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Send EmailOleic Acid, Red Oil, Oleoate, 112-80-1
OLEIC ACID
SECTION 1: PRODUCT IDENTITY AND CHEMICAL IDENTIFICATION
| Parameter | Information |
|---|---|
| Product Name | Oleic Acid |
| Chemical Name (IUPAC) | (9Z)-Octadec-9-enoic acid |
| Common Names | Oleic Acid, Red Oil, Oleoate, Metaupon |
| CAS Number | 112-80-1 |
| EC Number (EINECS) | 204-007-1 |
| Molecular Formula | C₁₈H₃₄O₂ / C₁₇H₃₃COOH |
| Molecular Weight | 282.46 g/mol |
| Chemical Class | Monounsaturated fatty acid (MUFA); Omega-9 fatty acid |
| Source | Vegetable and animal oils (olive oil, hazelnut oil, canola oil) |
| Appearance | Colorless to pale yellow, odorless liquid |
| Odor | Slight characteristic (rancidity upon oxidation) |
| Physical State (20°C) | Liquid |
| Solubility | Insoluble in water; slightly soluble in alcohol; soluble in ether and organic solvents |
SECTION 2: CHEMICAL STRUCTURE
Structure Description:
O
‖
HO—C—(CH₂)₇—CH = CH—(CH₂)₇—CH₃
cis-Δ9-Octadecenoic Acid
Oleic Acid
C₁₈H₃₄O₂
Simplified Structure:
CH₃—(CH₂)₇—CH = CH—(CH₂)₇—COOH
Oleic Acid
(Cis configuration - Omega-9)
| Parameter | Description |
|---|---|
| Molecular Formula | C₁₈H₃₄O₂ / C₁₇H₃₃COOH |
| Molecular Weight | 282.46 g/mol |
| Carbon Count | 18 |
| Double Bonds | 1 (monounsaturated) |
| Double Bond Position | C9-C10 (Δ9) |
| Configuration | Cis (natural form) |
| Omega Class | Omega-9 (9th carbon from methyl end) |
| Functional Groups | Carboxylic acid (-COOH), alkene (C=C) |
| SMILES | CCCCCCCC/C=C\CCCCCCCC(=O)O |
| InChI | InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9- |
| InChI Key | ZQPPMHVWECSIRJ-KTKRTIGZSA-N |
| Hydrogen Bond Donors | 1 |
| Hydrogen Bond Acceptors | 2 |
| Rotatable Bond Count | 15 |
| Polar Surface Area (PSA) | 37.3 Ų |
SECTION 3: PHYSICAL AND CHEMICAL PROPERTIES
| Property | Value | Test Method / Note |
|---|---|---|
| Appearance | Colorless to pale yellow, odorless liquid | Visual |
| Odor | Slight characteristic | Olfactometric |
| Molecular Weight | 282.46 g/mol | Calculated |
| Melting Point (α-form) | 13.4 °C | DSC |
| Melting Point (β-form) | 16.3 °C | DSC |
| Boiling Point | 360 °C | - |
| Boiling Point (13 mmHg) | 194-195 °C | - |
| Density (20°C) | 0.893-0.895 g/cm³ | ASTM D4052 |
| Refractive Index (n²⁰/D) | 1.458-1.460 | ASTM D1218 |
| Viscosity (25°C) | ~25-30 cP | - |
| Flash Point | 189 °C | ASTM D93 |
| Autoignition Temperature | 363 °C | - |
| Water Solubility (20°C) | Insoluble (~0.01 g/L) | General Method |
| Ethanol Solubility | Slightly soluble | General Method |
| Ether Solubility | Soluble | General Method |
| Chloroform Solubility | Soluble | General Method |
| Acetone, Benzene | Soluble | General Method |
| Log P (Octanol/Water) | ~7.6 (lipophilic) | Calculated / Experimental |
| pKa | ~4.8 (carboxylic acid) | Potentiometric |
| Iodine Value | 85-95 g I₂/100g | Titration |
| Acid Value | 195-205 mg KOH/g | Titration |
| Saponification Value | 195-205 mg KOH/g | Titration |
| Peroxide Value | ≤5 meq O₂/kg | Titration |
| Flammability | Combustible liquid | - |
SECTION 4: CRYSTAL FORMS (POLYMORPHISM)
| Form | Melting Point | Description |
|---|---|---|
| α-form (Alpha) | 13.4 °C | Stable at low temperatures |
| β-form (Beta) | 16.3 °C | Stable at higher temperatures |
SECTION 5: CHEMICAL PROPERTIES AND REACTIVITY
| Parameter | Information |
|---|---|
| Chemical Character | Weak acid (carboxylic acid); unsaturated fatty acid |
| Reactivity | Reactive due to carboxyl group and double bond |
| Addition Reactions | Addition of bromine, iodine, hydrogen to double bond (hydrogenation → stearic acid) |
| Oxidation | Slow rancidity upon air exposure (peroxide formation) |
| Isomerization | Cis → trans isomerization (elaidic acid) (with HNO₂ or sulfur compounds) |
| Esterification | Ester formation with alcohols (glycerol mono-oleate, E471) |
| Salt Formation | Oleate salts with bases (sodium oleate, potassium oleate) |
| Polymerization | Oxidative polymerization (drying oils) |
| Stability | Stable under normal conditions; degrades under light, heat and oxygen |
| Incompatible Materials | Strong oxidizing agents, strong acids, strong bases |
| Decomposition Products | CO, CO₂, aldehydes, ketones, peroxides |
SECTION 6: NATURAL SOURCES
| Source | Oleic Acid Content (%) |
|---|---|
| Vegetable Sources | |
| Olive Oil | 55 – 83% |
| Hazelnut Oil | 70 – 80% |
| High Oleic Sunflower Oil | 75 – 85% |
| Canola Oil | 55 – 65% |
| Avocado Oil | 60 – 70% |
| Almond Oil | 65 – 75% |
| Palm Oil | 40 – 50% |
| Soybean Oil | 20 – 25% |
| Animal Sources | |
| Lard | ~40% |
| Tallow | ~30% |
| Fish Oil | Variable |
| Human Body | |
| Adipose Tissue | Most abundant fatty acid |
SECTION 7: PRODUCTION AND PURIFICATION
| Step | Description |
|---|---|
| 1. Hydrolysis | Hydrolysis of vegetable/animal oils (triglycerides) with water (catalyst: zinc oxide or aromatic sulfonic acids) → Fatty acids + Glycerin |
| 2. Separation | The hydrolysis mixture is cooled. Saturated fatty acids (stearic, palmitic) are separated as solid phase by pressing. Liquid phase is rich in oleic acid. |
| 3. Purification | Fractional distillation under low pressure yields high-purity oleic acid (70-99%). |
| 4. Refining | Color removal (caustic, clay) and odor removal (steam distillation) |
SECTION 8: COMMERCIAL GRADES
| Grade / Type | Purity | Appearance | Primary Application |
|---|---|---|---|
| Technical Grade | 65-75% | Yellowish liquid | Soaps, textile, leather, industrial lubrication |
| Cosmetic Grade | ≥90% | Pale yellow liquid | Cosmetics, personal care, emulsifier |
| Food Grade (E471) | ≥95% | Colorless to pale yellow | Food additive, emulsifier |
| Pharmaceutical Grade | ≥98% | Colorless liquid | Drug carrier, ointment base |
| Analytical Grade | ≥99% | Colorless liquid | Laboratory, research |
| High Oleic (HO) | ≥75% | Pale yellow liquid | Cooking oil, biodiesel |
| Extra Olein | ≥90% | Colorless liquid | Premium cosmetics, pharmaceuticals |
SECTION 9: FUNCTIONAL PROPERTIES
| Property | Description |
|---|---|
| Emulsifier | Facilitates formation and stabilization of oil-water emulsions |
| Emollient | Forms protective layer on skin, prevents moisture loss |
| Solvent | Carrier for oil-soluble active ingredients |
| Lubricant | Lubricant in textile and leather processing |
| Preservative Aid | Synergistic effect with antioxidants |
| Penetration Enhancer | Enhances penetration of active ingredients in skin and hair |
| Flow Modifier | Viscosity control in paints, inks and coatings |
SECTION 10: APPLICATIONS AND USAGE
| Industry | Application | Function |
|---|---|---|
| Cosmetics | Creams, lotions, lipsticks, hair care | Emulsifier, emollient, carrier |
| Soap Industry | Bar and liquid soaps | Sodium/potassium oleate salts |
| Textile | Softener, finishing agent | Lubricant, softener |
| Leather | Tanning, fatliquoring | Lubricant, softener |
| Paints & Coatings | Alkyd resin production | Flow improver |
| Inks | Printing inks | Lubricant agent |
| Food | Cooking oils, emulsifier (E471) | Frying stability, emulsion |
| Pharmaceutical | Drug carrier, ointment base | Penetration enhancer |
| Metalworking | Cutting fluids, lubricants | Lubricant, cooling |
| Biodiesel | Biodiesel production | Fatty acid methyl ester (FAME) |
| Rubber | Rubber processing | Plasticizer |
| Research | ALI model (acute lung injury) | Experimental model |
SECTION 11: HEALTH EFFECTS
| Effect | Description | Evidence Level |
|---|---|---|
| Cardiovascular Health | Lowers LDL cholesterol; maintains/increases HDL; lowers blood pressure | Strong Clinical Evidence |
| Insulin Sensitivity | Reduces insulin resistance; helps manage Type 2 diabetes | Clinical Evidence |
| Anti-inflammatory | Suppresses pro-inflammatory cytokines; reduces chronic inflammation | Clinical Evidence |
| Breast Cancer | May suppress HER2 receptor expression (epidemiological) | Epidemiological |
| Colorectal Cancer | Slows proliferation effect | Preclinical |
| Neurodegeneration | May slow cognitive decline (Mediterranean diet) | Epidemiological |
| Skin Health | Strengthens skin barrier; increases moisture retention | Clinical Evidence |
SECTION 12: QUALITY SPECIFICATIONS
| Parameter | Technical Grade | Cosmetic Grade | Food Grade | Test Method |
|---|---|---|---|---|
| Appearance | Yellowish liquid | Pale yellow liquid | Colorless-pale yellow | Visual |
| Purity (Oleic Acid) | ≥65-75% | ≥90% | ≥95% | GC |
| Acid Value | 195-205 | 195-205 | 195-205 | Titration |
| Saponification Value | 195-205 | 195-205 | 195-205 | Titration |
| Iodine Value | 85-95 | 85-95 | 85-95 | Titration |
| Peroxide Value | ≤5 | ≤5 | ≤2 | Titration |
| Moisture Content | ≤0.5% | ≤0.3% | ≤0.1% | Karl Fischer |
| Color (Gardner) | ≤10 | ≤5 | ≤2 | ASTM D1544 |
| Density (20°C) | 0.893-0.895 | 0.893-0.895 | 0.893-0.895 | ASTM D4052 |
| Heavy Metals (Pb) | ≤10 ppm | ≤5 ppm | ≤2 ppm | ICP-MS |
| Arsenic (As) | ≤2 ppm | ≤1 ppm | ≤1 ppm | ICP-MS |
| Lead (Pb) | ≤2 ppm | ≤1 ppm | ≤1 ppm | ICP-MS |
SECTION 13: SAFETY AND TOXICOLOGICAL PROFILE
| Parameter | Value / Description |
|---|---|
| GHS Classification | Warning (irritant) |
| Signal Word | Warning |
| Hazard Pictograms | GHS07 (Exclamation mark) |
| Hazard Statements (H-Codes) | H315 (Causes skin irritation), H319 (Causes serious eye irritation), H413 (May cause long-lasting effects to aquatic life) |
| Precautionary Statements (P-Codes) | P264, P280, P302+P352, P305+P351+P338, P332+P313, P337+P313, P362+P364, P501 |
| Acute Oral Toxicity (LD50, Rat) | >5000 mg/kg (very low toxicity) |
| Acute Dermal Toxicity (LD50, Rabbit) | >2000 mg/kg (low toxicity) |
| Skin Irritation | Mild irritant |
| Eye Irritation | Mild-moderate irritant |
| Skin Sensitization | May cause sensitization (rare) |
| Carcinogenicity | Not classified as carcinogenic |
| Mutagenicity | Not mutagenic |
| Reproductive Toxicity | No reproductive toxicity |
| Target Organs | Skin, eyes |
SECTION 14: GHS CLASSIFICATION AND LABELING
GHS Classification (in accordance with 1272/2008/EC):
| Hazard Class | Category | H-Statement |
|---|---|---|
| Skin Irritation | Category 2 | H315 |
| Eye Irritation | Category 2 | H319 |
| Aquatic Chronic Toxicity | Category 3 | H412 |
Signal Word: Warning
Hazard Pictograms: GHS07 (Exclamation mark)
NFPA 704 Hazard Classification:
| Health | Flammability | Reactivity | Special |
|---|---|---|---|
| 1 | 1 | 0 | - |
| (Minimal health hazard) | (Combustible) | (Stable) | (None) |
SECTION 15: 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 and continue rinsing |
| P332+P313 | If skin irritation occurs: Get medical advice/attention |
| P337+P313 | If eye irritation persists: Get medical advice/attention |
| P362+P364 | Take off contaminated clothing and wash it before reuse |
| P403+P233 | Store in a well-ventilated place. Keep container tightly closed |
| P405 | Store locked up |
| P501 | Dispose of contents/container in accordance with local/regional/national/international regulations |
SECTION 16: FIRST AID MEASURES
| Route of Exposure | Action |
|---|---|
| Inhalation | Vapor not expected. If respiratory discomfort occurs, move to fresh air. |
| Skin Contact | Remove contaminated clothing. Wash with plenty of soap and water. Seek medical attention if irritation develops. |
| Eye Contact | Rinse thoroughly with plenty of water for at least 15 minutes. Keep eyelids open. Remove contact lenses if present. Seek medical attention if irritation persists. |
| Ingestion | Rinse mouth with water. Do NOT induce vomiting. Seek medical attention. Aspiration risk. |
| Note | Symptomatic treatment is administered. No specific antidote available. |
SECTION 17: FIREFIGHTING MEASURES
| Parameter | Information |
|---|---|
| Fire Hazard | Combustible liquid |
| Flash Point | 189 °C |
| Fire-Related Hazards | CO, CO₂, aldehydes, ketones |
| Suitable Extinguishing Media | Water mist, CO₂, dry chemical powder, foam |
| Unsuitable Extinguishing Media | Water jet (may spread burning liquid) |
| Special Protective Equipment | SCBA, full protective clothing |
SECTION 18: STORAGE AND SHELF LIFE
| Parameter | Information |
|---|---|
| Storage Conditions | Store in a cool (<25°C), dry, well-ventilated area; protect from light and oxygen. |
| Temperature Limits | 15-25°C (ideal); do not exceed 30°C |
| Humidity | Low humidity environment |
| Light | Protect from light (oxidation) |
| Oxygen | Store under inert atmosphere (nitrogen) to prevent oxidation |
| Container Requirements | Tightly closed, moisture and oxygen-resistant containers (stainless steel, lined steel, HDPE) |
| Incompatible Materials | Light, heat, oxygen, strong oxidizing agents |
| Shelf Life | 24-36 months (under proper storage conditions) |
| Signs of Degradation | Darkening color, odor change (rancidity), peroxide value increase |
SECTION 19: PACKAGING OPTIONS
| Packaging Type | Quantity / Capacity | Material | Application Area |
|---|---|---|---|
| Metal Drum (Lined) | 180 kg, 200 kg | Lined steel | Industrial, bulk supply |
| HDPE Drum | 25 kg, 50 kg, 180 kg, 200 kg | HDPE | Cosmetic, food, pharmaceutical |
| IBC Container | 500 kg, 1000 kg | HDPE | Large-scale industrial supply |
| Glass Bottle | 1 L, 5 L, 10 L | Amber glass | Laboratory, high purity |
| HDPE Bottle | 1 L, 5 L, 10 L | HDPE | Retail, laboratory |
| Flexibag | 1000 kg | PE | Bulk transport |
SECTION 20: TRANSPORTATION INFORMATION
| Parameter | Information |
|---|---|
| UN Number | Not applicable (not classified as dangerous substance) |
| Hazard Class | Not applicable |
| Packing Group | Not applicable |
| ADR/RID | Not classified as dangerous goods |
| IMDG Code | Not marine pollutant |
| IATA (Air) | Not classified as dangerous goods; can be transported by air |
| Transport Temperature | Ambient temperature; protect from heat, moisture, and light |
| Transport Precautions | Protect from leakage; keep away from oxidizing agents |
| Marine Pollutant | No |
SECTION 21: REGULATORY STATUS
| Region / Authority | Status |
|---|---|
| USA (FDA) | GRAS (21 CFR 184.1005); Approved as food additive |
| European Union (EC) | Approved as food additive (E471) |
| Turkey | Approved as food, cosmetic and industrial ingredient |
| ECHA (REACH) | Registered substance |
| TSCA (USA) | Listed |
| California (Prop 65) | Not listed |
| Halal | Yes (plant-derived, with certification) |
| Kosher | Yes (with certification) |
| Vegan | Yes (plant-derived) |
SECTION 22: OTHER NAMES AND SYNONYMS
| Type | Name |
|---|---|
| Turkish Names | Oleik Asit, Oleik, Red Oil |
| English Names | Oleic Acid, Red Oil, Oleoate, Metaupon |
| Chemical Names | (9Z)-Octadecenoic acid, cis-Δ9-Octadecenoic acid |
| Trans Isomer | Elaidic Acid (trans-9-Octadecenoic acid) |
| Trade Marks | Wecoline OO, Pamolyn 100, Emersol 211, Industrene 105, Priolene 6906, Edenor C 18:1 |
| CAS Number | 112-80-1 |
| EC Number | 204-007-1 |
| PubChem CID | 445639 |
| DrugBank ID | DB04204 |
| FDA UNII | 2UMI9U37CP |
| HS Code | 2916.15 |
SECTION 23: SUMMARY TABLE
| Property | Value |
|---|---|
| CAS Number | 112-80-1 |
| Molecular Formula | C₁₈H₃₄O₂ |
| Molecular Weight | 282.46 g/mol |
| Appearance | Colorless to pale yellow liquid |
| Melting Point | 13.4 °C (α-form) / 16.3 °C (β-form) |
| Boiling Point | 360 °C |
| Density (20°C) | 0.893-0.895 g/cm³ |
| Water Solubility | Insoluble |
| Log P | ~7.6 |
| Main Sources | Olive oil, hazelnut oil, canola oil |
| Primary Function | Emulsifier, emollient, carrier, intermediate |
| Main Applications | Cosmetics, food, soap, textile, pharmaceutical |
| Shelf Life | 24-36 months |
| Storage | Cool (<25°C), dry, light-protected |
| GHS Signal Word | Warning |
| UN Number | Not applicable |
| FDA Status | GRAS |
| Halal / Kosher / Vegan | Yes (plant-derived) |
SECTION 24: CRITICAL WARNINGS AND BEST PRACTICES
CRITICAL WARNINGS:
-
Oxidation Sensitivity: Oleic acid is sensitive to oxidation. Oxidation products (peroxides, aldehydes, ketones) cause color change, odor change (rancidity) and quality loss. Protect from light, heat and oxygen.
-
Storage Temperature: May solidify below melting point (13-16°C). Solidified product can be re-liquefied by warming (40-50°C).
-
Double Bond Sensitivity: Due to double bond content, undergoes addition reactions with bromine, iodine, hydrogen.
-
Strong Oxidizing Agents: Do not contact with strong oxidizing agents (violent reaction).
-
Aspiration Risk: Aspiration pneumonitis risk if swallowed. Do not induce vomiting.
-
Vapor Pressure: Low vapor pressure; inhalation risk is low.
-
Skin and Eye Contact: Prolonged contact may cause irritation.
BEST PRACTICE RECOMMENDATIONS:
-
Storage: Store in cool (<25°C), dry, dark place under inert atmosphere (nitrogen), in tightly closed containers. Antioxidants (BHT, BHA, Vitamin E) may be added to prevent oxidation.
-
Transportation: Use stainless steel or lined steel containers. Avoid copper, brass and iron (accelerate oxidation).
-
Formulation: Mix at 40-50°C; avoid high temperatures (>80°C) (oxidation).
-
Antioxidant Use: Add BHT (0.01-0.1%) or Vitamin E (0.05-0.2%) to formulations; prevents oxidation.
-
Temperature Control: Maintain temperature control during storage and transport in cold weather to prevent solidification.
-
Emulsion: Use in oil phase for O/W emulsions.
-
Quality Control: Regularly perform acid value, iodine value, peroxide value, color (Gardner) tests.
-
Personal Protective Equipment: Nitrile or neoprene gloves, safety goggles, protective clothing.
-
Hygiene: Wash hands thoroughly after handling.
-
Spill Cleanup: Collect with absorbent material; prevent entry into sewers or water bodies.
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 guarantee. This Technical Data Sheet is for informational purposes only. Users are responsible for testing suitability for their own applications and for complying with all local, regional, and national regulations. For complete safety, storage, use, handling, waste, and regulatory compliance information, please refer to the official Safety Data Sheet (SDS/MSDS) provided by the manufacturer/supplier.
