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 |
|---|---|---|
| Eight novel ABCD1 gene mutations and three polymorphisms in patients with X-linked adrenoleukodystrophy: The first polymorphism causing an amino acid exchange. | 2001 |
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| [Effect of various substrate nutrient on the spore germination and infective germ tube inducing of Pandora delphacis]. | 2001 Apr |
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| Glycoinositolphospholipids, free and as anchors of proteins, in Trypanosoma cruzi. | 2001 Aug |
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| Stable ordering in Langmuir-Blodgett films. | 2001 Aug 17 |
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| Diagnostic patterns of very-long-chain fatty acids in plasma of patients with X-linked adrenoleukodystrophy. | 2001 Aug 25 |
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| [Determination of fatty acids in Malania oleifera oil by gas chromatography-mass spectrometry]. | 2001 Mar |
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| Lipid composition and fluidity of plasma membranes isolated from corn (Zea mays L.) roots. | 2001 Mar 1 |
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| Lupeol esters from the twig bark of Japanese pear (Pyrus serotina Rehd.) cv. Shinko. | 2001 May |
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| [Studies on chemical constituents of two plants from Costus]. | 2002 Feb |
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| Constituents of Gnetum montanum. | 2002 Feb |
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| Detection of tissues of the central nervous system (CNS) as specified risk material (SRM) in meat products by means of gas chromatography-mass spectrometry (GC-MS). | 2002 Mar-Apr |
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| Flaxseed (Linum usitatissimum) supplementation associated with reduced skin test lesional area in horses with Culicoides hypersensitivity. | 2002 Oct |
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| Chemical and enzymatic transacylation of amide-linked FA of buttermilk gangliosides. | 2003 Aug |
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| In-house validation of an improved sample extraction and clean-up method for GC determination of isomers of nervonic acid in meat products. | 2003 Jun |
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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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| The human FA2H gene encodes a fatty acid 2-hydroxylase. | 2004 Nov 19 |
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| Natural killer T cells and rheumatoid arthritis: friend or foe? | 2005 |
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| Synthesis and evaluation of sphinganine analogues of KRN7000 and OCH. | 2005 Dec 9 |
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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 |
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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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| Uptake of the glycosphingolipid sulfatide in the gastrointestinal tract and pancreas in vivo and in isolated islets of Langerhans. | 2006 Oct 17 |
|
| 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 |
|
| Peroxisomal-mitochondrial oxidation in a rodent model of obesity-associated insulin resistance. | 2007 Oct |
|
| Prolongation of cardiac allograft survival by rapamycin and the invariant natural killer T cell glycolipid agonist OCH. | 2008 Aug 15 |
|
| Study of the lipidic and proteic composition of an industrial filmogenic yeast with applications as a nutritional supplement. | 2008 Dec 24 |
|
| [Chemical constituents of Changium smyrnioides]. | 2008 Jan |
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| [Chemical constituents from stems of Schisandra propinqua]. | 2008 Mar |
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| 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 |
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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 |
|
| Very long chain fatty acid levels in patients diagnosed with multiple sclerosis. | 2009 Dec |
|
| Dissecting the role of critical residues and substrate preference of a Fatty Acyl-CoA Synthetase (FadD13) of Mycobacterium tuberculosis. | 2009 Dec 21 |
|
| Quantitation of alpha-linolenic acid elongation to eicosapentaenoic and docosahexaenoic acid as affected by the ratio of n6/n3 fatty acids. | 2009 Feb 19 |
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| 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 |
|
| [Studies on the chemical constituents of Portulaca oleracea]. | 2009 Nov |
|
| Composition of diethyl ether flower extracts of Lonicera fragrantissima Lindl. & Paxton (caprifoliaceae). | 2009 Nov |
|
| Engineering and validation of a novel lipid thin film for biomembrane modeling in lipophilicity determination of drugs and xenobiotics. | 2009 Sep 7 |
|
| FPTIII mitigates peroxisome-mediated oxidative stress in kidneys of spontaneously hypertensive diabetic rats. | 2010 |
|
| 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 |
|
| Mechanisms for glycolipid antigen-driven cytokine polarization by Valpha14i NKT cells. | 2010 Jan 1 |
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| Lovastatin in X-linked adrenoleukodystrophy. | 2010 Jan 21 |
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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 Jun |
|
| Synthesis and biological activity of alpha-L-fucosyl ceramides, analogues of the potent agonist, alpha-D-galactosyl ceramide KRN7000. | 2010 Jun 1 |
|
| Plasma and erythrocyte fatty acid patterns in patients with recurrent depression: a matched case-control study. | 2010 May 14 |
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
Fri Dec 15 17:44:59 GMT 2023
by
admin
on
Fri Dec 15 17:44:59 GMT 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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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
Created by
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209-180-7
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m6811
Created by
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PRIMARY | Merck Index |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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LIPID -> FATTY ACID |
TUNISIAN SOURCE
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LIPID -> FATTY ACID |
Value was not available.
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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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