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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
Structure of LIGNOCERIC ACID

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)

HIDE SMILES / InChI

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

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Chemical and enzymatic transacylation of amide-linked FA of buttermilk gangliosides.
2003 Aug
Expression of the Arabidopsis ADS1 gene in Brassica juncea results in a decreased level of total saturated fatty acids.
2003 May
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
Alterations of fatty acid metabolism and membrane fluidity in peroxisome-defective mutant ZP102 cells.
2004 Jan
Evidence that oxidative stress is increased in patients with X-linked adrenoleukodystrophy.
2004 Jan 20
Structural elucidation of fritillahupehin from bulbs of Fritillaria hupehensis Hsiao et K.C. Hsia.
2004 Mar
Very long chain fatty acid synthesis in sunflower kernels.
2005 Apr 6
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
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
High-fat feeding reduces endothelium-dependent vasodilation in rats: differential mechanisms for saturated and unsaturated fatty acids?
2006 Aug
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
Bafoudiosbulbins A, and B, two anti-salmonellal clerodane diterpenoids from Dioscorea bulbifera L. var sativa.
2006 Sep
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
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
Patents

Sample Use Guides

Unknown
Route of Administration: Oral
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 Thu Jul 06 01:02:39 UTC 2023
Edited
by admin
on Thu Jul 06 01:02:39 UTC 2023
Record UNII
RK3VCW5Y1L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LIGNOCERIC ACID
MI  
Systematic Name English
FL-88(FATTY ACID)
Code English
N-TETRACOSANOIC ACID
Common Name English
TETRACOSANOIC ACID
Systematic Name English
LIGNOCERIC ACID [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C68439
Created by admin on Thu Jul 06 01:02:40 UTC 2023 , Edited by admin on Thu Jul 06 01:02:40 UTC 2023
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
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
Code System Code Type Description
PUBCHEM
11197
Created by admin on Thu Jul 06 01:02:40 UTC 2023 , Edited by admin on Thu Jul 06 01:02:40 UTC 2023
PRIMARY
CAS
557-59-5
Created by admin on Thu Jul 06 01:02:40 UTC 2023 , Edited by admin on Thu Jul 06 01:02:40 UTC 2023
PRIMARY
EPA CompTox
DTXSID6021664
Created by admin on Thu Jul 06 01:02:40 UTC 2023 , Edited by admin on Thu Jul 06 01:02:40 UTC 2023
PRIMARY
NCI_THESAURUS
C68387
Created by admin on Thu Jul 06 01:02:40 UTC 2023 , Edited by admin on Thu Jul 06 01:02:40 UTC 2023
PRIMARY
FDA UNII
RK3VCW5Y1L
Created by admin on Thu Jul 06 01:02:40 UTC 2023 , Edited by admin on Thu Jul 06 01:02:40 UTC 2023
PRIMARY
CHEBI
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
PRIMARY
WIKIPEDIA
LIGNOCERIC ACID
Created by admin on Thu Jul 06 01:02:40 UTC 2023 , Edited by admin on Thu Jul 06 01:02:40 UTC 2023
PRIMARY
ECHA (EC/EINECS)
209-180-7
Created by admin on Thu Jul 06 01:02:40 UTC 2023 , Edited by admin on Thu Jul 06 01:02:40 UTC 2023
PRIMARY
MERCK INDEX
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
PRIMARY Merck Index
Related Record Type Details
LIPID -> FATTY ACID
Value was not available.
LIPID -> FATTY ACID
TUNISIAN SOURCE
LIPID -> FATTY ACID
Range values as of FAO/WHO Codex Alimentarius Committee on commercial fats and oils.(unspecified percent)