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Record Information
Version1.0
Created at2006-05-22 14:17:31 UTC
Updated at2021-08-19 20:22:30 UTC
NP-MRD IDNP0000041
Secondary Accession NumbersNone
Natural Product Identification
Common NameTetracosanoic acid
DescriptionTetracosanoic acid is a C24 straight-chain saturated fatty acid. It has a role as a volatile oil component, a plant metabolite, a human metabolite and a Daphnia tenebrosa metabolite. It is a very long-chain fatty acid and a straight-chain saturated fatty acid. It is a conjugate acid of a tetracosanoate. Tetracosanoic acid, also known as N-tetracosanoate or lignoceric acid, 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. Tetracosanoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Tetracosanoic acid is a potentially toxic compound.
Structure
Thumb
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
FA(24:0)HMDB
Tetracosanoic acidMeSH
Chemical FormulaC24H48O2
Average Mass368.6367 Da
Monoisotopic Mass368.36543 Da
IUPAC Nametetracosanoic acid
Traditional Namelignoceric acid
CAS Registry Number557-59-5
SMILES
CCCCCCCCCCCCCCCCCCCCCCCC(O)=O
InChI Identifier
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)
InChI KeyQZZGJDVWLFXDLK-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated)V.dorna832021-08-13View Spectrum
Species
Species of Origin
Species NameSourceReference
Acacia auriculiformisLOTUS Database
Acacia polyacanthaLOTUS Database
Adenanthera pavoninaKNApSAcK Database
Ajania nubigenaLOTUS Database
Allium ampeloprasumLOTUS Database
Alpinia oxyphyllaKNApSAcK Database
Amaranthus dubiusLOTUS Database
Amphimedon compressaLOTUS Database
Angelica sinensisKNApSAcK Database
Anisomeles indicaKNApSAcK Database
Aplysina lacunosaLOTUS Database
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaLOTUS Database
Bredemeyera brevifoliaLOTUS Database
Broussonetia papyriferaLOTUS Database
Bupleurum chinenseKNApSAcK Database
Callyspongia fallaxLOTUS Database
Calophyllum calabaKNApSAcK Database
Calophyllum inophyllumKNApSAcK Database
Canavalia ensiformisLOTUS Database
Cannabis sativaCannabisDB
      Not Available
Cecropia pachystachyaLOTUS Database
Chlorophytum arundinaceumPlant
Cinnamosma madagascariensisLOTUS Database
Clitoria ternataKNApSAcK Database
Cornus capitataLOTUS Database
Cryptolepis buchananiiLOTUS Database
Dalbergia ecastaphyllumLOTUS Database
Dicliptera chinensisLOTUS Database
Dipteryx lacuniferaLOTUS Database
Duhaldea cappaLOTUS Database
Erylus formosusLOTUS Database
Fontinalis antipyreticaLOTUS Database
Fritillaria hupehensisLOTUS Database
Fritillaria monanthaLOTUS Database
Ganoderma australeLOTUS Database
Gnetum montanumLOTUS Database
Guazuma ulmifoliaLOTUS Database
Hedysarum sikkimenseLOTUS Database
Heptapleurum rhododendrifoliumLOTUS Database
Hibiscus cannabinusLOTUS Database
Hippomane mancinellaLOTUS Database
Hypericum perforatumLOTUS Database
Lantana strigocamaraLOTUS Database
Larix gmeliniLOTUS Database
Lippia sidoidesLOTUS Database
Lumbricus terrestrisLOTUS Database
Malva sylvestrisLOTUS Database
Malvaviscus arboreusLOTUS Database
Mangifera indicaKNApSAcK Database
Mirabilis jalapaLOTUS Database
Myrmekioderma reaLOTUS Database
Notopterygium incisumKNApSAcK Database
Penicillium javanicumLOTUS Database
Petiveria alliaceaLOTUS Database
Peucedanum govanianum var.bicoloKNApSAcK Database
Picea jezoensisLOTUS Database
Picea obovataLOTUS Database
Pinus koraiensisKNApSAcK Database
Pinus pumilaLOTUS Database
Pinus radiataLOTUS Database
Pinus sibiricaKNApSAcK Database
Populus tremuloidesLOTUS Database
Prunus africanaLOTUS Database
Prunus laurocerasusLOTUS Database
Psammosilene tunicoidesLOTUS Database
Rhizophora apiculataLOTUS Database
Ruscus aculeatusLOTUS Database
Saposhnikovia divaricataKNApSAcK Database
Scomber japonicusLOTUS Database
Scutellaria laterifloraLOTUS Database
Sideritis tauricaLOTUS Database
Sophora flavescensLOTUS Database
Streptomyces griseoincarnatusLOTUS Database
Strychnos nitidaKNApSAcK Database
Terminalia chebulaLOTUS Database
Tornabea scutelliferaLOTUS Database
Traversia baccharoidesLOTUS Database
Trichosanthes kirilowiiKNApSAcK Database
Tripneustes ventricosusLOTUS Database
Triticum aestivumKNApSAcK Database
Triticum turgidumLOTUS Database
Turraea niloticaLOTUS Database
Zataria multifloraLOTUS Database
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point84.2 °CNot Available
Boiling Point405.90 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility5.9e-06 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP11.400 (est)The Good Scents Company Information System
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002003
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004651
KNApSAcK IDC00001223
Chemspider ID10724
KEGG Compound IDC08320
BioCyc IDTETRACOSANOATE
BiGG ID2218057
Wikipedia LinkLignoceric_acid
METLIN ID6427
PubChem Compound11197
PDB IDNot Available
ChEBI ID28866
Good Scents IDrw1287001
References
General References
  1. 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. [PubMed:3572253 ]
  2. 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. [PubMed:15565636 ]
  3. 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. [PubMed:12865096 ]
  4. 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. [PubMed:23438684 ]
  5. 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. [PubMed:11913692 ]