stearidonic acid

moroctic acid

CAS: 20290-75-9 C18 H28 O2 MW: 276.41956000

Identification

Namestearidonic acid
CAS Number20290-75-9
FDA UNIIP4CEK3495O
Molecular FormulaC18 H28 O2
Molecular Weight276.41956000
MDL NumberMFCD00216036
Beilstein1712973

Regulatory

FDA/DG SANTE Petitions, Reviews, NoticesGRN 283

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 382.50 °C. @ 760.00 mm Hg (est)
Flash Point 535.00 °F. TCC ( 279.40 °C. ) (est)
logP (o/w) 5.890 (est)
Soluble in water, 0.03717 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for stearidonic acid usage levels up tonot for fragrance use.
Recommendation for stearidonic acid flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

cabbage savoy cabbage currant black currant seed oil fish oils PMC

Synonyms

moroctic acid (6Z,9Z,12Z,15Z)- octadeca-6,9,12,15-tetraenoic acid all-cis- octadeca-6,9,12,15-tetraenoic acid (6Z,9Z,12Z,15Z)-6,9,12,15- octadecatetraenoic acid 6Z,9Z,12Z,15Z- octadecatetraenoic acid 6,9,12,15- octadecatetraenoic acid, (6Z,9Z,12Z,15Z)- PubMed: Heterologous Reconstitution of Omega-3 Polyunsaturated Fatty Acids in Arabidopsis. PubMed: Lipids and Composition of Fatty Acids of Saccharina latissima Cultivated Year-Round in Integrated Multi-Trophic Aquaculture. PubMed: Preparation of Highly Purified Stearidonic Acid from Echium Oil via an Enzymatic Method Combined with Preparative High Performance Liquid Chromatography. PubMed: Validation of endogenous reference genes in Buglossoides arvensis for normalizing RT-qPCR-based gene expression data. PubMed: Lipid-Encapsulated Echium Oil (Echium plantagineum) Increases the Content of Stearidonic Acid in Plasma Lipid Fractions and Milk Fat of Dairy Cows. PubMed: Stearidonic acid, a plant-based dietary fatty acid, enhances the chemosensitivity of canine lymphoid tumor cells. PubMed: Antioxidant activity of phenolic compounds added to a functional emulsion containing omega-3 fatty acids and plant sterol esters. PubMed: Physico-chemical properties of Tecoma stans Linn. seed oil: a new crop for vegetable oil. PubMed: Feeding laying hens stearidonic acid-enriched soybean oil, as compared to flaxseed oil, more efficiently enriches eggs with very long-chain n-3 polyunsaturated fatty acids. PubMed: Oxidative stability of structured lipid-based infant formula emulsion: effect of antioxidants. PubMed: Development and Characterization of Somatic Hybrids of Ulva reticulata Forsskål (×) Monostroma oxyspermum (Kutz.)Doty. PubMed: Proinflammatory effects of arachidonic acid in a lipopolysaccharide-induced inflammatory microenvironment in 3T3-L1 adipocytes in vitro. PubMed: Flowering dynamics and pollinator visitation of oilseed echium (Echium plantagineum). PubMed: Stearidonic acid-enriched flax oil reduces the growth of human breast cancer in vitro and in vivo. PubMed: Relationship between cannabinoids content and composition of fatty acids in hempseed oils. PubMed: Echium oil is not protective against weight loss in head and neck cancer patients undergoing curative radio(chemo)therapy: a randomised-controlled trial. PubMed: Effects of stearidonic acid on serum triacylglycerol concentrations in overweight and obese subjects: a randomized controlled trial. PubMed: First use of the WAVE™ disposable rocking bioreactor for enhanced bioproduct synthesis by N2 -fixing cyanobacteria. PubMed: Benefits of foods supplemented with vegetable oils rich in α-linolenic, stearidonic or docosahexaenoic acid in hypertriglyceridemic subjects: a double-blind, randomized, controlled trail. PubMed: Novel elongase of Pythium sp. with high specificity on Δ(6)-18C desaturated fatty acids. PubMed: Prevalence and mechanism of polyunsaturated aldehydes production in the green tide forming macroalgal genus Ulva (Ulvales, Chlorophyta). PubMed: Effects of long chain fatty acid synthesis and associated gene expression in microalga Tetraselmis sp. PubMed: Achieving optimal n-3 fatty acid status: the vegetarian's challenge... or not. PubMed: Opportunities to enhance alternative sources of long-chain n-3 fatty acids within the diet. PubMed: DHA-containing oilseed: a timely solution for the sustainability issues surrounding fish oil sources of the health-benefitting long-chain omega-3 oils. PubMed: Pancreatic lipase selectively hydrolyses DPA over EPA and DHA due to location of double bonds in the fatty acid rather than regioselectivity. PubMed: Baseline plasma fatty acids profile and incident cardiovascular events in the SU.FOL.OM3 trial: the evidence revisited. PubMed: Transgenic expression of delta-6 and delta-15 fatty acid desaturases enhances omega-3 polyunsaturated fatty acid accumulation in Synechocystis sp. PCC6803. PubMed: Dietary echium oil increases long-chain n-3 PUFAs, including docosapentaenoic acid, in blood fractions and alters biochemical markers for cardiovascular disease independently of age, sex, and metabolic syndrome. PubMed: Identification and functional characterization of genes encoding omega-3 polyunsaturated fatty acid biosynthetic activities from unicellular microalgae. PubMed: Survey of the total fatty acid and triacylglycerol composition and content of 30 duckweed species and cloning of a Δ6-desaturase responsible for the production of γ-linolenic and stearidonic acids in Lemna gibba. PubMed: Altering n-3 to n-6 polyunsaturated fatty acid ratios affects prostaglandin production by ovine uterine endometrium. PubMed: Adipose tissue fatty acid composition and colon cancer: a case-control study. PubMed: Effect of stearidonic acid-enriched soybean oil on fatty acid profile and metabolic parameters in lean and obese Zucker rats. PubMed: Isolation and functional characterization of a delta 6-desaturase gene from the pike eel (Muraenesox cinereus). PubMed: Impact of botanical oils on polyunsaturated fatty acid metabolism and leukotriene generation in mild asthmatics. PubMed: Functional characterization of polyunsaturated fatty acid delta 6-desaturase and elongase genes from the black seabream (Acanthopagrus schlegelii). PubMed: Immunomodulatory and therapeutic effects of Hot-nature diet and co-supplemented hemp seed, evening primrose oils intervention in multiple sclerosis patients. PubMed: High lipid productivity of an Ankistrodesmus-Rhizobium artificial consortium. PubMed: Increase in stearidonic acid by increasing the supply of histidine to oleaginous Saccharomyces cerevisiae. PubMed: Consumption of stearidonic acid-rich oil in foods increases red blood cell eicosapentaenoic acid. PubMed: Characterisation and optimisation of physical and oxidative stability of structured lipid-based infant formula emulsion: effects of emulsifiers and biopolymer thickeners. PubMed: Long-chain polyunsaturated fatty acids may mutually benefit both obesity and osteoporosis. PubMed: Stearidonic and γ-linolenic acids in echium oil improves glucose disposal in insulin resistant monkeys. PubMed: Echium oil and linseed oil as alternatives for fish oil in the maternal diet: Blood fatty acid profiles and oxidative status of sows and piglets. PubMed: Alternative sources of omega-3 fats: can we find a sustainable substitute for fish? PubMed: Effect of metformin on the urinary metabolites of diet-induced-obese mice studied by ultra performance liquid chromatography coupled to time-of-flight mass spectrometry (UPLC-TOF/MS). PubMed: Effect of Echium oil compared with marine oils on lipid profile and inhibition of hepatic steatosis in LDLr knockout mice. PubMed: Dietary omega-3 PUFA and health: stearidonic acid-containing seed oils as effective and sustainable alternatives to traditional marine oils. PubMed: Variation in the fatty-acid content in seeds of various black, red, and white currant varieties. PubMed: Acyl migration evaluation in monoacylglycerols from Echium plantagineum seed oil and Marinol. PubMed: Identification of a fatty acid ∆(6)-desaturase gene from the eicosapentaenoic acid-producing fungus Pythium splendens RBB-5. PubMed: Identification of tocopherols, tocotrienols, and their fatty acid esters in residues and distillates of structured lipids purified by short-path distillation. PubMed: Influences of stearidonic acid-enriched soybean oil on the blood and organ biochemical parameters in rats. PubMed: Stearidonic acid as a supplemental source of ω-3 polyunsaturated fatty acids to enhance status for improved human health. PubMed: Erythrocyte stearidonic acid and other n-3 fatty acids and CHD in the Physicians' Health Study. PubMed: Production of trans-free margarine with stearidonic acid soybean and high-stearate soybean oils-based structured lipid. PubMed: The modification of plant oil composition via metabolic engineering--better nutrition by design. PubMed: The role of mediastinal adipose tissue 11β-hydroxysteroid d ehydrogenase type 1 and glucocorticoid expression in the development of coronary atherosclerosis in obese patients with ischemic heart disease. PubMed: Stearidonic acid acts in synergism with amphotericin B in inhibiting Candida albicans and Candida dubliniensis biofilms in vitro. PubMed: Searching for health beneficial n-3 and n-6 fatty acids in plant seeds. PubMed: Echium oil provides no benefit over linseed oil for (n-3) long-chain PUFA biosynthesis in rainbow trout. PubMed: Polyunsaturated fatty acids cause apoptosis in C. albicans and C. dubliniensis biofilms. PubMed: Regioisomer separation and identification of triacylglycerols containing vaccenic and oleic acids, and α- and γ-linolenic acids, in thermophilic cyanobacteria Mastigocladus laminosus and Tolypothrix sp. PubMed: Conclusions and recommendations from the symposium, Heart Healthy Omega-3s for Food: Stearidonic Acid (SDA) as a Sustainable Choice. PubMed: The omega-3 fatty acid nutritional landscape: health benefits and sources. PubMed: Stearidonic acid-enhanced soybean oil: a plant-based source of (n-3) fatty acids for foods. PubMed: Effects of dietary stearidonic acid on biomarkers of lipid metabolism. PubMed: Cost implications of alternative sources of (n-3) fatty acid consumption in the United States. PubMed: Incorporation of (n-3) fatty acids in foods: challenges and opportunities. PubMed: Mechanisms of action of (n-3) fatty acids. PubMed: Stearidonic acid raises red blood cell membrane eicosapentaenoic acid. PubMed: (n-3) fatty acids and cardiovascular health: are effects of EPA and DHA shared or complementary? PubMed: Stearidonic acid: is there a role in the prevention and management of type 2 diabetes mellitus? PubMed: Elongase reactions as control points in long-chain polyunsaturated fatty acid synthesis. PubMed: Stearidonic acid as a 'pro-eicosapentaenoic acid'. PubMed: The production of conjugated α-linolenic, γ-linolenic and stearidonic acids by strains of bifidobacteria and propionibacteria. PubMed: Identification of a Δ6 fatty acid elongase gene for arachidonic acid biosynthesis localized to the endoplasmic reticulum in the green microalga Myrmecia incisa Reisigl. PubMed: Echium oil reduces atherosclerosis in apoB100-only LDLrKO mice. PubMed: Modifications of stearidonic acid soybean oil by enzymatic acidolysis for the production of human milk fat analogues. PubMed: Effects of duration of treatment and dosage of eicosapentaenoic acid and stearidonic acid on red blood cell eicosapentaenoic acid content. PubMed: Identification of C18 intermediates formed during stearidonic acid biohydrogenation by rumen microorganisms in vitro. PubMed: Technical note: stearidonic acid metabolism by mixed ruminal microorganisms in vitro. PubMed: When balanced for precursor fatty acid supply echium oil is not superior to linseed oil in enriching lamb tissues with long-chain n-3 PUFA. PubMed: Characterization of stearidonic acid soybean oil enriched with palmitic acid produced by solvent-free enzymatic interesterification. PubMed: Up-regulated desaturase and elongase gene expression promoted accumulation of polyunsaturated fatty acid (PUFA) but not long-chain PUFA in Lates calcarifer, a tropical euryhaline fish, fed a stearidonic acid- and γ-linoleic acid-enriched diet. PubMed: Stearidonic and eicosapentaenoic acids inhibit interleukin-6 expression in ob/ob mouse adipose stem cells via Toll-like receptor-2-mediated pathways. PubMed: Echium acanthocarpum hairy root cultures, a suitable system for polyunsaturated fatty acid studies and production. PubMed: Stearidonic acid soybean oil enriched with palmitic acid at the sn-2 position by enzymatic interesterification for use as human milk fat analogues. PubMed: Functional characterization of a delta 6-desaturase gene from the black seabream (Acanthopagrus schlegeli). PubMed: Identification and functional characterisation of genes encoding the omega-3 polyunsaturated fatty acid biosynthetic pathway from the coccolithophore Emiliania huxleyi. PubMed: Effect of feeding Atlantic salmon (Salmo salar L.) a diet enriched with stearidonic acid from parr to smolt on growth and n-3 long-chain PUFA biosynthesis. PubMed: Separation of γ-linolenic and other polyunsaturated fatty acids from Boraginaceae via supercritical CO2. PubMed: Molecular analysis of ∆6 desaturase and ∆6 elongase from Conidiobolus obscurus in the biosynthesis of eicosatetraenoic acid, a ω3 fatty acid with nutraceutical potentials. PubMed: Fermentation process development of recombinant Hansenula polymorpha for gamma-linolenic acid production. PubMed: Effect of marine polyunsaturated fatty acids on biofilm formation of Candida albicans and Candida dubliniensis. PubMed: The effect of feeding modified soyabean oil enriched with C18 : 4 n-3 to broilers on the deposition of n-3 fatty acids in chicken meat. PubMed: Polyunsaturated fatty acids modulate prostaglandin synthesis by ovine amnion cells in vitro. PubMed: Dietary intake of stearidonic acid-enriched soybean oil increases the omega-3 index: randomized, double-blind clinical study of efficacy and safety. PubMed: Effect of chemical randomization on positional distribution and stability of omega-3 oil triacylglycerols. PubMed: Teratogenic effects of diatom metabolites on sea urchin Paracentrotus lividus embryos. PubMed: Specific protein regions influence substrate specificity and product length in polyunsaturated fatty acid condensing enzymes. PubMed: Reassessing the ichthyotoxin profile of cultured Prymnesium parvum (golden algae) and comparing it to samples collected from recent freshwater bloom and fish kill events in North America. PubMed: Heterotrophic growth and nutritional aspects of the diatom Cyclotella cryptica (Bacillariophyceae): Effect of some environmental factors. PubMed: Hot topic: Enhancing omega-3 fatty acids in milk fat of dairy cows by using stearidonic acid-enriched soybean oil from genetically modified soybeans. PubMed: Dietary source of stearidonic acid promotes higher muscle DHA concentrations than linolenic acid in hybrid striped bass. PubMed: Omega-3 fatty acids are oxygenated at the n-7 carbon by the lipoxygenase domain of a fusion protein in the cyanobacterium Acaryochloris marina. PubMed: The synthesis and accumulation of stearidonic acid in transgenic plants: a novel source of 'heart-healthy' omega-3 fatty acids. PubMed: Prostate tumor growth can be modulated by dietarily targeting the 15-lipoxygenase-1 and cyclooxygenase-2 enzymes. PubMed: Recent trends in the advanced analysis of bioactive fatty acids. PubMed: Improvement of Stearidonic acid production in Oleaginous Saccharomyces cerevisiae. PubMed: Dietary omega-3 fatty acids differentially influence ova release and ovarian cyclooxygenase-1 and cyclooxygenase-2 expression in rats. PubMed: Metabolic diversity in biohydrogenation of polyunsaturated fatty acids by lactic acid bacteria involving conjugated fatty acid production. PubMed: n-3 Oil sources for use in aquaculture--alternatives to the unsustainable harvest of wild fish. PubMed: Dietary stearidonic acid is a long chain (n-3) polyunsaturated fatty acid with potential health benefits. PubMed: Gamma-linolenic and stearidonic acids are required for basal immunity in Caenorhabditis elegans through their effects on p38 MAP kinase activity. PubMed: Increased elongase and desaturase gene expression with stearidonic acid enriched diet does not enhance long-chain (n-3) content of seawater Atlantic salmon (Salmo salar L.). PubMed: Safety assessment of SDA soybean oil: results of a 28-day gavage study and a 90-day/one generation reproduction feeding study in rats. PubMed: Stearidonic acid-enriched soybean oil increased the omega-3 index, an emerging cardiovascular risk marker. PubMed: Echium oil is better than rapeseed oil in enriching poultry meat with n-3 polyunsaturated fatty acids, including eicosapentaenoic acid and docosapentaenoic acid. PubMed: Effects of the brown seaweed Undaria pinnatifida on erythematous inflammation assessed using digital photo analysis. PubMed: Monoepoxy octadecadienoates and monoepoxy octadecatrienoates 1: NMR spectral characterization. PubMed: Monoepoxy octadecadienoates and monoepoxy octadecatrienoates 2: mass spectral characterization. PubMed: Mechanisms by which botanical lipids affect inflammatory disorders. PubMed: Echium oil reduces plasma lipids and hepatic lipogenic gene expression in apoB100-only LDL receptor knockout mice. PubMed: Changes in the content of gamma-linolenic C18:3 (n-6) and stearidonic C18:4 (n-3) acids in developing seeds of viper's bugloss Echium vulgare L. PubMed: Production of polyunsaturated fatty acids in transgenic plants. PubMed: Isolation of two anti-inflammatory and one pro-inflammatory polyunsaturated fatty acids from the brown seaweed Undaria pinnatifida. PubMed: Influence of low-dose polyunsaturated fatty acids supplementation on the inflammatory response of healthy adults. PubMed: Stearidonic acid increases the red blood cell and heart eicosapentaenoic acid content in dogs. PubMed: Replacement of dietary fish oil for Atlantic salmon parr (Salmo salar L.) with a stearidonic acid containing oil has no effect on omega-3 long-chain polyunsaturated fatty acid concentrations. PubMed: Self-reported health problems in young male subjects supplementing their diet with oils rich in eicosapentaenoic, gamma-linolenic and stearidonic acids. PubMed: Identification of Primula "front-end" desaturases with distinct n-6 or n-3 substrate preferences. PubMed: Identification of bifunctional delta12/omega3 fatty acid desaturases for improving the ratio of omega3 to omega6 fatty acids in microbes and plants. PubMed: Marine macroalgae as sources of polyunsaturated fatty acids. PubMed: Co-expression of the borage Delta 6 desaturase and the Arabidopsis Delta 15 desaturase results in high accumulation of stearidonic acid in the seeds of transgenic soybean. PubMed: Folded and unfolded conformations of the omega-3 polyunsaturated fatty acid family: ch(3)ch(2)[ch=chch(2)](b)[ch(2)](m)cooh: first principles study. PubMed: Effect of diets enriched in Delta6 desaturated fatty acids (18:3n-6 and 18:4n-3), on growth, fatty acid composition and highly unsaturated fatty acid synthesis in two populations of Arctic charr (Salvelinus alpinus L.). PubMed: Prostate tumor growth and recurrence can be modulated by the omega-6:omega-3 ratio in diet: athymic mouse xenograft model simulating radical prostatectomy. PubMed: Marine macroalgae analyzed by mass spectrometry are rich sources of polyunsaturated fatty acids. PubMed: [Progress on molecular biology of delta6-fatty acid desaturases]. PubMed: Comparison of stearidonic acid and alpha-linolenic acid on PGE2 production and COX-2 protein levels in MDA-MB-231 breast cancer cell cultures. PubMed: Novel fatty acid elongases and their use for the reconstitution of docosahexaenoic acid biosynthesis. PubMed: The influence of different combinations of gamma-linolenic acid, stearidonic acid and EPA on immune function in healthy young male subjects. PubMed: Dietary echium oil increases plasma and neutrophil long-chain (n-3) fatty acids and lowers serum triacylglycerols in hypertriglyceridemic humans. PubMed: The influence of different combinations of gamma-linolenic, stearidonic and eicosapentaenoic acids on the fatty acid composition of blood lipids and mononuclear cells in human volunteers. PubMed: Fatty acid content and juice characteristics in black currant (Ribes nigrum L.) genotypes. PubMed: Modification of plant lipids for human health: development of functional land-based omega-3 fatty acids. PubMed: Lipids of the hexane extract from the roots of medicinal boraginaceous species. PubMed: Metabolism of stearidonic acid in human subjects: comparison with the metabolism of other n-3 fatty acids. PubMed: Comparison of the effects of dietary alpha-linolenic, stearidonic, and eicosapentaenoic acids on production of inflammatory mediators in mice. PubMed: Genotypic variation in fatty acid content of blackcurrant seeds. PubMed: Occurrence and characterization of oils rich in gamma-linolenic acid (III): the taxonomical value of the fatty acids in Echium (Boraginaceae). PubMed: Purification of stearidonic acid (18:4(n-3)) and hexadecatetraenoic acid (16:4(n-3)) from algal fatty acid with lipase and medium pressure liquid chromatography. PubMed: Cloning and functional expression of the first plant fatty acid elongase specific for Delta(6)-polyunsaturated fatty acids. PubMed: Leaf lipids of Ribes nigrum: a plant containing 16:3, alpha-18:3, gamma-18:3 and 18:4 fatty acids. PubMed: Discovery of an 11 (R)- and 12(S)-lipoxygenase activity in ovaries of the mussel Mytilus edulis. PubMed: Fatty acid compositions of gonadal material and diets of the sea urchin, Psammechinus miliaris: trophic and nutritional implications. PubMed: Highly unsaturated (n-3) fatty acids, but not alpha-linolenic, conjugated linoleic or gamma-linolenic acids, reduce tumorigenesis in Apc(Min/+) mice. PubMed: Cloning of a human cDNA encoding a novel enzyme involved in the elongation of long-chain polyunsaturated fatty acids. PubMed: Identification and characterization of an enzyme involved in the elongation of n-6 and n-3 polyunsaturated fatty acids. PubMed: A bifunctional delta-fatty acyl acetylenase/desaturase from the moss Ceratodon purpureus. A new member of the cytochrome b5 superfamily. PubMed: Occurrence and characterization of oils rich in gamma-linolenic acid Part I: Echium seeds from Macaronesia. PubMed: The binding of arachidonic acid in the cyclooxygenase active site of mouse prostaglandin endoperoxide synthase-2 (COX-2). A putative L-shaped binding conformation utilizing the top channel region. PubMed: Low C18 to C20 fatty acid elongase activity and limited conversion of stearidonic acid, 18:4(n-3), to eicosapentaenoic acid, 20:5(n-3), in a cell line from the turbot, Scophthalmus maximus. PubMed: Metabolism of dietary alpha-linolenic acid vs. eicosapentaenoic acid in rat immune cell phospholipids during endotoxemia. PubMed: Capillary supercritical fluid chromatography--atmospheric pressure chemical ionization mass spectrometry of gamma- and alpha-linolenic acid containing triacylglycerols in berry oils. PubMed: Effect of the dietary fat type on arterial thrombosis tendency: systematic studies with a rat model. PubMed: Stearidonic acid, an inhibitor of the 5-lipoxygenase pathway. A comparison with timnodonic and dihomogammalinolenic acid. PubMed: Comparison of the metabolism of alpha-linolenic acid and its delta 6 desaturation product, stearidonic acid, in cultured NIH-3T3 cells. PubMed: Comparison of the conversion rates of alpha-linolenic acid (18:3(n - 3)) and stearidonic acid (18:4(n - 3)) to longer polyunsaturated fatty acids in rats. PubMed: Modification of liver fatty acid metabolism in mice by n-3 and n-6 delta 6-desaturase substrates and products. PubMed: Inhibitory effect of stearidonic acid (18:4 n-3) on platelet aggregation and arachidonate oxygenation. PubMed: Alternative lipids to usual omega 6 PUFAS: gamma-linolenic acid, alpha-linolenic acid, stearidonic acid, EPA, etc.