8,11,14-eicosatrienoic acid
homo-gamma-linolenic acid
 
Notes:
8,11,14-Eicosatrienoic acid is a 20-carbon-chain omega-6 fatty acid, unsaturated at positions 8, 11, and 14. It differs from arachidonic acid (5,8,11,14-eicosatetraenoic acid) only at position 5. 8,11,14-Eicosatrienoic acid is also known as Dihomo-gamma-linolenic acid (DGLA). In physiological literature, it is given the name 20:3(n-6). DGLA is the elongation product of the 18 carbon gamma-linolenic acid (GLA). DGLA can be converted into prostaglandin E1 (PGE1). PGE1 inhibits platelet aggregation and also exerts a vasodilatory effect. DGLA competes with arachadonic acid for COX and lipoxygenase, inhibiting the production of arachadonic acid's eicosanoids [HMDB]
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CAS Number: 7324-41-6Picture of molecule3D/inchi
Nikkaji Web: J986.594B
XlogP3: 7.20 (est)
Molecular Weight: 306.48938000
Formula: C20 H34 O2
NMR Predictor: Predict (works with chrome or firefox)
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:
 None found
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Safety Information:
 
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 8,11,14-eicosatrienoic acid usage levels up to:
 not for fragrance use.
 
Recommendation for 8,11,14-eicosatrienoic acid flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
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EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 5282826
National Institute of Allergy and Infectious Diseases: Data
 (8E,11E,14E)-icosa-8,11,14-trienoic acid
Chemidplus: 0007324416
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References:
 (8E,11E,14E)-icosa-8,11,14-trienoic acid
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 5282826
Pubchem (cas): 7324-41-6
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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
KEGG (GenomeNet): C03242
HMDB (The Human Metabolome Database): HMDB02925
FooDB: FDB023082
VCF-Online: VCF Volatile Compounds in Food
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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
 dichrostachys cinerea plant
Search Trop  Picture
 melittis melissophyllum plant
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Synonyms:
(8E,11E,14E)-icosa-8,11,14-trienoic acid
homo-gamma-linolenic acid
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Articles:
PubMed: Plasma phospholipids fatty acids, dietary fatty acids, and breast cancer risk.
PubMed: Metabolic engineering of long chain-polyunsaturated fatty acid biosynthetic pathway in oleaginous fungus for dihomo-gamma linolenic acid production.
PubMed: Pharmacokinetics, pharmacodynamics and adverse event profile of GSK2256294, a novel soluble epoxide hydrolase inhibitor.
PubMed: Effects of tung oilseed FAD2 and DGAT2 genes on unsaturated fatty acid accumulation in Rhodotorula glutinis and Arabidopsis thaliana.
PubMed: Plasma phospholipids, non-esterified plasma polyunsaturated fatty acids and oxylipids are associated with BMI.
PubMed: Epoxyeicosatrienoic acids attenuate cigarette smoke extract-induced interleukin-8 production in bronchial epithelial cells.
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: Serum phospholipid monounsaturated fatty acid composition and Δ-9-desaturase activity are associated with early alteration of fasting glycemic status.
PubMed: Dietary zinc deficiency affects blood linoleic acid: dihomo-γ-linolenic acid (LA:DGLA) ratio; a sensitive physiological marker of zinc status in vivo (Gallus gallus).
PubMed: EETs alleviate ox-LDL-induced inflammation by inhibiting LOX-1 receptor expression in rat pulmonary arterial endothelial cells.
PubMed: Pathogen induced chemo-attractant hepoxilin A3 drives neutrophils, but not eosinophils across epithelial barriers.
PubMed: Nutritional immunomodulation in critically ill children with acute lung injury: feasibility and impact on circulating biomarkers.
PubMed: Interrelated effects of dihomo-γ-linolenic and arachidonic acids, and sesamin on hepatic fatty acid synthesis and oxidation in rats.
PubMed: Serum cytokeratin 18 M30 antigen level and its correlation with nutritional parameters in middle-aged Japanese males with nonalcoholic fatty liver disease (NAFLD).
PubMed: Subchronic (13-week) oral toxicity study of dihomo-gamma-linolenic acid (DGLA) oil in rats.
PubMed: Fish oil prevents essential fatty acid deficiency and enhances growth: clinical and biochemical implications.
PubMed: Randomized clinical trial of the effects of perioperative use of immune-enhancing enteral formula on metabolic and immunological status in patients undergoing esophagectomy.
PubMed: Distribution and metabolism of dihomo-gamma-linolenic acid (DGLA, 20:3n-6) by oral supplementation in rats.
PubMed: Effects of long-term continuous use of immune-enhancing enteral formula on nutritional and immunologic status in non-surgical patients.
PubMed: Effects of sesamin and capsaicin on the mRNA expressions of delta6 and delta5 desaturases in rat primary cultured hepatocytes.
PubMed: Isolation and characterization of a delta5 FA desaturase from Pythium irregulare by heterologous expression in Saccharomyces cerevisiae and oilseed crops.
PubMed: Antioxidant and cyclooxygenase activities of fatty acids found in food.
PubMed: Hepoxilins raise circulating insulin levels in vivo.
PubMed: Evidence for age-related differences in the fatty acid composition of human adipose tissue, independent of diet.
PubMed: Dietary supplementation with gamma-linolenic acid alters fatty acid content and eicosanoid production in healthy humans.
PubMed: Influence of dietary arachidonic acid on metabolism in vivo of 8cis,11cis,14-eicosatrienoic acid in humans.
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: Effect of diet on the fatty acid composition of the major phospholipids of infant cerebral cortex.
PubMed: Borage or primrose oil added to standardized diets are equivalent sources for gamma-linolenic acid in rats.
PubMed: Infant brain lipids and diet.
PubMed: Fatty acid composition of serum phospholipids in an elderly institutionalized Japanese population.
PubMed: Phospholipid fatty acid composition of various mouse tissues after feeding alpha-linolenate (18:3n-3) or eicosatrienoate (20:3n-3).
PubMed: Plasma fatty acid composition during the first week of life following feeding with human milk or formula.
PubMed: The effect of essential fatty acid and specific vitamin supplements on vascular sensitivity in the mid-trimester of human pregnancy.
PubMed: Loss of delta-6-desaturase activity as a key factor in aging.
PubMed: The effect of dihomo-gamma-linolenic acid (20: 3,n-6) on the composition of phospholipid fatty acids in the liver of rats deficient in essential fatty acids.
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