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9,12-Octadecadienoic acid, (9Z,12Z)- is a naturally occurring polyunsaturated C18 fatty acid commonly known as linoleic acid.
9,12-Octadecadienoic acid, (9Z,12Z)- contains two cis double bonds at carbon positions 9 and 12 and belongs to the omega-6 fatty-acid family.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in food, nutritional, cosmetic, pharmaceutical, coating, polymer, surfactant, analytical, and organic-synthesis applications.
CAS Number: 60-33-3
EC Number: 200-470-9
Molecular Formula: C₁₈H₃₂O₂
Molecular Weight: 280.45 g/mol
SYNONYMS
Linoleic Acid, cis,cis-Linoleic Acid, cis-9,cis-12-Octadecadienoic Acid, cis,cis-9,12-Octadecadienoic Acid, 9-cis,12-cis-Linoleic Acid, 9Z,12Z-Linoleic Acid, all-cis-9,12-Octadecadienoic Acid, (9Z,12Z)-Octadeca-9,12-dienoic Acid, (Z,Z)-Octadeca-9,12-dienoic Acid, (Z,Z)-9,12-Octadecadienoic Acid, 9,12-Octadecadienoic Acid (Z,Z)-, 9,12-Octadecadienoic Acid, cis,cis-, 9,12-Linoleic Acid, cis-Δ9,12-Octadecadienoic Acid, cis-Delta-9,12-Octadecadienoic Acid, Octadecadienoic Acid, cis-9,cis-12-, Linolic Acid, Leinoleic Acid, Telfairic Acid, Linoleic, Linoleate Conjugate Acid, Omega-6 Fatty Acid, ω-6 Fatty Acid, n-6 Fatty Acid, C18:2 Fatty Acid, C18:2 n-6, C18:2 cis-9,cis-12, Fatty Acid 18:2 n-6, Polyunsaturated C18 Fatty Acid, Essential Omega-6 Fatty Acid, Diene Fatty Acid, Nonconjugated Diene Fatty Acid, cis,cis-Octadecadienoic Acid, (9Z,12Z)-9,12-Octadecadienoic Acid, 9-(Z),12-(Z)-Octadecadienoic Acid, Acide Linoléique, Acido Linoleico, Linoleinsäure, Linolsyra, Kwas Linolowy, Linolzuur, Ácido Linoleico, Linoleic Acid 95%, Linoleic Acid 99%, High-Purity Linoleic Acid, Technical Linoleic Acid, Food-Grade Linoleic Acid, Cosmetic-Grade Linoleic Acid, Pharmaceutical-Grade Linoleic Acid, Analytical-Grade Linoleic Acid, Linoleic Acid Analytical Standard, CAS 60-33-3, EC 200-470-9, FEMA 3380, JECFA 332, C₁₈H₃₂O₂, CH₃(CH₂)₄CH=CHCH₂CH=CH(CH₂)₇COOH, OYHQOLUKZRVURQ-HZJYTTRNSA-N, MFCD00004435, CHEBI 17351, Lipid Maps LMFA01030120
APPLICATIONS
9,12-Octadecadienoic acid, (9Z,12Z)- serves as a nutritional fatty-acid ingredient in products designed to supply omega-6 fatty acids.
9,12-Octadecadienoic acid, (9Z,12Z)- supports the preparation of dietary lipid blends in which the proportion of polyunsaturated fatty acids is carefully controlled.
9,12-Octadecadienoic acid, (9Z,12Z)- contributes an essential fatty-acid component that the human body cannot synthesize in sufficient quantity.
9,12-Octadecadienoic acid, (9Z,12Z)- requires food-grade purity, oxidation control, and compliance with the regulations applicable to the finished nutritional product.
9,12-Octadecadienoic acid, (9Z,12Z)- functions as a flavoring agent or flavoring adjuvant in authorized food applications.
9,12-Octadecadienoic acid, (9Z,12Z)- contributes fatty, oily, and background flavor characteristics at appropriately controlled use levels.
9,12-Octadecadienoic acid, (9Z,12Z)- supports flavor systems requiring a long-chain unsaturated fatty-acid component or carrier.
9,12-Octadecadienoic acid, (9Z,12Z)- must satisfy the applicable identity, purity, stability, and permitted-use requirements for food formulations.
9,12-Octadecadienoic acid, (9Z,12Z)- finds application in food-ingredient systems as a lipid-soluble carrier for compatible flavoring or nutritional materials.
9,12-Octadecadienoic acid, (9Z,12Z)- supports distribution of hydrophobic ingredients within oil-based concentrates and emulsified products.
9,12-Octadecadienoic acid, (9Z,12Z)- provides a low-volatility fatty phase capable of retaining suitable lipophilic substances.
9,12-Octadecadienoic acid, (9Z,12Z)- requires emulsification and antioxidant protection when incorporated into water-containing food systems.
9,12-Octadecadienoic acid, (9Z,12Z)- serves as an emollient and skin-conditioning ingredient in cosmetic and personal-care formulations.
9,12-Octadecadienoic acid, (9Z,12Z)- contributes a smooth, lubricious skin feel by forming a thin lipid layer over the treated surface.
9,12-Octadecadienoic acid, (9Z,12Z)- supports creams, lotions, serums, balms, oils, and anhydrous products requiring an unsaturated fatty-acid component.
9,12-Octadecadienoic acid, (9Z,12Z)- should be formulated to minimize irritation, sensitization, oxidation, and undesirable odor development.
9,12-Octadecadienoic acid, (9Z,12Z)- functions as a lipid-replenishing ingredient in dry-skin and barrier-support cosmetic products.
9,12-Octadecadienoic acid, (9Z,12Z)- contributes to the fatty phase of formulations intended to improve softness and flexibility of the skin surface.
9,12-Octadecadienoic acid, (9Z,12Z)- supports delivery of compatible oil-soluble vitamins, antioxidants, fragrances, and botanical extracts.
9,12-Octadecadienoic acid, (9Z,12Z)- requires careful stabilization because oxidation products can alter color, odor, and skin compatibility.
9,12-Octadecadienoic acid, (9Z,12Z)- finds application in hair conditioners, scalp oils, masks, and leave-on hair-care preparations.
9,12-Octadecadienoic acid, (9Z,12Z)- enhances lubrication of hair fibers and contributes to reduced friction during combing.
9,12-Octadecadienoic acid, (9Z,12Z)- supports incorporation of compatible lipophilic conditioning agents into oil phases and emulsions.
9,12-Octadecadienoic acid, (9Z,12Z)- must be balanced to avoid excessive greasiness, oxidation odor, or loss of formulation stability.
9,12-Octadecadienoic acid, (9Z,12Z)- serves as a raw material for producing linoleate soaps and surface-active salts.
9,12-Octadecadienoic acid, (9Z,12Z)- reacts with sodium, potassium, ammonium, and organic amine bases to form corresponding linoleate salts.
9,12-Octadecadienoic acid, (9Z,12Z)- enables adjustment of wetting, emulsification, detergency, lubrication, and dispersing behavior through controlled neutralization.
9,12-Octadecadienoic acid, (9Z,12Z)- requires oxidation and hydrolysis stability to be evaluated in the final surfactant system.
9,12-Octadecadienoic acid, (9Z,12Z)- functions as an intermediate in the production of linoleic-acid esters.
9,12-Octadecadienoic acid, (9Z,12Z)- reacts with monoalcohols, glycols, glycerol, polyglycerols, and other hydroxyl-containing materials.
9,12-Octadecadienoic acid, (9Z,12Z)- enables preparation of esters used as emollients, lubricants, solvents, plasticizing agents, dispersants, and formulation auxiliaries.
9,12-Octadecadienoic acid, (9Z,12Z)- provides unsaturation that can influence viscosity, low-temperature flow, oxidation, and film-forming behavior.
9,12-Octadecadienoic acid, (9Z,12Z)- serves as a starting material for producing linoleamides and related nitrogen-containing derivatives.
9,12-Octadecadienoic acid, (9Z,12Z)- reacts with ammonia or suitable amines to form amides having surfactant, conditioning, lubricating, and rheological functions.
9,12-Octadecadienoic acid, (9Z,12Z)- supports development of fatty amides used in personal care, coatings, adhesives, lubricants, and technical formulations.
9,12-Octadecadienoic acid, (9Z,12Z)- requires reaction conditions that limit oxidation, discoloration, residual amine, and unwanted side products.
9,12-Octadecadienoic acid, (9Z,12Z)- finds application as a fatty-acid modifier in alkyd-resin production.
9,12-Octadecadienoic acid, (9Z,12Z)- introduces unsaturated side chains that participate in oxidative crosslinking during air drying.
9,12-Octadecadienoic acid, (9Z,12Z)- supports coatings with useful film formation, adhesion, flexibility, gloss, hardness, and drying behavior.
9,12-Octadecadienoic acid, (9Z,12Z)- enables development of paints, varnishes, enamels, and coating binders when combined with suitable polyols and polybasic acids.
9,12-Octadecadienoic acid, (9Z,12Z)- functions as an unsaturated modifier in air-drying and baking alkyd coating systems.
9,12-Octadecadienoic acid, (9Z,12Z)- provides double bonds that undergo oxygen-initiated radical reactions and subsequent network formation.
9,12-Octadecadienoic acid, (9Z,12Z)- contributes to film hardness while retaining useful flexibility and adhesion to prepared surfaces.
9,12-Octadecadienoic acid, (9Z,12Z)- supports high-solids and reduced-solvent coating concepts when resin viscosity and curing behavior are properly controlled.
9,12-Octadecadienoic acid, (9Z,12Z)- serves as a modifier in printing-ink vehicles and oxidatively drying binder systems.
9,12-Octadecadienoic acid, (9Z,12Z)- contributes unsaturated fatty groups that promote gradual oxidative setting after application.
9,12-Octadecadienoic acid, (9Z,12Z)- supports pigment wetting and compatibility through its long hydrocarbon chain and carboxylic-acid functionality.
9,12-Octadecadienoic acid, (9Z,12Z)- requires drying rate, yellowing, odor, gloss, and storage stability to be optimized in the completed ink.
9,12-Octadecadienoic acid, (9Z,12Z)- finds application in resin synthesis for wood coatings, metal coatings, decorative paints, and industrial finishes.
9,12-Octadecadienoic acid, (9Z,12Z)- provides a flexible fatty segment that can reduce brittleness in highly crosslinked binder systems.
9,12-Octadecadienoic acid, (9Z,12Z)- promotes oxidative curing through its two nonconjugated carbon–carbon double bonds.
9,12-Octadecadienoic acid, (9Z,12Z)- enables coating developers to adjust oil length, viscosity, hardness, drying, and substrate adhesion.
9,12-Octadecadienoic acid, (9Z,12Z)- serves as a feedstock for producing dimerized fatty acids and oligomeric derivatives.
9,12-Octadecadienoic acid, (9Z,12Z)- undergoes controlled thermal or catalytic reactions through its unsaturated hydrocarbon chain.
9,12-Octadecadienoic acid, (9Z,12Z)- supports production of dimer-acid intermediates used in polyamides, adhesives, sealants, coatings, and specialty resins.
9,12-Octadecadienoic acid, (9Z,12Z)- contributes flexibility, hydrophobicity, chemical resistance, and low-temperature performance to suitable derivatives.
9,12-Octadecadienoic acid, (9Z,12Z)- functions as a precursor for flexible polyester and polyamide materials.
9,12-Octadecadienoic acid, (9Z,12Z)- provides a long aliphatic chain that increases hydrophobic character and segmental mobility.
9,12-Octadecadienoic acid, (9Z,12Z)- supports synthesis of resins used in hot-melt adhesives, reactive adhesives, sealants, and protective coatings.
9,12-Octadecadienoic acid, (9Z,12Z)- enables polymer properties to be adjusted through esterification, amidation, dimerization, and controlled crosslinking.
9,12-Octadecadienoic acid, (9Z,12Z)- serves as a renewable-carbon intermediate in specialty polymer development.
9,12-Octadecadienoic acid, (9Z,12Z)- introduces plant-derived hydrocarbon chains into resins, modifiers, and reactive additives.
9,12-Octadecadienoic acid, (9Z,12Z)- supports partial replacement of wholly petrochemical monomers in selected formulations.
9,12-Octadecadienoic acid, (9Z,12Z)- requires life-cycle, sourcing, purity, and performance data before specific sustainability claims are made.
9,12-Octadecadienoic acid, (9Z,12Z)- functions as a lubricity-enhancing fatty component in specialty lubricant formulations.
9,12-Octadecadienoic acid, (9Z,12Z)- adsorbs through its polar carboxyl group while its hydrocarbon chain contributes a low-shear boundary layer.
9,12-Octadecadienoic acid, (9Z,12Z)- supports metalworking, forming, drawing, rolling, and general industrial lubrication after compatibility testing.
9,12-Octadecadienoic acid, (9Z,12Z)- requires oxidation, corrosion, staining, thermal stability, and seal compatibility to be evaluated.
9,12-Octadecadienoic acid, (9Z,12Z)- finds application as an intermediate for lubricant esters with improved low-temperature flow.
9,12-Octadecadienoic acid, (9Z,12Z)- provides cis double bonds that prevent close molecular packing and reduce crystallization tendency.
9,12-Octadecadienoic acid, (9Z,12Z)- supports preparation of biodegradable or renewable-content lubricant bases and additives.
9,12-Octadecadienoic acid, (9Z,12Z)- requires antioxidant protection because its polyunsaturated chain is more oxidation-sensitive than saturated fatty chains.
9,12-Octadecadienoic acid, (9Z,12Z)- serves as a component or intermediate in corrosion-inhibitor systems for compatible metals.
9,12-Octadecadienoic acid, (9Z,12Z)- provides a carboxylic-acid group capable of interacting with metal surfaces or forming protective metal soaps.
9,12-Octadecadienoic acid, (9Z,12Z)- contributes hydrophobic surface coverage through its long C18 chain.
9,12-Octadecadienoic acid, (9Z,12Z)- requires metal-specific testing because free acidity, oxidation products, and water contamination can also promote corrosion.
9,12-Octadecadienoic acid, (9Z,12Z)- functions as a flotation, dispersing, and surface-modification intermediate in selected mineral-processing systems.
9,12-Octadecadienoic acid, (9Z,12Z)- interacts with mineral or metal surfaces through its carboxyl group.
9,12-Octadecadienoic acid, (9Z,12Z)- contributes hydrophobicity through its unsaturated C18 hydrocarbon chain.
9,12-Octadecadienoic acid, (9Z,12Z)- requires dosage, pH, water hardness, mineral composition, and froth behavior to be optimized.
9,12-Octadecadienoic acid, (9Z,12Z)- serves as a biochemical research standard for studies of omega-6 fatty-acid metabolism.
9,12-Octadecadienoic acid, (9Z,12Z)- supports investigations of fatty-acid uptake, esterification, membrane incorporation, oxidation, and enzymatic conversion.
9,12-Octadecadienoic acid, (9Z,12Z)- enables researchers to examine pathways leading to longer-chain polyunsaturated fatty acids and lipid mediators.
9,12-Octadecadienoic acid, (9Z,12Z)- requires high chemical and stereochemical purity for quantitative biochemical work.
9,12-Octadecadienoic acid, (9Z,12Z)- functions as an analytical reference material in gas chromatography and liquid chromatography.
9,12-Octadecadienoic acid, (9Z,12Z)- supports identification and quantification of fatty acids in foods, oils, biological samples, cosmetics, and industrial products.
9,12-Octadecadienoic acid, (9Z,12Z)- can be converted into methyl or trimethylsilyl derivatives for chromatographic analysis.
9,12-Octadecadienoic acid, (9Z,12Z)- provides characteristic infrared, mass-spectral, and chromatographic profiles for identity confirmation.
9,12-Octadecadienoic acid, (9Z,12Z)- finds application in lipid-oxidation studies as a representative polyunsaturated substrate.
9,12-Octadecadienoic acid, (9Z,12Z)- supports evaluation of antioxidants, radical inhibitors, oxygen barriers, packaging systems, and storage conditions.
9,12-Octadecadienoic acid, (9Z,12Z)- produces measurable oxidation products that can be followed through peroxide, anisidine, chromatographic, or spectroscopic methods.
9,12-Octadecadienoic acid, (9Z,12Z)- enables comparative assessment of oxidative stability in oils, emulsions, foods, cosmetics, and polymers.
9,12-Octadecadienoic acid, (9Z,12Z)- serves as a model fatty acid in membrane, micelle, liposome, and interfacial research.
9,12-Octadecadienoic acid, (9Z,12Z)- provides a hydrophobic chain and an ionizable carboxylic-acid head group.
9,12-Octadecadienoic acid, (9Z,12Z)- supports investigation of pH-dependent aggregation, protein binding, lipid packing, and membrane fluidity.
9,12-Octadecadienoic acid, (9Z,12Z)- requires controlled oxidation and concentration because degradation products can alter experimental results.
9,12-Octadecadienoic acid, (9Z,12Z)- functions as a substrate in enzyme research involving lipoxygenases, desaturases, elongases, oxidases, and esterifying enzymes.
9,12-Octadecadienoic acid, (9Z,12Z)- supports measurement of enzyme activity through substrate depletion or product formation.
9,12-Octadecadienoic acid, (9Z,12Z)- enables preparation of hydroxy, epoxy, oxo, and other functionalized fatty-acid derivatives.
9,12-Octadecadienoic acid, (9Z,12Z)- requires well-defined purity and peroxide content for reproducible enzymatic studies.
9,12-Octadecadienoic acid, (9Z,12Z)- serves as an organic-synthesis intermediate for epoxidized fatty acids and oxirane-containing derivatives.
9,12-Octadecadienoic acid, (9Z,12Z)- provides two double bonds capable of controlled epoxidation.
9,12-Octadecadienoic acid, (9Z,12Z)- supports preparation of reactive intermediates for plasticizers, coatings, lubricants, resins, and crosslinking agents.
9,12-Octadecadienoic acid, (9Z,12Z)- requires reaction selectivity to prevent excessive oxidation, ring opening, polymerization, and color formation.
9,12-Octadecadienoic acid, (9Z,12Z)- finds application as a precursor for hydroxylated, oxidized, conjugated, and functionalized fatty acids.
9,12-Octadecadienoic acid, (9Z,12Z)- enables chemical modification at the carboxyl group or either carbon–carbon double bond.
9,12-Octadecadienoic acid, (9Z,12Z)- supports creation of intermediates with altered polarity, reactivity, viscosity, adhesion, and biological behavior.
9,12-Octadecadienoic acid, (9Z,12Z)- provides a versatile renewable molecular platform for specialty chemical research.
DESCRIPTION
9,12-Octadecadienoic acid, (9Z,12Z)- is the systematic registry-style name for the naturally occurring cis,cis isomer commonly called linoleic acid.
9,12-Octadecadienoic acid, (9Z,12Z)- contains 18 carbon atoms, 32 hydrogen atoms, and two oxygen atoms.
9,12-Octadecadienoic acid, (9Z,12Z)- has a molecular formula of C₁₈H₃₂O₂ and a molecular weight of approximately 280.45 g/mol.
9,12-Octadecadienoic acid, (9Z,12Z)- is identified by CAS Number 60-33-3 and EC Number 200-470-9.
Structurally, 9,12-Octadecadienoic acid, (9Z,12Z)- contains a terminal carboxylic-acid group and a seventeen-carbon hydrocarbon chain.
The two carbon–carbon double bonds are located between carbons 9–10 and 12–13 when counted from the carboxyl carbon.
Both double bonds possess Z or cis geometry.
The first double bond is located at the omega-6 position when counted from the methyl end of the molecule.
The cis double bonds introduce bends into the hydrocarbon chain of 9,12-Octadecadienoic acid, (9Z,12Z)-.
These bends reduce close molecular packing compared with saturated C18 fatty acids.
Reduced packing contributes to the liquid physical state of 9,12-Octadecadienoic acid, (9Z,12Z)- at ordinary room temperature.
The separated nonconjugated double bonds also create a bis-allylic methylene group that is particularly susceptible to oxidation.
9,12-Octadecadienoic acid, (9Z,12Z)- normally appears as a colorless to pale-yellow or straw-colored oily liquid.
Commercial appearance depends on purity, source, oxidation history, storage conditions, and trace impurities.
Fresh high-purity material generally has a mild fatty odor.
Oxidized material may develop stronger rancid, paint-like, aldehydic, or otherwise undesirable odors.
9,12-Octadecadienoic acid, (9Z,12Z)- has a measured fusion temperature near 266.2–266.4 K, corresponding to approximately −7°C.
Published commercial values can vary because purity, isomer composition, oxidation, and analytical method influence the observed freezing or melting behavior.
9,12-Octadecadienoic acid, (9Z,12Z)- has a reduced-pressure boiling point near 502.7 K, or approximately 229.6°C, at about 0.021 bar.
Atmospheric-pressure distillation is generally avoided because prolonged high-temperature exposure can promote decomposition and oxidation.
9,12-Octadecadienoic acid, (9Z,12Z)- has a representative density near 0.90 g/cm³ at room temperature.
9,12-Octadecadienoic acid, (9Z,12Z)- is lighter than water and forms a separate oily phase when added without emulsification.
9,12-Octadecadienoic acid, (9Z,12Z)- is essentially insoluble in water but soluble in many organic solvents.
Compatible solvents can include ethanol, ether, acetone, hydrocarbons, aromatic solvents, dimethyl sulfoxide, and dimethylformamide.
9,12-Octadecadienoic acid, (9Z,12Z)- has a calculated XLogP value near 6.8, reflecting strong preference for organic and lipid phases over water.
The molecule contains one hydrogen-bond donor and two hydrogen-bond acceptors.
Its carboxyl group provides limited polarity and acid functionality, while the long hydrocarbon chain dominates bulk solubility behavior.
Neutralization to form linoleate salts substantially changes water dispersibility and interfacial behavior.
9,12-Octadecadienoic acid, (9Z,12Z)- has a theoretical acid value of approximately 200 mg KOH/g when chemically pure.
Commercial acid values can differ because of assay, water, neutral materials, oxidation products, and other fatty acids.
The iodine value is comparatively high because the molecule contains two carbon–carbon double bonds.
Acid value, iodine value, peroxide value, and chromatographic purity are important indicators of quality and storage condition.
9,12-Octadecadienoic acid, (9Z,12Z)- is commonly obtained from linoleic-acid-rich vegetable oils and other natural lipid feedstocks.
Production generally begins with hydrolysis or splitting of triglycerides to release free fatty acids.
The resulting fatty-acid mixture can be purified through distillation, crystallization, complexation, chromatography, or related separation processes.
High-purity production must control positional isomers, trans isomers, oleic acid, saturated fatty acids, linolenic acid, moisture, and oxidation products.
9,12-Octadecadienoic acid, (9Z,12Z)- is more oxidation-sensitive than oleic acid and saturated C18 fatty acids.
Oxygen exposure can initiate formation of lipid hydroperoxides at allylic and bis-allylic positions.
Hydroperoxides can decompose into aldehydes, ketones, acids, epoxides, and polymeric products.
These reactions can increase color, viscosity, acidity, odor, and instability during prolonged storage.
Light, elevated temperature, oxygen, trace metals, and radical-forming contaminants accelerate deterioration of 9,12-Octadecadienoic acid, (9Z,12Z)-.
Antioxidants, metal chelators, opaque packaging, low temperatures, and inert-gas blanketing can improve storage stability.
Repeated opening of containers increases exposure to oxygen and atmospheric moisture.
Partially used containers should therefore be tightly resealed with minimal headspace whenever practicable.
9,12-Octadecadienoic acid, (9Z,12Z)- undergoes esterification through its carboxylic-acid group.
9,12-Octadecadienoic acid, (9Z,12Z)- undergoes amidation with ammonia or amines under suitable reaction conditions.
Its double bonds permit oxidation, epoxidation, hydrogenation, conjugation, addition, polymerization, and crosslinking reactions.
This combined carboxyl and diene functionality accounts for its broad value as a chemical intermediate.
9,12-Octadecadienoic acid, (9Z,12Z)- can undergo oxidative curing when incorporated into alkyd resins and related binders.
Atmospheric oxygen reacts with unsaturated fatty chains to form hydroperoxides and radical intermediates.
The radical intermediates create carbon–carbon and carbon–oxygen crosslinks within the developing film.
The resulting network provides gradual increases in hardness, solvent resistance, and mechanical integrity.
9,12-Octadecadienoic acid, (9Z,12Z)- is combustible but has low volatility at ordinary ambient temperatures.
Representative commercial data place its flash point above approximately 110°C.
Fine mist, contaminated absorbent, heated material, and oxidation residues can present greater fire risk than an undisturbed bulk liquid.
Severe heating or combustion may produce carbon monoxide, carbon dioxide, smoke, aldehydes, and irritating organic decomposition products.
9,12-Octadecadienoic acid, (9Z,12Z)- is not uniformly assigned a severe hazard classification across available regulatory and supplier records.
Concentrated material can nevertheless irritate the eyes, skin, or respiratory tract, particularly as a heated mist or aerosol.
Oxidized material and impurities may produce a different irritation or sensitization profile from freshly purified material.
The current grade-specific Safety Data Sheet should therefore determine protective equipment, labeling, transport, and emergency procedures.
9,12-Octadecadienoic acid, (9Z,12Z)- quality control commonly includes appearance, odor, assay, fatty-acid composition, acid value, iodine value, peroxide value, water, color, density, and refractive index.
High-purity analytical grades may additionally require limits for positional isomers, trans isomers, residual solvents, and individual oxidation products.
Food, cosmetic, pharmaceutical, technical, and analytical grades are not automatically interchangeable.
The current specification and certificate of analysis should be reviewed before each regulated or sensitive application.
PROPERTIES
Chemical Name: 9,12-Octadecadienoic acid, (9Z,12Z)-
Common Name: Linoleic acid
IUPAC Name: (9Z,12Z)-Octadeca-9,12-dienoic acid
CAS Number: 60-33-3
EC Number: 200-470-9
PubChem CID: 5280450
JECFA Number: 332
FEMA Number: 3380
Molecular Formula: C₁₈H₃₂O₂
Condensed Structural Formula: CH₃(CH₂)₄CH=CHCH₂CH=CH(CH₂)₇COOH
Molecular Weight: 280.45 g/mol
Exact Mass: 280.24023 Da
Chemical Family: Polyunsaturated fatty acids
Fatty-Acid Classification: C18:2 n-6
Omega Classification: Omega-6
Double-Bond Positions: Carbon 9 and carbon 12
Double-Bond Geometry: Z,Z or cis,cis
Number of Double Bonds: 2
Conjugation: Nonconjugated
Functional Group: Carboxylic acid
Physical State: Oily liquid
Appearance: Colorless to pale-yellow or straw-colored liquid
Odor: Mild fatty odor when fresh
Melting or Fusion Point: Approximately −7°C
Reduced-Pressure Boiling Point: Approximately 229.6°C at 0.021 bar
Representative Density: Approximately 0.90–0.902 g/cm³
Water Solubility: Essentially insoluble
Organic-Solvent Solubility: Soluble in many alcohols, ethers, ketones, hydrocarbons, aromatic solvents, and polar aprotic solvents
XLogP: Approximately 6.8
Hydrogen-Bond Donor Count: 1
Hydrogen-Bond Acceptor Count: 2
Topological Polar Surface Area: Approximately 37.3 Ų
Representative Flash Point: Greater than approximately 110°C
Volatility: Low at ordinary ambient temperature
Theoretical Acid Value: Approximately 200 mg KOH/g
Iodine Value: High because of two carbon–carbon double bonds
Primary Functions: Nutritional fatty acid, flavoring adjuvant, emollient, chemical intermediate, resin modifier, lubricant intermediate, and analytical standard
Primary Applications: Food, nutritional products, cosmetics, personal care, pharmaceuticals, coatings, alkyd resins, inks, lubricants, surfactants, polymers, and laboratory research
Oxidation Stability: Sensitive to oxygen, heat, light, radicals, and trace metals
Combustibility: Combustible organic liquid
Chemical Stability: Stable when protected from oxidation and incompatible materials
Incompatible Materials: Strong oxidizing agents, strong bases, reactive metals, and radical-forming contaminants
Hazardous Decomposition Products: Carbon oxides, smoke, aldehydes, ketones, short-chain acids, and irritating organic fumes
Recommended Storage: Cool, dry, dark, and well-ventilated conditions in tightly closed containers
Preferred Storage Atmosphere: Air exposure minimized; inert-gas blanketing may be used for sensitive or high-purity grades
Current Data Requirement: Confirm grade-specific specifications, hazard classification, transport status, and shelf life from the current technical and safety documentation.
FIRST AID
Inhalation:
Move the affected person to fresh air.
Keep the person at rest in a position comfortable for breathing.
Avoid further exposure to 9,12-Octadecadienoic acid, (9Z,12Z)- mist, aerosol, vapor, or thermal-decomposition fumes.
Obtain medical attention if coughing, throat irritation, headache, nausea, dizziness, or breathing discomfort develops or persists.
Skin Contact:
Remove contaminated clothing and footwear.
Wash the affected skin thoroughly with soap and plenty of water.
Continue rinsing if redness, irritation, itching, or discomfort is present.
Obtain medical advice if symptoms persist or extensive exposure has occurred.
Wash contaminated clothing thoroughly before reuse.
Eye Contact:
Rinse the eyes immediately with plenty of clean, gently flowing water.
Hold the eyelids open to ensure complete irrigation.
Remove contact lenses when present and easy to do, then continue rinsing.
Continue rinsing for at least 15 minutes.
Obtain medical attention if pain, redness, tearing, blurred vision, or irritation persists.
Ingestion:
Rinse the mouth thoroughly with water.
Do not induce vomiting unless directed by qualified medical personnel.
Never give anything by mouth to an unconscious or convulsing person.
Obtain medical advice if a significant quantity has been swallowed or symptoms develop.
Provide the current Safety Data Sheet to medical personnel.
Note to Physicians:
No substance-specific antidote should be assumed.
Provide supportive care and treat according to the patient’s symptoms and clinical condition.
Assess the eyes, skin, respiratory tract, and gastrointestinal system following significant exposure.
Consider the possible presence of oxidation products, solvents, or other fatty acids when exposure involved technical-grade material.
Use the current grade-specific Safety Data Sheet as the primary medical reference.
HANDLING AND STORAGE
Handling:
Handle 9,12-Octadecadienoic acid, (9Z,12Z)- in accordance with good industrial hygiene and chemical-safety practices.
Review the current technical specification and Safety Data Sheet before opening or processing the material.
Avoid unnecessary contact with the skin, eyes, and clothing.
Do not breathe aerosol, mist, vapor, or fumes generated during heating or spraying.
Use closed or low-splash transfer systems wherever reasonably practicable.
Use clean, dry, and chemically compatible equipment for pumping, weighing, sampling, and transfer.
Minimize contact with air during prolonged processing.
Avoid contamination with metals, oxidants, bases, acids, water, and radical-forming substances.
Wash the hands, face, and exposed skin thoroughly after handling.
Do not eat, drink, or smoke in areas where 9,12-Octadecadienoic acid, (9Z,12Z)- is processed.
Keep containers tightly closed when the material is not being sampled or transferred.
Ventilation:
Provide adequate general ventilation in storage and processing areas.
Use local exhaust ventilation near heated vessels, mixers, filling points, spray equipment, and sampling stations.
Control mist and vapor at the source rather than allowing them to spread through the workplace.
Provide additional ventilation when 9,12-Octadecadienoic acid, (9Z,12Z)- is heated, atomized, or handled in confined spaces.
Use suitable respiratory protection when engineering controls cannot adequately limit exposure.
Select respiratory equipment through a documented workplace exposure assessment.
Ensure that ventilation and exhaust systems comply with occupational and environmental requirements.
Storage:
Store 9,12-Octadecadienoic acid, (9Z,12Z)- in its original or another chemically compatible, tightly closed container.
Keep the material in a cool, dry, dark, and adequately ventilated location.
Protect 9,12-Octadecadienoic acid, (9Z,12Z)- from direct sunlight, excessive heat, air, moisture, and physical damage.
Keep 9,12-Octadecadienoic acid, (9Z,12Z)- separated from strong oxidizing agents, strong bases, and incompatible chemicals.
Minimize container headspace and atmospheric exposure for oxidation-sensitive grades.
Use inert-gas blanketing where required by the grade specification or quality-control procedure.
Prevent dirt, rust, water, processing residues, and reactive chemicals from entering opened containers.
Carefully reseal partially used containers immediately after sampling or transfer.
Use first-in, first-out stock rotation within the applicable shelf life.
Inspect stored material for discoloration, rancid odor, increased viscosity, sediment, or elevated peroxide value before use.
Spill and Leak Procedures:
Restrict access to the affected area and remove unnecessary personnel.
Eliminate ignition sources when this can be done safely.
Provide effective ventilation before beginning spill recovery.
Wear suitable gloves, protective clothing, eye protection, and respiratory protection as required.
Stop the source of the leak only when this can be done without personal risk.
Prevent 9,12-Octadecadienoic acid, (9Z,12Z)- from entering drains, sewers, soil, groundwater, or surface water.
Recover pumpable liquid into suitable and correctly labeled containers whenever practicable.
Contain remaining material with sand, earth, vermiculite, or another compatible inert absorbent.
Collect recovered material and contaminated absorbent in tightly closed and correctly labeled waste containers.
Clean the affected surface thoroughly because residual fatty acid can create a severe slipping hazard.
Prevent contaminated wash water from entering uncontrolled drainage systems.
Dispose of recovered material and cleaning residues through an authorized waste-management route.
Handling Precautions:
Wear chemical-resistant gloves selected from documented compatibility and permeation data.
Use safety glasses with side protection or tightly fitting chemical goggles.
Wear a face shield in addition to goggles where splashing is reasonably foreseeable.
Use protective clothing and footwear capable of limiting repeated skin contact.
Provide accessible eyewash and emergency-shower equipment near major handling areas.
Inspect pumps, hoses, valves, seals, gaskets, tanks, and transfer connections before use.
Use equipment compatible with unsaturated fatty acids and the intended processing temperature.
Avoid copper, iron contamination, and other materials that can accelerate oxidation where product quality is critical.
Do not use open flames or uncontrolled direct heating to reduce viscosity.
Keep heated material, packaging, and contaminated absorbents away from ignition sources.
Monitor peroxide value, color, odor, and viscosity during prolonged storage of sensitive grades.
Review the current technical specification, Safety Data Sheet, certificate of analysis, and applicable regulatory requirements before production, transportation, storage, formulation, cleanup, or disposal.
