mead acid
5,8,11-eicosatrienoic acid
Identification
| Name | mead acid |
| IUPAC | (5E,8E,11E)-icosa-5,8,11-trienoic acid |
| CAS Number | 2751-14-6 |
| FDA UNII | Search |
| Molecular Formula | C20 H34 O2 |
| Molecular Weight | 306.48938000 |
| Nikkaji Number | J478.251H |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Soluble in | water, 0.002364 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for mead acid usage levels up to | not for fragrance use. |
| Recommendation for mead acid flavor usage levels up to | not for flavor use. |
No supplier data available
Potential Uses
Natural Occurrence
Synonyms
5,8,11-
eicosatrienoic acid
(5E,8E,11E)-
icosa-5,8,11-trienoic acid
PubMed:
Serum n-6 and n-9 Fatty Acids Correlate with Serum IGF-1 and Growth Up to Four Months of Age in Healthy Infants.
PubMed:
[Blood fatty acids in the development and correction of metabolic syndrome].
PubMed:
Whole Blood Levels of the n-6 Essential Fatty Acid Linoleic Acid Are Inversely Associated with Stunting in 2-to-6 Year Old Tanzanian Children: A Cross-Sectional Study.
PubMed:
Dietary effects of mead acid on N-methyl-N-nitrosourea-induced mammary cancers in female Sprague-Dawley rats.
PubMed:
De novo fatty acid biosynthesis and elongation in very long-chain acyl-CoA dehydrogenase-deficient mice supplemented with odd or even medium-chain fatty acids.
PubMed:
Essential Fatty Acid Deficiency in 2015: The Impact of Novel Intravenous Lipid Emulsions.
PubMed:
Mead acid supplementation does not rescue rats from cataract and retinal degeneration induced by N-methyl-N-nitrosourea.
PubMed:
Mead acid (20:3n-9) and n-3 polyunsaturated fatty acids are not associated with risk of posterior longitudinal ligament ossification: results of a case-control study.
PubMed:
Food allergy in small children carries a risk of essential fatty acid deficiency, as detected by elevated serum mead acid proportion of total fatty acids.
PubMed:
Mead acid inhibits the growth of KPL-1 human breast cancer cells in vitro and in vivo.
PubMed:
Prospective associations between plasma saturated, monounsaturated and polyunsaturated fatty acids and overall and breast cancer risk - modulation by antioxidants: a nested case-control study.
PubMed:
Identification of genes and pathways involved in the synthesis of Mead acid (20:3n-9), an indicator of essential fatty acid deficiency.
PubMed:
The eosinophil chemoattractant 5-oxo-ETE and the OXE receptor.
PubMed:
Plasma fatty acid lipidomics in amnestic mild cognitive impairment and Alzheimer's disease.
PubMed:
Hormone-sensitive lipase deficiency disturbs the fatty acid composition of mouse testis.
PubMed:
Lung transplantation in cystic fibrosis normalizes essential fatty acid profiles.
PubMed:
Essential polyunsaturated fatty acids, inflammation and mortality in dialysis patients.
PubMed:
NGF blocks polyunsaturated fatty acids biosynthesis in n-3 fatty acid-supplemented PC12 cells.
PubMed:
Inhibitory effect of 5,8,11-eicosatrienoic acid on angiogenesis.
PubMed:
Purified fish oil eliminating linoleic and alpha linolenic acid meets essential fatty acid requirements in rats.
PubMed:
Serum lipid and fatty acid profiles are highly changed in patients with alcohol induced acute pancreatitis.
PubMed:
Motor, mental and behavioral developments in infancy are associated with fatty acid pattern in breast milk and plasma of premature infants.
PubMed:
Elevated stearoyl-CoA desaturase in brains of patients with Alzheimer's disease.
PubMed:
Arachidonic acid and docosahexaenoic acid supplemented to an essential fatty acid-deficient diet alters the response to endotoxin in rats.
PubMed:
Increased elongase 6 and Î9-desaturase activity are associated with n-7 and n-9 fatty acid changes in cystic fibrosis.
PubMed:
The influence of supplemental docosahexaenoic and arachidonic acids during pregnancy and lactation on neurodevelopment at eighteen months.
PubMed:
Dietary cholesterol, female gender and n-3 fatty acid deficiency are more important factors in the development of non-alcoholic fatty liver disease than the saturation index of the fat.
PubMed:
[The role of modification of fatty acid composition of erythrocyte lipids in pathogenesis of arterial hypertension].
PubMed:
Early behaviour and development in breast-fed premature infants are influenced by omega-6 and omega-3 fatty acid status.
PubMed:
Mildly abnormal general movement quality in infants is associated with higher Mead acid and lower arachidonic acid and shows a U-shaped relation with the DHA/AA ratio.
PubMed:
Persistence of essential fatty acid deficiency in cystic fibrosis despite nutritional therapy.
PubMed:
Improved production of various polyunsaturated fatty acids through filamentous fungus Mortierella alpina breeding.
PubMed:
The essentiality of arachidonic acid and docosahexaenoic acid.
PubMed:
Fatty acid patterns early after premature birth, simultaneously analysed in mothers' food, breast milk and serum phospholipids of mothers and infants.
PubMed:
Fetal learning and memory: weak associations with the early essential polyunsaturated fatty acid status.
PubMed:
Identification of mutation sites on Delta12 desaturase genes from Mortierella alpina 1S-4 mutants.
PubMed:
The depressive effects of 5,8,11-eicosatrienoic Acid (20:3n-9) on osteoblasts.
PubMed:
Fish oil prevents essential fatty acid deficiency and enhances growth: clinical and biochemical implications.
PubMed:
Maternal and fetal brain contents of docosahexaenoic acid (DHA) and arachidonic acid (AA) at various essential fatty acid (EFA), DHA and AA dietary intakes during pregnancy in mice.
PubMed:
Structural requirements for activation of the 5-oxo-6E,8Z, 11Z,14Z-eicosatetraenoic acid (5-oxo-ETE) receptor: identification of a mead acid metabolite with potent agonist activity.
PubMed:
Oral DHA supplementation in DeltaF508 homozygous cystic fibrosis patients.
PubMed:
Relation between fatty acid composition and clinical status or genotype in cystic fibrosis patients.
PubMed:
Influence of pancreatic status and sex on polyunsaturated fatty acid profiles in cystic fibrosis.
PubMed:
Airway nitric oxide in patients with cystic fibrosis is associated with pancreatic function, Pseudomonas infection, and polyunsaturated fatty acids.
PubMed:
Plasma phospholipid fatty acids are influenced by a ketogenic diet enriched with n-3 fatty acids in children with epilepsy.
PubMed:
Chemical determinants involved in anandamide-induced inhibition of T-type calcium channels.
PubMed:
Acidolysis and glyceride synthesis reactions using fatty acids with two Pseudomonas lipases having different substrate specificities.
PubMed:
Identification and production of n-8 odd-numbered polyunsaturated fatty acids by a delta12 desaturation-defective mutant of Mortierella alpina 1S-4.
PubMed:
Abnormal fatty acid pattern in intestinal mucosa of children with celiac disease is not reflected in serum phospholipids.
PubMed:
Different specificity of two types of Pseudomonas lipases for C20 fatty acids with a Delta5 unsaturated double bond and their application for selective concentration of fatty acids.
PubMed:
Effects of arachidonic acid analogs on FcepsilonRI-mediated activation of mast cells.
PubMed:
Improvement of the fatty acid composition of an oil-producing filamentous fungus, Mortierella alpina 1S-4, through RNA interference with delta12-desaturase gene expression.
PubMed:
Plasma fatty acids of neonates born to mothers with and without gestational diabetes.
PubMed:
Tissue-specific, nutritional, and developmental regulation of rat fatty acid elongases.
PubMed:
Effects of eicosatrienoic acid (20:3 n-9, Mead's acid) on some promalignant-related properties of three human cancer cell lines.
PubMed:
Beneficial effects of n-9 eicosatrienoic acid on experimental bowel lesions.
PubMed:
Trans isomeric octadecenoic acids are related inversely to arachidonic acid and DHA and positively related to mead acid in umbilical vessel wall lipids.
PubMed:
Long-chain PUFA supplementation improves PUFA profile in infants with cholestasis.
PubMed:
Assessment of essential fatty acid and omega3-fatty acid status by measurement of erythrocyte 20:3omega9 (Mead acid), 22:5omega6/20:4omega6 and 22:5omega6/22:6omega3.
PubMed:
Production of 5,8,11-eicosatrienoic acid by a delta5 and delta6 desaturation activity-enhanced mutant derived from a delta12 desaturation activity-defective mutant of Mortierella alpina 1S-4.
PubMed:
Disturbances in essential fatty acid metabolism in patients receiving long-term home parenteral nutrition.
PubMed:
In vitro mimicry of essential fatty acid deficiency in human endothelial cells by TNFalpha impact of omega-3 versus omega-6 fatty acids.
PubMed:
Maternal-fetal n-6 and n-3 polyunsaturated fatty acids gradient in plasma and red cell phospholipids.
PubMed:
Competitive incorporation of arachidonic acid analogs by cultured rat keratinocytes.
PubMed:
Inhibitors of arachidonic acid metabolism have variable effects on calcium signaling pathways.
PubMed:
Electrospray/tandem mass spectrometry for quantitative analysis of lipid remodeling in essential fatty acid deficient mice.
PubMed:
Composition and permeability of syncytiotrophoblast plasma membranes in pregnancies complicated by intrauterine growth restriction.
PubMed:
Eicosatrienoic acid (20:3 n-9) inhibits the expression of E-cadherin and desmoglein in human squamous cell carcinoma in vitro.
PubMed:
Essential fatty acid metabolism in infants with cholestasis.
PubMed:
Modulation of adjuvant-induced arthritis by dietary arachidonic acid in essential fatty acid-deficient rats.
PubMed:
Serum n3 polyunsaturated fatty acids are depleted in Crohn's disease.
PubMed:
Production of 5,8,11-Eicosatrienoic Acid (Mead Acid) by a (Delta)6 Desaturation Activity-Enhanced Mutant Derived from a (Delta)12 Desaturase-Defective Mutant of an Arachidonic Acid-Producing Fungus, Mortierella alpina 1S-4.
PubMed:
Oxygenation of 5,8,11-eicosatrienoic acid by prostaglandin H synthase-2 of ovine placental cotyledons: isolation of 13-hydroxy-5,8,11-eicosatrienoic and 11-hydroxy-5,8,12-eicosatrienoic acids.
PubMed:
Effect of dietary n-9 eicosatrienoic acid on the fatty acid composition of plasma lipid fractions and tissue phospholipids.
PubMed:
Dietary (n-9) eicosatrienoic acid from a cultured fungus inhibits leukotriene B4 synthesis in rats and the effect is modified by dietary linoleic acid.
PubMed:
Functional and ultrastructural effects of essential fatty acid deficiency in kidney epithelial cells.
PubMed:
Essential fatty acid status in neonates after fish-oil supplementation during late pregnancy.
PubMed:
Studies on the metabolism of [1-14C]5.8.11-eicosatrienoic (Mead) acid in rat hepatocytes.
PubMed:
Mead ethanolamide, a novel eicosanoid, is an agonist for the central (CB1) and peripheral (CB2) cannabinoid receptors.
PubMed:
Occurrence of 22:3n-9 and 22:4n-9 in the lipids of the topminnow (Poeciliopsis lucida) hepatic tumor cell line, PLHC-1.
PubMed:
Effect of diet on the fatty acid composition of the major phospholipids of infant cerebral cortex.
PubMed:
Dietary lipids modify the fatty acid composition of cartilage, isolated chondrocytes and matrix vesicles.
PubMed:
Effect of dietary supplementation with n-9 eicosatrienoic acid on leukotriene B4 synthesis in rats: a novel approach to inhibition of eicosanoid synthesis.
PubMed:
Oxygenation of 5,8,11-eicosatrienoic acid by prostaglandin endoperoxide synthase and by cytochrome P450 monooxygenase: structure and mechanism of formation of major metabolites.
PubMed:
Phospholipid and phospholipid fatty acid composition of mixed murine spinal cord neuronal cultures.
PubMed:
Essential fatty acid deficiency in parenterally fed preterm infants.
PubMed:
An in vitro model for essential fatty acid deficiency: HepG2 cells permanently maintained in lipid-free medium.
PubMed:
Infant brain lipids and diet.
PubMed:
Infant cerebral cortex phospholipid fatty-acid composition and diet.
PubMed:
Essential fatty acid status of neonates born to Inuit mothers: comparison with Caucasian neonates and effect of diet.
PubMed:
Essential fatty acid deficiency in cultured SK-N-SH human neuroblastoma cells.
PubMed:
Unique fatty acid composition of normal cartilage: discovery of high levels of n-9 eicosatrienoic acid and low levels of n-6 polyunsaturated fatty acids.
PubMed:
Biochemical EFA status of mothers and their neonates after normal pregnancy.
PubMed:
Chain elongation of polyunsaturated fatty acids by vascular endothelial cells: studies with arachidonate analogues.
PubMed:
Fatty acid composition of umbilical arteries and veins: possible implications for the fetal EFA-status.
PubMed:
Modification of fluidity and lipid-protein relationships in pig intestinal brush-border membrane by dietary essential fatty acid deficiency.
PubMed:
n-6 and n-3 fatty acids during early human development.
PubMed:
Essential fatty acid deficiency in premature infants.
PubMed:
Fatty acid profiles in response to soybean oil lipid emulsion infusions in essential fatty acid-deficient miniature swine.
PubMed:
Soybean oil emulsion administration during parenteral nutrition in the preterm infant: effect on essential fatty acid, lipid, and glucose metabolism.
PubMed:
Criteria for essential fatty acid deficiency in plasma as assessed by capillary column gas-liquid chromatography.
PubMed:
[Progress of therapeutic agents for asthma--3) Trends in the development of leukotriene inhibitory agents].
PubMed:
Synergistic enhancement of mitogen responses of human lymphocytes by inhibitors of cyclo-oxygenase and 5,8,11-eicosatriynoic acid, an inhibitor of 12-lipoxygenase and leukotriene biosynthesis.
PubMed:
Elongation of C20 polyunsaturated fatty acids by human skin fibroblasts.
PubMed:
Calcium-dependent oxidation of 5,8,11-icosatrienoic acid by the cyclooxygenase enzyme system.
PubMed:
Manipulation of rat brain fatty acid composition alters volatile anesthetic potency.
PubMed:
Ovarian lipoxygenase activity and its regulation by gonadotropin in the rat.
PubMed:
A unique cardiac cytosolic acyltransferase with preferential selectivity for fatty acids that form cyclooxygenase/lipoxygenase metabolites and reverse essential fatty acid deficiency.
PubMed:
High-affinity incorporation of 20-carbon polyunsaturated fatty acids by human skin fibroblasts.
PubMed:
Incorporation of some eicosanoic acids into endothelial cells--effect on platelet inhibitory activity and prostacyclin production.
PubMed:
Prostaglandin E2-like activity of 20:3n-9 platelet lipoxygenase end-product.
PubMed:
Leukotriene B formation by neutrophils from essential fatty acid-deficient rats.
PubMed:
Arachidonic acid, 5,8,11-eicosatrienoic acid and 5,8,11,14, 17-eicosapentaenoic acid. Dietary manipulation of the levels of these acids in rat liver and platelet phospholipids and their incorporation into human platelet lipids.
PubMed:
Effects of non-steroidal anti-inflammatory agents on human neutrophil functions in vitro and in vivo.
PubMed:
The inactivation of lipoxygenases by acetylenic fatty acids.
PubMed:
Products derived from 5,8,11-eicosatrienoic acid by the 5-lipoxygenase-leukotriene pathway.
PubMed:
High affinity esterification of eicosanoid precursor fatty acids by platelets.
PubMed:
Potentiating effect of 5,8,11-eicosatrienoic acid on human platelet aggregation.
PubMed:
Energy intake and the appearance of 5,8,11-eicosatrienoic acid in serum lipids during parenteral nutrition without fat.
PubMed:
Formation of leukotrienes E3, E4 and E5 in rat basophilic leukemia cells.
PubMed:
Assessment of the essential fatty acid requirement in gerbils by polyunsaturated fatty acid ratio.
PubMed:
Inhibition of the eosinophil chemotactic factor (ECF) release from human PMNs and rat mast cells by arachidonic acid analogs.
PubMed:
New model of a scaling dermatosis: induction of hyperproliferation in hairless mice with eicosa-5,8,11-trienoic acid.
PubMed:
Conversion of 5,8,11-eicosatrienoic acid to leukotrienes C3 and D3.
PubMed:
Essential fatty acid deficiency during total parenteral nutrition.
PubMed:
The significance of cis, cis, cis 5,8,11 eicosatrienoic acid in essential fatty acid deficiency.
PubMed:
[ON THE BIOGENESIS OF 5,8,11-EICOSATRIENOIC ACID IN RATS FED A FAT-FREE DIET].
PubMed:
Metabolism of essential fatty acids. VIII. Origin of 5,8,11-eicosatrienoic acid in the fat-deficient rat.
PubMed:
Metabolism of essential fatty acids. III. Isolation of 5,8,11-eicosatrienoic acid from fat-deficient rats.