FComEx: Eicosanoic acid (PC000644)

Record Information

Version

1.0

Creation date

2015-10-09 22:31:45 UTC

Update date

2017-01-19 02:36:31 UTC

FoodComEx ID

PC000644

FoodDB Record

FDB002927

Chemical Information

Name

Eicosanoic acid

Description

Arachidic 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‚Äôs name derives from the Latin arachis‚Äîpeanut. It can be formed by the hydrogenation of arachidonic acid. Arachidic acid is a minor constituent of cupua√ßu butter (7%), perilla oil (0‚Äì1%), peanut oil (1.1‚Äì1.7%), 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 ÃäC -278.3 ÃäC 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 Number

506-30-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Arachate	biospider
Arachic acid	db_source
Arachidate	biospider
Arachidic acid	db_source
Arachidinate	Generator
Arachidinic acid	biospider
Arachinsaeure	ChEBI
CH3-[CH2]18-COOH	ChEBI
Eicosanoate	biospider
Eicosoate	Generator
Eicosoic acid	biospider
Icosanoate	biospider
Icosanoic acid	db_source
N-Eicosanoate	biospider
N-Eicosanoic acid	biospider

Chemical Formula

C20H40O2

IUPAC name

icosanoic acid

InChI Identifier

InChI=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 Key

VKOBVWXKNCXXDE-UHFFFAOYSA-N

Isomeric SMILES

CCCCCCCCCCCCCCCCCCCC(O)=O

Average Molecular Weight

312.5304

Monoisotopic Molecular Weight

312.302830524

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents