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

Details

Stereochemistry ACHIRAL
Molecular Formula C24H48O2
Molecular Weight 368.6376
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 368.6376
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
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
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 Sat Jun 26 04:28:10 UTC 2021
Edited
by admin
on Sat Jun 26 04:28:10 UTC 2021
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 Sat Jun 26 04:28:10 UTC 2021 , Edited by admin on Sat Jun 26 04:28:10 UTC 2021
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
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
Code System Code Type Description
PUBCHEM
11197
Created by admin on Sat Jun 26 04:28:10 UTC 2021 , Edited by admin on Sat Jun 26 04:28:10 UTC 2021
PRIMARY
CAS
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
PRIMARY
EPA CompTox
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
PRIMARY
NCI_THESAURUS
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
PRIMARY
FDA UNII
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
PRIMARY
WIKIPEDIA
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
PRIMARY
ECHA (EC/EINECS)
209-180-7
Created by admin on Sat Jun 26 04:28:10 UTC 2021 , Edited by admin on Sat Jun 26 04:28:10 UTC 2021
PRIMARY
MERCK INDEX
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
PRIMARY Merck Index
Related Record Type Details
LIPID -> FATTY ACID
Value was not available.
LIPID -> FATTY ACID
IOOC limits
LIPID -> FATTY ACID
Range values as of FAO/WHO Codex Alimentarius Committee on commercial fats and oils.(unspecified percent)