fbpx
Wikipedia

Oleic acid

October 15, 2023

Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, although commercial samples may be yellowish. In chemical terms, oleic acid is classified as a monounsaturated omega-9 fatty acid, abbreviated with a lipid number of 18:1 cis-9, and a main product of Δ9-desaturase.[2] It has the formula CH3−(CH2)7−CH=CH−(CH2)7−COOH.[3][page needed] The name derives from the Latin word oleum, which means oil.[4] It is the most common fatty acid in nature.[5] The salts and esters of oleic acid are called oleates. It is part of many oils and thus used in a lot of artificial food, as well as for soap.

Oleic acid
Names
Preferred IUPAC name
(9Z)-Octadec-9-enoic acid
Other names
Oleic acid
(9Z)-Octadecenoic acid
(Z)-Octadec-9-enoic acid
cis-9-Octadecenoic acid
cis-Δ9-Octadecenoic acid
18:1 cis-9
Identifiers
  • 112-80-1 Y
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL8659 N
ChemSpider
  • 393217 N
DrugBank
  • DB04224
ECHA InfoCard 100.003.643
  • 1054
  • 445639
UNII
  • 2UMI9U37CP Y
  • DTXSID1025809
  • InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9- N
    Key: ZQPPMHVWECSIRJ-KTKRTIGZSA-N N
  • InChI=1/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9-
    Key: ZQPPMHVWECSIRJ-KTKRTIGZBB
  • CCCCCCCC\C=C/CCCCCCCC(O)=O
Properties
C18H34O2
Molar mass 282.468 g·mol−1
Appearance colorless oily liquid with lard-like odor
Density 0.895 g/mL
Melting point 13 to 14 °C (55 to 57 °F; 286 to 287 K)
Boiling point 360 °C (680 °F; 633 K)[1]
Insoluble
Solubility in Ethanol Soluble
-208.5·10−6 cm3/mol
Hazards
NFPA 704 (fire diamond)
Health 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
1
0
Safety data sheet (SDS) JT Baker
Related compounds
Related compounds
 Elaidic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

Occurrence Edit

Fatty acids (or their salts) often do not occur as such in biological systems. Instead fatty acids such as oleic acid occur as their esters, commonly triglycerides, which are the greasy materials in many natural oils. Oleic acid is the most common monounsaturated fatty acid in nature. It is found in fats (triglycerides), the phospholipids that make membranes, cholesterol esters, and wax esters.[6]

Triglycerides of oleic acid comprise the majority of olive oil (about 70%). Olive oil exceeding 2% free oleic acid is graded unfit for human consumption.[7] It also makes up 59–75% of pecan oil,[8] 61% of canola oil,[9] 36–67% of peanut oil,[10] 60% of macadamia oil, 20–80% of sunflower oil,[11] 15–20% of grape seed oil, sea buckthorn oil, 40% of sesame oil,[3] and 14% of poppyseed oil. High oleic variants of plant sources such as sunflower (~80%) and canola oil (70%) also have been developed.[11] Karuka contains 52.39% oleic acid.[12] It is abundantly present in many animal fats, constituting 37 to 56% of chicken and turkey fat,[13] and 44 to 47% of lard.

Oleic acid is the most abundant fatty acid in human adipose tissue,[14] and second in abundance in human tissues overall, following palmitic acid.

Production and chemical behavior Edit

The biosynthesis of oleic acid involves the action of the enzyme stearoyl-CoA 9-desaturase acting on stearoyl-CoA. In effect, stearic acid is dehydrogenated to give the monounsaturated derivative, oleic acid.[6]

Oleic acid undergoes the reactions of carboxylic acids and alkenes. It is soluble in aqueous base to give soaps called oleates. Iodine adds across the double bond. Hydrogenation of the double bond yields the saturated derivative stearic acid. Oxidation at the double bond occurs slowly in air, and is known as rancidification in foodstuffs and as drying in coatings.

Reduction of the carboxylic acid group yields oleyl alcohol. Ozonolysis of oleic acid is an important route to azelaic acid. The coproduct is nonanoic acid:[15]

H17C8CH=CHC7H14CO2H + 4"O" → HO2CC7H14CO2H + H17C8CO2H

Esters of azelaic acid find applications in lubrication and plasticizers.

Neutralizing oleic acid with ethanolamines gives the protic ionic liquid monoethanolamine oleate.[16]

Related compounds Edit

The trans isomer of oleic acid is called elaidic acid or trans-9-octadecenoic acid. These isomers have distinct physical properties and biochemical properties. Elaidic acid, the most abundant trans fatty acid in diet, appears to have an adverse effect on health.[17] A reaction that converts oleic acid to elaidic acid is called elaidinization.

Another naturally occurring isomer of oleic acid is petroselinic acid.

In chemical analysis, fatty acids are separated by gas chromatography of their methyl ester derivatives. Alternatively, separation of unsaturated isomers is possible by argentation thin-layer chromatography.[18]

In ethenolysis, methyl oleate, the methyl ester of the acid, converts to 1-decene and methyl 9-decenoate:[19]

CH3(CH2)7CH=CH(CH2)7CO2Me + CH2=CH2 → CH3(CH2)7CH=CH2 + MeO2C(CH2)7CH=CH2

Dietary sources Edit

Properties of vegetable oils[20][21]
The nutritional values are expressed as percent (%) by mass of total fat.
Type Processing
treatment[22]		 Saturated
fatty acids		 Monounsaturated
fatty acids		 Polyunsaturated
fatty acids		 Smoke point
Total[20] Oleic
acid
(ω-9)		 Total[20] α-Linolenic
acid
(ω-3)		 Linoleic
acid
(ω-6)		 ω-6:3
ratio
Avocado[23] 11.6 70.6 52–66
[24]		 13.5 1 12.5 12.5:1 250 °C (482 °F)[25]
Brazil nut[26] 24.8 32.7 31.3 42.0 0.1 41.9 419:1 208 °C (406 °F)[27]
Canola[28] 7.4 63.3 61.8 28.1 9.1 18.6 2:1 204 °C (400 °F)[29]
Coconut[30] 82.5 6.3 6 1.7 175 °C (347 °F)[27]
Corn[31] 12.9 27.6 27.3 54.7 1 58 58:1 232 °C (450 °F)[29]
Cottonseed[32] 25.9 17.8 19 51.9 1 54 54:1 216 °C (420 °F)[29]
Cottonseed[33] hydrogenated 93.6 1.5 0.6 0.2 0.3 1.5:1
Flaxseed/linseed[34] 9.0 18.4 18 67.8 53 13 0.2:1 107 °C (225 °F)
Grape seed   10.4 14.8 14.3   74.9 0.15 74.7 very high 216 °C (421 °F)[35]
Hemp seed[36] 7.0 9.0 9.0 82.0 22.0 54.0 2.5:1 166 °C (330 °F)[37]
High-oleic safflower oil[38] 7.5 75.2 75.2 12.8 0 12.8 very high 212 °C (414 °F)[27]
Olive, Extra Virgin[39] 13.8 73.0 71.3 10.5 0.7 9.8 14:1 193 °C (380 °F)[27]
Palm[40] 49.3 37.0 40 9.3 0.2 9.1 45.5:1 235 °C (455 °F)
Palm[41] hydrogenated 88.2 5.7 0
Peanut[42] 16.2 57.1 55.4 19.9 0.318 19.6 61.6:1 232 °C (450 °F)[29]
Rice bran oil 25 38.4 38.4 36.6 2.2 34.4[43] 15.6:1 232 °C (450 °F)[44]
Sesame[45] 14.2 39.7 39.3 41.7 0.3 41.3 138:1
Soybean[46] 15.6 22.8 22.6 57.7 7 51 7.3:1 238 °C (460 °F)[29]
Soybean[47] partially hydrogenated 14.9 43.0 42.5 37.6 2.6 34.9 13.4:1
Sunflower[48] 8.99 63.4 62.9 20.7 0.16 20.5 128:1 227 °C (440 °F)[29]
Walnut oil[49] unrefined 9.1 22.8 22.2 63.3 10.4 52.9 5:1 160 °C (320 °F)[50]

Uses Edit

Oleic acid is used as a component in many foods, in the form of its triglycerides. It is a component of the normal human diet, being a part of animal fats and vegetable oils.

Oleic acid as its sodium salt is a major component of soap as an emulsifying agent. It is also used as an emollient.[51] Small amounts of oleic acid are used as an excipient in pharmaceuticals, and it is used as an emulsifying or solubilizing agent in aerosol products.[52]

E.O. Wilson found that oleic acid is used by ants; when a dead ant's corpse begins to emit oleic acid, other ants in the colony transport it away to the ant refuse pile.[53][54][55][56]

Niche uses Edit

Oleic acid is used to induce lung damage in certain types of animals for the purpose of testing new drugs and other means to treat lung diseases. Specifically in sheep, intravenous administration of oleic acid causes acute lung injury with corresponding pulmonary edema.[57]

Oleic acid is used as a soldering flux in stained glass work for joining lead came.[58]

Nanoparticles Edit

Oleic acid is widely used in the solution phase synthesis of nanoparticles, functioning as a kinetic knob[clarification needed] to control the size and morphology of nanoparticles.[59][60]

Health effects Edit

Oleic acid is the topmost monounsaturated fat in the human diet.[61] Monounsaturated fat consumption has been associated with decreased low-density lipoprotein (LDL) cholesterol, and possibly with increased high-density lipoprotein (HDL) cholesterol.[62] Oleic acid may be responsible for the hypotensive (blood pressure reducing) effects of olive oil that is considered a health benefit.[63] A 2017 review found that diets enriched in oleic acid are beneficial for regulating body weight.[64]

The United States FDA has approved a health claim on reduced risk of coronary heart disease for high oleic (> 70% oleic acid) oils.[65] Some oil plants have cultivars bred to increase the amount of oleic acid in the oils. In addition to providing a health claim, the heat stability and shelf life may also be improved, but only if the increase in monounsaturated oleic acid levels correspond to a substantial reduction in polyunsaturated fatty acid (especially α-linolenic acid) content.[66] When the saturated fat or trans fat in a fried food is replaced with a stable high oleic oil, consumers may be able to avoid certain health risks associated with consuming saturated fat and trans fat.[67][68]

See also Edit

References Edit

  1. ^ Young, Jay A. (2002). "Chemical Laboratory Information Profile: Oleic Acid". Journal of Chemical Education. 79 (1): 24. Bibcode:2002JChEd..79...24Y. doi:10.1021/ed079p24.
  2. ^ Nakamura, Manabu T.; Nara, Takayuki Y. (2004). "Structure, function, and dietary regulation of Δ6, Δ5, and Δ9 desaturases". Annual Review of Nutrition. 24: 345–376. doi:10.1146/annurev.nutr.24.121803.063211. PMID 15189125.
  3. ^ a b Thomas, Alfred (2000). "Fats and Fatty Oils". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a10_173. ISBN 978-3-527-30673-2.
  4. ^ Bailey and Bailey, Dorothy and Kenneth (1929). "An Etymological Dictionary of Chemistry and Mineralogy". Nature. 124 (3134): 789–790. Bibcode:1929Natur.124..789V. doi:10.1038/124789b0. S2CID 4024133.
  5. ^ "9-Octadecenoic acid". PubChem, National Center for Biotechnology Information, US National Library of Medicine. 14 July 2018. Retrieved 19 July 2018.
  6. ^ a b Ntambi, James M.; Miyazaki, Makoto (2003). "Recent insights into stearoyl-CoA desaturase-1". Current Opinion in Lipidology. 14 (3): 255–61. doi:10.1097/00041433-200306000-00005. PMID 12840656. S2CID 45954457.
  7. ^ "Olive Oil and Olive-Pomace Oil Grades and Standards | Agricultural Marketing Service". www.ams.usda.gov. Retrieved 2016-01-20.
  8. ^ Villarreal-Lozoya, Jose E.; Lombardini, Leonardo; Cisneros-Zevallos, Luis (2007). "Phytochemical constituents and antioxidant capacity of different pecan Carya illinoinensis (Wangenh.) K. Koch cultivars". Food Chemistry. 102 (4): 1241–1249. doi:10.1016/j.foodchem.2006.07.024. 
  9. ^ . Canola Council of Canada. Archived from the original on 2008-06-06. Retrieved 2008-09-03.
  10. ^ Moore, K. M.; Knauft, D. A. (1989). "The Inheritance of High Oleic Acid in Peanut". The Journal of Heredity. 80 (3): 252–3. doi:10.1093/oxfordjournals.jhered.a110845. 
  11. ^ a b "Nutrient database, Release 25". United States Department of Agriculture.(NDB ID: 04678, 04584)
  12. ^ Purwanto, Y.; Munawaroh, Esti (2010). [Ethnobotany Types of Pandanaceae as Foodstuffs in Indonesia]. Berkala Penelitian Hayati (in Indonesian). 5A: 97–108. doi:10.5072/FK2/Z6P0OQ. ISSN 2337-389X. OCLC 981032990. Archived from the original (PDF) on 29 October 2018. Retrieved 25 October 2018.
  13. ^ Nutter, Mary K.; Lockhart, Ernest E.; Harris, Robert S. (1943). "The chemical composition of depot fats in chickens and turkeys". Oil & Soap. 20 (11): 231–4. doi:10.1007/BF02630880. S2CID 84893770. 
  14. ^ Kokatnur, MG; Oalmann, MC; Johnson, WD; Malcom, GT; Strong, JP (1979). "Fatty acid composition of human adipose tissue from two anatomical sites in a biracial community". The American Journal of Clinical Nutrition. 32 (11): 2198–205. doi:10.1093/ajcn/32.11.2198. PMID 495536. 
  15. ^ Cornils, Boy; Lappe, Peter (2000). "Dicarboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a08_523. ISBN 978-3-527-30673-2.
  16. ^ Toledo Hijo, Ariel A. C.; Maximo, Guilherme J.; Costa, Mariana C.; Cunha, Rosiane L.; Pereira, Jorge F. B.; Kurnia, Kiki A.; Batista, Eduardo A. C.; Meirelles, Antonio J. A. (2017). "Phase Behavior and Physical Properties of New Biobased Ionic Liquid Crystals". The Journal of Physical Chemistry B. 121 (14): 3177–3189. doi:10.1021/acs.jpcb.7b01384. PMID 28332847.
  17. ^ Tardy, Anne-Laure; Morio, Beatrice; Chardigny, Jean-Michel; Malpuech-Brugere, Corinne (2011). "Ruminant and industrial sources of trans-fat and cardiovascular and diabetic diseases". Nutrition Research Reviews. 24 (1): 111–117. doi:10.1017/S0954422411000011. PMID 21320382.
  18. ^ Breuer, B.; Fock, H. P. (1987). "Separation of fatty acids or methyl esters including positional and geometric isomers by alumina argentation thin-layer chromatography". J. Chromatogr. Sci. 25 (7): 302–306. doi:10.1093/chromsci/25.7.302. PMID 3611285.
  19. ^ Marinescu, Smaranda C.; Schrock, Richard R.; Müller, Peter; Hoveyda, Amir H. (2009). "Ethenolysis Reactions Catalyzed by Imido Alkylidene Monoaryloxide Monopyrrolide (MAP) Complexes of Molybdenum". J. Am. Chem. Soc. 131 (31): 10840–10841. doi:10.1021/ja904786y. PMID 19618951.
  20. ^ a b c "US National Nutrient Database, Release 28". United States Department of Agriculture. May 2016. All values in this table are from this database unless otherwise cited or when italicized as the simple arithmetic sum of other component columns.
  21. ^ "Fats and fatty acids contents per 100 g (click for "more details"). Example: Avocado oil (user can search for other oils)". Nutritiondata.com, Conde Nast for the USDA National Nutrient Database, Standard Release 21. 2014. Retrieved 7 September 2017. Values from Nutritiondata.com (SR 21) may need to be reconciled with most recent release from the USDA SR 28 as of Sept 2017.
  22. ^ "USDA Specifications for Vegetable Oil Margarine Effective August 28, 1996" (PDF).
  23. ^ "Avocado oil, fat composition, 100 g". US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016. Retrieved 6 September 2017.
  24. ^ Ozdemir F, Topuz A (2004). "Changes in dry matter, oil content and fatty acids composition of avocado during harvesting time and post-harvesting ripening period" (PDF). Food Chemistry. Elsevier. pp. 79–83. Archived from the original (PDF) on 2020-01-16. Retrieved 15 January 2020.
  25. ^ Wong M, Requejo-Jackman C, Woolf A (April 2010). "What is unrefined, extra virgin cold-pressed avocado oil?". Aocs.org. The American Oil Chemists' Society. Retrieved 26 December 2019.
  26. ^ "Brazil nut oil, fat composition, 100 g". US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016. Retrieved 6 September 2017.
  27. ^ a b c d Katragadda HR, Fullana A, Sidhu S, Carbonell-Barrachina ÁA (2010). "Emissions of volatile aldehydes from heated cooking oils". Food Chemistry. 120: 59–65. doi:10.1016/j.foodchem.2009.09.070.
  28. ^ "Canola oil, fat composition, 100 g". US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016. Retrieved 6 September 2017.
  29. ^ a b c d e f Wolke RL (May 16, 2007). "Where There's Smoke, There's a Fryer". The Washington Post. Retrieved March 5, 2011.
  30. ^ "Coconut oil, fat composition, 100 g". US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016. Retrieved 6 September 2017.
  31. ^ "Corn oil, industrial and retail, all purpose salad or cooking, fat composition, 100 g". US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016. Retrieved 6 September 2017.
  32. ^ "Cottonseed oil, salad or cooking, fat composition, 100 g". US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016. Retrieved 6 September 2017.
  33. ^ "Cottonseed oil, industrial, fully hydrogenated, fat composition, 100 g". US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016. Retrieved 6 September 2017.
  34. ^ "Linseed/Flaxseed oil, cold pressed, fat composition, 100 g". US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016. Retrieved 6 September 2017.
  35. ^ Garavaglia J, Markoski MM, Oliveira A, Marcadenti A (2016). "Grape Seed Oil Compounds: Biological and Chemical Actions for Health". Nutrition and Metabolic Insights. 9: 59–64. doi:10.4137/NMI.S32910. PMC 4988453. PMID 27559299.
  36. ^ Callaway J, Schwab U, Harvima I, Halonen P, Mykkänen O, Hyvönen P, Järvinen T (April 2005). "Efficacy of dietary hempseed oil in patients with atopic dermatitis". The Journal of Dermatological Treatment. 16 (2): 87–94. doi:10.1080/09546630510035832. PMID 16019622. S2CID 18445488.
  37. ^ Melina V. "Smoke points of oils" (PDF). veghealth.com. The Vegetarian Health Institute.
  38. ^ "Safflower oil, salad or cooking, high oleic, primary commerce, fat composition, 100 g". US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016. Retrieved 6 September 2017.
  39. ^ "Olive oil, salad or cooking, fat composition, 100 g". US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016. Retrieved 6 September 2017.
  40. ^ "Palm oil, fat composition, 100 g". US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016. Retrieved 6 September 2017.
  41. ^ "Palm oil, industrial, fully hydrogenated, filling fat, fat composition, 100 g". US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016. Retrieved 6 September 2017.
  42. ^ "Oil, peanut". FoodData Central. usda.gov.
  43. ^ Orthoefer FT (2005). "Chapter 10: Rice Bran Oil". In Shahidi F (ed.). Bailey's Industrial Oil and Fat Products. Vol. 2 (6th ed.). John Wiley & Sons, Inc. p. 465. doi:10.1002/047167849X. ISBN 978-0-471-38552-3.
  44. ^ "Rice bran oil". RITO Partnership. Retrieved 22 January 2021.
  45. ^ "Oil, sesame, salad or cooking". FoodData Central. fdc.nal.usda.gov. 1 April 2019.
  46. ^ "Soybean oil, salad or cooking, fat composition, 100 g". US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016. Retrieved 6 September 2017.
  47. ^ "Soybean oil, salad or cooking, (partially hydrogenated), fat composition, 100 g". US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016. Retrieved 6 September 2017.
  48. ^ "FoodData Central". fdc.nal.usda.gov.
  49. ^ "Walnut oil, fat composition, 100 g". US National Nutrient Database, United States Department of Agriculture.
  50. ^ "Smoke Point of Oils". Baseline of Health. Jonbarron.org.
  51. ^ Carrasco, F. (2009). "Ingredientes Cosméticos". Diccionario de Ingredientes (4th ed.). Francisco Carrasco Otero. p. 428. ISBN 978-84-613-4979-1.
  52. ^ Smolinske, Susan C. (1992). Handbook of Food, Drug, and Cosmetic Excipients. CRC Press. pp. 247–8. ISBN 978-0-8493-3585-3.
  53. ^ Wilson, E. O.; Durlach, N. I.; Roth, L. M. (December 1958). "Chemical Releasers of Necrophoric Behavior in Ants". Psyche: A Journal of Entomology. 65 (4): 108–114. doi:10.1155/1958/69391. ISSN 0033-2615.
  54. ^ "'Hey I'm Dead!' The Story Of The Very Lively Ant". NPR.
  55. ^ "How ants determine the death of another ant | Britannica". www.britannica.com. Retrieved 2023-07-03.
  56. ^ Diez, Lise; Moquet, Laura; Detrain, Claire (2013-12-01). "Post-mortem Changes in Chemical Profile and their Influence on Corpse Removal in Ants". Journal of Chemical Ecology. 39 (11): 1424–1432. doi:10.1007/s10886-013-0365-1. ISSN 1573-1561. PMID 24242873. S2CID 254654298.
  57. ^ Julien, M; Hoeffel, JM; Flick, MR (1986). "Oleic acid lung injury in sheep". Journal of Applied Physiology. 60 (2): 433–40. doi:10.1152/jappl.1986.60.2.433. PMID 3949648.
  58. ^ Duncan, Alastair (2003). The Technique of Leaded Glass. Dover Publications. p. 77. ISBN 978-0-486-42607-5.
  59. ^ Yin, Xi; Shi, Miao; Wu, Jianbo; Pan, Yung-Tin; Gray, Danielle L.; Bertke, Jeffery A.; Yang, Hong (11 September 2017). "Quantitative Analysis of Different Formation Modes of Platinum Nanocrystals Controlled by Ligand Chemistry". Nano Letters. 17 (10): 6146–6150. Bibcode:2017NanoL..17.6146Y. doi:10.1021/acs.nanolett.7b02751. PMID 28873317.
  60. ^ Wei, Yan; Han, Bing; Hu, Xiaoyang; Lin, Yuanhua; Wang, Xinzhi; Deng, Xuliang (2012). "Synthesis of Fe3O4 Nanoparticles and their Magnetic Properties". Procedia Engineering. 27: 632–637. doi:10.1016/j.proeng.2011.12.498.
  61. ^ Schwingshackl L, Hoffmann G (2014). "Monounsaturated fatty acids, olive oil and health status: a systematic review and meta-analysis of cohort studies". Lipids in Health and Disease. 13: 154. doi:10.1186/1476-511X-13-154. PMC 4198773. PMID 25274026.
  62. ^ . Merck & Co. Inc. Archived from the original on 2009-03-03. Retrieved 2009-03-14.
  63. ^ Teres, S.; Barcelo-Coblijn, G.; Benet, M.; Alvarez, R.; Bressani, R.; Halver, J. E.; Escriba, P. V. (2008). "Oleic acid content is responsible for the reduction in blood pressure induced by olive oil". Proceedings of the National Academy of Sciences. 105 (37): 13811–6. Bibcode:2008PNAS..10513811T. doi:10.1073/pnas.0807500105. JSTOR 25464133. PMC 2544536. PMID 18772370.
  64. ^ Tutunchi, Helda; Ostadrahimi, Alireza; Saghafi-Asl, Maryam (2020). "The Effects of Diets Enriched in Monounsaturated Oleic Acid on the Management and Prevention of Obesity: a Systematic Review of Human Intervention Studies". Advances in Nutrition. 11 (4): 864–877. doi:10.1093/advances/nmaa013. PMC 7360458. PMID 32135008.
  65. ^ Nutrition, Center for Food Safety and Applied (20 December 2019). "FDA Completes Review of Qualified Health Claim Petition for Oleic Acid and the Risk of Coronary Heart Disease". FDA.
  66. ^ Aladedunye, Felix; Przybylski, Roman (December 2013). "Frying stability of high oleic sunflower oils as affected by composition of tocopherol isomers and linoleic acid content". Food Chemistry. 141 (3): 2373–2378. doi:10.1016/j.foodchem.2013.05.061. PMID 23870970.
  67. ^ "High-oleic canola oils and their food applications". The American Oil Chemists' Society.
  68. ^ Trans Fat Task Force (June 2006). TRANSforming the Food Supply. Trans Fat Task Force. ISBN 0-662-43689-X. Retrieved 7 January 2007.

External links Edit

  • (The AOCS Lipid Library)
  • 9-octadecenoic acid (NIST Chemistry Webbook)

October 15, 2023
oleic, acid, fatty, acid, that, occurs, naturally, various, animal, vegetable, fats, oils, odorless, colorless, although, commercial, samples, yellowish, chemical, terms, oleic, acid, classified, monounsaturated, omega, fatty, acid, abbreviated, with, lipid, n. Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils It is an odorless colorless oil although commercial samples may be yellowish In chemical terms oleic acid is classified as a monounsaturated omega 9 fatty acid abbreviated with a lipid number of 18 1 cis 9 and a main product of D9 desaturase 2 It has the formula CH3 CH2 7 CH CH CH2 7 COOH 3 page needed The name derives from the Latin word oleum which means oil 4 It is the most common fatty acid in nature 5 The salts and esters of oleic acid are called oleates It is part of many oils and thus used in a lot of artificial food as well as for soap Oleic acid NamesPreferred IUPAC name 9Z Octadec 9 enoic acidOther names Oleic acid 9Z Octadecenoic acid Z Octadec 9 enoic acidcis 9 Octadecenoic acidcis D9 Octadecenoic acid18 1 cis 9IdentifiersCAS Number 112 80 1 Y3D model JSmol Interactive imageChEMBL ChEMBL8659 NChemSpider 393217 NDrugBank DB04224ECHA InfoCard 100 003 643IUPHAR BPS 1054PubChem CID 445639UNII 2UMI9U37CP YCompTox Dashboard EPA DTXSID1025809InChI InChI 1S C18H34O2 c1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 h9 10H 2 8 11 17H2 1H3 H 19 20 b10 9 NKey ZQPPMHVWECSIRJ KTKRTIGZSA N NInChI 1 C18H34O2 c1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 h9 10H 2 8 11 17H2 1H3 H 19 20 b10 9 Key ZQPPMHVWECSIRJ KTKRTIGZBBSMILES CCCCCCCC C C CCCCCCCC O OPropertiesChemical formula C 18H 34O 2Molar mass 282 468 g mol 1Appearance colorless oily liquid with lard like odorDensity 0 895 g mLMelting point 13 to 14 C 55 to 57 F 286 to 287 K Boiling point 360 C 680 F 633 K 1 Solubility in water InsolubleSolubility in Ethanol SolubleMagnetic susceptibility x 208 5 10 6 cm3 molHazardsNFPA 704 fire diamond 010Safety data sheet SDS JT BakerRelated compoundsRelated compounds Elaidic acidExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Occurrence 2 Production and chemical behavior 3 Related compounds 4 Dietary sources 5 Uses 5 1 Niche uses 5 2 Nanoparticles 6 Health effects 7 See also 8 References 9 External linksOccurrence EditFatty acids or their salts often do not occur as such in biological systems Instead fatty acids such as oleic acid occur as their esters commonly triglycerides which are the greasy materials in many natural oils Oleic acid is the most common monounsaturated fatty acid in nature It is found in fats triglycerides the phospholipids that make membranes cholesterol esters and wax esters 6 Triglycerides of oleic acid comprise the majority of olive oil about 70 Olive oil exceeding 2 free oleic acid is graded unfit for human consumption 7 It also makes up 59 75 of pecan oil 8 61 of canola oil 9 36 67 of peanut oil 10 60 of macadamia oil 20 80 of sunflower oil 11 15 20 of grape seed oil sea buckthorn oil 40 of sesame oil 3 and 14 of poppyseed oil High oleic variants of plant sources such as sunflower 80 and canola oil 70 also have been developed 11 Karuka contains 52 39 oleic acid 12 It is abundantly present in many animal fats constituting 37 to 56 of chicken and turkey fat 13 and 44 to 47 of lard Oleic acid is the most abundant fatty acid in human adipose tissue 14 and second in abundance in human tissues overall following palmitic acid Production and chemical behavior EditThe biosynthesis of oleic acid involves the action of the enzyme stearoyl CoA 9 desaturase acting on stearoyl CoA In effect stearic acid is dehydrogenated to give the monounsaturated derivative oleic acid 6 Oleic acid undergoes the reactions of carboxylic acids and alkenes It is soluble in aqueous base to give soaps called oleates Iodine adds across the double bond Hydrogenation of the double bond yields the saturated derivative stearic acid Oxidation at the double bond occurs slowly in air and is known as rancidification in foodstuffs and as drying in coatings Reduction of the carboxylic acid group yields oleyl alcohol Ozonolysis of oleic acid is an important route to azelaic acid The coproduct is nonanoic acid 15 H17C8CH CHC7H14CO2H 4 O HO2CC7H14CO2H H17C8CO2HEsters of azelaic acid find applications in lubrication and plasticizers Neutralizing oleic acid with ethanolamines gives the protic ionic liquid monoethanolamine oleate 16 Related compounds EditThe trans isomer of oleic acid is called elaidic acid or trans 9 octadecenoic acid These isomers have distinct physical properties and biochemical properties Elaidic acid the most abundant trans fatty acid in diet appears to have an adverse effect on health 17 A reaction that converts oleic acid to elaidic acid is called elaidinization Another naturally occurring isomer of oleic acid is petroselinic acid In chemical analysis fatty acids are separated by gas chromatography of their methyl ester derivatives Alternatively separation of unsaturated isomers is possible by argentation thin layer chromatography 18 In ethenolysis methyl oleate the methyl ester of the acid converts to 1 decene and methyl 9 decenoate 19 CH3 CH2 7CH CH CH2 7CO2Me CH2 CH2 CH3 CH2 7CH CH2 MeO2C CH2 7CH CH2Dietary sources EditProperties of vegetable oils 20 21 The nutritional values are expressed as percent by mass of total fat Type Processingtreatment 22 Saturatedfatty acids Monounsaturatedfatty acids Polyunsaturatedfatty acids Smoke pointTotal 20 Oleicacid w 9 Total 20 a Linolenicacid w 3 Linoleicacid w 6 w 6 3ratioAvocado 23 11 6 70 6 52 66 24 13 5 1 12 5 12 5 1 250 C 482 F 25 Brazil nut 26 24 8 32 7 31 3 42 0 0 1 41 9 419 1 208 C 406 F 27 Canola 28 7 4 63 3 61 8 28 1 9 1 18 6 2 1 204 C 400 F 29 Coconut 30 82 5 6 3 6 1 7 175 C 347 F 27 Corn 31 12 9 27 6 27 3 54 7 1 58 58 1 232 C 450 F 29 Cottonseed 32 25 9 17 8 19 51 9 1 54 54 1 216 C 420 F 29 Cottonseed 33 hydrogenated 93 6 1 5 0 6 0 2 0 3 1 5 1Flaxseed linseed 34 9 0 18 4 18 67 8 53 13 0 2 1 107 C 225 F Grape seed 10 4 14 8 14 3 74 9 0 15 74 7 very high 216 C 421 F 35 Hemp seed 36 7 0 9 0 9 0 82 0 22 0 54 0 2 5 1 166 C 330 F 37 High oleic safflower oil 38 7 5 75 2 75 2 12 8 0 12 8 very high 212 C 414 F 27 Olive Extra Virgin 39 13 8 73 0 71 3 10 5 0 7 9 8 14 1 193 C 380 F 27 Palm 40 49 3 37 0 40 9 3 0 2 9 1 45 5 1 235 C 455 F Palm 41 hydrogenated 88 2 5 7 0Peanut 42 16 2 57 1 55 4 19 9 0 318 19 6 61 6 1 232 C 450 F 29 Rice bran oil 25 38 4 38 4 36 6 2 2 34 4 43 15 6 1 232 C 450 F 44 Sesame 45 14 2 39 7 39 3 41 7 0 3 41 3 138 1Soybean 46 15 6 22 8 22 6 57 7 7 51 7 3 1 238 C 460 F 29 Soybean 47 partially hydrogenated 14 9 43 0 42 5 37 6 2 6 34 9 13 4 1Sunflower 48 8 99 63 4 62 9 20 7 0 16 20 5 128 1 227 C 440 F 29 Walnut oil 49 unrefined 9 1 22 8 22 2 63 3 10 4 52 9 5 1 160 C 320 F 50 Uses EditOleic acid is used as a component in many foods in the form of its triglycerides It is a component of the normal human diet being a part of animal fats and vegetable oils Oleic acid as its sodium salt is a major component of soap as an emulsifying agent It is also used as an emollient 51 Small amounts of oleic acid are used as an excipient in pharmaceuticals and it is used as an emulsifying or solubilizing agent in aerosol products 52 E O Wilson found that oleic acid is used by ants when a dead ant s corpse begins to emit oleic acid other ants in the colony transport it away to the ant refuse pile 53 54 55 56 Niche uses Edit Oleic acid is used to induce lung damage in certain types of animals for the purpose of testing new drugs and other means to treat lung diseases Specifically in sheep intravenous administration of oleic acid causes acute lung injury with corresponding pulmonary edema 57 Oleic acid is used as a soldering flux in stained glass work for joining lead came 58 Nanoparticles Edit Oleic acid is widely used in the solution phase synthesis of nanoparticles functioning as a kinetic knob clarification needed to control the size and morphology of nanoparticles 59 60 Health effects EditOleic acid is the topmost monounsaturated fat in the human diet 61 Monounsaturated fat consumption has been associated with decreased low density lipoprotein LDL cholesterol and possibly with increased high density lipoprotein HDL cholesterol 62 Oleic acid may be responsible for the hypotensive blood pressure reducing effects of olive oil that is considered a health benefit 63 A 2017 review found that diets enriched in oleic acid are beneficial for regulating body weight 64 The United States FDA has approved a health claim on reduced risk of coronary heart disease for high oleic gt 70 oleic acid oils 65 Some oil plants have cultivars bred to increase the amount of oleic acid in the oils In addition to providing a health claim the heat stability and shelf life may also be improved but only if the increase in monounsaturated oleic acid levels correspond to a substantial reduction in polyunsaturated fatty acid especially a linolenic acid content 66 When the saturated fat or trans fat in a fried food is replaced with a stable high oleic oil consumers may be able to avoid certain health risks associated with consuming saturated fat and trans fat 67 68 See also EditOleylamine the corresponding amine Oleamide the corresponding amideReferences Edit Young Jay A 2002 Chemical Laboratory Information Profile Oleic Acid Journal of Chemical Education 79 1 24 Bibcode 2002JChEd 79 24Y doi 10 1021 ed079p24 Nakamura Manabu T Nara Takayuki Y 2004 Structure function and dietary regulation of D6 D5 and D9 desaturases Annual Review of Nutrition 24 345 376 doi 10 1146 annurev nutr 24 121803 063211 PMID 15189125 a b Thomas Alfred 2000 Fats and Fatty Oils Ullmann s Encyclopedia of Industrial Chemistry doi 10 1002 14356007 a10 173 ISBN 978 3 527 30673 2 Bailey and Bailey Dorothy and Kenneth 1929 An Etymological Dictionary of Chemistry and Mineralogy Nature 124 3134 789 790 Bibcode 1929Natur 124 789V doi 10 1038 124789b0 S2CID 4024133 9 Octadecenoic acid PubChem National Center for Biotechnology Information US National Library of Medicine 14 July 2018 Retrieved 19 July 2018 a b Ntambi James M Miyazaki Makoto 2003 Recent insights into stearoyl CoA desaturase 1 Current Opinion in Lipidology 14 3 255 61 doi 10 1097 00041433 200306000 00005 PMID 12840656 S2CID 45954457 Olive Oil and Olive Pomace Oil Grades and Standards Agricultural Marketing Service www ams usda gov Retrieved 2016 01 20 Villarreal Lozoya Jose E Lombardini Leonardo Cisneros Zevallos Luis 2007 Phytochemical constituents and antioxidant capacity of different pecan Carya illinoinensis Wangenh K Koch cultivars Food Chemistry 102 4 1241 1249 doi 10 1016 j foodchem 2006 07 024 nbsp Comparison of Dietary Fats Chart Canola Council of Canada Archived from the original on 2008 06 06 Retrieved 2008 09 03 Moore K M Knauft D A 1989 The Inheritance of High Oleic Acid in Peanut The Journal of Heredity 80 3 252 3 doi 10 1093 oxfordjournals jhered a110845 nbsp a b Nutrient database Release 25 United States Department of Agriculture NDB ID 04678 04584 Purwanto Y Munawaroh Esti 2010 Etnobotani Jenis Jenis Pandanaceae Sebagai Bahan Pangan di Indonesia Ethnobotany Types of Pandanaceae as Foodstuffs in Indonesia Berkala Penelitian Hayati in Indonesian 5A 97 108 doi 10 5072 FK2 Z6P0OQ ISSN 2337 389X OCLC 981032990 Archived from the original PDF on 29 October 2018 Retrieved 25 October 2018 Nutter Mary K Lockhart Ernest E Harris Robert S 1943 The chemical composition of depot fats in chickens and turkeys Oil amp Soap 20 11 231 4 doi 10 1007 BF02630880 S2CID 84893770 nbsp Kokatnur MG Oalmann MC Johnson WD Malcom GT Strong JP 1979 Fatty acid composition of human adipose tissue from two anatomical sites in a biracial community The American Journal of Clinical Nutrition 32 11 2198 205 doi 10 1093 ajcn 32 11 2198 PMID 495536 nbsp Cornils Boy Lappe Peter 2000 Dicarboxylic Acids Aliphatic Ullmann s Encyclopedia of Industrial Chemistry doi 10 1002 14356007 a08 523 ISBN 978 3 527 30673 2 Toledo Hijo Ariel A C Maximo Guilherme J Costa Mariana C Cunha Rosiane L Pereira Jorge F B Kurnia Kiki A Batista Eduardo A C Meirelles Antonio J A 2017 Phase Behavior and Physical Properties of New Biobased Ionic Liquid Crystals The Journal of Physical Chemistry B 121 14 3177 3189 doi 10 1021 acs jpcb 7b01384 PMID 28332847 Tardy Anne Laure Morio Beatrice Chardigny Jean Michel Malpuech Brugere Corinne 2011 Ruminant and industrial sources of trans fat and cardiovascular and diabetic diseases Nutrition Research Reviews 24 1 111 117 doi 10 1017 S0954422411000011 PMID 21320382 Breuer B Fock H P 1987 Separation of fatty acids or methyl esters including positional and geometric isomers by alumina argentation thin layer chromatography J Chromatogr Sci 25 7 302 306 doi 10 1093 chromsci 25 7 302 PMID 3611285 Marinescu Smaranda C Schrock Richard R Muller Peter Hoveyda Amir H 2009 Ethenolysis Reactions Catalyzed by Imido Alkylidene Monoaryloxide Monopyrrolide MAP Complexes of Molybdenum J Am Chem Soc 131 31 10840 10841 doi 10 1021 ja904786y PMID 19618951 a b c US National Nutrient Database Release 28 United States Department of Agriculture May 2016 All values in this table are from this database unless otherwise cited or when italicized as the simple arithmetic sum of other component columns Fats and fatty acids contents per 100 g click for more details Example Avocado oil user can search for other oils Nutritiondata com Conde Nast for the USDA National Nutrient Database Standard Release 21 2014 Retrieved 7 September 2017 Values from Nutritiondata com SR 21 may need to be reconciled with most recent release from the USDA SR 28 as of Sept 2017 USDA Specifications for Vegetable Oil Margarine Effective August 28 1996 PDF Avocado oil fat composition 100 g US National Nutrient Database Release 28 United States Department of Agriculture May 2016 Retrieved 6 September 2017 Ozdemir F Topuz A 2004 Changes in dry matter oil content and fatty acids composition of avocado during harvesting time and post harvesting ripening period PDF Food Chemistry Elsevier pp 79 83 Archived from the original PDF on 2020 01 16 Retrieved 15 January 2020 Wong M Requejo Jackman C Woolf A April 2010 What is unrefined extra virgin cold pressed avocado oil Aocs org The American Oil Chemists Society Retrieved 26 December 2019 Brazil nut oil fat composition 100 g US National Nutrient Database Release 28 United States Department of Agriculture May 2016 Retrieved 6 September 2017 a b c d Katragadda HR Fullana A Sidhu S Carbonell Barrachina AA 2010 Emissions of volatile aldehydes from heated cooking oils Food Chemistry 120 59 65 doi 10 1016 j foodchem 2009 09 070 Canola oil fat composition 100 g US National Nutrient Database Release 28 United States Department of Agriculture May 2016 Retrieved 6 September 2017 a b c d e f Wolke RL May 16 2007 Where There s Smoke There s a Fryer The Washington Post Retrieved March 5 2011 Coconut oil fat composition 100 g US National Nutrient Database Release 28 United States Department of Agriculture May 2016 Retrieved 6 September 2017 Corn oil industrial and retail all purpose salad or cooking fat composition 100 g US National Nutrient Database Release 28 United States Department of Agriculture May 2016 Retrieved 6 September 2017 Cottonseed oil salad or cooking fat composition 100 g US National Nutrient Database Release 28 United States Department of Agriculture May 2016 Retrieved 6 September 2017 Cottonseed oil industrial fully hydrogenated fat composition 100 g US National Nutrient Database Release 28 United States Department of Agriculture May 2016 Retrieved 6 September 2017 Linseed Flaxseed oil cold pressed fat composition 100 g US National Nutrient Database Release 28 United States Department of Agriculture May 2016 Retrieved 6 September 2017 Garavaglia J Markoski MM Oliveira A Marcadenti A 2016 Grape Seed Oil Compounds Biological and Chemical Actions for Health Nutrition and Metabolic Insights 9 59 64 doi 10 4137 NMI S32910 PMC 4988453 PMID 27559299 Callaway J Schwab U Harvima I Halonen P Mykkanen O Hyvonen P Jarvinen T April 2005 Efficacy of dietary hempseed oil in patients with atopic dermatitis The Journal of Dermatological Treatment 16 2 87 94 doi 10 1080 09546630510035832 PMID 16019622 S2CID 18445488 Melina V Smoke points of oils PDF veghealth com The Vegetarian Health Institute Safflower oil salad or cooking high oleic primary commerce fat composition 100 g US National Nutrient Database Release 28 United States Department of Agriculture May 2016 Retrieved 6 September 2017 Olive oil salad or cooking fat composition 100 g US National Nutrient Database Release 28 United States Department of Agriculture May 2016 Retrieved 6 September 2017 Palm oil fat composition 100 g US National Nutrient Database Release 28 United States Department of Agriculture May 2016 Retrieved 6 September 2017 Palm oil industrial fully hydrogenated filling fat fat composition 100 g US National Nutrient Database Release 28 United States Department of Agriculture May 2016 Retrieved 6 September 2017 Oil peanut FoodData Central usda gov Orthoefer FT 2005 Chapter 10 Rice Bran Oil In Shahidi F ed Bailey s Industrial Oil and Fat Products Vol 2 6th ed John Wiley amp Sons Inc p 465 doi 10 1002 047167849X ISBN 978 0 471 38552 3 Rice bran oil RITO Partnership Retrieved 22 January 2021 Oil sesame salad or cooking FoodData Central fdc nal usda gov 1 April 2019 Soybean oil salad or cooking fat composition 100 g US National Nutrient Database Release 28 United States Department of Agriculture May 2016 Retrieved 6 September 2017 Soybean oil salad or cooking partially hydrogenated fat composition 100 g US National Nutrient Database Release 28 United States Department of Agriculture May 2016 Retrieved 6 September 2017 FoodData Central fdc nal usda gov Walnut oil fat composition 100 g US National Nutrient Database United States Department of Agriculture Smoke Point of Oils Baseline of Health Jonbarron org Carrasco F 2009 Ingredientes Cosmeticos Diccionario de Ingredientes 4th ed Francisco Carrasco Otero p 428 ISBN 978 84 613 4979 1 Smolinske Susan C 1992 Handbook of Food Drug and Cosmetic Excipients CRC Press pp 247 8 ISBN 978 0 8493 3585 3 Wilson E O Durlach N I Roth L M December 1958 Chemical Releasers of Necrophoric Behavior in Ants Psyche A Journal of Entomology 65 4 108 114 doi 10 1155 1958 69391 ISSN 0033 2615 Hey I m Dead The Story Of The Very Lively Ant NPR How ants determine the death of another ant Britannica www britannica com Retrieved 2023 07 03 Diez Lise Moquet Laura Detrain Claire 2013 12 01 Post mortem Changes in Chemical Profile and their Influence on Corpse Removal in Ants Journal of Chemical Ecology 39 11 1424 1432 doi 10 1007 s10886 013 0365 1 ISSN 1573 1561 PMID 24242873 S2CID 254654298 Julien M Hoeffel JM Flick MR 1986 Oleic acid lung injury in sheep Journal of Applied Physiology 60 2 433 40 doi 10 1152 jappl 1986 60 2 433 PMID 3949648 Duncan Alastair 2003 The Technique of Leaded Glass Dover Publications p 77 ISBN 978 0 486 42607 5 Yin Xi Shi Miao Wu Jianbo Pan Yung Tin Gray Danielle L Bertke Jeffery A Yang Hong 11 September 2017 Quantitative Analysis of Different Formation Modes of Platinum Nanocrystals Controlled by Ligand Chemistry Nano Letters 17 10 6146 6150 Bibcode 2017NanoL 17 6146Y doi 10 1021 acs nanolett 7b02751 PMID 28873317 Wei Yan Han Bing Hu Xiaoyang Lin Yuanhua Wang Xinzhi Deng Xuliang 2012 Synthesis of Fe3O4 Nanoparticles and their Magnetic Properties Procedia Engineering 27 632 637 doi 10 1016 j proeng 2011 12 498 Schwingshackl L Hoffmann G 2014 Monounsaturated fatty acids olive oil and health status a systematic review and meta analysis of cohort studies Lipids in Health and Disease 13 154 doi 10 1186 1476 511X 13 154 PMC 4198773 PMID 25274026 You Can Control Your Cholesterol A Guide to Low Cholesterol Living Merck amp Co Inc Archived from the original on 2009 03 03 Retrieved 2009 03 14 Teres S Barcelo Coblijn G Benet M Alvarez R Bressani R Halver J E Escriba P V 2008 Oleic acid content is responsible for the reduction in blood pressure induced by olive oil Proceedings of the National Academy of Sciences 105 37 13811 6 Bibcode 2008PNAS 10513811T doi 10 1073 pnas 0807500105 JSTOR 25464133 PMC 2544536 PMID 18772370 Tutunchi Helda Ostadrahimi Alireza Saghafi Asl Maryam 2020 The Effects of Diets Enriched in Monounsaturated Oleic Acid on the Management and Prevention of Obesity a Systematic Review of Human Intervention Studies Advances in Nutrition 11 4 864 877 doi 10 1093 advances nmaa013 PMC 7360458 PMID 32135008 Nutrition Center for Food Safety and Applied 20 December 2019 FDA Completes Review of Qualified Health Claim Petition for Oleic Acid and the Risk of Coronary Heart Disease FDA Aladedunye Felix Przybylski Roman December 2013 Frying stability of high oleic sunflower oils as affected by composition of tocopherol isomers and linoleic acid content Food Chemistry 141 3 2373 2378 doi 10 1016 j foodchem 2013 05 061 PMID 23870970 High oleic canola oils and their food applications The American Oil Chemists Society Trans Fat Task Force June 2006 TRANSforming the Food Supply Trans Fat Task Force ISBN 0 662 43689 X Retrieved 7 January 2007 External links EditFATTY ACIDS STRAIGHT CHAIN MONOENOIC The AOCS Lipid Library 9 octadecenoic acid NIST Chemistry Webbook Retrieved from https en wikipedia org w index php title Oleic acid amp oldid 1177232502, wikipedia, wiki, book, books, library,

article

, read, download, free, free download, mp3, video, mp4, 3gp, jpg, jpeg, gif, png, picture, music, song, movie, book, game, games.