Linoleic acid

Description

Linoleic acid is an essential ω-6 polyunsaturated fatty acid (PUFA). It is the most abundant PUFA in a variety of foods, and dietary sources of linoleic acid include vegetable oils, meats, nuts, seeds, and eggs. Linoleic acid (30 μM) increases migration of IEC-6 rat intestinal epithelial cells in a wound healing assay. Rats fed a linoleate-deficient diet exhibit decreased body weight and an increased ratio of eicosatrienoate to arachidonate in liver and serum phospholipids compared with rats fed a control diet, as well as mild scaling of forepaw skin.

Chemical properties

Liquid at room temperature, colorless

Chemical properties

Linoleic acid occurs as a colorless to light-yellow-colored oil.

The Uses of Linoleic acid

linoleic acid (vitamin F) is also known as omega-6. An emulsifier, it is also cleansing, emollient, and skin conditioning. Some formulations incorporate it as a surfactant. Linoleic acid prevents dryness and roughness. A deficiency of linoleic acid in the skin is associated with symptoms similar to those characterizing eczema, psoriasis, and a generally poor skin condition. In numerous laboratory studies where a linoleic acid deficiency was induced, a topical application of linoleic acid in its free or esterified form quickly reversed this condition. In addition, there is some evidence in laboratory tests that linoleic acid may inhibit melanin production by decreasing tyrosinase activity and suppressing melanin polymer formation within melanosomes. Linoleic acid is an essential fatty acid found in a variety of plant oils, including soybean and sunflower.

The Uses of Linoleic acid

Linoleic acid(cis-9, cis-12-octadecadienoic acid), an essential fatty acid, can act as a radioprotective agent of BM while being toxic to certain tumor cells.

The Uses of Linoleic acid

Unsaturated μ-6 fatty acid Linoleic acid is involved in the production of quick-drying oils which are used in oil paints and varnishes. It is also used in beauty products due to its beneficial properties on the skin such as moisture retention. It is a key starting material for the synthesis of linoleyl alcohol and octadecanoic acid. It is used as a precursor of arachidonic acid (AA) and various prostaglandins. It may be used to improve the delivery and efficacy of anti-cancer drugs and in cancer protection.

What are the applications of Application

Linoleic Acid is a fatty acid with cytotoxic activity that influences the inflammatory process

What are the applications of Application

Linoleic Acid, water soluble is a complex of linoleic acid and methyl-β-cyclodextrin

Definition

ChEBI: An octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry.

Production Methods

Linoleic acid is obtained by extraction from various vegetable oils such as safflower oil.

Definition

An unsaturated carboxylic acid that occurs in LINSEED OIL and other plant oils. It is used in making paints and varnishes.

Definition

linoleic acid: A liquid polyunsaturatedfatty acid with two doublebonds, CH₃(CH₂)₄CH:CHCH_2-CH:CH(CH₂)₇COOH.Linoleic acid isabundant in plant fats and oils,e.g.linseed oil, groundnut oil,and soyabeanoil.It is an essential fatty acid.

General Description

Colorless to straw colored liquid. A polyunsaturated fatty acid essential to human diet.

Air & Water Reactions

Sensitive to air and light. . Oxidizes across carbon double bonds

Reactivity Profile

Linoleic acid reacts to neutralize bases. May react vigorously with oxidizing agents. May react exothermically with reducing agents to release hydrogen gas.

Fire Hazard

Flash point data for Linoleic acid are not available. Linoleic acid is probably combustible.

Pharmaceutical Applications

Linoleic acid is used in topical transdermal formulations, in oral formulations as an absorption enhancer, and in topical cosmetic formulations as an emulsifying agent, and in aqueous microemulsions.It is also used in parenteral emulsions for total parenteral nutrition and in nonprescription oral dietary supplements.

Biochem/physiol Actions

Linoleic acid increases cell proliferation and gene expression of PPARα and its target genes such as acyl-CoA oxidase in primary duck hepatocytes .

Safety

Linoleic acid is widely used in cosmetics and topical pharmaceutical formulations, and is generally regarded as a nontoxic material. On exposure to the eyes, skin, and mucous membranes, linoleic acid can cause mild irritation.

Metabolism

Not Available

storage

Linoleic acid is sensitive to air, light, moisture, and heat. It should be stored in a tightly sealed container under an inert atmosphere and refrigerated.

Incompatibilities

Linoleic acid is incompatible with bases, strong oxidizing agents, and reducing agents.

Regulatory Status

GRAS listed. Approved for use in foods in Europe and the USA.