Record Information
Version1.0
Creation date2010-04-08 22:06:20 UTC
Update date2019-11-26 03:00:09 UTC
Primary IDFDB004651
Secondary Accession Numbers
  • FDB021823
Chemical Information
FooDB NameCarnaubic acid
DescriptionLignoceric acid, also known as N-tetracosanoic acid or tetraeicosanoate, is a member of the class of compounds known as very long-chain fatty acids. Very long-chain fatty acids are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Thus, lignoceric acid is considered to be a fatty acid lipid molecule. Lignoceric acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Lignoceric acid can be found in a number of food items such as hazelnut, cheese, rye bread, and cetacea (dolphin, porpoise, whale), which makes lignoceric acid a potential biomarker for the consumption of these food products. Lignoceric acid can be found primarily in blood and feces, as well as in human fibroblasts tissue. Lignoceric acid exists in all eukaryotes, ranging from yeast to humans. In humans, lignoceric acid is involved in a couple of metabolic pathways, which include adrenoleukodystrophy, x-linked and beta oxidation of very long chain fatty acids. Lignoceric acid is also involved in carnitine-acylcarnitine translocase deficiency, which is a metabolic disorder. Lignoceric acid, or tetracosanoic acid, is the saturated fatty acid with formula C23H47COOH. It is found in wood tar, various cerebrosides, and in small amounts in most natural fats. The fatty acids of peanut oil contain small amounts of lignoceric acid (1.1% – 2.2%). This fatty acid is also a byproduct of lignin production .
CAS Number557-59-5
Structure
Thumb
Synonyms
SynonymSource
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
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
Chemical FormulaC24H48O2
IUPAC nametetracosanoic acid
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
Isomeric SMILESCCCCCCCCCCCCCCCCCCCCCCCC(O)=O
Average Molecular Weight368.6367
Monoisotopic Molecular Weight368.36543078
Classification
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0avl-9200000000-6a6f857b59886189b246Spectrum
GC-MSCarnaubic acid, non-derivatized, GC-MS Spectrumsplash10-0159-1900000000-3507c183bf018486d18fSpectrum
GC-MSCarnaubic acid, 1 TMS, GC-MS Spectrumsplash10-0159-2900000000-9dedfb3583ae4e553948Spectrum
GC-MSCarnaubic acid, non-derivatized, GC-MS Spectrumsplash10-07bf-9000000000-2ae141518702212751a7Spectrum
GC-MSCarnaubic acid, non-derivatized, GC-MS Spectrumsplash10-0159-1900000000-3507c183bf018486d18fSpectrum
GC-MSCarnaubic acid, non-derivatized, GC-MS Spectrumsplash10-0159-2900000000-9dedfb3583ae4e553948Spectrum
GC-MSCarnaubic acid, non-derivatized, GC-MS Spectrumsplash10-0159-1900000000-2826f8c66ba3647dda0fSpectrum
Predicted GC-MSCarnaubic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-7690000000-51ad38c3eba8f98c3565Spectrum
Predicted GC-MSCarnaubic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00g0-9550000000-6d38b4af18d7872e12a9Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004r-0791000000-10ab351997f48e512657Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004r-0791000000-10ab351997f48e512657Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004r-0791000000-10ab351997f48e512657Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0009000000-5c9df57aa4e8e48bd80fSpectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0009000000-a22a23dbfe780a163a38Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0009000000-7907c6ab3ef19e9cdf86Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0009000000-847587fdc96a653e9651Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0009000000-5c9df57aa4e8e48bd80fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0009000000-a22a23dbfe780a163a38Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0009000000-847587fdc96a653e9651Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-016r-0509000000-b590f3868a4aa3c86803Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-0903000000-a6d1b482b61c2d36ee1dSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-0900000000-4ef3dd8c92115a6d4e0cSpectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-07bf-9000000000-2ae141518702212751a7Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0a4i-0900000000-3c3e69329be8a7148076Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0900000000-3c3e69329be8a7148076Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-249bc2a1e0da9132abb1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ba-0009000000-bb2e8d3e4fc1a5f88c77Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9113000000-18bb969031b0d8959a2fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-48bd2e6f8cbaa8fda6bdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kmi-2339000000-6881995e14be93cee803Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-6982000000-bcce0a5d41ac456500c7Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDCARNAUBIC-ACID
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).