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nervonic acid
15-tetracosenoic acid, (15Z)-

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Name:(Z)-tetracos-15-enoic acid
CAS Number: 506-37-6Picture of molecule3D/inchi
FDA UNII: 91OQS788BE
Nikkaji Web:J11.357C
Beilstein Number:1728551
MDL:MFCD00010507
XlogP3:9.80 (est)
Molecular Weight:366.62902000
Formula:C24 H46 O2
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 479.20 °C. @ 760.00 mm Hg (est)
Flash Point:> 230.00 °F. TCC ( > 110.00 °C. )
logP (o/w): 10.890 (est)
Soluble in:
 water, 9.308e-006 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Nervonic Acid >95.0%(GC)
Santa Cruz Biotechnology
For experimental / research use only.
Nervonic Acid
Shaanxi Y-Herb Biotechnology
Nervonic Acid Powder Maple Seed Oil 90% 95% Acer Truncatum Extract CAS 506-37-6
Sigma-Aldrich
For experimental / research use only.
Nervonic Acid
analytical standard
TCI AMERICA
For experimental / research use only.
cis-15-Tetracosenoic Acid >95.0%(GC)
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for nervonic acid usage levels up to:
 not for fragrance use.
 
Recommendation for nervonic acid flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5281120
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(Z)-tetracos-15-enoic acid
Chemidplus:0000506376
 
References:
 (Z)-tetracos-15-enoic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5281120
Pubchem (sid):135023121
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
Golm Metabolome Database:Search
KEGG (GenomeNet):C08323
HMDB (The Human Metabolome Database):HMDB02368
FooDB:FDB002934
Export Tariff Code:2916.19.3000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 fish
Search PMC Picture
 rape
Search Trop Picture
 rape seed oil
Search Trop Picture
 safflower
Search Trop Picture
 
Synonyms:
 nervonoyl acid
cis-selacholeic acid
cis-15-teracosenoic acid
(15Z)-tetracos-15-enoic acid
(Z)-tetracos-15-enoic acid
cis-15-tetracosenic acid
(15Z)-tetracosenoic acid
(15Z)-15-tetracosenoic acid
(Z)-15-tetracosenoic acid
15Z-tetracosenoic acid
cis-15-tetracosenoic acid
15-tetracosenoic acid, (15Z)-
 tetracosenoic acid, 15-(Z)-
 

Articles:

PubMed:Plasma phospholipids, non-esterified plasma polyunsaturated fatty acids and oxylipids are associated with BMI.
PubMed:A polyaromatic molecular tube that binds long hydrocarbons with high selectivity.
PubMed:Differential levels of long chain polyunsaturated fatty acids in women with preeclampsia delivering male and female babies.
PubMed:Fermentative production of nervonic acid by Mortierella capitata RD000969.
PubMed:Proportion of nervonic acid in serum lipids is associated with serum plasmalogen levels and metabolic syndrome.
PubMed:Characterizing plasma phospholipid fatty acid profiles of polycystic ovary syndrome patients with and without insulin resistance using GC-MS and chemometrics approach.
PubMed:Identification of saturated and unsaturated fatty acids released during microsomal incubations.
PubMed:[Effect of docosahexaenoic acid and nervonic acid on the damage of learning and memory abilities in rats induced by 1-bromopropane].
PubMed:Dietary fat in relation to erythrocyte fatty acid composition in men.
PubMed:Nervonic acid is much lower in donor milk than in milk from mothers delivering premature infants--of neglected importance?
PubMed:Altered heart and kidney phospholipid fatty acid composition are associated with cardiac hypertrophy in hypertensive rats.
PubMed:Detection and identification of extra virgin olive oil adulteration by GC-MS combined with chemometrics.
PubMed:Lipid biomarkers of lens aging.
PubMed:Polyunsaturated fatty acid concentration predicts myelin integrity in early-phase psychosis.
PubMed:Effects of diet and behavioral enrichment on free fatty acids in the aged canine brain.
PubMed:Decreased nervonic acid levels in erythrocyte membranes predict psychosis in help-seeking ultra-high-risk individuals.
PubMed:Mychonastes afer HSO-3-1 as a potential new source of biodiesel.
PubMed:Aberrant lipid metabolism in hepatocellular carcinoma revealed by plasma metabolomics and lipid profiling.
PubMed:Reduced levels of placental long chain polyunsaturated fatty acids in preterm deliveries.
PubMed:Plasma fatty acid composition in continuous ambulatory peritoneal dialysis patients: an increased omega-6/omega-3 ratio and deficiency of essential fatty acids.
PubMed:Plasma fatty acids in chronic kidney disease: nervonic acid predicts mortality.
PubMed:Circulating sphingolipid biomarkers in models of type 1 diabetes.
PubMed:Synthesis and characterization of poly(3-hydroxyalkanoates) from Brassica carinata oil with high content of erucic acid and from very long chain fatty acids.
PubMed:Effects of weight loss on erythrocyte membrane composition and fluidity in overweight and moderately obese women.
PubMed:Domain growth, pattern formation, and morphology transitions in Langmuir monolayers. A new growth instability.
PubMed:Serum fatty acids and cardiovascular risk factors in sudden sensorineural hearing loss: a case-control study.
PubMed:Reversal of mouse Acyl-CoA oxidase 1 (ACOX1) null phenotype by human ACOX1b isoform [corrected].
PubMed:Metabolite profiling identifies candidate markers reflecting the clinical adaptations associated with Roux-en-Y gastric bypass surgery.
PubMed:Molecular cloning and characterization of a KCS gene from Cardamine graeca and its heterologous expression in Brassica oilseeds to engineer high nervonic acid oils for potential medical and industrial use.
PubMed:Study of the inhibitory effect of fatty acids on the interaction between DNA and polymerase beta.
PubMed:Project DyAdd: Fatty acids in adult dyslexia, ADHD, and their comorbid combination.
PubMed:The metabolic syndrome of omega3-depleted rats. I. Liver data.
PubMed:Increase in nervonic acid content in transformed yeast and transgenic plants by introduction of a Lunaria annua L. 3-ketoacyl-CoA synthase (KCS) gene.
PubMed:Perturbation of 11-eicosenoate metabolism in female diabetic rats.
PubMed:Imaging MALDI mass spectrometry using an oscillating capillary nebulizer matrix coating system and its application to analysis of lipids in brain from a mouse model of Tay-Sachs/Sandhoff disease.
PubMed:Lipophilic components of different therapeutic mud species.
PubMed:Relationship between serum concentrations of saturated fatty acids and unsaturated fatty acids and the homeostasis model insulin resistance index in Japanese patients with type 2 diabetes mellitus.
PubMed:Early dietary treatments with Lorenzo's oil and docosahexaenoic acid for neurological development in a case with Zellweger syndrome.
PubMed:Expression of the Arabidopsis ADS1 gene in Brassica juncea results in a decreased level of total saturated fatty acids.
PubMed:Serum phospholipid fatty acids, adipose tissue, and metabolic markers in obese adolescents.
PubMed:Site-directed mutational analysis of structural interactions of low molecule compounds binding to the N-terminal 8 kDa domain of DNA polymerase beta.
PubMed:Isolation, structure elucidation and in vivo hepatoprotective potential of trans-tetracos-15-enoic acid from Indigofera tinctoria Linn.
PubMed:Sequential pressurized liquid extraction to determine brain-originating fatty acids in meat products as markers in bovine spongiform encephalopathy risk assessment studies.
PubMed:Relationships between serum unsaturated fatty acids and coronary risk factors: negative relations between nervonic acid and obesity-related risk factors.
PubMed:Arachidonic acid predominates in the membrane phosphoglycerides of the early and term human placenta.
PubMed:Association between school performance, breast milk intake and fatty acid profile of serum lipids in ten-year-old cleft children.
PubMed:Sulfoquinovosylmonoacylglycerol inhibitory mode analysis of rat DNA polymerase beta.
PubMed:Role of the posterior vacuole in Spraguea lophii (Microsporidia) spore hatching.
PubMed:Lipid composition in human breast milk from Granada (Spain): changes during lactation.
PubMed:Effect of borage oil consumption on fatty acid metabolism, transepidermal water loss and skin parameters in elderly people.
PubMed:Dietary patterns and blood fatty acid composition in children with attention-deficit hyperactivity disorder in Taiwan.
PubMed:Structural characterisation of some fatty acids from the brain as biomarkers of BSE risk material.
PubMed:Relationship between insulin sensitivity and sphingomyelin signaling pathway in human skeletal muscle.
PubMed:The source of long-chain PUFA in formula supplements does not affect the fatty acid composition of plasma lipids in full-term infants.
PubMed:Red blood cell membrane essential fatty acid metabolism in early psychotic patients following antipsychotic drug treatment.
PubMed:Catalase in microsporidian spores before and during discharge.
PubMed:Fatty acid composition of serum phospholipid of premenopausal women and postmenopausal women receiving and not receiving hormone replacement therapy.
PubMed:Nervonic acid is transferred from the maternal diet to milk and tissues of suckling rat pups.
PubMed:In-house validation of an improved sample extraction and clean-up method for GC determination of isomers of nervonic acid in meat products.
PubMed:[Determination of nervonic acid in oral tonic by GC].
PubMed:Inhibition of hyaluronidases and chondroitinases by fatty acids.
PubMed:Three-dimensional structural model analysis of the binding site of an inhibitor, nervonic acid, of both DNA polymerase beta and HIV-1 reverse transcriptase.
PubMed:Accumulation of specific ceramides in ischemic/reperfused rat heart; effect of ischemic preconditioning.
PubMed:Peroxisomal fatty acid oxidation and cellular redox.
PubMed:Detection of tissues of the central nervous system (CNS) as specified risk material (SRM) in meat products by means of gas chromatography-mass spectrometry (GC-MS).
PubMed:Antioxidant and cyclooxygenase activities of fatty acids found in food.
PubMed:The effect of a Tropaeolum speciosum oil supplement on the nervonic acid content of sphingomyelin in rat tissues.
PubMed:Significantly reduced docosahexaenoic and docosapentaenoic acid concentrations in erythrocyte membranes from schizophrenic patients compared with a carefully matched control group.
PubMed:Structural homology between DNA binding sites of DNA polymerase beta and DNA topoisomerase II.
PubMed:Long-chain aliphatic beta-diketones from epicuticular wax of Vanilla bean species. Synthesis of nervonoylacetone.
PubMed:Mode analysis of binding of fatty acids to mammalian DNA polymerases.
PubMed:Infant cerebellar gray and white matter fatty acids in relation to age and diet.
PubMed:Mode analysis of a fatty acid molecule binding to the N-terminal 8-kDa domain of DNA polymerase beta. A 1:1 complex and binding surface.
PubMed:Composition and permeability of syncytiotrophoblast plasma membranes in pregnancies complicated by intrauterine growth restriction.
PubMed:Enhancement of propylene glycol distribution in the skin by high purity cis-unsaturated fatty acids with different alkyl chain lengths having different double bond position.
PubMed:Fatty acid composition of human brain phospholipids during normal development.
PubMed:Effects of feeding Lunaria oil rich in nervonic and erucic acids on the fatty acid compositions of sphingomyelins from erythrocytes, liver, and brain of the quaking mouse mutant.
PubMed:Localization of nervonic acid beta-oxidation in human and rodent peroxisomes: impaired oxidation in Zellweger syndrome and X-linked adrenoleukodystrophy.
PubMed:Charge-remote fragmentations are energy-dependent processes.
PubMed:Implication of hydrogen peroxide generation and apoptosis in the neoplastic transformation of mouse fibroblasts overexpressing peroxisomal fatty acyl-CoA oxidase.
PubMed:The inhibitory action of fatty acids on DNA polymerase beta.
PubMed:Lack of promotion of colon carcinogenesis by high-oleic safflower oil.
PubMed:Nervonic acid and demyelinating disease.
PubMed:Intertribal somatic hybrids between Brassica napus and Thlaspi perfoliatum with high content of the T. perfoliatum-specific nervonic acid.
PubMed:Nervonic acid in red blood cell sphingomyelin in premature infants: an index of myelin maturation?
PubMed:Nasu-Hakola disease. A case accompanied by abnormalities in fatty acid composition of serum total lipids and amino acid analysis.
PubMed:Inhibition of steroid 5 alpha-reductase by specific aliphatic unsaturated fatty acids.
PubMed:The effect of borage oil consumption on the composition of individual phospholipids in human platelets.
PubMed:Dietary taurine content changes liver lipids in cats.
PubMed:Incorporation of very-long-chain fatty acids into sphingolipids of cultured neural cells.
PubMed:Nervonic acid versus tricosanoic acid as internal standards in quantitative gas chromatographic analyses of fish oil longer-chain n-3 polyunsaturated fatty acid methyl esters.
PubMed:Molecular species composition of the major phospholipids in brain and retina from rainbow trout (Salmo gairdneri). Occurrence of high levels of di-(n-3)polyunsaturated fatty acid species.
PubMed:Influence of structural modifications on the phase behavior of semi-synthetic cerebroside sulfate.
PubMed:Ganglioside composition in human cataractous nuclei.
PubMed:Cardiac lipid changes in rats fed oils enriched in saturates and their apparent relationship to focal heart lesions.
PubMed:Ageing and compositional changes of rat lens.
PubMed:Phospholipid and fatty acid composition of erythrocyte membrane from wild Japanese serow (Capricornis crispus).
PubMed:Comparative study of acidic glycosphingolipids by field desorption and secondary ion mass spectrometry.
PubMed:Peripheral nerve cells in culture rich in Schwann cells incorporate and metabolize trans-unsaturated fatty acid (elaidic acid) as well as physiological dis isomer (oleic acid).
PubMed:[Conversion of erucic acid in subcellular fractions from liver, kidneys and heart of rat, 8 min after intravenous injection (author's transl)].
PubMed:Comparison of the development of the fatty acid content and composition of the brain of a precocial species (guinea pig) and a non-precocial species (rat).
PubMed:Evidence of accumulation of ceramides containing [14C]nervonic acid in the rat lung following injection of [14C]erucic acid.
PubMed:Fatty acid composition and thermal behavior of natural sphingomyelins.
PubMed:Lipid abnormalities in hereditary neuropathy. Part 2. Serum phospholipids.
PubMed:The triglyceride fatty acid pattern in arterial wall, adipose tissue and serum of amputated diabetic subjects.
PubMed:Molecular arrangements of sphingolipids. The monolayer behaviour of ceramides.
PubMed:The fatty acid composition of triglycerides in arteries, depot fat and serum of amputated diabetics.
PubMed:The effects of biotin and fatty acids on SV3T3 cell growth in the presence of normal calf serum.
PubMed:Effect of early postnatal dietary sterculate on the fatty acid composition of rat liver and brain lipids.
PubMed:Alpha-Hydroxylation of lignoceric and nervonic acids in the brain. Effects of altered thyroid function on postnatal development of the hydroxylase activity.
PubMed:Elongation of (omega-14C)oleic acid and (omega-14C)nervonic acid.
PubMed:Modification of the fatty acid composition of Ehrlich ascites tumor cell plasma membranes.
PubMed:Nervonic acid biosynthesis by erucyl-CoA elongation in normal and quaking mouse brain microsomes. Elongation of other unsaturated fatty acyl-CoAs (mono and poly-unsaturated).
PubMed:Glycolipids of the fish testis.
PubMed:[Effect of alcohol on the metabolic conversion of 14C erucic acid in the liver of rats receiving rapeseed or peanut oil].
PubMed:Biochemical studies in Nevin-Jones syndrome.
PubMed:Composition of human serum sphingomyelins.
PubMed:Abnormalities of high density lipoproteins in abetalipoproteinemia.
PubMed:Metabolism of(14)C-labelled oleic acid, erucic acid and nervonic acid in rats.
PubMed:The isolation and partial characterization of glycolipids of normal human leucocytes.
PubMed:THE ISOLATION AND PARTIAL CHARACTERIZATION OF THE GLYCOLIPIDS OF BP8/C3H ASCITES-SARCOMA CELLS.
PubMed:BIOSYNTHESIS OF NERVONIC ACID AND ITS HOMOLOGUES FROM CARBOXYL-LABELED OLEIC ACID.
PubMed:Levels of radioactivity in tissues and in expired carbon dioxide after administration of 1-C14-labelled palmitic acid, 2-C14-labelled erucic acid, or 2-C14-labelled nervonic acid to rats.
 
Notes:
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.
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