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 |
|---|---|---|
| Synthesis and biological activity of alpha-L-fucosyl ceramides, analogues of the potent agonist, alpha-D-galactosyl ceramide KRN7000. | 2010-06-01 |
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| A comparative analysis of the distribution and composition of lipidic constituents and associated enzymes in pollen and stigma of sunflower. | 2010-06 |
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| Plasma and erythrocyte fatty acid patterns in patients with recurrent depression: a matched case-control study. | 2010-05-14 |
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| Lovastatin in X-linked adrenoleukodystrophy. | 2010-01-21 |
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| Mechanisms for glycolipid antigen-driven cytokine polarization by Valpha14i NKT cells. | 2010-01-01 |
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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. | 2010-01 |
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| FPTIII mitigates peroxisome-mediated oxidative stress in kidneys of spontaneously hypertensive diabetic rats. | 2010 |
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| Dissecting the role of critical residues and substrate preference of a Fatty Acyl-CoA Synthetase (FadD13) of Mycobacterium tuberculosis. | 2009-12-21 |
|
| Very long chain fatty acid levels in patients diagnosed with multiple sclerosis. | 2009-12 |
|
| [Studies on the chemical constituents of Portulaca oleracea]. | 2009-11 |
|
| Composition of diethyl ether flower extracts of Lonicera fragrantissima Lindl. & Paxton (caprifoliaceae). | 2009-11 |
|
| Persistence of essential fatty acid deficiency in cystic fibrosis despite nutritional therapy. | 2009-11 |
|
| Engineering and validation of a novel lipid thin film for biomembrane modeling in lipophilicity determination of drugs and xenobiotics. | 2009-09-07 |
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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. | 2009-07-12 |
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| Application of GC-MS for the detection of lipophilic compounds in diverse plant tissues. | 2009-04-24 |
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| Quantitation of alpha-linolenic acid elongation to eicosapentaenoic and docosahexaenoic acid as affected by the ratio of n6/n3 fatty acids. | 2009-02-19 |
|
| Odd-numbered very-long-chain fatty acids from the microbial, animal and plant kingdoms. | 2009-02-02 |
|
| Comparative evaluation of rice bran wax as an ointment base with standard base. | 2009-01 |
|
| Metabolomics of the interaction between PPAR-alpha and age in the PPAR-alpha-null mouse. | 2009 |
|
| Study of the lipidic and proteic composition of an industrial filmogenic yeast with applications as a nutritional supplement. | 2008-12-24 |
|
| [Chemical constituents from dried sorophore of cultured Cordyceps militaris]. | 2008-12 |
|
| Enhanced production of nitric oxide, reactive oxygen species, and pro-inflammatory cytokines in very long chain saturated fatty acid-accumulated macrophages. | 2008-11-28 |
|
| Petiveria alliacea extracts uses multiple mechanisms to inhibit growth of human and mouse tumoral cells. | 2008-11-18 |
|
| [Chemical constituents of Solanum cathayanum]. | 2008-09 |
|
| Prolongation of cardiac allograft survival by rapamycin and the invariant natural killer T cell glycolipid agonist OCH. | 2008-08-15 |
|
| [Study on chemical constituents in roots and rhizomes of Ligularia duciforms II]. | 2008-05 |
|
| A simple and sensitive liquid chromatographic method for the analysis of free docosanoic, tetracosanoic and hexacosanoic acids in human plasma as fluorescent derivatives. | 2008-03-17 |
|
| [Chemical constituents from stems of Schisandra propinqua]. | 2008-03 |
|
| Functional domains of the fatty acid transport proteins: studies using protein chimeras. | 2008-03 |
|
| Phage display-derived recombinant antibodies with TCR-like specificity against alpha-galactosylceramide and its analogues in complex with human CD1d molecules. | 2008-03 |
|
| [Chemical constituents of Changium smyrnioides]. | 2008-01 |
|
| Secondary metabolites of Cinnamosma madagascariensis and their alpha-glucosidase inhibitory properties. | 2008-01 |
|
| Molecular cloning, expression profiling, and yeast complementation of 19 beta-tubulin cDNAs from developing cotton ovules. | 2008 |
|
| Isolation and characterization of thermotolerant fungi producing lignoceric acid from glycerol. | 2008 |
|
| Comparison between different hydrolysis processes of vine-trimming waste to obtain hemicellulosic sugars for further lactic acid conversion. | 2007-12 |
|
| Down-regulation of fatty acid synthase increases the resistance of Saccharomyces cerevisiae cells to H2O2. | 2007-11-15 |
|
| Saturated very-long-chain fatty acids promote cotton fiber and Arabidopsis cell elongation by activating ethylene biosynthesis. | 2007-11 |
|
| Induction of lipid peroxidation and decrease of antioxidant defenses in symptomatic and asymptomatic patients with X-linked adrenoleukodystrophy. | 2007-11 |
|
| Fatty acid and carotenoid production by Sporobolomyces ruberrimus when using technical glycerol and ammonium sulfate. | 2007-10 |
|
| Peroxisomal-mitochondrial oxidation in a rodent model of obesity-associated insulin resistance. | 2007-10 |
|
| 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. | 2007-08 |
|
| [Chemical constituents from root of Psammosilene tunicoides]. | 2007-05 |
|
| [Immunomodulation by modified glycolipid ligand-stimulated invariant natural killer T (iNKT) cells]. | 2007-04 |
|
| Novel free ceramides as components of the soldier defense gland of the Formosan subterranean termite (Coptotermes formosanus). | 2007-03 |
|
| Uptake of the glycosphingolipid sulfatide in the gastrointestinal tract and pancreas in vivo and in isolated islets of Langerhans. | 2006-10-17 |
|
| Bafoudiosbulbins A, and B, two anti-salmonellal clerodane diterpenoids from Dioscorea bulbifera L. var sativa. | 2006-09 |
|
| [Studies on chemical constituents from roots of Peucedanum praeruptorum II]. | 2006-08 |
|
| High-fat feeding reduces endothelium-dependent vasodilation in rats: differential mechanisms for saturated and unsaturated fatty acids? | 2006-08 |
|
| Analysis of fatty acids in lung tissues using gas chromatography-mass spectrometry preceded by derivatization-solid-phase microextraction with a novel fiber. | 2006-07-14 |
|
| Expression of the Arabidopsis ADS1 gene in Brassica juncea results in a decreased level of total saturated fatty acids. | 2003-05 |
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
Mon Mar 31 18:51:21 GMT 2025
by
admin
on
Mon Mar 31 18:51:21 GMT 2025
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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
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DSLD |
1506 (Number of products:1)
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| Code System | Code | Type | Description | ||
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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
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PRIMARY | Merck Index |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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LIPID -> FATTY ACID | |||
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LIPID -> FATTY ACID | |||
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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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