Linoleic acid

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Linoleic acid
IUPAC name	cis, cis-9,12-octadecadienoic acid.[1]
Identifiers
CAS number	[60-33-3]
SMILES	CCCCCC=CCC=CCCCCCCCC(=O)O
Properties
Molecular formula	C18H32O2
Molar mass	280.45 g mol−1
Density	0.9 g/cm3
Melting point	-5 °C
Boiling point	229°C
Solubility in methanol	methanol 3.22 M [2]
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references

Linoleic acid (LA) is an unsaturated omega-6 fatty acid. It is a colorless liquid. In physiological literature, it is called 18:2(n-6). Chemically, linoleic acid is a carboxylic acid with an 18-carbon chain and two cis double bonds; the first double bond is located at the sixth carbon from the omega end.

The word linoleic comes from the Greek word linon (flax). Oleic means of, relating to, or derived from oil or olive or of or relating to oleic acid since removing the omega-6 double bond produces oleic acid.

Contents 1 In Physiology 2 Industrial uses 3 Dietary Sources 4 See also 5 References

[edit] In Physiology

Linoleic acid (LA) is a polyunsaturated fatty acid used in the biosynthesis of arachidonic acid (AA) and thus some prostaglandins. It is found in the lipids of cell membranes. It is abundant in many vegetable oils, especially safflower and sunflower oils.

Linoleic acid is a member of the group of essential fatty acids called omega-6 fatty acids, so called because they are an essential dietary requirement for all mammals. The other group of essential fatty acids is the omega-3 fatty acids, for example Alpha-linolenic acid. Omega-6 deficiency symptoms include dry hair, hair loss,^[3] and poor wound healing.^[4]

Metabolism and Eicosanoids

The first step in the metabolism of Linoleic Acid (LA) is performed by Δ-6-desaturase, which converts LA into gamma-Linolenic acid (GLA).

There is evidence suggesting that infants lack Δ-6-desaturase of their own, and must acquire it through breast milk. Studies show that breast-milk fed babies have higher concentrations of GLA than formula-fed babies, while formula-fed babies have elevated concentrations of LA. ^[5]

GLA is converted to Dihomo-gamma-linolenic acid (DGLA), which in turn is converted to Arachidonic acid (AA). One of the possible fates of AA is to be transformed into a group of metabolites called eicosanoids, a class of paracrine hormones. The three types of eicosanoids are prostaglandins, thromboxanes, and leukotrienes. Eicosanoids are only produced from AA and tend to be pro-inflammatory. ^[6]

For example, both Thrombaxane and Leukotriene_B4 are proaggretory and vasoconstrictive eicosanoids. An increased intake of Omega 3 fatty acids with a decrease in Omega 6 fatty acids has been shown to attenuate inflammation due to reduced production of these eicosanoids.^[7]

One study monitoring two groups of survivors of myocardial infarction concluded that “the concentration of alpha-linolenic acid was increased by 68%, in the experimental group, and that of linoleic acid reduced by 7%...the survivors of a first myocardial infarction, assigned to a Mediterranean alpha-linolenic acid rich diet, had a markedly reduced rate of recurrence, other cardiac events and overall mortality.” ^[8]

Possible Roles in Disease

Cancer Prevention

A study in mice has shown that dietary intake of Conjugated Linoleic Acid (CLA) can help prevent cancer in mice. The study looked at a specific isomer of LA and studied its effect on cancer induced by dimethylbenz(a)anthracene. The study suggested a significant effect of CLA intake on the reduction of carcinogenesis. ^[9]

Cystic fibrosis

Since children with cystic fibrosis suffer from Essential Fatty Acid Deficiency due to malabsorption, it was hypothesized that high doses of LA might aid in their growth. The study looked at two groups of infants with cystic fibrosis on diets with two different levels of LA. It was shown that supplementary LA, indeed, has a positive effect on the growth of infants with cystic fibrosis, especially between 6 and 9 months of age.^[10]

Dermatitis

Dermatitis is one of the first signs of an Essential Fatty Acid deficiency in both humans and animals. Until 1955, one of the most widely applied treatments for atopic eczema was a high dose of GLA. ^[11]

Diabetes

A number of studies have shown that diabetics require higher than normal intakes of LA. Because diabetics have consistently been shown to have above normal levels of LA while having lower than normal levels of GLA, it is believed that diabetics have impaired Δ-6-desaturase activity. Increased intakes of LA have been shown to attenuate diabetic complications in numerous studies.^[12]

[edit] Industrial uses

Linoleic acid is used in making soaps, emulsifiers, and quick-drying oils. Reduction of linoleic acid yields linoleyl alcohol. Linoleic acid has become increasingly popular in the beauty products industry because of its beneficial properties on the skin. Research points to linoleic acid's effective properties when applied topically on the skin, i.e. anti-inflammatory, acne reduction, moisture retention properties.^[13][14][15]

[edit] Dietary Sources

Name	% ALA†	ref.
Safflower Oil	78%
Grape Seed Oil	73%
Poppy Seed Oil	70%
Sunflower Oil	68%
Hemp Oil	60%
Corn Oil	59%
Wheat Germ Oil	55%
Cottonseed Oil	54%
Soybean Oil	51%
Walnut Oil	51%
Peanut Oil	48%
Sesame Oil	45%
Rice Bran Oil	39%
Pistachio Oil	32.7%
Canola Oil	21%
Egg Yolk	16%
Lard	10%
Olive Oil	10%
Palm Oil	10%
Cocoa Butter	3%
Macadamia Oil	2%
Butter	2%
Coconut Oil	2%
	†average val

[edit] See also

• alpha-Linolenic acid
• Conjugated linoleic acid
• Essential fatty acids
• Essential fatty acid interactions
• Eicosanoids
• Essential nutrients
• Linolein

[edit] References

v • d • e Lipids: fatty acids Saturated Acetic • Propionic • Butyric • Valeric • Hexanoic • Caprylic • Decanoic • Lauric • Myristic • Palmitic • Heptadecanoic • Stearic • Arachidic • Behenic • Lignoceric n−3 Unsaturated α-Linolenic • Stearidonic • Eicosapentaenoic • Docosahexaenoic n−6 Unsaturated Linoleic • γ-Linolenic • Dihomo-γ-linolenic • Arachidonic n−9 Unsaturated Oleic • Elaidic • Erucic • Nervonic