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EC / List no.: 610-549-3
CAS no.: 506-37-6
Mol. formula: C24H46O2
Nervonic acid (24:1, n−9) is a fatty acid.
Nervonic acid is a monounsaturated analog of lignoceric acid (24:0).
Nervonic acid is also known as selacholeic acid and cis-15-tetracosenoic acid.
Its name derives from the Latin word nervus, meaning nerve or sinew.
Nervonic acid exists in nature as an elongation product of oleic acid (18:1 Δ9), its immediate precursor being erucic acid.
Nervonic acid is particularly abundant in the white matter of animal brains and in peripheral nervous tissue where nervonyl sphingolipids are enriched in the myelin sheath of nerve fibers.
In the same way, recent studies have concluded that nervonic acid is implicated as an intermediate in the biosynthesis of nerve cell myelin.
This acid is an important member of the group of the cerebrosides, which are fatty acids of the glycosphingolipids group, important components of the muscles and the central nervous system and peripheral.
Indeed, it is one of the major fatty acids in brain sphingolipids, normally accounting for approximately 40% of the total fatty acids in sphingolipids.
Structure
As it is defined as a monounsaturated fatty acid, it has one double bond in the fatty acid chain and all the remaining carbon atoms are single-bonded.
Nervonic acid is classified in the sub-group of very long chain fatty acids (VLCFA), which includes molecules containing more than 20 carbon atoms.
Nervonic acid has specifically 24-carbon backbone and the sole C=C double bond originating from the methyl end is in n-9 or omega-9 (ω-9).
Functions
Nervonic acid is an essential nutrient for the growth and maintenance of the brain.
This acid has been found in breast-milk:
Nervonic acid is said it can speed the development in infants.
Nervonic acid is the reason why it is recommended to pregnant and nursing women.
This acid is a regulator of the Ca2+ ion channel in the cell membrane of nerve tissues, so nervonic acid plays an important role in the control of the levels of calcium of the cytosol.
Nervonic acid can regulate the function of brain cell membranes and have a neuroprotective effect which is important to high-level training adults or athletes: it is an energy supplement.
Moreover, due to its function as an intermediate in myelin biosynthesis, dietary therapy with nervonic acid-containing fats has been studied: nervonic acid appears to be beneficial for the treatment of genetic disorders of the lipid metabolism, such as Zellweger syndrome or adrenoleukodistrophy.
Nervonic acid beta-oxidation takes place in peroxisomes, and this oxidation is impaired in X-ALD patients.
Due to different mutations, people having these disorders have ineffective peroxisomes.
Nervonic acid causes an important accumulation of very long chain fatty acids, that can be treated with oils enriched with 24:1 (Lorenzo's oil, Lunaria's oil).
Nervonic acid is also used as a biomarker to predict who will suffer some psychoses.
For instance, there is evidence of abnormal levels of fatty acids in individuals with schizophrenia.
In particular, decreased levels of 24:1 are related with prodromal psychosis symptoms so it can be beneficial in the prevention and treatment of this kind of disorders.
Nervonic acid can be an indicator of future neurodevelopmental disorders in male babies whose mother has preeclampsia.
Recent studies show that cord nervonic acid levels were lower in women with preeclampsia delivering male babies as compared to normotensive control group.
But this does not happen with girl babies.
These results suggest that male babies born to mothers with preeclampsia may be at an increased risk of developing neurodevelopmental disorders as compared to female babies.
This acid is present in the composition of aged eye lens, but it does not appear in normal eye lens.
This data shows that we can use the presence of nervonic acid (together with heneicosylic acid and docosahexaenoic acid) as biomarkers of aging lens, which is the most vulnerable stage for cataract development.
Sources
Nervonic acid occurs in seed oil of plants, where significant amounts are contained.
Indeed, more than 10% of the lipids contain nervonic acid, usually in the form of triglycerides.
The seed oils of Lunaria species (Lunaria biennis or Lunaria annua, for example) are a quite important source of this long chain fatty acid, since they contain over 20% of it in the triglyceride lipid.
Nervonic acid is also found in Cardamine gracea, Heliophila longifola, and Malania oleifera.
In all these species, 24:1 usually is esterified at the sn-1 and sn-3 positions on the glycerol backbone.
Other sources can be the molds Neocallimastix frontalis, the bacterium Pseudomonas atlantica, the yeast Saccharomyces cerevisiae, and the marine diatom Nitzschia cylindrus.
Description
Nervonic acid is a monounsaturated omega-9 fatty acid.
Nervonic acid has been identified as important in the biosynthesis of nerve cell myelin.
Nervonic acid 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.
Occurrence
Nervonic acid is abundant in King Salmon ( Chinook ) with 140 mg/100g, yellow mustard seed 83 mg/100g , flaxseed 64 mg/ 100g, Sockeye salmon 40 mg/100g, sesame seed 35mg/100g, and macadamia nuts 18 mg/100g.
Uses:
Nervonic acid is a fatty acid.
Nervonic acid is particularly abundant in the white matter of animal brains and in peripheral nervous tissue where nervonyl sphingolipids are enriched in the myelin sheath of nerve fibers.
Nervonic acid is one of the major fatty acids in brain sphingolipids, normally accounting for approximately 40% of the total fatty acids in sphingolipids.
General Description
Nervonic acids are the products of the desaturation and elongation processes of various fatty acids such as palmitic acid, stearic acid, oleic acid, etc.
Biochem/physiol Actions
Nervonic acid (C24:1), a component of membrane sphingolipids and phosphatidylethanolamines, may be a useful predictor of chronic kidney disease mortality and diabetes.
Nervonic acid oils are being studied for pharmaceutical, nutraceutical and industrial applications. Nervonic acid is a major component of Lunaria oil.
Nervonic Acid is a monounsaturated fatty acid with a 24-carbon backbone and the sole double bond originating from the 9th carbon from the methyl end, with this bond in the cis- configuration.
Nervonic acid is a natural product found in Tropaeolum speciosum, Calophyllum calaba, and other organisms with data available.
General description
Nervonic acids are the products of the desaturation and elongation processes of various fatty acids such as palmitic acid, stearic acid, oleic acid, etc.
Nervonic acid (24:1n-9) is a very long-chain fatty acid produced by elongation of oleic acid (18:1n-9) (Item No. 90260) and derived from erucic acid (22:1n-9) (Item No. 90175).
Nervonic acid is enriched in nervous tissue and is particularly abundant in sphingolipids, such as sphingomyelin in the myelin sheath of nerve fibers.
Nervonic acid is poorly produced in demyelinating disorders, including multiple sclerosis and adrenoleukodystrophy, suggesting that dietary supplementation may be beneficial.
In addition, it is deficient in mice that are homozygous for the quaking mutation, a model of Parkinson’s disease.
Nervonic acid is a long chain of unsaturated fatty acids that is enriched in sphingomyelin.
Nervonic acid consists of choline, sphingosine, phosphoric acid, and fatty acid.
Nervonic acid may enhance brain functions and prevent demyelination.
Research shows that there is a negative relationship between nervonic acid and obesity-related risk factors.
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.
Nervonic acid (C24:1), a component of membrane sphingolipids and phosphatidylethanolamines, may be a useful predictor of chronic kidney disease mortality and diabetes.
Nervonic acid oils are being studied for pharmaceutical, nutraceutical and industrial applications.
Nervonic acid is a major component of Lunaria oil.
There is increasing evidence that dietary supplementation with nervonic acid is healthy for babies and infants during the early stage of brain development.
Nervonic acid has been reported to reduce the shaking associated with Parkinson’s disease and the numbness caused by multiple sclerosis.
Nervonic acid also has the potential for treating schizophrenia and reducing early Alzheimer’s symptoms.
Nervonic acid (cis-15-Tetracosenoic acid) is a long-chain unsaturated fatty acid that is enriched in sphingomyelin and may enhance brain functions and prevent demyelination.
Nervonic acid is a fatty acid.
Nervonic acid is particularly abundant in the white matter of animal brains and in peripheral nervous tissue where nervonic sphingolipids are enriched in the myelin sheath of nerve fibers.
Nervonic acid is one of the major fatty acids in brain sphingolipids, normally accounting for approximately 40% of the total fatty acids in sphingolipids.
Nervonic acid (24:1n-9) is a very long-chain fatty acid produced by elongation of oleic acid (18:1n-9) (Cay-90260) and derived from erucic acid.
Nervonic acid is enriched in nervous tissue and is particularly abundant in sphingolipids, such as sphingomyelin in the myelin sheath of nerve fibers.
Nervonic acid is poorly produced in demyelinating disorders, including multiple sclerosis and adrenoleukodystrophy, suggesting that dietary supplementation may be beneficial.
In addition, it is deficient in mice that are homozygous for the quaking mutation, a model of Parkinson's disease.
Nervonic acid also binds and inhibits DNA polymerase beta (Ki = 4.0 uM) and HIV-1 reverse transcriptase (Ki = 1.2 uM). Formal Name: 15Z-tetracosenoic acid. CAS Number: 506-37-6. Synonyms: Selacholeic Acid. Molecular Formula: C24H46O2
Nervonic acid (NA) is a very-long-chain monounsaturated fatty acid that plays a crucial role in brain development and has attracted widespread research interest.
The markets encouraged the development of a refined, Nervonic acid-enriched plant oil as feedstocks for the needed further studies of Nervonic acid biological functions to the end commercial application.
Plant seed oils offer a renewable and environmentally friendly source of Nervonic acid, but their industrial production is presently hindered by various factors.
This review focuses on the Nervonic acid biosynthesis and assembly, Nervonic acid resources from plants, and the genetic engineering of Nervonic acid biosynthesis in oil crops, discusses the factors that affect Nervonic acid production in genetically engineered oil crops, and provides prospects for the application of Nervonic acid and prospective trends in the engineering of Nervonic acid.
This review emphasizes the progress made toward various Nervonic acid-related topics and explores the limitations and trends, thereby providing integrated and comprehensive insight into the nature of Nervonic acid production mechanisms during genetic engineering.
Furthermore, this report supports further work involving the manipulation of Nervonic acid production through transgenic technologies and molecular breeding for the enhancement of crop nutritional quality or creation of plant biochemical factories to produce Nervonic acid for use in nutraceutical, pharmaceutical, and chemical industries.
A very long-chain fatty acid-enriched in nervous tissue and particularly abundant in sphingolipids, such as sphingomyelin; poorly produced in demyelinating disorders, including multiple sclerosis and adrenoleukodystrophy; binds and inhibits DNA polymerase beta (Ki = 4.0 uM) and HIV-1 reverse transcriptase (Ki = 1.2 uM)
IUPAC NAMES:
(15Z)-tetracos-15-enoic acid
(Z)-Tetracos-15-enoic acid
cis-15-Tetracosenoic Acid
Nervonic acid
SYNONYMS:
15-TETRACOSENOICACID,STANDARDFORGC
selacholeic
CIS-15-TETRACOSENOIC ACID
C24:1 (CIS-15) ACID
DELTA 15 CIS TETRACOSENOIC ACID
15-TETRACOSENOIC ACID
NERVONIC ACID
NERVONIC ACID (CIS)
SELACHOLEIC ACID
15-Tetracosenoic acid,(15Z)-
cis-15-Teracosenoic acid
(E)-tetracos-15-enoic acid
NERVONIC ACID 98%(RG)
CIS-15-TETRACOSENICACID
tetracosenic acid
Selacholeic Acid 15Z-Tetracosenic Acid
cis-15-Tetracosenoic acid, Selacholeic acid
(15Z)-Tetracosenoic acid
(Z)-Tetracos-15-enoic acid
(15Z)-15-Tetracosenoic acid
(Z)-15-Tetracosenoic acid
Nervonic acid,cis-15-Tetracosenoic acid, Selacholeic acid
8-Pentadecene-1-carboxylic acid
Physetolic acid
15-cis-Tetracosenoic acid
Nervonic Acid Selacholeic Acid
Nervonic acid SynonyMs cis-15-Tetracosenoic acid
Nervonic aCld
Nervonic aci
Nervonic acid 506-37-6
neuro acid
Nervonic acid(C24:1)
Nervonic acid fandachem
Natural Neronic acid
Nervonic aci 90%?
Nerve acid 90%
Nervonic acid
506-37-6
cis-15-tetracosenoic acid
(Z)-tetracos-15-enoic acid
selacholeic acid
cis-selacholeic acid
15Z-tetracosenoic acid
(15Z)-Tetracosenoic acid
UNII-91OQS788BE
(15Z)-tetracos-15-enoic acid
(Z)-15-Tetracosenoic acid
15-Tetracosenoic acid
15-Tetracosenoic acid, (15Z)-
(Z)-15-tetracosenoate
(15e)-Tetracos-15-Enoic Acid
(15Z)-tetracos-15-enoate
cis-Delta(15)-tetracosenoate
C24:1n-9
selacholeate
Nervonsaeure
Hervonic acid
cis-selacholeate
Nevonic acid
15-Tetracosenoate
15Z-tetracosenoate
cis-15-Teracosenoate
cis-15-Tetracosenate
ISOCONAZOLENITRATE
15cis-tetracosenoic acid
z-15-Tetracosenoic acid
cis-15-Teracosenoic acid
cis-15-Tetracosenic acid
SCHEMBL21103
Tetracosenoic acid, 15-(Z)-
CHEMBL1173379
cis-Delta(15)-tetracosenoic acid
DTXSID801009308
Nervonic acid, analytical standard
Nervonic acid, >=99% (capillary GC)
Nervonic acid, analytical reference material
