components of the soldier defense gland of the Formosan subterranean termite (Coptotermes formosanus). | 2007 Mar |
|
| [Chemical constituents from root of Psammosilene tunicoides]. | 2007 May |
|
| Saturated very-long-chain fatty acids promote cotton fiber and Arabidopsis cell elongation by activating ethylene biosynthesis. | 2007 Nov |
|
| Induction of lipid peroxidation and decrease of antioxidant defenses in symptomatic and asymptomatic patients with X-linked adrenoleukodystrophy. | 2007 Nov |
|
| Down-regulation of fatty acid synthase increases the resistance of Saccharomyces cerevisiae cells to H2O2. | 2007 Nov 15 |
|
| Fatty acid and carotenoid production by Sporobolomyces ruberrimus when using technical glycerol and ammonium sulfate. | 2007 Oct |
|
| Peroxisomal-mitochondrial oxidation in a rodent model of obesity-associated insulin resistance. | 2007 Oct |
|
| Molecular cloning, expression profiling, and yeast complementation of 19 beta-tubulin cDNAs from developing cotton ovules. | 2008 |
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| Prolongation of cardiac allograft survival by rapamycin and the invariant natural killer T cell glycolipid agonist OCH. | 2008 Aug 15 |
|
| [Chemical constituents from dried sorophore of cultured Cordyceps militaris]. | 2008 Dec |
|
| Study of the lipidic and proteic composition of an industrial filmogenic yeast with applications as a nutritional supplement. | 2008 Dec 24 |
|
| Functional domains of the fatty acid transport proteins: studies using protein chimeras. | 2008 Mar |
|
| Phage display-derived recombinant antibodies with TCR-like specificity against alpha-galactosylceramide and its analogues in complex with human CD1d molecules. | 2008 Mar |
|
| A simple and sensitive liquid chromatographic method for the analysis of free docosanoic, tetracosanoic and hexacosanoic acids in human plasma as fluorescent derivatives. | 2008 Mar 17 |
|
| [Study on chemical constituents in roots and rhizomes of Ligularia duciforms II]. | 2008 May |
|
| Petiveria alliacea extracts uses multiple mechanisms to inhibit growth of human and mouse tumoral cells. | 2008 Nov 18 |
|
| Enhanced production of nitric oxide, reactive oxygen species, and pro-inflammatory cytokines in very long chain saturated fatty acid-accumulated macrophages. | 2008 Nov 28 |
|
| [Chemical constituents of Solanum cathayanum]. | 2008 Sep |
|
| Metabolomics of the interaction between PPAR-alpha and age in the PPAR-alpha-null mouse. | 2009 |
|
| Application of GC-MS for the detection of lipophilic compounds in diverse plant tissues. | 2009 Apr 24 |
|
| Quantitation of alpha-linolenic acid elongation to eicosapentaenoic and docosahexaenoic acid as affected by the ratio of n6/n3 fatty acids. | 2009 Feb 19 |
|
| Comparative evaluation of rice bran wax as an ointment base with standard base. | 2009 Jan |
|
| Odd-numbered very-long-chain fatty acids from the microbial, animal and plant kingdoms. | 2009 May-Jul |
|
| Persistence of essential fatty acid deficiency in cystic fibrosis despite nutritional therapy. | 2009 Nov |
|
| Engineering and validation of a novel lipid thin film for biomembrane modeling in lipophilicity determination of drugs and xenobiotics. | 2009 Sep 7 |
|
| Mechanisms for glycolipid antigen-driven cytokine polarization by Valpha14i NKT cells. | 2010 Jan 1 |
|
| A comparative analysis of the distribution and composition of lipidic constituents and associated enzymes in pollen and stigma of sunflower. | 2010 Jun |
Sample Use Guides
Human skin fibroblasts were used for activity evaluation. Cell cultures were washed twice with serum-free DMEM F-12 and cultured for another 24 h in DMEM F-12 (supplemented with 1% FBS) medium before treatment with VLCFAs. Varying concentrations (0.5–10 mg/ml) of lignoceric acid (a 24-carbon compound) or cerotic acid (a 26-carbon compound) were added to the cell cultures and cells were further cultured for 48 h. Culture medium containing VLCFAs was changed once after 24 h. of treatment and replaced with fresh culture medium containing the same concentrations of VLCFAs as originally added. NADPH oxidase (NOX) activity was measured in cell homogenates at 37C using lucigenin and NADPH. Enzymic activity of NOX was significantly ( p<0.001) increased in dermal fibroblasts following treatment with lignoceric acid or cerotic acid.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 01:02:39 UTC 2023
by
admin
on
Thu Jul 06 01:02:39 UTC 2023
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| Record UNII |
RK3VCW5Y1L
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| Record Status |
Validated (UNII)
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| Record Version |
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C68439
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NCI_THESAURUS |
C68421
Created by
admin on Thu Jul 06 01:02:40 UTC 2023 , Edited by admin on Thu Jul 06 01:02:40 UTC 2023
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DSLD |
1506 (Number of products:1)
Created by
admin on Thu Jul 06 01:02:40 UTC 2023 , Edited by admin on Thu Jul 06 01:02:40 UTC 2023
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| Code System | Code | Type | Description | ||
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11197
Created by
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557-59-5
Created by
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DTXSID6021664
Created by
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C68387
Created by
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RK3VCW5Y1L
Created by
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PRIMARY | |||
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28866
Created by
admin on Thu Jul 06 01:02:40 UTC 2023 , Edited by admin on Thu Jul 06 01:02:40 UTC 2023
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LIGNOCERIC ACID
Created by
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209-180-7
Created by
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PRIMARY | |||
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M6811
Created by
admin on Thu Jul 06 01:02:40 UTC 2023 , Edited by admin on Thu Jul 06 01:02:40 UTC 2023
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PRIMARY | Merck Index |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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LIPID -> FATTY ACID |
Value was not available.
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LIPID -> FATTY ACID |
TUNISIAN SOURCE
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LIPID -> FATTY ACID |
Range values as of FAO/WHO Codex Alimentarius Committee on commercial fats and oils.(unspecified percent)
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