Tetracosanoic acid (CHEM003568)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-09-05 17:13:21 UTC
Update Date2026-04-17 17:44:34 UTC
Accession NumberCHEM003568
Identification
Common NameTetracosanoic acid
ClassSmall Molecule
DescriptionLignoceric acid, also tetracosanoic acid, is a normal carboxylic acid, a very long chain fatty acid (VLCFA). Very long chain fatty acids (VLCFAs) are exclusively oxidized in peroxisomes and their levels are significantly increased in tissues of patients with peroxisomal disorders. (2).
Contaminant Sources
  • FooDB Chemicals
  • HPV EPA Chemicals
  • T3DB toxins
Contaminant Type
  • Animal Toxin
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
CH3-[CH2]22-COOHChEBI
Lignoceric acidChEBI
LignozerinsaeureChEBI
N-Tetracosanoic acidChEBI
Tetracosanic acidChEBI
TetracosansaeureChEBI
Tetracosoic acidChEBI
Tetraeicosanoic acidChEBI
Tetraicosanoic acidChEBI
LignocerateGenerator
N-TetracosanoateGenerator
TetracosanateGenerator
TetracosoateGenerator
TetraeicosanoateGenerator
TetraicosanoateGenerator
TetracosanoateGenerator
Lignoceric acid, silver (1+) saltHMDB
Lignoceric acid, sodium saltHMDB
Lignoceric acid, potassium saltHMDB
Tetracosanoic acid, potassium salt (1:1)HMDB
Potassium tetracosanoateHMDB
Tetracosanoic acidMeSH
FA(24:0)PhytoBank
Chemical FormulaC24H48O2
Average Molecular Mass368.637 g/mol
Monoisotopic Mass368.365 g/mol
CAS Registry Number557-59-5
IUPAC Nametetracosanoic acid
Traditional Namelignoceric acid
SMILESCCCCCCCCCCCCCCCCCCCCCCCC(O)=O
InChI IdentifierInChI=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)
InChI KeyQZZGJDVWLFXDLK-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentVery long-chain fatty acids
Alternative Parents
Substituents
  • Very long-chain fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Peroxisome
Biofluid LocationsNot Available
Tissue Locations
  • Fibroblasts
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point84.2 °C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.3e-05 g/LALOGPS
logP9.56ALOGPS
logP9.81ChemAxon
logS-7.2ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity113.89 m³·mol⁻¹ChemAxon
Polarizability51.57 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0159-1900000000-3507c183bf018486d18fSpectrum
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0159-2900000000-9dedfb3583ae4e553948Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-07bf-9000000000-2ae141518702212751a7Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0159-1900000000-3507c183bf018486d18fSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0159-2900000000-9dedfb3583ae4e553948Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0159-1900000000-2826f8c66ba3647dda0fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-7690000000-51ad38c3eba8f98c3565Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00g0-9550000000-6d38b4af18d7872e12a9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-016r-0509000000-b590f3868a4aa3c86803Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-0903000000-a6d1b482b61c2d36ee1dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-0900000000-4ef3dd8c92115a6d4e0cSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-07bf-9000000000-2ae141518702212751a7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0a4i-0900000000-3c3e69329be8a7148076Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004r-0791000000-10ab351997f48e512657Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004r-0791000000-10ab351997f48e512657Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004r-0791000000-10ab351997f48e512657Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0009000000-5c9df57aa4e8e48bd80fSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0009000000-a22a23dbfe780a163a38Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0009000000-7907c6ab3ef19e9cdf86Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0009000000-847587fdc96a653e9651Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0009000000-5c9df57aa4e8e48bd80fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0009000000-a22a23dbfe780a163a38Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0009000000-847587fdc96a653e9651Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0900000000-3c3e69329be8a7148076Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-0009000000-847587fdc96a653e9651Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-014i-0009000000-7bccb707d42bca681a58Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-a22a23dbfe780a163a38Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-48bd2e6f8cbaa8fda6bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kmi-2339000000-6881995e14be93cee803Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-6982000000-bcce0a5d41ac456500c7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-249bc2a1e0da9132abb1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ba-0009000000-bb2e8d3e4fc1a5f88c77Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9113000000-18bb969031b0d8959a2fSpectrum
MSMass Spectrum (Electron Ionization)splash10-0avl-9200000000-6a6f857b59886189b246Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002003
FooDB IDFDB004651
Phenol Explorer IDNot Available
KNApSAcK IDC00001223
BiGG ID2218057
BioCyc IDTETRACOSANOATE
METLIN ID6427
PDB IDNot Available
Wikipedia LinkLignoceric_acid
Chemspider ID10724
ChEBI ID28866
PubChem Compound ID11197
Kegg Compound IDC08320
YMDB IDYMDB00684
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21781003
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23019902
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23157011
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23394615
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23871298
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=24491713
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=3174658
8. Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.
9. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.
10. Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987.
11. Galloway JH, Cartwright IJ, Bennett MJ: Abnormal myocardial lipid composition in an infant with type II glutaric aciduria. J Lipid Res. 1987 Mar;28(3):279-84.
12. Dhaunsi GS, Kaur J, Alsaeid K, Turner RB, Bitar MS: Very long chain fatty acids activate NADPH oxidase in human dermal fibroblasts. Cell Biochem Funct. 2005 Jan-Feb;23(1):65-8.
13. Petroni A, Blasevich M, Uziel G: 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. Life Sci. 2003 Aug 8;73(12):1567-75.