Cis-9-octadecenoic acid is a monounsaturated omega-9 fatty acid widely found in nature, especially in olive oil, where it constitutes 55–83% of the composition, and it is prized for its stability and resistance to oxidative degradation.

In cosmetics and skincare, Cis-9-octadecenoic acid acts as an emollient and penetration enhancer, promoting absorption of active ingredients and providing softening and conditioning benefits for the skin and hair.

Nutritionally, Cis-9-octadecenoic acid is associated with improved heart health, as it helps lower LDL ("bad") cholesterol and increases HDL ("good") cholesterol, making it a cornerstone of heart-healthy diets like the Mediterranean diet.

CAS Number: 112-80-1

EC Number: 204-007-1

Molecular Formula: C18H34O2

Molar Mass: 282.47 g/mol

Synonyms: Oleic acid, cis-9-Octadecenoic acid, Elainic acid, C18H34O2, oleic acid, 112-80-1, cis-Oleic acid, oleate, Elaidoic acid, (Z)-Octadec-9-enoic acid, cis-Octadec-9-enoic acid, Z-9-Octadecenoic acid, Oleinic acid, 9-Octadecenoic acid (Z)-, White oleic acid, (9Z)-octadec-9-enoic acid, 9Z-Octadecenoic acid, Elainicacid, cis-Oleate, Elaic acid, delta9-cis-Oleic acid, 9-Octadecenoic acid (9Z)-, 9-Octadecenoic acid, (Z)-, 9-octadecenoic acid, (9Z)-Octadecenoic acid, Oleic acid, pure, D 100 (fatty acid), Oleic acid (natural),  Red oil, D 100, 9-octadecylenic acid, cis-delta(sup 9)-Octadecenoic acid, 9,10-Octadecenoic acid, EINECS 204-007-1, C18:1n-9, delta.9-cis-Oleic acid, 9-(Z)-octadecenoic acid,  (Z)-9-Octadecanoic acid, 9-Octadecenoic acid, cis-, cis-.delta.9-Octadecenoate, cis-.delta.9-Octadecenoic acid, cis-Delta(9)-octadecenoic acid, Oleic acid (NF), Oleic acid, 97%, C18:1 n-9,  Octadec-9-enoic acid, 18:1 n-9, C18:1, cis-9 octadecenoate, (9Z)- Octadecenoic acid, cis-delta9-octadecenoic acid, CAS-112-80-1, Sulfurized oleic acid, Sulphurized oleic acid,  Oleic acid, sulfurized, (9Z)-9-Octadecenoic acid, 9-Octadecenoic acid (9Z)-, sulfurized, Distoline, Oleinate, oleaic acid, Rapinic acid, oleic acid group, Z-9-Octadecenoate,  EINECS 270-164-8, Oleic acid, p.a., OLEICACID, 9,10-Octadecenoate, 9-Octadecenoic acid (Z)-, sulfurized, Oleic acid (8CI), oleic acid extra pure, cis-Octadec-9-enoate, 9-(Z)-octadecenoate, (Z)-9-Octadecanoate, (Z)-octadec-9-enoate, Oleic acid-9,10-t, (9Z)-9-Octadecenoate, 9-cis-Octadecenoic acid, z-octadeca-9-enoic acid, 10402-16-1, Oleic Acid (18:1), Oleic acid, natural, FCC, (9Z)octadec-9-enoic acid, Oleic acid, technical grade, Delta9-cis-Octadecenoic acid, 68412-07-7, MLS001056779, MLS002153498, MLS002454427, 9-octadecenoic acid, (9Z)-, (9Z)-9-Octadecenoic acid,  Oleic acid, analytical standard, Oleic acid, >=93% (GC), Oleic acid, >=99% (GC), HMS2234O13, HMS3649H21, Oleic acid, technical grade, 90%, HY-N1446, ZINC6845860, Tox21_111086, Tox21_201967, Tox21_303324, BDBM50150484, HSCI1_000362, LMFA01030002, LS-560, s4707, SBB058695, 9-Octadecenoic acid (9Z)- (9CI), cis-9-Octadecenoic-9,10-3H2 acid, Low Titer White Oleate, AKOS017343225,  cis-.delta.(sup 9)-Octadecenoic acid, CCG-267270, FA 18:1, 9-Octadecenoic-9,10-t2 acid, (Z)-, NCGC00091119-01, NCGC00091119-03, NCGC00257233-01, NCGC00259516-01, AK187813, AS-16066, BP-24023, CC-33313, SC-19057, Oleic acid, SAJ first grade, >=70.0%, Oleic acid, >=99.0%, CS-0016886, NS00010823, O0011, O0180, C00712, D02315, K-0971, Oleic acid, from suet, natural, >=60% (GC),  AB00641912_08, Fatty acids C7 to C20: cis-9-Octadecenoic Acid, 9-Octadecenoic-9,10-t2 acid, (9Z)- (9CI), Oleic acid, suitable for cell culture, Q207688, SR-01000780573, SR-01000780573-6,  F0001-0262, Oleic acid, certified reference material, Oleic acid, European Pharmacopoeia (EP) Reference Standard, UNII-13FB83DEYU component ZQPPMHVWECSIRJ-KTKRTIGZSA-N,  UNII-44NH37HHP9 component ZQPPMHVWECSIRJ-KTKRTIGZSA-N, UNII-5U9XZ261ER component ZQPPMHVWECSIRJ-KTKRTIGZSA-N, UNII-7N137Q0QYJ component ZQPPMHVWECSIRJ-KTKRTIGZSA-N, UNII-96GS7P39SN component ZQPPMHVWECSIRJ-KTKRTIGZSA-N, UNII-9B22238JYI component ZQPPMHVWECSIRJ-KTKRTIGZSA-N, UNII-B6G0Y5Z616 component ZQPPMHVWECSIRJ-KTKRTIGZSA-N, UNII-HBA528N3PW component ZQPPMHVWECSIRJ-KTKRTIGZSA-N, UNII-MO7HV04S9Y component ZQPPMHVWECSIRJ-KTKRTIGZSA-N, UNII-ODL221H4AM component ZQPPMHVWECSIRJ-KTKRTIGZSA-N, UNII-UDR641JW8W component ZQPPMHVWECSIRJ-KTKRTIGZSA-N, UNII-V1PY73ZXPE component ZQPPMHVWECSIRJ-KTKRTIGZSA-N, 459CE4C0-C836-4249-8E2D-69874B714E9C, UNII-79P21R4317 component ZQPPMHVWECSIRJ-KTKRTIGZSA-N, Oleic acid, United States Pharmacopeia (USP) Reference Standard, Oleic acid, meets analytical specification of Ph, Eur., 65.0-88.0% (GC), Oleic Acid, Pharmaceutical Secondary Standard, Certified Reference Material, Oleic Acid-Water Soluble, powder, BioReagent, suitable for cell culture, A6L, Elaidic acid, 112-79-8, trans-Oleic acid, trans-9-Octadecenoic acid, 9-octadecenoic acid, (E)-octadec-9-enoic acid, (E)-Oleic acid, 9-Octadecenoic acid, (E)-, 9-octadecenoic acid, (9E)-, trans-Octadec-9-enoic acid, (9E)-octadec-9-enoic acid, trans-Elaidic acid, 9-elaidic acid, Octadec-9-enoic acid, 9E-octadecenoic acid, UNII-4837010H8C, trans-.DELTA.9-Octadecenoic acid, (9E)-Octadecenoic acid, MFCD00063954, NSC 26988, 9-trans-Octadecenoic acid, (E)-9-Octadecenoic acid, trans-delta(sup 9)-Octadecenoic acid, D9-trans-Octadecenoic acid, trans-D9-Octadecenoic acid, Delta(9)-octadecenoic acid, 9-Octadecenoic acid,(9E)-, trans-Delta(9)-octadecenoic acid, Elaidic acid, 98%, C18:1, n-9, trans-.delta.(sup 9)-Octadecenoic acid, 4837010H8C, 18:1, n-9, 2027-47-6, Q-201508, 9 Octadecenoic Acid, delta9-Octadecenoic acid, Delta(9)-octadecenoate, Elaidinic acid, oleic_acid, Elaidic acid group, EINECS 217-977-6, Oleic Acid 213 NF, Oleic Acid 221 NF, Oleic Acid 233 LL, cis 9 Octadecenoic Acid, cis-9-Octadecenoic Acid., bmse000643, (9E)octadec-9-enoic acid, Octadec-9-enoic acid anion, SCHEMBL1139, SCHEMBL6693, WLN: QV8U9-T, Oleic acid, tall oil derived, 9-elaidic acid, DTXSID8058619, CHEBI:36021, Elaidic acid, analytical standard, HMS3649H19, Elaidic acid, >=99.0% (GC), ZINC8217338, 1749AH, 6479AF, BDBM50250904, CCG-35462, LMFA01030073, NSC-26988, STL282737, 9-Octadecenoic acid, (E)- (9CI), Elaidic acid, analytical sample grade, AKOS000278123, Oleic acid, from tall oil fatty acids, cis-9-Octadecenoic Acid, Elainic Acid, DB04224, FS-4659, NCGC00344330-02, LS-63810, ST098716, HY-113016, LS-181026, CS-0059361, Oleic acid derived from tall oil fatty acids, EN300-19543, C01712, W-1404, L001099, Q413491, SR-01000946663, J-002839, Oleic Acid, 99% min (animal-origin free, vegetal-derived)

Cis-9-octadecenoic acid is a naturally occurring monounsaturated fatty acid with the molecular formula C18H34O2.

Cis-9-octadecenoic acid is classified as an omega-9 fatty acid due to the position of its single double bond, which is located at the ninth carbon from the methyl end of the carbon chain.

Cis-9-octadecenoic acid is a major component of various animal and vegetable fats, most notably in olive oil, where it constitutes a significant portion of the oil’s composition.

This fatty acid is liquid at room temperature and has a slightly greasy texture.

Known for its stability and non-drying properties, Cis-9-octadecenoic acid is widely used in the production of soaps, cosmetics, and industrial lubricants.

Moreover, Cis-9-octadecenoic acid plays an essential role in human health, being associated with improved cardiovascular health due to its ability to reduce LDL cholesterol while maintaining or increasing HDL cholesterol.

Cis-9-octadecenoic acid is also a precursor for the biosynthesis of other important lipids in the body.

Cis-9-octadecenoic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils.

Cis-9-octadecenoic acid is an odorless, colorless oil, although commercial samples may be yellowish.

In chemical terms, Cis-9-octadecenoic acid is classified as a monounsaturated omega-9 fatty acid, abbreviated with a lipid number of 18:1 cis-9.

Cis-9-octadecenoic acid has the formula CH3(CH2)7CH=CH(CH2)7COOH.

The name derives from the Latin word oleum, which means oil.

Cis-9-octadecenoic acid is the most common fatty acid in Cis-9-octadecenoic acid is an octadec-9-enoic acid in which the double bond at C-9 has the Z (cis) stereochemistry.

Cis-9-octadecenoic acid acts as an EC 3.1.1.1 (carboxylesterase) inhibitor, an Escherichia coli metabolite, a plant metabolite, a Daphnia galeata metabolite, a solvent, an antioxidant and a mouse metabolite.

Cis-9-octadecenoic acid is the conjugate acid of an oleate.

Cis-9-octadecenoic acid is derived from a cis-octadec-9-ene hydride.

Cis-9-octadecenoic acid is one of the most abundant fatty acids found in nature.

Cis-9-octadecenoic acid's structure consists of an 18-carbon chain with a single cis double bond between the ninth and tenth carbons.

This configuration gives Cis-9-octadecenoic acid its characteristic bend, making it less prone to solidify at room temperature compared to saturated fats.

Cis-9-octadecenoic acid is primarily sourced from plant-based oils such as olive oil, canola oil, and sunflower oil, though it is also present in animal fats like lard and tallow.

Cis-9-octadecenoic acid is not only prized for its culinary uses but also for its remarkable stability, which makes it resistant to oxidative rancidity.

This stability is one reason Cis-9-octadecenoic acid is a key ingredient in many food preservation techniques and industrial formulations.

In the pharmaceutical and cosmetic industries, Cis-9-octadecenoic acid acts as an emollient, skin-conditioning agent, and penetration enhancer, making it a valuable component of creams, lotions, and ointments.

From a biological perspective, Cis-9-octadecenoic acid is an essential part of the human diet and contributes to membrane fluidity and cell signaling.

Cis-9-octadecenoic acid is often associated with the Mediterranean diet, which is linked to reduced risks of chronic diseases such as heart disease, type 2 diabetes, and certain cancers.

Recent studies suggest that Cis-9-octadecenoic acid may possess anti-inflammatory and antioxidative properties, further solidifying its role in promoting overall health.

Cis-9-octadecenoic acid is a monounsaturated omega-9 fatty acid that is widely recognized for its prevalence in both natural and industrial applications.

With the molecular formula C18H34O2, Cis-9-octadecenoic acid consists of an 18-carbon chain featuring a single cis double bond between the ninth and tenth carbons.

This specific structural configuration imparts a bend in the molecule, reducing Cis-9-octadecenoic acid's tendency to solidify at room temperature, distinguishing it from saturated fatty acids.

Cis-9-octadecenoic acid is abundantly found in various plant-based oils, such as olive oil, where it typically makes up 55–83% of the composition, as well as canola, peanut, and sunflower oils.

Cis-9-octadecenoic acid is also present in animal-derived fats like lard and tallow, although in lower concentrations.

In addition to its widespread occurrence in food sources, Cis-9-octadecenoic acid is extensively used in industrial, cosmetic, and pharmaceutical applications due to its chemical stability and versatile properties.

Cis-9-octadecenoic acid's resistance to oxidative degradation makes it a key ingredient in the formulation of products such as soaps, lubricants, and biodiesel.

In the cosmetic and skincare industry, Cis-9-octadecenoic acid is valued as an effective emollient and a penetration enhancer, promoting the absorption of active ingredients into the skin.

Cis-9-octadecenoic acid's ability to soften and condition skin is why it is often found in moisturizers, ointments, and hair care products.

Nutritionally, Cis-9-octadecenoic acid plays a significant role in human health and is considered beneficial for maintaining heart health.

Research has shown that replacing saturated fats in the diet with monounsaturated fats like Cis-9-octadecenoic acid can help lower LDL ("bad") cholesterol levels while preserving or even increasing HDL ("good") cholesterol.

This is a major factor in Cis-9-octadecenoic acid's association with the Mediterranean diet, which is frequently linked to reduced risks of cardiovascular diseases, stroke, and type 2 diabetes.

Emerging scientific studies also suggest that Cis-9-octadecenoic acid has anti-inflammatory and antioxidant properties, which may contribute to its protective effects against chronic illnesses, including certain types of cancer.

Beyond its biological and nutritional importance, Cis-9-octadecenoic acid serves as a precursor for the biosynthesis of numerous complex lipids, including phospholipids and triglycerides.

These compounds are crucial for maintaining cellular membrane integrity, signaling pathways, and energy storage within the body.

Cis-9-octadecenoic acid's involvement in these processes highlights its essential role in maintaining physiological homeostasis.

Additionally, Cis-9-octadecenoic acid's presence in natural oil-based products has made it a popular choice in environmentally friendly alternatives to synthetic chemicals, particularly in the development of biodegradable lubricants and eco-friendly biofuels.

Overall, Cis-9-octadecenoic acid represents a multifaceted fatty acid with applications and benefits spanning health, nutrition, industry, and sustainability.

Cis-9-octadecenoic acid's ubiquity in nature, combined with its chemical and biological versatility, underscores its importance as both a fundamental component of human nutrition and a valuable resource in various commercial industries.

Uses of Cis-9-Octadecenoic Acid:

Cis-9-octadecenoic acid is a highly versatile compound with a broad range of applications across industries due to its stability, non-toxic nature, and beneficial properties.

In the food industry, Cis-9-octadecenoic acid is a primary component of healthy cooking oils, such as olive and sunflower oil, and contributes to food preservation by enhancing shelf life.

Cis-9-octadecenoic acid's nutritional benefits, particularly in lowering LDL cholesterol and improving HDL cholesterol, make it an essential ingredient in heart-healthy diets like the Mediterranean diet.

In cosmetics and personal care, Cis-9-octadecenoic acid is valued for its emollient properties, softening and moisturizing the skin while promoting the absorption of active ingredients in creams and lotions.

Cis-9-octadecenoic acid is also a key ingredient in hair care products for conditioning and adding shine.

In pharmaceuticals, Cis-9-octadecenoic acid is used as an excipient in drug formulations and topical treatments.

Industrially, Cis-9-octadecenoic acid is a critical component in soap production, biodegradable lubricants, and biodiesel, supporting eco-friendly and sustainable practices.

Additionally, Cis-9-octadecenoic acid is utilized in research as a model compound for lipid metabolism and is investigated for its anti-inflammatory and antioxidant properties.

Cis-9-octadecenoic acid's multifaceted uses across health, industry, and sustainability highlight its indispensable role in modern life.

Cis-9-octadecenoic acid has a wide range of uses across various industries, owing to its chemical stability, non-toxic nature, and versatile properties.

Here are Cis-9-Octadecenoic Acid's primary applications:

Food Industry:

Cooking Oils:

Found in olive oil, sunflower oil, and canola oil, Cis-9-octadecenoic acid is a key component of healthy cooking oils used for frying, baking, and salad dressings.

Food Preservation:

Cis-9-octadecenoic acid's oxidative stability helps extend the shelf life of food products.

Nutritional Benefits:

Cis-9-octadecenoic acid is used in products marketed for heart health due to its ability to lower LDL cholesterol and increase HDL cholesterol.

Cosmetics and Personal Care:

Emollient:

Softens and moisturizes the skin, making it a popular ingredient in creams, lotions, and ointments.

Penetration Enhancer:

Promotes the absorption of active ingredients in skincare products.

Hair Care:

Conditions hair and adds shine in shampoos and conditioners.

Pharmaceuticals:

Drug Formulations:

Cis-9-octadecenoic acid is used as an excipient to enhance drug delivery and stability.

Topical Applications:

Acts as a carrier in medicinal ointments and transdermal patches.

Industrial Applications:

Soap Production:

Cis-9-octadecenoic acid is used in manufacturing soaps and detergents for its lathering and cleansing properties.

Lubricants:

Serves as a component in eco-friendly and biodegradable lubricants.

Biodiesel:

Plays a role in the production of biofuels due to its renewable nature and energy efficiency.

Plastics and Coatings:

Functions as a plasticizer and stabilizer in certain industrial materials.

Environmental Applications:

Eco-Friendly Alternatives:

Incorporated into green chemistry processes for biodegradable and sustainable products.

Biodegradable Surfactants:

Cis-9-octadecenoic acid is used in the production of cleaning agents that break down naturally in the environment.

Research and Biotechnology:

Model Compound:

Cis-9-octadecenoic acid is used in studies on lipid metabolism and membrane structure due to its role in biological systems.

Bioactive Agent:

Investigated for Cis-9-octadecenoic acid's anti-inflammatory and antioxidant properties in biomedical research.

Traditional and Folk Uses:

Skin Remedies:

Applied topically in traditional medicine to treat dry skin, minor wounds, and irritation.

Cooking and Preservation:

Historically used in Mediterranean and other diets for flavor and health benefits.

Features of Cis-9-Octadecenoic Acid:

Monounsaturated Structure:

Contains a single double bond, which enhances its stability and health benefits.

Omega-9 Fatty Acid:

Naturally occurring and essential for various biological processes.

High Oxidative Stability:

Resistant to rancidity, making it suitable for long-lasting products.

Biodegradable:

Environmentally friendly and breaks down naturally.

Versatile Solubility:

Compatible with oils, fats, and emulsifiers, enabling diverse applications.

Non-Toxic:

Safe for use in food, cosmetics, and pharmaceuticals.

Skin-Friendly:

Non-irritating and penetrates skin easily, promoting active ingredient delivery.

Natural Occurrence:

Found in abundance in plant and animal fats, particularly olive oil.

Benefits of Cis-9-Octadecenoic Acid:

Heart Health:

Cis-9-octadecenoic acid helps lower LDL cholesterol and raise HDL cholesterol, reducing cardiovascular risks.

Skin Hydration:

Cis-9-octadecenoic acid acts as an emollient to soften and moisturize the skin.

Nutritional Value:

Provides a healthy source of energy and supports cell membrane integrity.

Eco-Friendly Applications:

Cis-9-octadecenoic acid is used in biodegradable lubricants, biodiesel, and cleaning agents, promoting sustainability.

Long Shelf Life:

High stability enhances the durability of food and cosmetic products.

Improved Product Performance:

Enhances the texture, spreadability, and absorption of cosmetics and pharmaceuticals.

Industrial Utility:

Cis-9-octadecenoic acid offers a renewable and efficient base for soaps, plastics, and coatings.

Health Protection:

Cis-9-octadecenoic acid exhibits anti-inflammatory and antioxidant properties, potentially reducing chronic disease risks.

Occurence of Cis-9-Octadecenoic Acid:

Cis-9-octadecenoic acid is one of the most abundant fatty acids found in nature, occurring widely in both plant-based and animal-derived sources.

Cis-9-octadecenoic acid is a major component of many edible oils, particularly olive oil, where it constitutes 55–83% of the oil’s fatty acid content.

Other plant oils rich in Cis-9-octadecenoic acid include sunflower, canola, peanut, and avocado oil.

In animal-derived fats, Cis-9-octadecenoic acid is present in lard, tallow, and poultry fat, though typically in lower concentrations than in vegetable oils.

Cis-9-octadecenoic acid is also found in various nuts and seeds, such as almonds, macadamia nuts, and sesame seeds.

Beyond food sources, Cis-9-octadecenoic acid occurs in waxes and esters, such as beeswax and lanolin.

In biological systems, Cis-9-octadecenoic acid is synthesized naturally as a key component of cell membranes, where it plays a role in maintaining fluidity and structural integrity.

Cis-9-octadecenoic acid's widespread occurrence in both natural and industrial contexts highlights its versatility and importance.

Production of Cis-9-Octadecenoic Acid:

Cis-9-octadecenoic acid is produced both naturally and industrially.

Naturally, Cis-9-octadecenoic acid is synthesized in plants and animals through the desaturation of stearic acid, a saturated fatty acid.

This process involves the action of stearoyl-CoA desaturase enzymes, which introduce a double bond at the ninth carbon position, forming the monounsaturated structure characteristic of Cis-9-octadecenoic acid.

In commercial oils like olive, sunflower, and canola oil, Cis-9-octadecenoic acid is extracted as a natural component.

Industrially, Cis-9-octadecenoic acid is often separated from animal fats or vegetable oils through hydrolysis or saponification.

These processes break down triglycerides into their constituent fatty acids and glycerol.

After separation, Cis-9-octadecenoic acid is purified via fractional distillation or crystallization to achieve the desired purity levels for various applications.

A growing area of production involves biotechnological methods, where genetically engineered microorganisms, such as yeast or algae, are used to produce Cis-9-octadecenoic acid sustainably.

This approach is particularly valuable for creating high-purity Cis-9-octadecenoic acid for specialized uses in food, pharmaceuticals, and cosmetics.

Overall, Cis-9-octadecenoic acid production leverages both natural sources and innovative technologies to meet the diverse demands of modern industries.

Synthesis of Cis-9-Octadecenoic Acid:

The synthesis of Cis-9-octadecenoic acid can occur naturally in biological systems or artificially in laboratory and industrial settings.

Natural Synthesis:

Cis-9-octadecenoic acid is synthesized in plants, animals, and microorganisms as part of lipid metabolism.

The process begins with stearic acid (a saturated fatty acid), which undergoes desaturation catalyzed by the enzyme stearoyl-CoA desaturase (SCD).

This enzyme introduces a cis double bond at the ninth carbon position of the stearic acid chain, forming Cis-9-octadecenoic acid.

This biosynthetic pathway is essential for producing unsaturated fatty acids that maintain the fluidity and functionality of biological membranes.

Laboratory Synthesis:

In a laboratory setting, Cis-9-octadecenoic acid can be synthesized through chemical or catalytic methods:

Partial Hydrogenation of LinCis-9-octadecenoic acid:

LinCis-9-octadecenoic acid (C18:2) can be selectively hydrogenated to reduce one of its double bonds, converting it into Cis-9-octadecenoic acid (C18:1).

Desaturation of Stearic Acid:

Using chemical catalysts or enzymes, stearic acid can be selectively desaturated to form Cis-9-octadecenoic acid.

Grignard Reaction:

A less common synthetic route involves using carbon chain precursors and Grignard reagents to build an 18-carbon chain with a single cis double bond.

Industrial Synthesis

Industrially, Cis-9-octadecenoic acid is primarily derived from natural triglyceride sources like vegetable oils or animal fats through processes such as:

Hydrolysis or Saponification:

Triglycerides are hydrolyzed with water or reacted with alkali to release free fatty acids, including Cis-9-octadecenoic acid.

Fractional Distillation:

Cis-9-octadecenoic acid is purified from the mixture of fatty acids based on its boiling point or solubility differences.

Biotechnological Methods:

Engineered microorganisms, such as yeast or algae, are employed to biosynthesize Cis-9-octadecenoic acid from simple carbon sources in a sustainable and controlled manner.

Applications of Synthesis:

These synthetic methods produce Cis-9-octadecenoic acid for use in food, cosmetics, pharmaceuticals, and industrial products.

Advances in enzymatic and biotechnological techniques are paving the way for more sustainable and efficient production, especially for high-purity applications.

Handling and Storage of Cis-9-Octadecenoic Acid:

Handling:

Avoid direct contact with skin and eyes.

Use in well-ventilated areas.

Keep away from sources of heat, sparks, or open flames.

Wear appropriate protective equipment (gloves, goggles, and apron).

Storage:

Store in a cool, dry, and well-ventilated area.

Keep containers tightly closed and protect from direct sunlight.

Use corrosion-resistant storage materials (e.g., stainless steel or HDPE).

Avoid exposure to air to prevent oxidation.

Stability and Reactivity of Cis-9-Octadecenoic Acid:

Chemical Stability:

Stable under normal conditions when stored properly.

Conditions to Avoid:

Exposure to heat, light, and air can cause oxidation.

Avoid moisture to prevent hydrolysis.

Incompatible Materials:

Strong oxidizing agents (e.g., peroxides, chlorates).

Strong bases or acids in uncontrolled environments.

Hazardous Decomposition Products:

Carbon monoxide, carbon dioxide, and irritating fumes under fire conditions.

First Aid Measures of Cis-9-Octadecenoic Acid:

Inhalation:

Move to fresh air.

If symptoms persist, seek medical attention.

Skin Contact:

Wash affected area with soap and water.

Seek medical advice if irritation occurs.

Eye Contact:

Rinse thoroughly with water for at least 15 minutes.

Seek medical attention if irritation persists.

Ingestion:

Do not induce vomiting.

Rinse mouth with water and seek medical advice if discomfort occurs.

Firefighting Measures of Cis-9-Octadecenoic Acid:

Suitable Extinguishing Media:

Foam, dry chemical powder, carbon dioxide, or water spray.

Specific Hazards:

May release toxic fumes (e.g., CO, CO₂) when burned.

Combustible at high temperatures.

Protective Equipment for Firefighters:

Wear self-contained breathing apparatus (SCBA) and full protective clothing.

Special Instructions:

Cool exposed containers with water spray to prevent pressure buildup.

Accidental Release Measures of Cis-9-Octadecenoic Acid:

Personal Precautions:

Wear protective equipment (gloves, goggles, and respirator).

Avoid skin and eye contact.

Environmental Precautions:

Prevent spillage from entering drains or waterways.

Contain spill using sand, earth, or other inert materials.

Cleanup Methods:

Absorb spills with non-combustible absorbent materials (e.g., sand, vermiculite).

Place waste in appropriate containers for disposal.

Clean the area with detergent and water.

Exposure Controls/Personal Protective Measures of Cis-9-Octadecenoic Acid:

Engineering Controls:

Ensure adequate ventilation, especially in confined areas.

Use local exhaust systems to minimize exposure.

Personal Protective Equipment (PPE):

Eyes:

Safety goggles or face shield.

Skin:

Chemical-resistant gloves (e.g., nitrile or neoprene).

Respiratory:

Mask or respirator if vapors are present in high concentrations.

Clothing:

Long-sleeved protective clothing.

Hygiene Measures:

Wash hands and face after handling.

Do not eat, drink, or smoke in work areas.

Identifiers of Cis-9-Octadecenoic Acid:

Molecular Formula: C18H34O2

Molar Mass: 282.47 g/mol

CAS Number: 112-80-1

PubChem CID: 445639

SMILES Representation: CCCCCCCC=CCCCCCCCC(=O)O

InChI Key: ZQPPMHVWECSIRJ-KTKRTIGZSA-N

EINECS Number: 204-007-1

UNII (FDA): 2UMI9U37CP

Beilstein Reference: 1728571

Common Name: Cis-9-octadecenoic acid

Chemical Abstracts Service (CAS): 112-80-1

Reaxys Registry Number: 1728571

ChemSpider ID: 393217

KEGG Compound ID: C06424

Molecular Weight: 282.467 g/mol

Omega-9 fatty acid

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-

Canonical SMILES: CCCCCCCC=CCCCCCCCC(=O)O

ChEBI ID: 16196

MeSH Unique ID (NLM): D010016

HS Code: 291619 (for fatty acids, including Cis-9-octadecenoic acid)

ZINC Database ID: ZINC03870991

Properties of Cis-9-Octadecenoic Acid:

Formula: C18H34O2

Molar mass: 282.47 g / mol

Density: 895 kg / m³

Solubility in water: Insoluble

Solubility in ethanol: Solubility

Appearance Form: liquid, clear

Colour: colourless

Melting point/freezing Melting point/range: 13 - 14 °C 

Initial boiling point and 194 - 195 °C at 1,6 hPa 

Flash point > 113 °C - closed cup

Vapour pressure 1 hPa at 176 °C

Relative density 0,89 g/cm3 at 25 °C

Appearance: Colorless to pale yellow liquid

Density: ~0.895 g/cm³ at 25°C

Melting Point: 13–14°C

Boiling Point: ~360°C (decomposes)

Solubility: Insoluble in water; soluble in organic solvents like ethanol and chloroform

Flash Point: >110°C

Refractive Index: 1.461–1.465 (at 20°C)

Acidity (pKa): ~4.75 (carboxylic acid group)

Vapor Pressure: Negligible at room temperature

Specifications of Cis-9-Octadecenoic Acid:

Purity (Cis-9-octadecenoic acid Content): ≥ 65% to ≥ 95%, depending on grade

Acid Value: 198–202 mg KOH/g

Iodine Value: 85–95 g I2/100 g (indicative of unsaturation level)

Saponification Value: 198–202 mg KOH/g

Peroxide Value: ≤ 5 meq/kg (indicates oxidative stability)

Free Fatty Acids (FFA): ≤ 0.5% to ≤ 5% (varies by application)

Moisture Content: ≤ 0.5%

Names of Cis-9-Octadecenoic Acid:

IUPAC Names:

(9Z) -Octadec-9-enoic acid

(9Z) -octadec-9-enoic acid

(Z) -octadec-9-enoic acid

9-Octadecanoic acid

9-Octadecenoic acid (9Z) -

9-Octadecenoic acid, (Z) -

C18H34O2

cis-9-octadecenoic acid

Kyselina olejová

octadec-9-enoic acid

Octadecanoic acid

Olajsav

OLEIC ACID