Oleic acid

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
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.003.643
Properties
C18H34O2
Molar mass 282.47 g·mol−1
Appearance Pale yellow or brownish yellow 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
Safety data sheet JT Baker
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oilHealth code 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g., sodium chlorideReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
1
0
0
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).
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Infobox references

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. It has the formula CH3(CH2)7CH=CH(CH2)7COOH.[2] The name derives from the Latin word oleum, which means oil.[3] It is the most common fatty acid in nature.[4]

Occurrence

Fatty acids (or their salts) do not often occur as such in biological systems. Instead fatty acids like oleic acid occur as their esters, commonly triglycerides, which are the greasy materials in many natural oils. Fatty acids can be obtained by the saponification of triglycerides.

Triglycerides of oleic acid comprise the majority of olive oil. Free oleic acid render olive oil inedible.[5] It also makes up 59-75% of pecan oil,[6] 61% of canola oil,[7] 36-67% of peanut oil,[8] 60% of macadamia oil, 20-85% of sunflower oil (the latter in the high oleic variant),[9] 15-20% of grape seed oil, sea buckthorn oil, and sesame oil,[2] and 14% of poppyseed oil. It also comprises 22.18% of the fats from the fruit of the durian species Durio graveolens.[10] It is abundantly present in many animal fats, constituting 37 to 56% of chicken and turkey fat[11] and 44 to 47% of lard.

Oleic acid is the most abundant fatty acid in human adipose tissue,[12] and second in abundance in human tissues overall only to palmitic acid.[13]

As an insect pheromone

Oleic acid is emitted by the decaying corpses of a number of insects, including bees and Pogonomyrmex ants, and triggers the instincts of living workers to remove the dead bodies from the hive. If a live bee[14] or ant[15][16] is dabbed with oleic acid, it is dragged off for disposal as if it were dead. The oleic acid smell also may indicate danger to living insects, prompting them to avoid others who have succumbed to disease or places where predators lurk.[17]

Production and chemical behavior

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.

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 or 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:[18]

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

Esters of azelaic acid find applications in lubrication and plasticizers.

The stereoisomer 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.[19] 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.[20]

Uses

The principal use of oleic acid is as a component in many foods, in the form of its triglycerides. It is a component of the normal human diet as 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.[21] 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.[22]

Niche uses

Oleic acid is also 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.[23] This sort of research has been of particular benefit to premature newborns, for whom treatment for underdeveloped lungs (and associated complications) is often a matter of life and death.

Oleic acid is used as a soldering flux in stained glass work for joining lead came.[24]

Oleic acid is also widely used in the solution phase synthesis of nanoparticles, functioning as a kinetic knob to control the size and morphology of nanoparticles.[25]

Health effects

Oleic acid is a common monounsaturated fat in human diet. Monounsaturated fat consumption has been associated with decreased low-density lipoprotein (LDL) cholesterol, and possibly increased high-density lipoprotein (HDL) cholesterol.[26] However, its ability to raise HDL is still debated.

Oleic acid may be responsible for the hypotensive (blood pressure reducing) effects of olive oil.[27] Adverse effects also have been documented, however, since both oleic and monounsaturated fatty acid levels in the membranes of red blood cells have been associated with increased risk of breast cancer,[28] although the consumption of oleate in olive oil has been associated with a decreased risk of breast cancer.[29]

See also

References

  1. ↑ Young, Jay A. (2002). "Chemical Laboratory Information Profile: Oleic Acid". Journal of Chemical Education. 79: 24. Bibcode:2002JChEd..79...24Y. doi:10.1021/ed079p24.
  2. 1 2 Thomas, Alfred (2000). "Fats and Fatty Oils". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a10_173. ISBN 3-527-30673-0.
  3. ↑ Bailey and Bailey, Dorothy and Kenneth (1929). An Etymological Dictionary of Chemistry and Minerology. London: Edward Arnold & co. p. 190.
  4. ↑ "9-Octadecenoic acid". PubChem, National Center for Biotechnology Information, US National Library of Medicine. 14 July 2018. Retrieved 19 July 2018.
  5. ↑ "Olive Oil and Olive-Pomace Oil Grades and Standards | Agricultural Marketing Service". www.ams.usda.gov. Retrieved 2016-01-20.
  6. ↑ 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.
  7. ↑ "Comparison of Dietary Fats Chart". Canola Council of Canada. Archived from the original on 2008-06-06. Retrieved 2008-09-03.
  8. ↑ "The Inheritance of High Oleic Acid in Peanut". The Journal of Heredity. 80 (3): 252–3. 1989.
  9. ↑ "Nutrient database, Release 25". United States Department of Agriculture.
  10. ↑ Nasaruddin, Mohd hanif; Noor, Noor Qhairul Izzreen Mohd; Mamat, Hasmadi (2013). "Komposisi Proksimat dan Komponen Asid Lemak Durian Kuning (Durio graveolens) Sabah" [Proximate and Fatty Acid Composition of Sabah Yellow Durian (Durio graveolens)] (PDF). Sains Malaysiana (in Malay). 42 (9): 1283–1288. ISSN 0126-6039. OCLC 857479186. Retrieved 28 November 2017.
  11. ↑ 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.
  12. ↑ 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. PMID 495536.
  13. ↑ Oliveira, AF; Chunha, DA; Ladriere, L; et al. (May 2015). "In vitro use of free fatty acids bound to albumin: A comparison of protocols". BioFeedback. BioTechniques (Letter to the Editor). 58 (5): 228–33. doi:10.2144/000114285. PMID 25967901.
  14. ↑ Purnamadjaja, Anies Hannawati; Russell, R. Andrew (2005). "Pheromone communication in a robot swarm: Necrophoric bee behaviour and its replication". Robotica. 23 (6): 731–42. doi:10.1017/S0263574704001225.
  15. ↑ Ayasse, M.; Paxton, R. (2002). "Brood protection in social insects". In Hilker, M.; Meiners, T. Chemoecology of Insect Eggs and Egg Deposition. Berlin: Blackwell. pp. 117–48. ISBN 1-4051-0694-8.
  16. ↑ Krulwich, Robert (2009). "Hey I'm Dead! The Story Of The Very Lively Ant". NPR.
  17. ↑ Walker, Matt (2009-09-09). "Ancient 'smell of death' revealed". BBC - Earth News. Retrieved 2009-09-13.
  18. ↑ Cornils, Boy; Lappe, Peter (2000). "Dicarboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a08_523. ISBN 3-527-30673-0.
  19. ↑ Tardy, Anne-Laure; Morio, Beatrice; Chardigny, Jean-Michel; Malpuech-Brugere, Corinne "Ruminant and industrial sources of trans-fat and cardiovascular and diabetic diseases" Nutrition Research Reviews 2011, volume 24, pp. 111-117. doi:10.1017/S0954422411000011
  20. ↑ 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.
  21. ↑ Carrasco, F. (2009). "Ingredientes Cosméticos". Diccionario de Ingredientes (4th ed.). p. 428. ISBN 978-84-613-4979-1.
  22. ↑ Smolinske, Susan C. (1992). Handbook of Food, Drug, and Cosmetic Excipients. pp. 247–8. ISBN 978-0-8493-3585-3.
  23. ↑ Julien, M; Hoeffel, JM; Flick, MR (1986). "Oleic acid lung injury in sheep". Journal of Applied Physiology. 60 (2): 433–40. PMID 3949648.
  24. ↑ Duncan, Alastair (2003). The Technique of Leaded Glass. p. 77. ISBN 0-486-42607-6.
  25. ↑ 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.
  26. ↑ "You Can Control Your Cholesterol: A Guide to Low-Cholesterol Living". Merck & Co. Inc. Archived from the original on 2009-03-03. Retrieved 2009-03-14.
  27. ↑ 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.
  28. ↑ Pala, V.; Krogh, V.; Muti, P.; Chajes, V.; Riboli, E.; Micheli, A.; Saadatian, M.; Sieri, S.; Berrino, F. (2001). "Erythrocyte Membrane Fatty Acids and Subsequent Breast Cancer: A Prospective Italian Study". JNCI Journal of the National Cancer Institute. 93 (14): 1088–95. doi:10.1093/jnci/93.14.1088. PMID 11459870.
  29. ↑ Martin-Moreno JM, Willett WC, Gorgojo L, Banegas JR, Rodriguez-Artalejo F, Fernandez-Rodriguez JC, Maisonneuve P, Boyle P (1994). "Dietary fat, olive oil intake and breast cancer risk". International Journal of Cancer. 58 (6): 774–780. doi:10.1002/ijc.2910580604. PMID 7927867.
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