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Sodium linoleate is an organic fatty acid salt that belongs to the class of unsaturated carboxylate soaps and is chemically defined as the sodium salt of linoleic acid, an essential polyunsaturated omega-6 fatty acid commonly found in vegetable oils.
Sodium linoleate is produced through the neutralization or saponification of linoleic acid with sodium hydroxide, yielding an amphiphilic molecule composed of a hydrophilic carboxylate head group (–COO⁻ Na⁺) and a long C18 hydrophobic hydrocarbon chain containing two cis double bonds at the 9 and 12 positions.
Sodium linoleate has anti-inflammatory, immune-regulating, and tumor cell growth-affecting activities.
CAS Number: 822-17-3
Molecular Formula: C18H33NaO2
Molecular Weight: 304.45
EINECS Number: 212-491-0
Synonyms:Sodium linoleate, Sodium (9Z,12Z)-octadeca-9,12-dienoate, Linoleic acid sodium salt, PRISAVON L, 872C9A1W9I, EINECS 212-491-0, 9,12-Octadecadienoic acid (Z,Z) sodium salt, 9,12-Octadecadienoic acid (9Z,12Z) sodium salt, DTXSID5041562, 9,12-Octadecadienoic acid (9Z,12Z) sodium salt (1:1), 9,12-Octadecadienoic acid sodium salt, RefChem:887660, SODIUM LINOLEATE [INCI], DTXCID3021562, Linoleic acid sodium salt, 822-17-3, Sodium linolate, sodium;(9Z,12Z)-octadeca-9,12-dienoate, Linoleic acid (sodium salt), MFCD00063202, C18H31NaO2, UNII-872C9A1W9I, SCHEMBL107358, CHEMBL571449, WYPBVHPKMJYUEO-NBTZWHCOSA-M, EBC-75061, CS-W012114, HY-W011398, AC-33772, FS159638, SY110510, Linoleic acid sodium salt ≥98% (GC), Sodium(9Z,12Z)-octadeca-9,12-dienoate, L0056, NS00079542, cis-9,cis-12-Octadecadienoic acid sodium salt, A916196, 9,12-Octadecadienoic acid (9Z,12Z) sodium salt, Q27269782, 12-octadecadienoicacid(z,z)-sodiumsalt;CIS-9,CIS-12-OCTADECADIENOIC ACID SODIUM SALT;LINOLEIC ACID SODIUM SALT;linoleic acid sodium;sodium (9Z,12Z)-octadeca-9,12-dienoate;(9Z,12Z)-9,12-Octadecadienoic acid sodium salt;Linoleic acid sodium salt,cis-9,cis-12-Octadecadienoic acid sodium salt;(Z,Z)-9,12-Octadecadienoic acid sodium salt
Sodium linoleate can change the composition of fatty acids and the production of metabolites in cells.
Sodium linoleate is an organic fatty acid salt that belongs to the class of unsaturated carboxylate soaps and is chemically defined as the sodium salt of linoleic acid, an essential polyunsaturated omega-6 fatty acid.
Sodium linoleate is produced by neutralization (saponification) of linoleic acid with sodium hydroxide, yielding an amphiphilic molecule composed of a hydrophilic carboxylate head group (–COO⁻ Na⁺) and a long hydrophobic hydrocarbon chain containing two cis double bonds.
This molecular structure gives sodium linoleate surface-active properties, enabling it to act as an emulsifier and surfactant by interacting with both aqueous phases and non-polar oils or lipids.
This structural combination allows sodium linoleate to interact efficiently with both aqueous phases and non-polar lipid or oil phases.
Sodium linoleate is an orally active IL8 regulator via the JNK and NF-κB pathway.
The presence of two cis double bonds introduces flexibility and kinks into the hydrocarbon chain, which strongly influences its packing behavior and interfacial properties.
In water, sodium linoleate readily forms micelles, emulsions, and interfacial films, reducing surface and interfacial tension and stabilizing oil–water dispersions.
These surface-active properties make it an effective emulsifier, wetting agent, and dispersant in a wide range of systems.
From a physicochemical standpoint, sodium linoleate exhibits soap-like behavior, including foaming and cleansing action, while being generally milder than salts of saturated fatty acids.
However, due to the unsaturated nature of its hydrocarbon chain, it is more susceptible to oxidative degradation when exposed to oxygen, heat, or light, which can affect shelf life and performance if not properly stabilized.
Antioxidants are therefore often used in formulations containing sodium linoleate to improve oxidative stability.
Biologically and environmentally, sodium linoleate is derived from naturally occurring fatty acids and is typically biodegradable and compatible with biological systems.
These characteristics, combined with its amphiphilic structure and surface activity, make sodium linoleate an important compound in cosmetic, pharmaceutical, biochemical, and industrial applications where gentle emulsification and effective interfacial control are required.
Melting point : 192 °C
Storage temperature : −20 °C
Solubility : Soluble in ethanol
Form : Powder to crystal
Color : White to orange to green
Biological source : Plant oil (safflower)
Major application : General analytical; life science and biopharma
Cosmetic ingredient functions : Viscosity controlling; surfactant – cleansing; surfactant – emulsifying; cleansing
InChI : 1S/C18H32O2.Na/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20;/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20);/q;+1/p-1/b7-6-,10-9-;
InChIKey : WYPBVHPKMJYUEO-NBTZWHCOSA-M
SMILES : [Na+].CCCCCC=C/CC=C/CCCCCCCC([O-])=
Sodium linoleate is an organic fatty acid salt that belongs to the class of unsaturated carboxylate soaps and is chemically defined as the sodium salt of linoleic acid, a naturally occurring polyunsaturated omega-6 fatty acid.
It is typically produced by the neutralization (saponification) of linoleic acid with sodium hydroxide, resulting in an amphiphilic compound that contains a hydrophilic carboxylate head group (–COO⁻ Na⁺) and a long hydrophobic C18 hydrocarbon chain with two cis double bonds at the 9 and 12 positions.
This amphiphilic structure gives sodium linoleate strong surface-active behavior, allowing it to interact simultaneously with water and non-polar substances such as oils, fats, and lipid phases.
The presence of unsaturation in the hydrocarbon chain increases molecular flexibility and influences its interfacial behavior compared with saturated fatty acid salts.
In aqueous systems, sodium linoleate can form micelles and emulsions, reducing surface and interfacial tension and stabilizing dispersed oil–water systems.
These properties make it effective as a mild surfactant, emulsifier, and dispersing agent in a variety of formulations.
Sodium linoleate is sensitive to oxidation due to its unsaturated double bonds, which can affect stability under exposure to air, light, or elevated temperatures.
Nevertheless, under controlled conditions it remains compatible with many biological and industrial systems, reflecting its origin from naturally occurring fatty acids.
Sodium linoleates fatty acid backbone, amphiphilic character, and surface activity makes sodium linoleate an important compound in chemical, cosmetic, pharmaceutical, and biochemical applications.
Sodium linoleate, as a component of acylglycosyl ceramides, plays a physiological role in maintaining the water permeability barrier of the skin.
The deficiency of linoleic acid may cause poor growth or development, scaly dermatitis, and an impaired immune response in infants.
Sodium linoleate is used in cosmetic and personal care products.
Sodium linoleate is mainly used as emollients or moisturizers for skin, nails, and hair.
Uses:
Sodium linoleate can be used for cell culture materials, fluidic device module, drug testing, and fluidic device
Sodium linoleate is widely used as a surfactant and emulsifying agent due to its strong amphiphilic character and ability to reduce surface and interfacial tension.
In cosmetic and personal care products, it is commonly included in soaps, cleansers, creams, and lotions where it helps emulsify oils, improve cleansing efficiency, and provide mild skin-compatible surfactant action.
In pharmaceutical and biomedical formulations, Sodium linoleate is used as an excipient or emulsifier to enhance the solubility and dispersion of lipophilic active ingredients in aqueous systems.
Its biocompatibility and origin from naturally occurring fatty acids make it suitable for topical and oral formulations under controlled conditions.
Sodium linoleate is also applied in biochemical and biological research as a model fatty acid salt, particularly in studies involving lipid–protein interactions, membrane behavior, and micelle formation.
Sodium linoleate is frequently used to solubilize hydrophobic molecules or to mimic biological lipid environments in laboratory systems.
In food and nutritional research, sodium linoleate may be used in controlled experimental formulations as an emulsifying or dispersing agent, although its use is regulated depending on application and concentration.
In industrial and chemical formulations, it serves as a dispersant, wetting agent, or soap component in specialized cleaning products and processing aids.
Sodium linoleate is valued for its natural fatty acid origin, amphiphilic structure, emulsifying capability, and biodegradability, making it useful in cosmetic, pharmaceutical, biochemical, and specialty industrial applications.
Sodium linoleate is extensively used as a surfactant and emulsifying agent because of its strong amphiphilic structure and ability to reduce surface and interfacial tension.
In cosmetic and personal care formulations, it is commonly incorporated into soaps, facial cleansers, body washes, creams, and lotions, where it helps emulsify oils, improve cleansing performance, and provide a relatively mild, skin-compatible surfactant effect compared with harsher synthetic detergents.
In pharmaceutical applications, sodium linoleate is used as an excipient, emulsifier, or solubilizing agent to enhance the dispersion and bioavailability of lipophilic active ingredients in aqueous dosage forms.
Its compatibility with biological systems and fatty-acid origin make it suitable for topical, oral, and experimental drug-delivery formulations when properly stabilized.
In biochemical and biomedical research, sodium linoleate is widely employed as a model unsaturated fatty acid salt.
Sodium linoleate is used in studies of lipid metabolism, enzyme activity, membrane dynamics, micelle formation, and lipid–protein interactions, as well as for solubilizing hydrophobic compounds in laboratory assays.
Sodium linoleate also finds use in food and nutrition research, where it may be applied in controlled experimental systems as an emulsifying or dispersing agent for oils and fats, subject to regulatory limitations.
In industrial and chemical formulations, it functions as a dispersant, wetting agent, or soap component in specialty cleaning products, textile processing aids, and surface-active formulations.
Sodium linoleate is used in agriculture and environmental applications as an emulsifier in formulations that require effective dispersion of hydrophobic substances in water.
Sodium linoleates combination of natural fatty-acid origin, biodegradability, emulsifying efficiency, and compatibility with biological and aqueous systems makes sodium linoleate valuable across cosmetic, pharmaceutical, research, food-related, and specialized industrial applications.
Safety Profile:
Sodium linoleate is generally considered a low-hazard fatty acid salt, but appropriate safety precautions should still be observed during handling and formulation.
As a surfactant, Sodium linoleate can cause skin and eye irritation upon direct contact, particularly at high concentrations or with prolonged exposure, leading to redness, dryness, or discomfort.
Inhalation of dust or aerosols, if generated during processing, may cause mild respiratory irritation, such as coughing or throat discomfort, especially in poorly ventilated environments.
Ingestion is not considered highly toxic, but it may result in gastrointestinal irritation, including nausea or diarrhea, due to its soap-like and surfactant properties.
Because sodium linoleate contains unsaturated double bonds, it is susceptible to oxidative degradation when exposed to air, light, or heat, which may lead to the formation of irritating oxidation products over time.
Proper storage in tightly closed containers, away from heat and light, is therefore recommended to maintain stability and safety.
