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9,12-Octadecadienoic acid, (9Z,12Z)- is the systematic chemical name for linoleic acid, an eighteen-carbon polyunsaturated omega-6 fatty acid containing two cis double bonds.
9,12-Octadecadienoic acid, (9Z,12Z)- occurs naturally in many vegetable oils, seeds, plant lipids, foods, biological membranes, and metabolic systems.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in food, nutrition, cosmetics, personal care, pharmaceutical research, analytical chemistry, specialty lubricants, metalworking fluids, coatings, adhesives, and fatty-acid derivative manufacture.
CAS Number: 60-33-3
EC Number: 200-470-9
Molecular Formula: C18H32O2
Molecular Weight: 280.45 g/mol
Synonyms: 9,12-Octadecadienoic acid, (9Z,12Z)-, Linoleic Acid, cis,cis-Linoleic Acid, All-cis-9,12-Octadecadienoic Acid, cis-9,cis-12-Octadecadienoic Acid, 9-cis,12-cis-Octadecadienoic Acid, (9Z,12Z)-Octadeca-9,12-dienoic Acid, (9Z,12Z)-9,12-Octadecadienoic Acid, (Z,Z)-9,12-Octadecadienoic Acid, (Z,Z)-Octadeca-9,12-dienoic Acid, cis-Δ9,12-Octadecadienoic Acid, Delta-9,12-Linoleic Acid, C18:2 n-6, C18:2 Omega-6, Omega-6 Linoleic Acid, Linolic Acid, Telfairic Acid, Vitamin F Component, Essential Fatty Acid, Polyunsaturated Fatty Acid, PUFA, Linoleate Precursor, JECFA 332, FEMA 3380, CAS 60-33-3, EC 200-470-9, PubChem CID 5280450, ChEBI 17351, UNII 9KJL21T0QJ, Lipid Maps LMFA01030120
APPLICATIONS
9,12-Octadecadienoic acid, (9Z,12Z)- is used as a food ingredient under applicable purity and good-manufacturing-practice requirements.
9,12-Octadecadienoic acid, (9Z,12Z)- is used as a nutrient supplement in food formulations.
9,12-Octadecadienoic acid, (9Z,12Z)- is used as a flavoring agent or flavoring adjuvant.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in food only at levels appropriate to the intended technical effect.
9,12-Octadecadienoic acid, (9Z,12Z)- is used to provide omega-6 fatty-acid content in nutritional formulations.
9,12-Octadecadienoic acid, (9Z,12Z)- is used as an essential-fatty-acid component in appropriate dietary products.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in adult-nutrition products after oxidative stability has been established.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in infant formula only under the applicable compositional and regulatory requirements.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in edible-oil and lipid formulations.
9,12-Octadecadienoic acid, (9Z,12Z)- is used to standardize the fatty-acid profile of selected food oils.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in nutritional-oil blends containing omega-6 fatty acids.
9,12-Octadecadienoic acid, (9Z,12Z)- is used after peroxide value, anisidine value, flavor, and storage stability have been tested.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in encapsulated lipid ingredients.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in spray-dried or microencapsulated oil preparations.
9,12-Octadecadienoic acid, (9Z,12Z)- is used with antioxidant and oxygen-barrier systems.
9,12-Octadecadienoic acid, (9Z,12Z)- is used after release, oxidation, and shelf-life testing.
9,12-Octadecadienoic acid, (9Z,12Z)- is used as a reference fatty acid in nutrition research.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in studies of omega-6 fatty-acid metabolism.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in investigations of membrane-lipid composition.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in studies involving prostaglandin and eicosanoid biosynthetic pathways.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in pharmaceutical and biomedical research.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in lipid-metabolism experiments.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in cell-culture and biochemical studies requiring a defined omega-6 fatty acid.
9,12-Octadecadienoic acid, (9Z,12Z)- is used at a purity and concentration suitable for the experimental method.
9,12-Octadecadienoic acid, (9Z,12Z)- is used as an analytical reference standard.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in gas-chromatography fatty-acid profiling.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in liquid-chromatography and mass-spectrometry method development.
9,12-Octadecadienoic acid, (9Z,12Z)- is used to identify and quantify linoleic acid in oils, foods, tissues, and biological samples.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in fatty-acid methyl-ester analysis.
9,12-Octadecadienoic acid, (9Z,12Z)- is used to prepare methyl linoleate standards.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in comparative studies of cis and trans fatty-acid isomers.
9,12-Octadecadienoic acid, (9Z,12Z)- is used to distinguish natural cis,cis linoleic acid from linoelaidic and mixed-trans isomers.
9,12-Octadecadienoic acid, (9Z,12Z)- is used as an emollient in cosmetic formulations.
9,12-Octadecadienoic acid, (9Z,12Z)- is used to improve softness and flexibility of the skin surface.
9,12-Octadecadienoic acid, (9Z,12Z)- is used to reduce the dry or rough feel of cosmetic products.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in products formulated to be non-irritating and non-sensitizing.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in facial creams.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in body lotions.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in hand creams and moisturizing emulsions.
9,12-Octadecadienoic acid, (9Z,12Z)- is used after emulsion stability, odor, color, and oxidation have been evaluated.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in facial serums and oil concentrates.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in dry-skin and barrier-support cosmetic products.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in night creams and facial oils.
9,12-Octadecadienoic acid, (9Z,12Z)- is used at levels supported by finished-product safety testing.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in lip-care products.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in lip balms, lip oils, and conditioning lip formulations.
9,12-Octadecadienoic acid, (9Z,12Z)- is used to provide emollience and spreadability.
9,12-Octadecadienoic acid, (9Z,12Z)- is used after flavor, odor, rancidity, and packaging compatibility have been assessed.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in body oils.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in massage-oil formulations.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in bath oils and oil-serum products.
9,12-Octadecadienoic acid, (9Z,12Z)- is used with suitable antioxidants to limit oxidative deterioration.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in facial-cleansing oils.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in cleansing balms.
9,12-Octadecadienoic acid, (9Z,12Z)- is used to dissolve oily makeup and sebum-compatible soils.
9,12-Octadecadienoic acid, (9Z,12Z)- is used after surfactant, rinse-feel, and oxidation testing.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in soaps and cleansing bars.
9,12-Octadecadienoic acid, (9Z,12Z)- is neutralized to form sodium, potassium, ammonium, or amine linoleates.
9,12-Octadecadienoic acid, (9Z,12Z)- is used to modify lather, cleansing, and conditioning properties.
9,12-Octadecadienoic acid, (9Z,12Z)- is used after product stability and odor development have been evaluated.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in body washes and shower products.
9,12-Octadecadienoic acid, (9Z,12Z)- is used as an emollient lipid in surfactant systems.
9,12-Octadecadienoic acid, (9Z,12Z)- is used to reduce the perception of dryness after cleansing.
9,12-Octadecadienoic acid, (9Z,12Z)- is used after solubilization and phase-stability testing.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in shampoos.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in hair conditioners.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in hair masks and scalp-treatment formulations.
9,12-Octadecadienoic acid, (9Z,12Z)- is used to provide lipid conditioning and improved hair feel.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in leave-in hair treatments.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in hair oils and anti-frizz products.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in products for dry, chemically treated, or textured hair.
9,12-Octadecadienoic acid, (9Z,12Z)- is used after deposition, oxidation, and sensory performance have been measured.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in color-cosmetic products.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in foundations, concealers, blushes, and cream makeup.
9,12-Octadecadienoic acid, (9Z,12Z)- is used to improve pigment wetting and product spread.
9,12-Octadecadienoic acid, (9Z,12Z)- is used after color, odor, and long-term stability have been confirmed.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in nail and cuticle-care products.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in cuticle oils and nail-conditioning formulations.
9,12-Octadecadienoic acid, (9Z,12Z)- is used to provide an emollient film.
9,12-Octadecadienoic acid, (9Z,12Z)- is used after compatibility with fragrances, antioxidants, and packaging has been tested.
9,12-Octadecadienoic acid, (9Z,12Z)- is used as a chemical intermediate.
9,12-Octadecadienoic acid, (9Z,12Z)- is used to manufacture linoleate salts.
9,12-Octadecadienoic acid, (9Z,12Z)- is used to manufacture linoleate esters and amides.
9,12-Octadecadienoic acid, (9Z,12Z)- is used to manufacture specialty surfactants, emulsifiers, and functional lipid derivatives.
9,12-Octadecadienoic acid, (9Z,12Z)- is used to produce methyl linoleate.
9,12-Octadecadienoic acid, (9Z,12Z)- is used to produce ethyl linoleate.
9,12-Octadecadienoic acid, (9Z,12Z)- is used to produce glycerol and polyol linoleate esters.
9,12-Octadecadienoic acid, (9Z,12Z)- is used after ester purity, residual acidity, and oxidation stability have been specified.
9,12-Octadecadienoic acid, (9Z,12Z)- is used to produce metal linoleate salts.
9,12-Octadecadienoic acid, (9Z,12Z)- is used to produce calcium, zinc, potassium, and sodium linoleates.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in derivative manufacture for coatings, lubricants, soaps, and specialty formulations.
9,12-Octadecadienoic acid, (9Z,12Z)- is used only after the intended salt composition and regulatory status have been verified.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in alkyd-resin and coating research.
9,12-Octadecadienoic acid, (9Z,12Z)- is used as an unsaturated fatty-acid component in oxidative-curing resin systems.
9,12-Octadecadienoic acid, (9Z,12Z)- is used to introduce flexible hydrophobic chains and reactive double bonds.
9,12-Octadecadienoic acid, (9Z,12Z)- is used after drying rate, yellowing, hardness, and film durability have been evaluated.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in paint and arts-and-crafts product formulations.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in specialty oils, binders, and fatty-acid-derived coating components.
9,12-Octadecadienoic acid, (9Z,12Z)- is used where oxidative reactivity contributes to film formation.
9,12-Octadecadienoic acid, (9Z,12Z)- is used after storage stability and spontaneous-heating risks have been assessed.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in adhesive and sealant development.
9,12-Octadecadienoic acid, (9Z,12Z)- is used as a fatty-acid intermediate in selected construction-adhesive systems.
9,12-Octadecadienoic acid, (9Z,12Z)- is used to modify flexibility, hydrophobicity, and substrate wetting.
9,12-Octadecadienoic acid, (9Z,12Z)- is used after bond strength, aging, and migration testing.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in metalworking-fluid formulations.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in lubricity additives and emulsifier intermediates.
9,12-Octadecadienoic acid, (9Z,12Z)- is used to improve boundary lubrication in suitable systems.
9,12-Octadecadienoic acid, (9Z,12Z)- is used after corrosion, microbial stability, foaming, and emulsion testing.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in specialty lubricant-esters.
9,12-Octadecadienoic acid, (9Z,12Z)- is used to introduce renewable fatty-acid content into lubricant molecules.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in formulations requiring low-temperature fluidity and surface affinity.
9,12-Octadecadienoic acid, (9Z,12Z)- is used after oxidation resistance and thermal stability have been improved appropriately.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in epoxidation research.
9,12-Octadecadienoic acid, (9Z,12Z)- is used to manufacture epoxidized fatty-acid derivatives.
9,12-Octadecadienoic acid, (9Z,12Z)- is used to introduce oxirane functionality through reactions at its carbon-carbon double bonds.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in derivative development for plasticizers, stabilizers, coatings, and reactive intermediates.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in dimer-acid and polymer-intermediate research.
9,12-Octadecadienoic acid, (9Z,12Z)- is used as an unsaturated feedstock for oligomerization and functionalization.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in the development of polyamide, polyester, and resin intermediates.
9,12-Octadecadienoic acid, (9Z,12Z)- is used after molecular-weight distribution and residual monomer have been controlled.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in oxidation and antioxidant research.
9,12-Octadecadienoic acid, (9Z,12Z)- is used as a model polyunsaturated lipid in lipid-peroxidation experiments.
9,12-Octadecadienoic acid, (9Z,12Z)- is used to evaluate antioxidant performance.
9,12-Octadecadienoic acid, (9Z,12Z)- is used to study hydroperoxide, aldehyde, and secondary oxidation-product formation.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in membrane and liposome research.
9,12-Octadecadienoic acid, (9Z,12Z)- is used to prepare phospholipid and triglyceride model systems.
9,12-Octadecadienoic acid, (9Z,12Z)- is used to examine the effects of unsaturation on membrane fluidity.
9,12-Octadecadienoic acid, (9Z,12Z)- is used under controlled oxygen, temperature, and antioxidant conditions.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in commercial manufacturing after identity and purity testing.
9,12-Octadecadienoic acid, (9Z,12Z)- is used after acid value, iodine value, water, color, and peroxide value have been reviewed.
9,12-Octadecadienoic acid, (9Z,12Z)- is used after cis-isomer content and other fatty-acid impurities have been determined.
9,12-Octadecadienoic acid, (9Z,12Z)- is used according to the current specification, certificate of analysis, and safety data sheet.
DESCRIPTION
9,12-Octadecadienoic acid, (9Z,12Z)- is commonly known as linoleic acid.
9,12-Octadecadienoic acid, (9Z,12Z)- is an eighteen-carbon straight-chain carboxylic acid.
9,12-Octadecadienoic acid, (9Z,12Z)- contains two carbon-carbon double bonds.
9,12-Octadecadienoic acid, (9Z,12Z)- has cis geometry at both double bonds.
9,12-Octadecadienoic acid, (9Z,12Z)- has double bonds between carbons 9 and 10 and between carbons 12 and 13.
9,12-Octadecadienoic acid, (9Z,12Z)- is described by lipid shorthand as C18:2 n-6.
9,12-Octadecadienoic acid, (9Z,12Z)- belongs to the omega-6 fatty-acid family.
9,12-Octadecadienoic acid, (9Z,12Z)- is classified as a polyunsaturated fatty acid.
9,12-Octadecadienoic acid, (9Z,12Z)- has the molecular formula C18H32O2.
9,12-Octadecadienoic acid, (9Z,12Z)- has a molecular weight of approximately 280.45 g/mol.
9,12-Octadecadienoic acid, (9Z,12Z)- has CAS number 60-33-3.
9,12-Octadecadienoic acid, (9Z,12Z)- has EC number 200-470-9.
9,12-Octadecadienoic acid, (9Z,12Z)- has PubChem CID 5280450.
9,12-Octadecadienoic acid, (9Z,12Z)- has the InChIKey OYHQOLUKZRVURQ-HZJYTTRNSA-N.
9,12-Octadecadienoic acid, (9Z,12Z)- has one carboxylic-acid functional group.
9,12-Octadecadienoic acid, (9Z,12Z)- has a long hydrophobic hydrocarbon chain.
9,12-Octadecadienoic acid, (9Z,12Z)- is generally a colorless to pale-yellow or straw-colored oily liquid.
9,12-Octadecadienoic acid, (9Z,12Z)- may develop a darker color as oxidation progresses.
9,12-Octadecadienoic acid, (9Z,12Z)- has a mild fatty odor when fresh.
9,12-Octadecadienoic acid, (9Z,12Z)- can develop rancid or paint-like odors after oxidative deterioration.
9,12-Octadecadienoic acid, (9Z,12Z)- is practically insoluble in water.
9,12-Octadecadienoic acid, (9Z,12Z)- is soluble in alcohol, ether, oils, and many organic fat solvents.
9,12-Octadecadienoic acid, (9Z,12Z)- is strongly lipophilic.
9,12-Octadecadienoic acid, (9Z,12Z)- has a calculated XLogP value near 6.8.
9,12-Octadecadienoic acid, (9Z,12Z)- has a representative melting point near −5°C.
9,12-Octadecadienoic acid, (9Z,12Z)- remains liquid under ordinary room-temperature conditions.
9,12-Octadecadienoic acid, (9Z,12Z)- has a representative boiling point near 229°C at approximately 16 mmHg.
9,12-Octadecadienoic acid, (9Z,12Z)- can decompose or oxidize if strongly heated in air.
9,12-Octadecadienoic acid, (9Z,12Z)- has a representative specific gravity of approximately 0.898–0.904.
9,12-Octadecadienoic acid, (9Z,12Z)- has a representative refractive index of approximately 1.469–1.473.
9,12-Octadecadienoic acid, (9Z,12Z)- has a representative iodine value of approximately 145–160 for the cited flavoring specification.
9,12-Octadecadienoic acid, (9Z,12Z)- physical values vary with purity, temperature, oxidation, and fatty-acid composition.
9,12-Octadecadienoic acid, (9Z,12Z)- is an essential fatty acid in mammalian nutrition.
9,12-Octadecadienoic acid, (9Z,12Z)- contributes to biological membrane lipid composition.
9,12-Octadecadienoic acid, (9Z,12Z)- serves as a biochemical precursor within omega-6 metabolic pathways.
9,12-Octadecadienoic acid, (9Z,12Z)- should not be presented as providing a guaranteed therapeutic effect in isolated commercial products.
9,12-Octadecadienoic acid, (9Z,12Z)- occurs in many plant and seed oils.
9,12-Octadecadienoic acid, (9Z,12Z)- may be isolated from edible fats and oils by hydrolysis, saponification, or fat-splitting processes.
9,12-Octadecadienoic acid, (9Z,12Z)- commercial grades may be produced through fractional separation and purification of fatty-acid mixtures.
9,12-Octadecadienoic acid, (9Z,12Z)- natural-source claims require supplier documentation and fatty-acid-composition data.
9,12-Octadecadienoic acid, (9Z,12Z)- is more oxidation sensitive than oleic acid because it contains two double bonds.
9,12-Octadecadienoic acid, (9Z,12Z)- can form lipid hydroperoxides during exposure to oxygen.
9,12-Octadecadienoic acid, (9Z,12Z)- oxidation is accelerated by heat, light, air, and trace transition metals.
9,12-Octadecadienoic acid, (9Z,12Z)- oxidation can be slowed through antioxidants, chelating agents, inert gas, and protective packaging.
9,12-Octadecadienoic acid, (9Z,12Z)- can undergo autoxidation during prolonged storage.
9,12-Octadecadienoic acid, (9Z,12Z)- can generate aldehydes, ketones, acids, and polymeric oxidation products.
9,12-Octadecadienoic acid, (9Z,12Z)- oxidation can change odor, color, viscosity, and biological performance.
9,12-Octadecadienoic acid, (9Z,12Z)- should therefore be monitored using appropriate peroxide and secondary-oxidation tests.
9,12-Octadecadienoic acid, (9Z,12Z)- can react through its carboxylic-acid group.
9,12-Octadecadienoic acid, (9Z,12Z)- can form salts through neutralization.
9,12-Octadecadienoic acid, (9Z,12Z)- can form esters through reaction with alcohols and polyols.
9,12-Octadecadienoic acid, (9Z,12Z)- can form amides through reaction with suitable nitrogen-containing reagents.
9,12-Octadecadienoic acid, (9Z,12Z)- can react at either carbon-carbon double bond.
9,12-Octadecadienoic acid, (9Z,12Z)- can undergo hydrogenation, epoxidation, oxidation, polymerization, and addition reactions.
9,12-Octadecadienoic acid, (9Z,12Z)- can be converted into functional intermediates for coatings, lubricants, polymers, and surfactants.
9,12-Octadecadienoic acid, (9Z,12Z)- derivative properties depend on reaction selectivity and residual unsaturation.
9,12-Octadecadienoic acid, (9Z,12Z)- differs from linoelaidic acid.
9,12-Octadecadienoic acid, (9Z,12Z)- contains cis,cis double bonds.
9,12-Octadecadienoic acid, (9Z,12Z)- linoelaidic counterparts contain trans geometry.
9,12-Octadecadienoic acid, (9Z,12Z)- cis geometry produces a lower melting point and a more flexible molecular chain.
9,12-Octadecadienoic acid, (9Z,12Z)- is affirmed by United States regulation as GRAS for specified food functions under current good manufacturing practice.
9,12-Octadecadienoic acid, (9Z,12Z)- may function as a flavoring agent or adjuvant.
9,12-Octadecadienoic acid, (9Z,12Z)- may function as a nutrient supplement.
9,12-Octadecadienoic acid, (9Z,12Z)- food-grade material must have purity suitable for its intended use.
9,12-Octadecadienoic acid, (9Z,12Z)- is present in numerous personal-care product categories.
9,12-Octadecadienoic acid, (9Z,12Z)- is used in face, body, hair, eye-area, cleansing, moisturizing, and color-cosmetic products.
9,12-Octadecadienoic acid, (9Z,12Z)- cosmetic safety depends on purity, oxidation state, use concentration, and formulation.
9,12-Octadecadienoic acid, (9Z,12Z)- cosmetic products should be formulated to be non-irritating and non-sensitizing.
9,12-Octadecadienoic acid, (9Z,12Z)- may be classified differently by suppliers depending on purity and additives.
9,12-Octadecadienoic acid, (9Z,12Z)- is not assigned a universal severe hazard classification in the PubChem summary.
9,12-Octadecadienoic acid, (9Z,12Z)- may nevertheless irritate eyes or skin after substantial or prolonged contact.
9,12-Octadecadienoic acid, (9Z,12Z)- mists, heated vapors, and oxidation products should not be inhaled.
9,12-Octadecadienoic acid, (9Z,12Z)- is combustible.
9,12-Octadecadienoic acid, (9Z,12Z)- can burn after sufficient heating and ignition.
9,12-Octadecadienoic acid, (9Z,12Z)- combustion can generate carbon monoxide, carbon dioxide, smoke, and irritating decomposition products.
9,12-Octadecadienoic acid, (9Z,12Z)- contaminated absorbents and oil-soaked materials may present spontaneous-heating risks.
9,12-Octadecadienoic acid, (9Z,12Z)- should be stored under cool and dry conditions.
9,12-Octadecadienoic acid, (9Z,12Z)- should be protected from oxygen, direct sunlight, heat, and reactive metals.
9,12-Octadecadienoic acid, (9Z,12Z)- should be stored in tightly closed compatible containers.
9,12-Octadecadienoic acid, (9Z,12Z)- high-purity or oxidation-sensitive grades may benefit from nitrogen blanketing.
9,12-Octadecadienoic acid, (9Z,12Z)- commercial grades can differ substantially.
9,12-Octadecadienoic acid, (9Z,12Z)- technical grades may contain oleic, palmitic, stearic, or other fatty acids.
9,12-Octadecadienoic acid, (9Z,12Z)- food, cosmetic, pharmaceutical, and analytical grades have different purity requirements.
9,12-Octadecadienoic acid, (9Z,12Z)- grade selection must be based on the intended regulated application.
PROPERTIES
Chemical Name: (9Z,12Z)-Octadeca-9,12-dienoic acid
Product Name: 9,12-Octadecadienoic acid, (9Z,12Z)-
Common Name: Linoleic Acid
Chemical Family: Polyunsaturated fatty acids
Lipid Classification: Omega-6 fatty acid
Lipid Shorthand: C18:2 n-6
CAS Number: 60-33-3
EC Number: 200-470-9
PubChem CID: 5280450
ChEBI Identifier: CHEBI:17351
Lipid Maps Identifier: LMFA01030120
JECFA Number: 332
FEMA Number: 3380
Molecular Formula: C18H32O2
Molecular Weight: 280.45 g/mol
Structural Description: Eighteen-carbon carboxylic acid with cis double bonds at positions 9 and 12
Condensed Formula: CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOH
Double-Bond Geometry: 9Z and 12Z
Physical State: Oily liquid at room temperature
Typical Appearance: Colorless to pale-yellow or straw-colored liquid
Odor: Mild fatty odor when fresh
Water Solubility: Practically insoluble
Organic-Solvent Solubility: Soluble in ether, alcohol, oils, and many fat solvents
Representative Melting Point: Approximately −5°C
Representative Reduced-Pressure Boiling Point: Approximately 229°C at 16 mmHg
Representative Specific Gravity: Approximately 0.898–0.904
Representative Refractive Index: Approximately 1.469–1.473
Calculated XLogP: Approximately 6.8
Hydrogen-Bond Donors: 1
Hydrogen-Bond Acceptors: 2
Representative Iodine Value: Approximately 145–160 for the cited flavoring specification
Representative Saponification Value: Approximately 194–202 for the cited flavoring specification
Oxidation Stability: Low relative to saturated and monounsaturated fatty acids
Light Stability: Protect from direct light
Air Stability: Protect from prolonged oxygen exposure
Metal Sensitivity: Trace copper and iron can accelerate oxidation
Combustibility: Combustible organic liquid
Primary Food Functions: Flavoring agent, flavoring adjuvant, and nutrient supplement
Primary Cosmetic Functions: Emollient, skin-conditioning agent, hair-conditioning lipid, and formulation intermediate
Primary Industrial Functions: Chemical intermediate, metalworking-fluid component, lubricant intermediate, coating intermediate, and adhesive ingredient
Primary Analytical Uses: Fatty-acid standard, chromatography standard, and lipid-metabolism reference
Food Regulatory Status in the United States: GRAS under current good manufacturing practice for specified uses
European Regulatory Identity: Listed under EC number 200-470-9
Hazard Classification: Grade, purity, oxidation state, additives, supplier, and jurisdiction dependent
Storage Conditions: Cool, dry, dark storage in tightly closed compatible containers
Preferred Storage Protection: Minimize air, heat, light, moisture, and metal contamination
Optional Storage Control: Nitrogen or another inert-gas blanket for sensitive high-purity grades
Shelf Life: Grade, antioxidant system, packaging, oxygen exposure, and manufacturer dependent
Regulatory Suitability: Purity, origin, grade, product category, use level, and jurisdiction dependent
FIRST AID
Inhalation:
Move the affected person to fresh air after substantial mist, heated-vapor, smoke, or decomposition-product exposure.
Obtain medical attention if coughing, headache, nausea, or breathing discomfort persists.
Skin Contact:
Remove contaminated clothing and wash the affected skin thoroughly with soap and water.
Obtain medical advice if redness or irritation continues.
Eye Contact:
Rinse cautiously with clean water for at least 15 minutes.
Remove contact lenses if easy to do and obtain medical attention if discomfort persists.
Ingestion:
Rinse the mouth and do not induce vomiting unless instructed by medical personnel.
Obtain medical advice after significant accidental ingestion of non-food-grade or industrial material.
Note to Physicians:
Treat symptomatically and provide supportive care.
Consider exposure to oxidation products or other fatty acids and additives present in the commercial grade.
HANDLING AND STORAGE
Handling:
Wear suitable gloves and eye protection during bulk transfer, heating, sampling, and formulation.
Avoid prolonged skin contact, eye contact, mist formation, and unnecessary exposure to heated material.
Ventilation:
Provide effective general ventilation and local exhaust where the material is heated, sprayed, or aerosolized.
Use suitable respiratory protection when mist or decomposition-product exposure cannot be controlled adequately.
Storage:
Store in tightly closed compatible containers in a cool, dry, dark, and well-ventilated area.
Protect the material from direct sunlight, oxygen, excessive heat, oxidizing agents, copper, iron, and contamination.
Spill and Leak Procedures:
Contain the liquid and absorb it with a suitable inert material.
Prevent uncontrolled entry into drains and place recovered material and oily absorbents in appropriate labeled containers.
Handling Precautions:
Do not leave oil-soaked cloths, filters, or absorbents in uncontrolled piles because oxidation may generate heat.
Use food-, cosmetic-, pharmaceutical-, or analytical-grade material only for the corresponding regulated application.
Follow the current specification, certificate of analysis, safety data sheet, and applicable regulatory requirements.
