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Omega-3 Fatty Acids, Eicosa Pentaenoic Acid, Docosa Hexaenoic Acid, EPA, DHA, 10417-94-4, 6217-54-5

Omega-3 Fatty Acids, Eicosa Pentaenoic Acid, Docosa Hexaenoic Acid, EPA, DHA, 10417-94-4, 6217-54-5

OMEGA-3 FATTY ACIDS (EPA/DHA)

Omega-3 Fatty Acids / Eicosapentaenoic Acid (EPA) / Docosahexaenoic Acid (DHA)
CAS Numbers: 10417-94-4 (EPA); 6217-54-5 (DHA)

1. PRODUCT IDENTIFICATION AND CHEMICAL IDENTITY

Parameter Detail
Product Name Omega-3 Fatty Acids (EPA/DHA)
Chemical Definition Eicosapentaenoic Acid (EPA) and Docosahexaenoic Acid (DHA)
EPA CAS Number 10417-94-4
DHA CAS Number 6217-54-5
EPA Molecular Formula C₂₀H₃₀O₂
DHA Molecular Formula C₂₂H₃₂O₂
EPA Molecular Weight 302.46 g/mol
DHA Molecular Weight 328.49 g/mol
Chemical Class Long-chain polyunsaturated fatty acids (PUFA)
Appearance Colorless to light yellow oily liquid
Odor Slight fishy odor (source-dependent)
Solubility Fat-soluble; insoluble in water

Omega-3 fatty acids are essential fatty acids belonging to the class of polyunsaturated fatty acids (PUFA). Eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) are the two most important omega-3 fatty acids for human health. They cannot be synthesized in sufficient amounts by the body and must be obtained through diet or supplementation. EPA and DHA are known for their cardiovascular health benefits, brain function support, eye health, and anti-inflammatory effects. Their primary sources include fish oil, algal oil, and krill oil. They are widely used in dietary supplements, functional foods, infant formulas, and pharmaceutical preparations.

2. SYNONYMS AND OTHER NAMES

Type Name
EPA Names Eicosapentaenoic Acid, Timnodonic Acid, Icosapentaenoic Acid, EPA
DHA Names Docosahexaenoic Acid, Cervonic Acid, DHA
Chemical Class Polyunsaturated fatty acids (PUFA), Omega-3 fatty acids
EPA CAS Number 10417-94-4
DHA CAS Number 6217-54-5
EPA Molecular Formula C₂₀H₃₀O₂
DHA Molecular Formula C₂₂H₃₂O₂
E Number Not applicable

3. CHEMICAL STRUCTURE

3.1. EPA (Eicosapentaenoic Acid) Structure

EPA is a 20-carbon omega-3 fatty acid with 5 double bonds (C20:5 n-3). The final double bond is located at the third carbon atom from the omega (methyl) end.

Structural Formula:

CH₃ - CH₂ - CH = CH - CH₂ - CH = CH - CH₂ - CH = CH - CH₂ - CH = CH - CH₂ - CH = CH - (CH₂)₃ - COOH

Abbreviated Notation:
C20:5 n-3 (or 20:5ω-3)

3.2. DHA (Docosahexaenoic Acid) Structure

DHA is a 22-carbon omega-3 fatty acid with 6 double bonds (C22:6 n-3). The final double bond is located at the third carbon atom from the omega (methyl) end.

Structural Formula:

CH₃ - CH₂ - CH = CH - CH₂ - CH = CH - CH₂ - CH = CH - CH₂ - CH = CH - CH₂ - CH = CH - CH₂ - CH = CH - (CH₂)₂ - COOH

Abbreviated Notation:
C22:6 n-3 (or 22:6ω-3)

3.3. Key Structural Features

Feature EPA DHA
Carbon Count 20 22
Double Bond Count 5 6
Omega Position n-3 (ω-3) n-3 (ω-3)
Molecular Formula C₂₀H₃₀O₂ C₂₂H₃₂O₂
Molecular Weight 302.46 g/mol 328.49 g/mol
Carboxyl Group Present (-COOH) Present (-COOH)
Structure Long-chain, polyunsaturated Long-chain, polyunsaturated

4. PHYSICAL AND CHEMICAL PROPERTIES

Property EPA DHA Omega-3 Mixture
Appearance Colorless to light yellow oily liquid Colorless to light yellow oily liquid Colorless to light yellow oily liquid
Odor Slight fishy odor Slight fishy odor Slight fishy odor (source-dependent)
Solubility Fat-soluble; water-insoluble Fat-soluble; water-insoluble Fat-soluble; water-insoluble
Melting Point -54°C -44°C Variable
Boiling Point Decomposes Decomposes Decomposes
Density (20°C) ~0.91 g/cm³ ~0.93 g/cm³ 0.90 – 0.95 g/cm³
Refractive Index ~1.47 ~1.48 1.47 – 1.49
Iodine Value High High High
Oxidation Sensitivity High (polyunsaturated) High (polyunsaturated) High
pH Neutral Neutral Neutral

5. SOLUBILITY PROFILE

Solvent EPA DHA Conditions
Water Insoluble Insoluble 20°C
Vegetable Oils Soluble Soluble 20°C
Ethanol Soluble Soluble 20°C
Chloroform Soluble Soluble 20°C
Hexane Soluble Soluble 20°C
Acetone Soluble Soluble 20°C
Ether Soluble Soluble 20°C

6. CHEMICAL PROPERTIES AND REACTIVITY

Property Description
Chemical Character Weakly acidic (carboxylic acid)
Polyunsaturated Structure Contains multiple cis-double bonds
Oxidation Undergoes autoxidation in air; causes fishy odor and rancidity
Isomerization Double bonds in cis configuration; trans isomerization possible with heat and light
Esterification Forms triglycerides, phospholipids, and ethyl esters
Incompatible Materials Strong oxidizers, heat, light, oxygen, heavy metals

7. REACTION EQUATIONS

7.1. Oxidation (Rancidity)

Omega-3 + O₂ → Peroxides → Aldehydes → Ketones (off-odor)

7.2. Esterification (Triglyceride Formation)

Omega-3 + Glycerol → Triglyceride + H₂O

7.3. Hydrogenation (Saturation)

Omega-3 + H₂ (catalyst) → Saturated Fatty Acid (double bonds saturated)

7.4. Saponification

Omega-3 + NaOH → Sodium Salt (Soap) + Glycerol

8. BIOLOGICAL AND BIOCHEMICAL PROPERTIES

Property Description
Essentiality Cannot be synthesized sufficiently by the body; must be obtained from diet
Cell Membrane Structure Found in cell membrane phospholipids; regulates membrane fluidity
Eicosanoid Synthesis Precursor to anti-inflammatory eicosanoids (prostaglandins, thromboxanes)
Metabolism Participates in energy metabolism via beta-oxidation
Tissue Distribution Concentrated in brain, retina, and nervous tissue (especially DHA)
Placental Transfer Crosses the placenta for fetal development

9. BIOLOGICAL MECHANISMS OF ACTION

Effect Mechanism
Triglyceride Reduction Reduces VLDL synthesis in the liver; inhibits triglyceride synthesis
Anti-inflammatory Effect Reduces pro-inflammatory eicosanoids; promotes formation of anti-inflammatory mediators (resolvins, protectins)
Blood Pressure Reduction Increases vasodilation; improves vascular tone
Platelet Aggregation Reduces blood clotting by decreasing thromboxane A2 synthesis
Brain Function Increases neuronal membrane fluidity; supports synaptogenesis and neurotransmission
Anti-arrhythmic Effect Modulates ion channel activity in cardiac myocytes

10. SOURCES

Source EPA Content DHA Content Description
Fish Oil High High Most common source; cold-water fish (salmon, mackerel, sardines)
Algal Oil Medium High Vegetarian/vegan source; derived from microalgae
Krill Oil High Medium Derived from Antarctic krill; phospholipid form
Fish Meat Medium Medium Obtained through consumption of oily fish
Flaxseed Oil None (ALA) None (ALA) Contains ALA; conversion to EPA/DHA in the body is limited

11. FUNCTIONAL PROPERTIES AND HEALTH EFFECTS

Function Description
Heart Health Lowers triglyceride levels, supports vascular elasticity, regulates blood pressure
Brain Function Plays a critical role in cell membrane structure, supports memory and learning, may reduce risk of neurodegenerative diseases
Anti-inflammatory Effect Reduces inflammation in the body; supports joint health
Eye Health Plays an important role in retinal health; may reduce risk of age-related macular degeneration
Pregnancy and Fetal Development Plays a critical role in fetal brain and eye development
Immune System Modulates immune response

12. APPLICATIONS AND INDUSTRIAL USES

12.1. Dietary Supplements

Application Description
Capsule Form Commonly used in soft gelatin capsules.
Liquid Form Used as liquid supplements in bottles or dropper forms.
Powder Form Microencapsulated powder form; can be added to food products.

12.2. Functional Foods

Application Description
Infant Formula Added to infant formulations for brain development.
Dairy Products Used in fortified milk, yogurt, and cheese products.
Beverages Used in functional beverages (fruit juices, cold drinks).
Bakery Products Omega-3 enriched bread and cereal products.

12.3. Clinical Nutrition and Pharmaceutical Preparations

Application Description
Clinical Nutrition Used in enteral and parenteral nutrition products in hospitals.
Pharmaceutical Preparations Prescription omega-3 products (e.g., triglyceride-lowering drugs).
Dermatological Products Used in creams and lotions to support skin barrier.

12.4. Animal Nutrition

Application Description
Fish Feed Added to fish feeds in aquaculture.
Pet Food Used as a health supplement in dog and cat foods.

13. EPA AND DHA COMPARISON

Property EPA (Eicosapentaenoic Acid) DHA (Docosahexaenoic Acid)
Carbon Count 20 22
Double Bond Count 5 6
Molecular Weight 302.46 g/mol 328.49 g/mol
Melting Point -54°C -44°C
Primary Role Anti-inflammatory, triglyceride reduction Brain development, eye health, neuroprotection
Tissue Distribution More widespread (blood, heart) Brain, retina, nervous tissue
Eicosanoid Precursor Yes (anti-inflammatory eicosanoids) Limited (neuroprotectins, resolvins)

14. CHEMICAL COMPATIBILITY TABLE

Substance / Environment Compatibility Description
Vegetable Oils COMPATIBLE Easily miscible; forms solution.
Water INCOMPATIBLE Insoluble; forms two phases.
Oxygen / Air LIMITED Susceptible to oxidation; inert atmosphere required.
Light (UV) LIMITED Accelerates oxidation; dark-colored containers recommended.
Heat LIMITED Oxidation accelerates at high temperatures; store in cool place.
Antioxidants COMPATIBLE Vitamin E and other antioxidants should be added for stability.
Heavy Metals INCOMPATIBLE Catalyze oxidation.
Plastic (HDPE, PET) COMPATIBLE Suitable as packaging material (oxygen barrier).
Glass COMPATIBLE Suitable for storage and packaging.

15. STABILITY AND SHELF LIFE

Parameter Information
Stability Susceptible to oxidation; must be stabilized with antioxidants (e.g., vitamin E).
Storage Conditions Store in a cool (15-25°C), dry, and well-ventilated area; protect from light and oxygen.
Temperature Effect Storage at low temperature (refrigerator) extends shelf life.
Light Effect UV light accelerates oxidation; use dark-colored glass or opaque packaging.
Oxygen Effect Oxygen accelerates oxidation; package under inert atmosphere (nitrogen).
Shelf Life 12-24 months (under proper storage conditions, stabilized with antioxidants).

16. TOXICOLOGICAL PROFILE

Parameter Value
Acute Oral Toxicity (LD50, Rat) > 5000 mg/kg (low toxicity)
Acute Dermal Toxicity Low
Acute Inhalation Toxicity Low risk
Skin Irritation Mild irritant (liquid form)
Eye Irritation Mild irritant
High Dose Effects Blood-thinning effect; interaction with anticoagulant drugs; gastrointestinal discomfort
Mutagenicity Negative
Carcinogenicity Not classified
Reproductive Toxicity Not classified
Recommended Daily Dose 250-1000 mg (EPA+DHA)

17. GHS CLASSIFICATION AND LABELING

GHS Classification (Generally Not Classified as Hazardous):

Hazard Class Category H-Statement
Not classified as hazardous - -

Signal Word: None (not classified as hazardous)

Hazard Pictograms: None

Hazard Statements (H-Codes): None

Safety Phrases (Historically):

Code Statement
S24/25 Avoid contact with skin and eyes.
S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39 Wear suitable protective clothing, gloves, and eye/face protection.

18. PRECAUTIONARY STATEMENTS (P-CODES)

Code Statement
P264 Wash hands thoroughly after handling.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352 IF ON SKIN: Wash with plenty of soap and water.
P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present.
P337+P313 If eye irritation persists: Get medical advice/attention.
P501 Dispose of contents/container in accordance with local regulations.

19. FIRST AID MEASURES

Route of Exposure Action to Be Taken
Inhalation Move to fresh air. If breathing difficulty occurs, seek medical attention.
Skin Contact Wash with plenty of soap and water. Remove contaminated clothing.
Eye Contact Rinse thoroughly with plenty of water for at least 15 minutes. Remove contact lenses. Seek medical attention.
Ingestion Rinse mouth with water. Do not induce vomiting. If large amount is swallowed, seek medical attention.
General Note If symptoms persist, always consult a healthcare facility.

20. FIRE-FIGHTING MEASURES

Parameter Information
Fire Hazard Flammable liquid; keep away from heat, sparks, and flames.
Hazards During Fire Thermal decomposition produces carbon monoxide, carbon dioxide, and toxic fumes.
Suitable Extinguishing Media Dry chemical powder, CO₂, alcohol-resistant foam, water spray.
Special Protective Equipment Self-contained breathing apparatus (SCBA), full protective clothing.
Special Precautions Prevent fire-fighting water from entering the environment.

21. ACCIDENTAL RELEASE MEASURES

Parameter Information
Personal Protection Protective gloves, goggles, coverall.
Ventilation Increase ventilation; use local exhaust in confined spaces.
Containment Cover spilled area with inert material (sand, vermiculite).
Cleaning Methods Collect with inert absorbent material and place in appropriate waste container.
Environmental Precautions Prevent entry into drains, sewers, and water bodies.
Waste Disposal Dispose of in accordance with local regulations.

22. STORAGE AND SHELF LIFE

Parameter Information
Storage Conditions Store in a cool (15-25°C), dry, and well-ventilated area; protect from light and oxygen.
Container Requirements Tightly closed, under inert atmosphere (nitrogen), in dark-colored glass or oxygen-barrier plastic containers.
Materials to Avoid Light, oxygen, heat, heavy metals, strong oxidizers.
Shelf Life 12-24 months (under proper storage conditions, stabilized with antioxidants).
Stability Note Susceptible to oxidation; antioxidants (vitamin E, ascorbyl palmitate) should be added.
Packaging Options 1 kg, 5 kg, 10 kg, 25 kg, 200 kg (drums, IBC tanks).

23. PACKAGING OPTIONS

Packaging Type Quantity Material
Dark-colored glass bottle 1 – 5 kg Glass (dark-colored)
Plastic drum (oxygen barrier) 10 – 25 kg HDPE / Aluminum foil-lined
Metal drum (stainless steel) 25 – 200 kg Stainless steel
IBC Tank 1000 kg HDPE / Stainless steel
Capsule / Softgel Variable Gelatin / Vegetable capsule

24. TRANSPORT INFORMATION

Parameter Information
UN Number Not applicable (not classified as dangerous goods).
Hazard Class Not classified as hazardous for transport.
Packing Group Not applicable.
ADR/RID Not classified as dangerous goods.
IMDG Code Not classified as dangerous goods.
IATA (Air) Not classified as dangerous goods.
Marine Pollutant No.
Transport Temperature Ambient temperature; protect from light and oxygen.

25. REGULATORY STATUS

Region / Authority Status
European Union Approved as a dietary supplement and functional food ingredient.
USA (FDA) Recognized as GRAS (Generally Recognized as Safe).
Turkey Approved as a dietary supplement; regulated by Turkish Food Codex.
EFSA Health claims (heart health, brain function) have been approved.
WHO/FAO Recommended daily intake levels have been established.
Pharmaceutical Used as an active ingredient in prescription products.

26. SECTORAL SUITABILITY TABLE

Sector Suitability Description
Dietary Supplements HIGH Widespread use in capsules, liquid, and powder forms.
Functional Foods HIGH Infant formulas, dairy products, beverages, bakery.
Clinical Nutrition HIGH Enteral and parenteral nutrition products.
Pharmaceutical HIGH Prescription triglyceride-lowering drugs.
Cosmetics MEDIUM Skin care products (anti-inflammatory, barrier support).
Animal Nutrition MEDIUM Fish feed and pet food.

27. QUICK REFERENCE TABLE

Property EPA DHA
CAS Number 10417-94-4 6217-54-5
Molecular Formula C₂₀H₃₀O₂ C₂₂H₃₂O₂
Molecular Weight 302.46 g/mol 328.49 g/mol
Carbon Count 20 22
Double Bond Count 5 6
Omega Position n-3 (ω-3) n-3 (ω-3)
Melting Point -54°C -44°C
Appearance Colorless to light yellow oily liquid Colorless to light yellow oily liquid
Primary Role Anti-inflammatory, triglyceride reduction Brain development, eye health
Shelf Life 12-24 months (with antioxidants) 12-24 months (with antioxidants)

28. CRITICAL NOTICES AND BEST PRACTICES

CRITICAL NOTICES:

  1. Oxidation Sensitivity: Omega-3 fatty acids are highly unsaturated and very sensitive to oxidation. Air, light, heat, and heavy metals accelerate oxidation. Stabilization with antioxidants (vitamin E, ascorbyl palmitate) is essential.

  2. Fishy Odor: Oxidative degradation produces aldehydes and ketones, causing fishy odor. This is an indicator of quality loss. Microencapsulation or odor removal technologies may be used.

  3. Anticoagulant Effect: High doses of omega-3 may have a blood-thinning effect. Individuals taking blood-thinning medications (warfarin, aspirin, clopidogrel) should use under medical supervision.

  4. Dosage: Doses of 250-1000 mg (EPA+DHA) daily are recommended for general health. High doses (>3 g/day) require medical supervision.

  5. Source Quality: Products derived from fish oil should be tested for heavy metal (mercury, PCB) contamination. Molecularly distilled products are preferred.

  6. Pregnancy and Lactation: DHA is critical for fetal brain and eye development. Special formulations should be preferred for pregnant and lactating women.

  7. Regulation: Health claims (heart health, brain function) are subject to varying regulations by country. Check local regulations before use.

BEST PRACTICE RECOMMENDATIONS:

  • Storage: Store in a cool (15-25°C), dry, and well-ventilated area, protected from light and oxygen. Refrigeration (2-8°C) is recommended for long-term storage.

  • Packaging: Use dark-colored glass or oxygen-barrier containers. Use promptly after opening to minimize air exposure.

  • Antioxidant Addition: Add natural antioxidants (vitamin E, ascorbyl palmitate, rosemary extract) to the product for stabilization.

  • Quality Control: Monitor quality with peroxide value (PV), anisidine value (AV), total oxidation value (TOTOX), and heavy metal analysis.

  • Personnel Protection: Use protective gloves and goggles. Ensure adequate ventilation.

  • Waste Management: Dispose of waste in accordance with local regulations. Do not pour down drains.

LEGAL DISCLAIMER:

The information provided in this document is based on our current knowledge and experience and is presented in good faith; however, as all conditions of use are beyond our control, it does not constitute a binding specification or warranty. This Technical Data Sheet is for informational purposes only. Users are obligated to test the suitability of the product for their own applications. For complete safety, storage, handling, transport, waste, and regulatory compliance information, the official Safety Data Sheet (SDS/MSDS) provided by the manufacturer/supplier must be consulted.

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