FComEx: Nervonic acid (PC000778)

Record Information

Version

1.0

Creation date

2015-10-09 22:32:38 UTC

Update date

2017-01-19 02:36:36 UTC

FoodComEx ID

PC000778

FoodDB Record

FDB002934

Chemical Information

Name

Nervonic acid

Description

Present in fish and rape seed oils Nervonic acid is a long chain unsaturated fatty acid that is enriched in sphingomyelin. It consists of choline, sphingosine, phosphoric acid, and fatty acid. Nervonic acid may enhance the brain functions and prevent demyelination (Chemical Land21). Research shows that there is negative relationship between nervonic acid and obesity-related risk factors (PMID: 16394593); Demyelination in adrenoleukodystrophy (ALD) is associated with an accumulation of very long chain saturated fatty acids stemming from a genetic defect in the peroxisomal beta oxidation system responsible for the chain shortening of these fatty acids. Sphingolipids from post mortem ALD brain have decreased levels of nervonic acid, 24:1(n-9), and increased levels of stearic acid, 18:0. (PMID: 8072429); Nervonic acid is a monounsaturated omega-9 fatty acid. Nervonic acid has been identified as important in the biosynthesis of nerve cell myelin. It is found in the sphingolipids of white matter in human brain.; Nervonic acid is used in the treatment of disorders involving demyelination, such as adrenoleukodystrophy and multiple sclerosis where there is a decreased level of nervonic acid in sphingolipids.

CAS Number

506-37-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(15Z)-tetracos-15-enoate	biospider
(15Z)-tetracos-15-enoic acid	biospider
(15Z)-Tetracosenoate	biospider
(15Z)-Tetracosenoic acid	biospider
(Z)-15-Tetracosenoate	biospider
(z)-15-tetracosenoic acid	biospider
(Z)-Tetracos-15-enoate	Generator
(Z)-Tetracos-15-enoic acid	ChEBI
15-Tetracosenoate	biospider
15-Tetracosenoic acid	biospider
15cis-Tetracosenoate	Generator
15cis-Tetracosenoic acid	ChEBI
15Z-tetracosenoate	biospider
15Z-tetracosenoic acid	biospider
cis-15-Teracosenoate	biospider
cis-15-Teracosenoic acid	biospider
cis-15-Tetracosenate	biospider
cis-15-Tetracosenic acid	biospider
cis-15-tetracosenoate	biospider
cis-15-tetracosenoic acid	biospider
cis-Delta(15)-tetracosenoate	biospider
cis-Delta(15)-tetracosenoic acid	biospider
Cis-selacholeate	biospider
Cis-selacholeic acid	biospider
cis-δ(15)-tetracosenoate	Generator
cis-δ(15)-tetracosenoic acid	Generator
Nervonate	biospider
Nervonic acid	db_source
Nervonsaeure	ChEBI
Selacholeate	biospider
Selacholeic acid	db_source
tetracos-15-enoic acid	biospider

Chemical Formula

C24H46O2

IUPAC name

(15E)-tetracos-15-enoic acid

InChI Identifier

InChI=1S/C24H46O2/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/h9-10H,2-8,11-23H2,1H3,(H,25,26)/b10-9+

InChI Key

GWHCXVQVJPWHRF-MDZDMXLPSA-N

Isomeric SMILES

CCCCCCCC\C=C\CCCCCCCCCCCCCC(O)=O

Average Molecular Weight

366.6208

Monoisotopic Molecular Weight

366.349780716

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Very long-chain fatty acids

Alternative Parents