mead acid
5,8,11-eicosatrienoic acid
 
Notes:
None found
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CAS Number: 2751-14-6Picture of molecule3D/inchi
Nikkaji Web: J478.251H
XlogP3-AA: 7.00 (est)
Molecular Weight: 306.48938000
Formula: C20 H34 O2
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Category: natural substances and extractives
 
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Soluble in:
 water, 0.002364 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
Santa Cruz Biotechnology
For experimental / research use only.
Mead Acid ≥95%
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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
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Safety in Use Information:
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.
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Safety References:
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 5282825
National Institute of Allergy and Infectious Diseases: Data
 (5E,8E,11E)-icosa-5,8,11-trienoic acid
Chemidplus: 0002751146
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References:
 (5E,8E,11E)-icosa-5,8,11-trienoic acid
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 5282825
Pubchem (cas): 2751-14-6
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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
HMDB (The Human Metabolome Database): Search
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 undaria pinnatifida
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Synonyms:
5,8,11-eicosatrienoic acid
(5E,8E,11E)-icosa-5,8,11-trienoic acid
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Articles:
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 Δ9-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.
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