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Showing Compound Eicosanoic acid (FDB002927)

Record Information
Version1.0
Creation date2010-04-08 22:05:35 UTC
Update date2020-09-17 15:29:58 UTC
Primary IDFDB002927
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameEicosanoic acid
DescriptionArachidic acid, also known as eicosanoic acid, is a saturated fatty acid with a 20-carbon chain. It belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Arachidic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It is a white crystalline solid. Arachidic acid’s name derives from the Latin arachis—peanut. It can be formed by the hydrogenation of arachidonic acid. Arachidic acid is a minor constituent of cupuaçu butter (7%), perilla oil (0–1%), peanut oil (1.1–1.7%), corn oil (3%), Arabica coffee oil and cocoa butter (1%). It also constitutes 7.1% of the fats from the durian fruit. Arachidic acid is also found in cannabis (PMID:6991645). Arachidic acid occurs naturally in fish and vegetable oils. The salts and esters of arachidic acid are known as arachidates. Diets rich in saturated fats like arachidic acid are associated with increased levels of serum low density lipoproteins. In a study of arachidic acid on Arabica coffee oil (PMID: 29995918), the influence of high-temperature heating on composition and thermo-oxidative stability was studied. The investigated samples showed a stability to oxidation up to approx. 276.8 ̊C -278.3 ̊C and the heat treatment of the beans during the roasting process did not significantly affect the composition in fatty acids. Arabica coffee oil may be used in processes which require high-temperature heating, such as those employed by the food industry, or in the production of pastries. Arachidic acid is also used for the production of detergents, photographic materials and lubricants.
CAS Number506-30-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility5.0e-05 g/LALOGPS
logP8.53ALOGPS
logP8.03ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity95.49 m³·mol⁻¹ChemAxon
Polarizability42.91 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H40O2
IUPAC nameicosanoic acid
InChI IdentifierInChI=1S/C20H40O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h2-19H2,1H3,(H,21,22)
InChI KeyVKOBVWXKNCXXDE-UHFFFAOYSA-N
Isomeric SMILESCCCCCCCCCCCCCCCCCCCC(O)=O
Average Molecular Weight312.5304
Monoisotopic Molecular Weight312.302830524
Classification
Description Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • 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
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0596-9100000000-091619221e36a7a177ff2014-09-20View Spectrum
GC-MSEicosanoic acid, non-derivatized, GC-MS Spectrumsplash10-0159-0900000000-cc7f30812c4ef45583b1Spectrum
GC-MSEicosanoic acid, 1 TMS, GC-MS Spectrumsplash10-0159-2901000000-7d146c5d993118307ce5Spectrum
GC-MSEicosanoic acid, non-derivatized, GC-MS Spectrumsplash10-0596-9100000000-53a544b7fbf2ee3b176aSpectrum
GC-MSEicosanoic acid, non-derivatized, GC-MS Spectrumsplash10-0159-0900000000-cc7f30812c4ef45583b1Spectrum
GC-MSEicosanoic acid, non-derivatized, GC-MS Spectrumsplash10-0159-2901000000-7d146c5d993118307ce5Spectrum
GC-MSEicosanoic acid, non-derivatized, GC-MS Spectrumsplash10-014i-1900000000-33733dae76fd89dc7394Spectrum
Predicted GC-MSEicosanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9450000000-ff95bd6be578f2c72ce9Spectrum
Predicted GC-MSEicosanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0109-9560000000-d2d19ad6d5ef54fdf90aSpectrum
Predicted GC-MSEicosanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0029000000-273e657da59fa67385c22012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9200000000-84b07a6d22109c4413362012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-9100000000-9d6e321e2bf8cd1f20e42012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-0009000000-d7e3408b3b2e854229b02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-0109000000-c0ed9d28e54855b400692017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a6r-0013493000-832a78a9cf97d74660ea2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-06vi-0012391000-e4dcf31aba99059fcf392017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4i-0193000000-031626259c4a170161652017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4i-0091000000-9389b44ea9cfe1afe40b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-03di-0009000000-6bf31eaaa3592667dc532021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-03di-0009000000-32767cc19095158402612021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-03e9-3409000000-c86c0c5c2a80a4d1a6d62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-545adcea3fffd230d8c72021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0092000000-c40a8544a31d253f26c62015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0i01-2491000000-60bf2b9a6912f287f6f02015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfu-8970000000-fd0569abd03da6142ee22015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0092000000-c40a8544a31d253f26c62015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0i01-2491000000-60bf2b9a6912f287f6f02015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfu-8970000000-fd0569abd03da6142ee22015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0049000000-54fd1cf54bdd386d406e2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xu-1095000000-2584a862e47ea0cb88f22015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9140000000-2caaff4da05fbcb0fdf72015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0049000000-54fd1cf54bdd386d406e2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xu-1095000000-2584a862e47ea0cb88f22015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9140000000-2caaff4da05fbcb0fdf72015-05-27View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Spectrum
ChemSpider ID10035
ChEMBL IDCHEMBL1173381
KEGG Compound IDC06425
Pubchem Compound ID10467
Pubchem Substance IDNot Available
ChEBI ID28822
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02212
CRC / DFC (Dictionary of Food Compounds) IDCPG46-Q:CPG46-Q
EAFUS IDNot Available
Dr. Duke IDARACHIC-ACID|ARACHIDIC-ACID|EICOSANOIC-ACID
BIGG ID48230
KNApSAcK IDC00001209
HET IDDCR
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDArachidic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.