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Omega-3 Fatty Acids

HCID 56842239
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GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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Grundinformationen

CAS
329042-31-1
Standard-SMILES
CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O.CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O.CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)O
InChIKey
QPEOIOLHJXXJFN-GNGJDXFDSA-N
Summenformel
C60H92O6
Durchschnittliche Molmasse
909,4 g/mol
Monoisotopische Masse
908,68939065

Überblick

Omega-3 fatty acids are polyunsaturated fatty acids (PUFAs) with a double bond at the third carbon atom from the end of the carbon chain. The three types of omega-3 fatty acids involved in human physiology are α-linolenic acid (ALA) (found in plant oils), eicosapentaenoic acid (EPA), and docosahexaenoic acid (DHA) (both commonly found in fish oil that originally come from microalgae that is further consumed by phytoplankton, a source of diet for fish). Omega-3 fatty acids play a critical role in metabolism and cellular function and they are available as daily supplements. On September 8, 2004, the U.S. Food and Drug Administration gave "qualified health claim" status to EPA and DHA omega-3 fatty acids. Therapeutic products containing omega-3 fatty acid and its derivatives for treatment of hypertriglyceridemia include Lovaza, Omtryg, Epanova, and Vascepa.

Namen und Bezeichner

Bevorzugter Name
Omega-3 Fatty Acids
IUPAC
(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid;(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid;(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid

Namen und Synonyme

n-3 PUFAn3 PUFAn 3 PUFAPUFA, n3PUFA, n-3Omega-3 acidOmega-3Omega-3 PUFAOmega-3 phospholipidsOmega-3 triglyceridesomega-3-Fatty AcidsRefChem:55772
Weitere Namen anzeigen
Omega-3 acid triglyceridesOmega-3-acid triglycerides71M78END5SCHEBI:25681NDI 441Omega-3 Polyunsaturated Fatty Acid(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid;(5E,8E,11E,14E,17E)-henicosa-5,8,11,14,17-pentaenoic acidn-3 PUFAs

Datenbank-Bezeichner

CAS
329042-31-1
PubChem CID
56842239
ChEMBL
CHEMBL4298065

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA)
112 Ų
H-Brücken-Donoren
3
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
40
Schwere Atome
66
Formalladung
0
Komplexität
1.160

Experimentelle und physikochemische Eigenschaften

Dietary IngredientsOmega-3 fatty acids

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Toxikologische Informationen

Adverse Effects · 1 Eintrag

The FDA-approved fatty acid prescriptions (icosapent ethyl, omega-3-acid ethyl esters, omega-3-carboxylic acids, and omega-3-acid ethyl esters A) are generally safe with benign effects such as fishy taste, eructation, dyspepsia, diarrhea, gas, nausea, and arthralgia. Researchers noted adverse reactions in clinical trials for each FDA-approved omega-3 fatty acid product.

Toxicity SummaryEPA and DHA are considered generally safe. The FDA recommends that daily intake not exceed 3 g/d of EPA and DHA combined, with no more than 2 g/d deriving from supplements.

Chemie und Industrie

Pharmakologische Informationen

Pharmacodynamics · 1 Eintrag

Omega-3 fatty acids are triglycerides that get broken down into smaller fatty acid units. They act to reduce plasma triglyceride levels however increase the cholesterol levels and are thought to possess potent antiarrythmic effects. Polyunsaturated fatty acids including eicosapentaenoic and docosahexaenoic acid mediate important cellular function such as inhibition of platelet function, prolongation of bleeding time, anti-inflammatory effects and reduction of plasma fibrinogen. Polyunsaturated fatty acids are components of the phospholipids that form the structures of the cell membranes and also serve as energy source. They form eicosanoids which are important signalling molecules with wide-ranging functions in the body's cardiovascular, pulmonary, immune and endocrine systems. DHA tends to exist in high concentrations in the retina, brain (via uptake by Mfsd2a as a transporter), and sperm.

Mechanism of Action · 1 Eintrag

Omega-3 fatty acids mediate anti-inflammatory effects and increased levels of EPA or DHA has shown to decrease the levels of PGE2 and 4 series-LT. Eicosapentaenoic acids compete with constitutive levels of arachidonic acid in cell membranes for the same desaturation enzymes and produce 3-series prostaglandins and thromboxanes, and 5-series leukotrienes which have low pro-inflammatory potential. The alteration in leukotriene biosynthesis due to higher concentration of omega-3 fatty acids compared to arachidonic acid underlies the anti-inflammatory effects. EPA and DHA also give rise to resolvins and related lipid signalling molecules such as protectins via cyclooxygenase and lipoxygenase pathways, which have anti-inflammatory effects. They inhibit transendothelial migration of neutrophils and inhibit TNF and IL-1β production. Omega-3 fatty acids also decrease adhesion molecule expression on leukocytes and on endothelial cells and decrease intercellular adhesive interactions. Omega-3 (or n-3) polyunsaturated fatty acids (PUFAs) and their metabolites are natural ligands for peroxisome proliferator-activated receptor (PPAR) gamma that regulates inflammatory gene expression and NFκB activation. PPAR alpha activation is also associated with induction of COX-2 expression. The role of EPA and DHA in reducing triglyceride levels include inhibition of acyl-CoA:1,2-diacylglycerol acyltransferase, increased mitochondrial and peroxisomal-beta-oxidation in the liver, decreased lipogenesis in the liver, and increased plasma lipoprotein lipase activity. They also may reduce triglyceride synthesis because they are poor substrates for the enzymes responsible for TG synthesis, and EPA and DHA inhibit esterification of other fatty acids.

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Biological Half-LifeApproximate half-life values in a compartmental study of ALA, EPA and DHA are 1h, 39-67h and 20h, respectively.
Metabolism/Metabolites · 1 Eintrag

ALA, DHA and EPA are metabolized and oxidized in the liver, which is the site of biosynthesis of n-3 fatty acid intermediates, synthesizing VLDL that transport fatty acids in the plasma to tissues. Major enzymes that generate lipid signalling molecules from EPA, DHA and ALA are lipoxygenases and cyclooxygenase.

FDA Pharmacological Classification · 5 Einträge

71M78END5S

OMEGA-3 FATTY ACIDS

Chemical Structure [CS] - Fatty Acids, Omega-3

Established Pharmacologic Class [EPC] - Omega-3 Fatty Acid

Omega-3 fatty acids is an Omega-3 Fatty Acid.

Absorption, Distribution and Excretion · 3 Einträge

After ingestion, dietary lipids are hydrolyzed in the intestinal lumen. The hydrolysis products—monoglycerides and free fatty acids—are then incorporated into bile-salt– containing micelles and absorbed into enterocytes, largely by passive diffusion. The absorption rate is about 95%. Within intestinal cells, free fatty acids are primarily incorporated into chylomicrons and enter the circulation via the lymphatic system where they are delivered to various tissues for metabolism, oxidation and storage.

Vd of EPA is aproximately 82L

Clearance of EPA is approximately 757mL/h.