U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Characterization of novel structures of mannosylinositolphosphorylceramides from the yeast forms of Sporothrix schenckii.
2001 Aug
Stable ordering in Langmuir-Blodgett films.
2001 Aug 17
Diagnostic patterns of very-long-chain fatty acids in plasma of patients with X-linked adrenoleukodystrophy.
2001 Aug 25
Lupeol esters from the twig bark of Japanese pear (Pyrus serotina Rehd.) cv. Shinko.
2001 May
Peroxisomal fatty acid oxidation and cellular redox.
2002
Constituents of Gnetum montanum.
2002 Feb
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
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
Expression of the Arabidopsis ADS1 gene in Brassica juncea results in a decreased level of total saturated fatty acids.
2003 May
Structural elucidation of fritillahupehin from bulbs of Fritillaria hupehensis Hsiao et K.C. Hsia.
2004 Mar
Natural killer T cells and rheumatoid arthritis: friend or foe?
2005
[Studies on chemical constituents from roots of Peucedanum praeruptorum II].
2006 Aug
Uptake of the glycosphingolipid sulfatide in the gastrointestinal tract and pancreas in vivo and in isolated islets of Langerhans.
2006 Oct 17
Induction of lipid peroxidation and decrease of antioxidant defenses in symptomatic and asymptomatic patients with X-linked adrenoleukodystrophy.
2007 Nov
Fatty acid and carotenoid production by Sporobolomyces ruberrimus when using technical glycerol and ammonium sulfate.
2007 Oct
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
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
[Chemical constituents of Solanum cathayanum].
2008 Sep
Very long chain fatty acid levels in patients diagnosed with multiple sclerosis.
2009 Dec
Engineering and validation of a novel lipid thin film for biomembrane modeling in lipophilicity determination of drugs and xenobiotics.
2009 Sep 7
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
Synthesis and biological activity of alpha-L-fucosyl ceramides, analogues of the potent agonist, alpha-D-galactosyl ceramide KRN7000.
2010 Jun 1
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 Fri Dec 15 17:44:59 GMT 2023
Edited
by admin
on Fri Dec 15 17:44:59 GMT 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 Fri Dec 15 17:45:00 GMT 2023 , Edited by admin on Fri Dec 15 17:45:00 GMT 2023
NCI_THESAURUS C68421
Created by admin on Fri Dec 15 17:45:00 GMT 2023 , Edited by admin on Fri Dec 15 17:45:00 GMT 2023
DSLD 1506 (Number of products:1)
Created by admin on Fri Dec 15 17:45:00 GMT 2023 , Edited by admin on Fri Dec 15 17:45:00 GMT 2023
Code System Code Type Description
PUBCHEM
11197
Created by admin on Fri Dec 15 17:45:00 GMT 2023 , Edited by admin on Fri Dec 15 17:45:00 GMT 2023
PRIMARY
CAS
557-59-5
Created by admin on Fri Dec 15 17:45:00 GMT 2023 , Edited by admin on Fri Dec 15 17:45:00 GMT 2023
PRIMARY
EPA CompTox
DTXSID6021664
Created by admin on Fri Dec 15 17:45:00 GMT 2023 , Edited by admin on Fri Dec 15 17:45:00 GMT 2023
PRIMARY
NCI_THESAURUS
C68387
Created by admin on Fri Dec 15 17:45:00 GMT 2023 , Edited by admin on Fri Dec 15 17:45:00 GMT 2023
PRIMARY
FDA UNII
RK3VCW5Y1L
Created by admin on Fri Dec 15 17:45:00 GMT 2023 , Edited by admin on Fri Dec 15 17:45:00 GMT 2023
PRIMARY
CHEBI
28866
Created by admin on Fri Dec 15 17:45:00 GMT 2023 , Edited by admin on Fri Dec 15 17:45:00 GMT 2023
PRIMARY
WIKIPEDIA
LIGNOCERIC ACID
Created by admin on Fri Dec 15 17:45:00 GMT 2023 , Edited by admin on Fri Dec 15 17:45:00 GMT 2023
PRIMARY
ECHA (EC/EINECS)
209-180-7
Created by admin on Fri Dec 15 17:45:00 GMT 2023 , Edited by admin on Fri Dec 15 17:45:00 GMT 2023
PRIMARY
MERCK INDEX
m6811
Created by admin on Fri Dec 15 17:45:00 GMT 2023 , Edited by admin on Fri Dec 15 17:45:00 GMT 2023
PRIMARY Merck Index
Related Record Type Details
LIPID -> FATTY ACID
TUNISIAN SOURCE
LIPID -> FATTY ACID
Value was not available.
LIPID -> FATTY ACID
Range values as of FAO/WHO Codex Alimentarius Committee on commercial fats and oils.(unspecified percent)