Linoleic acid
From Wikipedia, the free encyclopedia
| Linoleic acid | |
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| IUPAC name | cis, cis-9,12-octadecadienoic acid.[1] |
| Identifiers | |
| CAS number | 60-33-3  |
| SMILES | CCCCC/C=C\C/C=C\CCCCCCCC(=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] |
 (what is this?) (verify)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 |
[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 LeukotrieneB4 are proaggretory and vasoconstrictive eicosanoids. Another important clinical effect is that the oxidized metabolic products of linolenic acid such as 9--hydroxyoctadecanoic acid and 13-hydroxyoctadecanoic acid have also been shown to activate TRPV1, the capsaicin receptor and through this might play a major role in hyperalgesia and allodynia.[7]
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.[8]
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.” [9]
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. [10]
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.[11]
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. [12]
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.[13]
[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.[14][15][16]
[edit] Dietary Sources
| Name | % LA† | 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% | |
| Linseed oil | 15% | |
| 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
- ^ Beare-Rogers (2001). "IUPAC Lexicon of Lipid Nutrition" (pdf). http://www.iupac.org/publications/pac/2001/pdf/7304x0685.pdf. Retrieved 2006-02-22.
- ^ Solubility of linoleic acid in methanol
- ^ Cunnane S, Anderson M (01 Apr 1997). "Pure linoleate deficiency in the rat: influence on growth, accumulation of n-6 polyunsaturates, and (1-14C) linoleate oxidation". J Lipid Res 38 (4): 805–12. PMID 9144095. http://www.jlr.org/cgi/reprint/38/4/805. Retrieved 2007-01-15.
- ^ Ruthig DJ & Meckling-Gill KA. (01 Oct 1999). "Both (n-3) and (n-6) fatty acids stimulate wound healing in the rat intestinal epithelial cell line, IEC-6". Journal of Nutrition 129 (10): 1791–8. PMID 10498749. http://jn.nutrition.org/cgi/content/full/129/10/1791. Retrieved 2007-01-15.
- ^ David F. Horrobin (1993).“Fatty acid metabolism in health and disease: the role of Δ-6-desaturase.” American Journal of Clinical Nutrition. 57: 732S-7S.
- ^ Piomelli, Daniele (2000). "Arachidonic Acid". Neuropsychopharmacology: The Fifth Generation of Progress. http://www.acnp.org/g4/GN401000059/Default.htm. Retrieved on 4/16/09.
- ^ Patwardhan AM, Scotland PE, Akopian AN, Hargreaves KM. (2009). Activation of TRPV1 in the spinal cord by oxidized linoleic acid metabolites contributes to inflammatory hyperalgesia. Proc Natl Acad Sci U S A. 2009 Nov 3;106(44):18820-4. PMID 19843694
- ^ John E. Kinsella, Belur Lokesh, and Richard A. Stone (1990) “Dietary n-3 polyunsatruated fatty acids and amelioration of cardiovascular disease: possible mechanisms.” American Journal of Clinical Nutrition. 52: 1-28.
- ^ Michel de Lorgeril, and Serge Renaud (6/11/94). “Mediterranean alpha-linolenic acid-rich diet in secondary prevention of coronary heart disease.” Lancet 343: 8911.
- ^ Mammary Cancer Prevention by Conjugated Dienoic Derivative of Linoleic Acid Cancer Research 51, 6118-6124, November 15, 1991
- ^ Effect of linoleic acid intake on growth of infants with cystic fibrosis, The American Journal of Clinical Nutrition, 1996, vol. 63, no5, pp. 746-752.
- ^ David F. Horrobin (1993).“Fatty acid metabolism in health and disease: the role of Δ-6-desaturase.” American Journal of Clinical Nutrition. 57: 732S-7S.
- ^ David F. Horrobin (1993).“Fatty acid metabolism in health and disease: the role of Δ-6-desaturase.” American Journal of Clinical Nutrition. 57: 732S-7S.
- ^ "Plant oils: Topical application and anti-inflammatory effects (croton oil test)". Dermatol. Monatsschr 179: 173. 1993.
- ^ Letawe,; Letawe C, Boone M, Pierard GE (March 1998). "Digital image analysis of the effect of topically applied linoleic acid on acne microcomedones". Clinical & Experimental Dermatology 23 (2): 56–58. doi:. PMID 9692305 : 9692305. http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=pubmed&cmd=Retrieve&dopt=AbstractPlus&list_uids=9692305&itool=iconabstr&query_hl=17&itool=pubmed_docsum.
- ^ Darmstadt, G L; Darmstadt GL, Mao-Qiang M, Chi E, Saha SK, Ziboh VA, Black RE, Santosham M, Elias PM (2002). "Impact of topical oils on the skin barrier: possible implications for neonatal health in developing countries". Acta Paediatrica 91 (5): 546–554. doi:.
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