Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C24H48O2 |
| Molecular Weight | 368.6376 |
| 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 | 368.6376 |
| 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 |
|---|---|---|
| Final report on the safety assessment of Corylus Avellana (Hazel) Seed Oil, Corylus Americana (Hazel) Seed Oil, Corylus Avellana (Hazel) Seed Extract, Corylus Americana (Hazel) Seed Extract, Corylus Avellana (Hazel) Leaf Extract, Corylus Americana (Hazel) Leaf Extract, and Corylus Rostrata (Hazel) Leaf Extract. | 2001 |
|
| Stable ordering in Langmuir-Blodgett films. | 2001 Aug 17 |
|
| [Determination of fatty acids in Malania oleifera oil by gas chromatography-mass spectrometry]. | 2001 Mar |
|
| [Studies on chemical constituents of two plants from Costus]. | 2002 Feb |
|
| Structure of a novel diterpenoid ester, fritillahupehin from bulbs of Fritillaria hupehensis Hsiao and K.C. Hsia. | 2002 Jul |
|
| 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 |
|
| Flaxseed (Linum usitatissimum) supplementation associated with reduced skin test lesional area in horses with Culicoides hypersensitivity. | 2002 Oct |
|
| 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. | 2003 Aug 8 |
|
| The determination of air/water partition coefficients for alkyl carboxylic acids by a new indirect method. | 2003 Oct |
|
| Characterization of the cuticular surface wax pores and the waxy particles of the dustywing, Semidalis flinti (Neuroptera: Coniopterygidae). | 2003 Oct |
|
| Characterization of the Acyl-CoA synthetase activity of purified murine fatty acid transport protein 1. | 2003 Oct 31 |
|
| Synthetic glycolipid OCH prevents insulitis and diabetes in NOD mice. | 2004 Dec |
|
| 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 |
|
| Very-long-chain fatty acids activate lysosomal hydrolases in neonatal human skin tissue. | 2005 |
|
| 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 |
|
| Glycosylphosphatidylinositol-anchored fungal polysaccharide in Aspergillus fumigatus. | 2005 Dec 2 |
|
| Synthesis and evaluation of sphinganine analogues of KRN7000 and OCH. | 2005 Dec 9 |
|
| sn-position determination of phospholipid-linked fatty acids derived from erythrocytes by liquid chromatography electrospray ionization ion-trap mass spectrometry. | 2005 Feb |
|
| Very long chain fatty acids activate NADPH oxidase in human dermal fibroblasts. | 2005 Jan-Feb |
|
| [Synthetic glycolipid ligands as novel therapeutics for multiple sclerosis]. | 2005 Nov |
|
| [Chemical components in essential oils from tender branches and leaves of Rhododendron]. | 2005 Sep |
|
| High-fat feeding reduces endothelium-dependent vasodilation in rats: differential mechanisms for saturated and unsaturated fatty acids? | 2006 Aug |
|
| [Studies on the chemical constituents of Lagotis yunnanensis (II)]. | 2006 Feb |
|
| 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 |
|
| A new sesquiterpene lactone from the roots of Lasianthus acuminatissimus. | 2006 May |
|
| Bafoudiosbulbins A, and B, two anti-salmonellal clerodane diterpenoids from Dioscorea bulbifera L. var sativa. | 2006 Sep |
|
| 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 |
|
| The effect of Lorenzo's oil on oxidative stress in X-linked adrenoleukodystrophy. | 2006 Sep 25 |
|
| Saturated very-long-chain fatty acids promote cotton fiber and Arabidopsis cell elongation by activating ethylene biosynthesis. | 2007 Nov |
|
| Isolation and characterization of thermotolerant fungi producing lignoceric acid from glycerol. | 2008 |
|
| 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 |
|
| Secondary metabolites of Cinnamosma madagascariensis and their alpha-glucosidase inhibitory properties. | 2008 Jan |
|
| [Chemical constituents from stems of Schisandra propinqua]. | 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 |
|
| 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 |
|
| Application of GC-MS for the detection of lipophilic compounds in diverse plant tissues. | 2009 Apr 24 |
|
| Dissecting the role of critical residues and substrate preference of a Fatty Acyl-CoA Synthetase (FadD13) of Mycobacterium tuberculosis. | 2009 Dec 21 |
|
| Comparative evaluation of rice bran wax as an ointment base with standard base. | 2009 Jan |
|
| [Studies on the chemical constituents of Portulaca oleracea]. | 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 |
|
| Lovastatin in X-linked adrenoleukodystrophy. | 2010 Jan 21 |
|
| 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
Sat Jun 26 04:28:10 UTC 2021
by
admin
on
Sat Jun 26 04:28:10 UTC 2021
|
| Record UNII |
RK3VCW5Y1L
|
| Record Status |
Validated (UNII)
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| Record Version |
|
-
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| Name | Type | Language | ||
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Systematic Name | English | ||
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Code | English | ||
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Common Name | English | ||
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Systematic Name | English | ||
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Common Name | English |
| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C68439
Created by
admin on Sat Jun 26 04:28:10 UTC 2021 , Edited by admin on Sat Jun 26 04:28:10 UTC 2021
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NCI_THESAURUS |
C68421
Created by
admin on Sat Jun 26 04:28:10 UTC 2021 , Edited by admin on Sat Jun 26 04:28:10 UTC 2021
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DSLD |
1506 (Number of products:1)
Created by
admin on Sat Jun 26 04:28:10 UTC 2021 , Edited by admin on Sat Jun 26 04:28:10 UTC 2021
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| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
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11197
Created by
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PRIMARY | |||
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557-59-5
Created by
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PRIMARY | |||
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557-59-5
Created by
admin on Sat Jun 26 04:28:10 UTC 2021 , Edited by admin on Sat Jun 26 04:28:10 UTC 2021
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PRIMARY | |||
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C68387
Created by
admin on Sat Jun 26 04:28:10 UTC 2021 , Edited by admin on Sat Jun 26 04:28:10 UTC 2021
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PRIMARY | |||
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RK3VCW5Y1L
Created by
admin on Sat Jun 26 04:28:10 UTC 2021 , Edited by admin on Sat Jun 26 04:28:10 UTC 2021
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PRIMARY | |||
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LIGNOCERIC ACID
Created by
admin on Sat Jun 26 04:28:10 UTC 2021 , Edited by admin on Sat Jun 26 04:28:10 UTC 2021
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PRIMARY | |||
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209-180-7
Created by
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PRIMARY | |||
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M6811
Created by
admin on Sat Jun 26 04:28:10 UTC 2021 , Edited by admin on Sat Jun 26 04:28:10 UTC 2021
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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 |
IOOC limits
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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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