n.

(化合物や官能基として)リノール酸、リノール酸エステル

関: linoleic acid

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/01/12 05:19:46」(JST)

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Linoleic acid (LA) is a polyunsaturated omega-6 fatty acid. It is a colorless liquid at room temperature. In physiological literature, it has a lipid number of 18:2 cis,cis-9,12. From the chemistry perspective, linoleic acid is a carboxylic acid with an 18-carbon chain and two cis double bonds; with the first double bond located at the sixth carbon from the methyl end.^[3]

Linoleic acid belongs to one of the two families of essential fatty acids, which means that the human body cannot synthesize it from other food components.^[4]

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

In physiology

LA is a polyunsaturated fatty acid used in the biosynthesis of arachidonic acid (AA) and thus some prostaglandins, leukotrienes (LTA, LTB, LTC), and thromboxane (TXA). It is found in the lipids of cell membranes. It is abundant in many nuts, fatty seeds (flax seeds, hemp seeds, poppy seeds, sesame seeds, etc.) and their derived vegetable oils; comprising over half (by weight) of poppy seed, safflower, sunflower, corn, and soybean oils.^[5]

Linoleic acid is an essential fatty acid that must be consumed for proper health. A diet only deficient in linoleate (the salt form of the acid) causes mild skin scaling, hair loss,^[6] and poor wound healing in rats.^[7]

Along with oleic acid, linoleic acid is released by cockroaches upon death which has the effect of preventing other roaches from entering the area. This is similar to the mechanism found in ants and bees, which release oleic acid upon death.^[8]

Metabolism and eicosanoids

The first step in the metabolism of LA is performed by Δ⁶desaturase, which converts LA into gamma-linolenic acid (GLA).

There is evidence suggesting that infants lack Δ⁶desaturase 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.^[9]

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 during the inflammatory response and during physical activity; eicosanoids are a class of paracrine hormones. The three types of eicosanoids are prostaglandins, thromboxanes, and leukotrienes. Eicosanoids produced from AA tend to promote (not cause) inflammation and promote growth during and after physical activity in healthy humans.^[10] For example, both AA-derived thrombaxane and leukotriene_B4 are proaggregatory and vasoconstrictive eicosanoids during inflammation. The oxidized metabolic products of linoleic 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.^[11]

An increased intake of certain ^[12] 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.^[13]

One study monitoring two groups of survivors of myocardial infarction concluded “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.” ^[14]

Uses

Industrial uses

Linoleic acid is used in making quick-drying oils, which are useful in oil paints and varnishes. These applications exploit the easy reaction of the linoleic acid with oxygen in air, which leads to crosslinking and formation of a stable film.

Reduction of linoleic acid yields linoleyl alcohol. Linoleic acid is a surfactant with a critical micelle concentration of 1.5 x 10⁻⁴ M @ pH 7.5.

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 anti-inflammatory, acne reductive, and moisture retentive properties when applied topically on the skin.^[15]^[16]^[17]

Use in research

Linoleic acid lipid radicals can be used to show the antioxidant effect of natural phenols. Experiments on linoleic acid subjected to 2,2′-azobis (2-amidinopropane) dihydrochloride induced oxidation of linoleic acid; hence producing lipid radicals and then the use of different combinations of phenolics show that binary mixtures can lead to either a synergetic antioxidant effect or to an antagonistic effect towards the lipid radicals. Research like this is useful in discovering which phenols prevent the autoxidation of lipids in vegetable oils.^[18]

Linoleic acid may be linked to obesity by promoting overeating and damaging the arcuate nucleus in the brain's hypothalamus.^[19]

Dietary sources

Note: Unless cited, none of these percentages have been verified by scientific research.

Name	% LA^†	ref.
Salicornia oil	75%
Safflower oil	74.62%
Evening Primrose oil	73%
Poppyseed oil	70%
Grape seed oil	69.6%
Sunflower oil	65.7%
Barbary Fig Seed Oil	65%
Hemp oil	60%
Corn oil	59%
Wheat germ oil	55%
Cottonseed oil	54%
Soybean oil	51%
Walnut oil	51%
Sesame oil	45%
Rice bran oil	39%
Argan oil	37%
Pistachio oil	32.7%
Peanut oil	32%	^[20]
Almonds	24%
Canola oil	21%
Chicken fat	18-23%	^[21]
Egg yolk	16%
Linseed oil	15%
Lard	10%
Olive oil	10% (3.5 - 21%)	^[22]^[23]
Palm oil	10%
Cocoa butter	3%
Macadamia oil	2%
Butter	2%
Coconut oil	2%
	^†average val

References

^ ^a ^b ^c The Merck Index, 11th Edition, 5382
^ ^a ^b ^c ^d Record of CAS RN 60-33-3 in the GESTIS Substance Database of the IFA
^ David J. Anneken, Sabine Both, Ralf Christoph, Georg Fieg, Udo Steinberner, Alfred Westfechtel "Fatty Acids" in Ullmann's Encyclopedia of Industrial Chemistry, 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a10_245.pub2
^ Burr, G.O., Burr, M.M. and Miller, E. (1930). "On the nature and role of the fatty acids essential in nutrition" (PDF). J. Biol. Chem. 86 (587): 1–9.
^ "Nutrient Data Laboratory Home Page". USDA National Nutrient Database for Standard Reference, Release 20. U.S. Department of Agriculture, Agricultural Research Service. 2007.
^ Cunnane S, Anderson M (1 April 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. Retrieved 2007-01-15.
^ Ruthig DJ & Meckling-Gill KA. (1 October 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. Retrieved 2007-01-15.
^ "Earth News: Ancient 'smell of death' revealed". BBC.
^ 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. Retrieved 2009-04-16.
^ 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". Proceedings of the National Academy of Sciences of the United States of America 106 (44): 18820–4. doi:10.1073/pnas.0905415106. PMC 2764734. PMID 19843694.
^ Kinsella, JE; Lokesh, B; Stone, RA (1990). "Dietary n-3 polyunsaturated fatty acids and amelioration of cardiovascular disease: possible mechanisms". The American journal of clinical nutrition 52 (1): 1–28. PMID 2193500.
^ Kinsella, John E.; Lokesh, Belur; Stone, Richard A. (1990). "Dietary n-3 polyunsatruated fatty acids and amelioration of cardiovascular disease: possible mechanisms". American Journal of Clinical Nutrition 52 (1): 1–28. PMID 2193500.
^ de Lorgeril, M; Renaud, Serge; Salen, P; Monjaud, I; Mamelle, N; Martin, J.L.; Guidollet, J; Touboul, P; Delaye, J (1994). "Mediterranean alpha-linolenic acid-rich diet in secondary prevention of coronary heart disease". Lancet 343: 8911. doi:10.1016/s0140-6736(94)92580-1.
^ Diezel, W.E.; Schulz, E.; Skanks, M.; Heise, H. (1993). "Plant oils: Topical application and anti-inflammatory effects (croton oil test)". Dermatologische Monatsschrift 179: 173.
^ 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:10.1046/j.1365-2230.1998.00315.x. PMID 9692305.
^ 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:10.1080/080352502753711678. PMID 12113324.
^ Peyrat-Maillard, M. N.; Cuvelier, M. E.; Berset, C. (2003). "Antioxidant activity of phenolic compounds in 2,2′-azobis (2-amidinopropane) dihydrochloride (AAPH)-induced oxidation: Synergistic and antagonistic effects". Journal of the American Oil Chemists' Society 80 (10): 1007–1012. doi:10.1007/s11746-003-0812-z.
^ Janet Raloff (2012). "Tricks Foods Play". Science News Magazine 182 (7): 25–28. doi:10.1002/scin.5591820727.
^ Oil, peanut, salad or cooking: search for peanut oil on http://www.nal.usda.gov/fnic/foodcomp/search/
^ M. K. Nutter, E. E. Lockhart and R. S. Harris (1943). "The chemical composition of depot fats in chickens and turkeys". Journal of the American Oil Chemists' Society 20 (11): 231–234. doi:10.1007/BF02630880.
^ "Olive Oil : Chemical Characteristics".
^ Beltran; Del Rio, C; Sánchez, S; Martínez, L (2004). "Influence of Harvest Date and Crop Yield on the Fatty Acid Composition of Virgin Olive Oils from Cv. Picual" (PDF). J. Agric. Food Chem. 52 (11): 3434–3440. doi:10.1021/jf049894n. PMID 15161211.

External links

Linoleic acid MS Spectrum
Fatty Acids: Methylene-Interrupted Double Bonds, AOCS Lipid Library

English Journal

Physicochemical properties, nutritional value and techno-functional properties of goldenberry (Physalis peruviana) waste powder concise title: Composition of goldenberry juice waste.

Mokhtar SM1, Swailam HM2, Embaby HE3.
Food chemistry.Food Chem.2018 May 15;248:1-7. doi: 10.1016/j.foodchem.2017.11.117. Epub 2017 Dec 2.
PMID 29329831

Enzymatic esterification of acylglycerols rich in omega-3 from flaxseed oil by an immobilized solvent-tolerant lipase from Actinomadura sediminis UTMC 2870 isolated from oil-contaminated soil.

Imanparast S1, Hamedi J2, Faramarzi MA3.
Food chemistry.Food Chem.2018 Apr 15;245:934-942. doi: 10.1016/j.foodchem.2017.11.080. Epub 2017 Nov 22.
PMID 29287462

Effect of regulated deficit irrigation on fatty acids and their derived volatiles in 'Cabernet Sauvignon' grapes and wines of Ningxia, China.

Ju YL1, Liu M2, Tu TY2, Zhao XF3, Yue XF4, Zhang JX5, Fang YL6, Meng JF7.
Food chemistry.Food Chem.2018 Apr 15;245:667-675. doi: 10.1016/j.foodchem.2017.10.018. Epub 2017 Oct 7.
PMID 29287424

Japanese Journal

オクタン酸メチル,ラウリン酸メチルまたはパルミチン酸メチルを混合したリノール酸メチルの酸化

馬鉄錚,高橋朋子,小林敬 [他]
日本食品工学会誌 13(2), 25-29, 2012-06
NAID 40019373723

蛍光検出を用いたヒト皮脂に含まれる過酸化脂質の高感度迅速フローインジェクション分析

小倉悠紀,小山純一,福原忠雄
分析化学 61(5), 397-401, 2012-05
NAID 40019324467

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リンク元	「リノール酸」「リノール酸エステル」
拡張検索	「calcium linoleate」

「リノール酸」

Linoleic acid
Names
	IUPAC name (9Z,12Z)-9,12-Octadecadienoic acid
	Other names C18:2 (Lipid numbers)
Identifiers
CAS Number	60-33-3
ChEBI	CHEBI:17351
ChEMBL	ChEMBL267476
ChemSpider	4444105
IUPHAR/BPS	1052
Jmol interactive 3D	Image
KEGG	C01595
UNII	9KJL21T0QJ
	InChI InChI=1S/C18H32O2/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)/b7-6-,10-9- Key: OYHQOLUKZRVURQ-HZJYTTRNSA-N ; InChI=1/C18H32O2/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)/b7-6-,10-9- Key: OYHQOLUKZRVURQ-HZJYTTRNBX ;
	SMILES CCCCC/C=C\C/C=C\CCCCCCCC(=O)O ;
Properties
Chemical formula	C18H32O2
Molar mass	280.45 g·mol−1
Appearance	Colorless oil
Density	0.9 g/cm3
Melting point	−5 °C (23 °F); −12 °C (10 °F)
Boiling point	230 °C (446 °F) at 21 mbar; 230 °C (446 °F) at 16 mmHg
Solubility in water	0.139 mg/L
Vapor pressure	16 Torr at 229 °C[citation needed]
Hazards
NFPA 704	1 2 0
Flash point	112 °C (234 °F)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

　　[★]

英: linoleate, linolic acid
関: 脂肪酸

「リノール酸エステル」

　　[★]

英: linoleate
関: リノール酸

「calcium linoleate」

　　[★]

リノール酸カルシウム

[Merck-1] The Merck Index, 11th Edition, 5382

[GESTIS-2] Record of CAS RN 60-33-3 in the GESTIS Substance Database of the IFA

[Ullmann-3] David J. Anneken, Sabine Both, Ralf Christoph, Georg Fieg, Udo Steinberner, Alfred Westfechtel "Fatty Acids" in Ullmann's Encyclopedia of Industrial Chemistry, 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a10_245.pub2

[4] Burr, G.O., Burr, M.M. and Miller, E. (1930). "On the nature and role of the fatty acids essential in nutrition" (PDF). J. Biol. Chem. 86 (587): 1–9.

[USDA-5] "Nutrient Data Laboratory Home Page". USDA National Nutrient Database for Standard Reference, Release 20. U.S. Department of Agriculture, Agricultural Research Service. 2007.

[Cunnane-6] Cunnane S, Anderson M (1 April 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. Retrieved 2007-01-15.

[Ruthig-7] Ruthig DJ & Meckling-Gill KA. (1 October 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. Retrieved 2007-01-15.

[BBC-8] "Earth News: Ancient 'smell of death' revealed". BBC.

[David_F._Horrobin_1993-9] 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.

[10] Piomelli, Daniele (2000). "Arachidonic Acid". Neuropsychopharmacology: The Fifth Generation of Progress. Retrieved 2009-04-16.

[11] 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". Proceedings of the National Academy of Sciences of the United States of America 106 (44): 18820–4. doi:10.1073/pnas.0905415106. PMC 2764734. PMID 19843694.

[12] Kinsella, JE; Lokesh, B; Stone, RA (1990). "Dietary n-3 polyunsaturated fatty acids and amelioration of cardiovascular disease: possible mechanisms". The American journal of clinical nutrition 52 (1): 1–28. PMID 2193500.

[13] Kinsella, John E.; Lokesh, Belur; Stone, Richard A. (1990). "Dietary n-3 polyunsatruated fatty acids and amelioration of cardiovascular disease: possible mechanisms". American Journal of Clinical Nutrition 52 (1): 1–28. PMID 2193500.

[14] Lorgeril, M; Renaud, Serge; Salen, P; Monjaud, I; Mamelle, N; Martin, J.L.; Guidollet, J; Touboul, P; Delaye, J (1994). "Mediterranean alpha-linolenic acid-rich diet in secondary prevention of coronary heart disease". Lancet 343: 8911. doi:10.1016/s0140-6736(94)92580-1.

[15] Diezel, W.E.; Schulz, E.; Skanks, M.; Heise, H. (1993). "Plant oils: Topical application and anti-inflammatory effects (croton oil test)". Dermatologische Monatsschrift 179: 173.

[16] 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:10.1046/j.1365-2230.1998.00315.x. PMID 9692305.

[17] 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:10.1080/080352502753711678. PMID 12113324.

[18] Peyrat-Maillard, M. N.; Cuvelier, M. E.; Berset, C. (2003). "Antioxidant activity of phenolic compounds in 2,2′-azobis (2-amidinopropane) dihydrochloride (AAPH)-induced oxidation: Synergistic and antagonistic effects". Journal of the American Oil Chemists' Society 80 (10): 1007–1012. doi:10.1007/s11746-003-0812-z.

[19] Janet Raloff (2012). "Tricks Foods Play". Science News Magazine 182 (7): 25–28. doi:10.1002/scin.5591820727.

[20] Oil, peanut, salad or cooking: search for peanut oil on http://www.nal.usda.gov/fnic/foodcomp/search/

[21] M. K. Nutter, E. E. Lockhart and R. S. Harris (1943). "The chemical composition of depot fats in chickens and turkeys". Journal of the American Oil Chemists' Society 20 (11): 231–234. doi:10.1007/BF02630880.

[oos-22] "Olive Oil : Chemical Characteristics".

[Beltran2004-23] Beltran; Del Rio, C; Sánchez, S; Martínez, L (2004). "Influence of Harvest Date and Crop Yield on the Fatty Acid Composition of Virgin Olive Oils from Cv. Picual" (PDF). J. Agric. Food Chem. 52 (11): 3434–3440. doi:10.1021/jf049894n. PMID 15161211.

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linoleate