Record Information
Version1.0
Creation date2015-10-09 22:31:45 UTC
Update date2017-01-19 02:36:31 UTC
FoodComEx IDPC000644
FoodDB RecordFDB002927
Chemical Information
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
Synonyms
SynonymSource
Arachatebiospider
Arachic aciddb_source
Arachidatebiospider
Arachidic aciddb_source
ArachidinateGenerator
Arachidinic acidbiospider
ArachinsaeureChEBI
CH3-[CH2]18-COOHChEBI
Eicosanoatebiospider
EicosoateGenerator
Eicosoic acidbiospider
Icosanoatebiospider
Icosanoic aciddb_source
N-Eicosanoatebiospider
N-Eicosanoic acidbiospider
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
Chemical Taxonomy
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
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logP9.29SANGSTER (1993)
Experimental Water SolubilityNot Available
Melting PointMp 77°DFC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 200 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci J10948
AKSci J92310
AKSci L983
Cayman Chemical 9000339
MetaSci HMDB0002212
Sigma-Aldrich HMDB0002212
Toronto Research Chemicals A764990