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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
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
[Effect of various substrate nutrient on the spore germination and infective germ tube inducing of Pandora delphacis].
2001 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
Characterization of the cuticular surface wax pores and the waxy particles of the dustywing, Semidalis flinti (Neuroptera: Coniopterygidae).
2003 Oct
The human FA2H gene encodes a fatty acid 2-hydroxylase.
2004 Nov 19
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
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
Synthesis and evaluation of sphinganine analogues of KRN7000 and OCH.
2005 Dec 9
A novel method for the measurement of in vitro fatty acid 2-hydroxylase activity by gas chromatography-mass spectrometry.
2005 Jul
[Chemical components in essential oils from tender branches and leaves of Rhododendron].
2005 Sep
A new sesquiterpene lactone from the roots of Lasianthus acuminatissimus.
2006 May
The effect of Lorenzo's oil on oxidative stress in X-linked adrenoleukodystrophy.
2006 Sep 25
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
Induction of lipid peroxidation and decrease of antioxidant defenses in symptomatic and asymptomatic patients with X-linked adrenoleukodystrophy.
2007 Nov
Isolation and characterization of thermotolerant fungi producing lignoceric acid from glycerol.
2008
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
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
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
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
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
FPTIII mitigates peroxisome-mediated oxidative stress in kidneys of spontaneously hypertensive diabetic rats.
2010
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
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
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)