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)
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 |
|---|---|---|
| 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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| Synthetic glycolipid OCH prevents insulitis and diabetes in NOD mice. | 2004 Dec |
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| The human FA2H gene encodes a fatty acid 2-hydroxylase. | 2004 Nov 19 |
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| Method for measurement of peroxisomal very-long-chain fatty acid beta-oxidation in human skin fibroblasts using stable-isotope-labeled tetracosanoic acid. | 2004 Oct |
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| Transmissible spongiform encephalopathies: assessment of exposure risk in the histological working environment using GC-MS detection of fatty acids as marker for central nervous tissues. | 2005 |
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| Very-long-chain fatty acids activate lysosomal hydrolases in neonatal human skin tissue. | 2005 |
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| Natural killer T cells and rheumatoid arthritis: friend or foe? | 2005 |
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| Very long chain fatty acid synthesis in sunflower kernels. | 2005 Apr 6 |
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| Preferential T(h)2 polarization by OCH is supported by incompetent NKT cell induction of CD40L and following production of inflammatory cytokines by bystander cells in vivo. | 2005 Dec |
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| Glycosylphosphatidylinositol-anchored fungal polysaccharide in Aspergillus fumigatus. | 2005 Dec 2 |
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| Synthesis and evaluation of sphinganine analogues of KRN7000 and OCH. | 2005 Dec 9 |
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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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| A novel method for the measurement of in vitro fatty acid 2-hydroxylase activity by gas chromatography-mass spectrometry. | 2005 Jul |
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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 |
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| [Synthetic glycolipid ligands as novel therapeutics for multiple sclerosis]. | 2005 Nov |
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| 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 |
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| [Chemical components in essential oils from tender branches and leaves of Rhododendron]. | 2005 Sep |
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| Chemical constituents of Selinum cryptotaenium. | 2006 Apr-May |
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| [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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| [Studies on the chemical constituents of Lagotis yunnanensis (II)]. | 2006 Feb |
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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 |
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| A new sesquiterpene lactone from the roots of Lasianthus acuminatissimus. | 2006 May |
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| 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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| Sequential pressurized liquid extraction to determine brain-originating fatty acids in meat products as markers in bovine spongiform encephalopathy risk assessment studies. | 2006 Sep 15 |
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| The effect of Lorenzo's oil on oxidative stress in X-linked adrenoleukodystrophy. | 2006 Sep 25 |
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| [Immunomodulation by modified glycolipid ligand-stimulated invariant natural killer T (iNKT) cells]. | 2007 Apr |
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| 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 |
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| Comparison between different hydrolysis processes of vine-trimming waste to obtain hemicellulosic sugars for further lactic acid conversion. | 2007 Dec |
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| Novel free ceramides as components of the soldier defense gland of the Formosan subterranean termite (Coptotermes formosanus). | 2007 Mar |
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| [Chemical constituents from root of Psammosilene tunicoides]. | 2007 May |
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| Fatty acid and carotenoid production by Sporobolomyces ruberrimus when using technical glycerol and ammonium sulfate. | 2007 Oct |
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| Peroxisomal-mitochondrial oxidation in a rodent model of obesity-associated insulin resistance. | 2007 Oct |
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| Molecular cloning, expression profiling, and yeast complementation of 19 beta-tubulin cDNAs from developing cotton ovules. | 2008 |
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| Isolation and characterization of thermotolerant fungi producing lignoceric acid from glycerol. | 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 |
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| [Chemical constituents from dried sorophore of cultured Cordyceps militaris]. | 2008 Dec |
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| [Chemical constituents from stems of Schisandra propinqua]. | 2008 Mar |
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| Petiveria alliacea extracts uses multiple mechanisms to inhibit growth of human and mouse tumoral cells. | 2008 Nov 18 |
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| Enhanced production of nitric oxide, reactive oxygen species, and pro-inflammatory cytokines in very long chain saturated fatty acid-accumulated macrophages. | 2008 Nov 28 |
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| Application of GC-MS for the detection of lipophilic compounds in diverse plant tissues. | 2009 Apr 24 |
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| Very long chain fatty acid levels in patients diagnosed with multiple sclerosis. | 2009 Dec |
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| Comparative evaluation of rice bran wax as an ointment base with standard base. | 2009 Jan |
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| Analysis of sterols and fatty acids in natural and cultured Cordyceps by one-step derivatization followed with gas chromatography-mass spectrometry. | 2009 Jul 12 |
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| Odd-numbered very-long-chain fatty acids from the microbial, animal and plant kingdoms. | 2009 May-Jul |
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| Composition of diethyl ether flower extracts of Lonicera fragrantissima Lindl. & Paxton (caprifoliaceae). | 2009 Nov |
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| Cytochrome P450 family member CYP704B2 catalyzes the {omega}-hydroxylation of fatty acids and is required for anther cutin biosynthesis and pollen exine formation in rice. | 2010 Jan |
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| Synthesis and biological activity of alpha-L-fucosyl ceramides, analogues of the potent agonist, alpha-D-galactosyl ceramide KRN7000. | 2010 Jun 1 |
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.
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NCI_THESAURUS |
C68439
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NCI_THESAURUS |
C68421
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DSLD |
1506 (Number of products:1)
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11197
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557-59-5
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DTXSID6021664
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C68387
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RK3VCW5Y1L
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28866
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LIGNOCERIC ACID
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209-180-7
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m6811
Created by
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PRIMARY | Merck Index |
SUBSTANCE RECORD
