Oleic acid

Oleic acid
Oleic acid
CAS number 112-80-1 YesY
Jmol-3D images Image 1
Molecular formula C18H34O2
Molar mass 282.4614 g/mol
Appearance Pale yellow or brownish yellow oily liquid with lard-like odor
Density 0.895 g/mL
Melting point

13-14 °C (286 K)

Boiling point

360 °C (633 K) (760mm Hg)[1]

Solubility in water Insoluble
Solubility in methanol Soluble
 N acid (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Oleic acid is a monounsaturated omega-9 fatty acid found in various animal and vegetable fats. It has the formula CH3(CH2)7CH=CH(CH2)7COOH.[2] It is an odorless, colourless oil, although commercial samples may be yellowish. The trans isomer of oleic acid is called elaidic acid (hence the name elaidinization for a reaction that switches cis isomers to trans isomers). The term "oleic" means related to, or derived from, oil or olive.



Triglyceride esters of oleic acid compose the majority of olive oil, although there may be less than 2.0% as free acid in the virgin olive oil, with higher concentrations making the olive oil inedible. It also makes up 59-75% of pecan oil,[3] 36-67% of peanut oil,[4] 15-20% of grape seed oil, sea buckthorn oil, and sesame oil,[2] and 14% of poppyseed oil.[5] It is abundantly present in many animal fats, constituting 37 to 56% of chicken and turkey fat,[6] and 44 to 47% of lard, etc.

Oleic acid is the most abundant fatty acid in human adipose tissue.[7]

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[8] or ant[9][10] is daubed 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.[11]

Production and chemical behavior

The biosynthesis of oleic acid results from 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:[12]

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

Esters of azelaic acid find applications in lubrication and plasticizers.


The dominant use of oleic acid is as its sodium salt, which a major component of many kinds of soap. Small amounts of oleic acid are used as an excipient in pharmaceuticals, oleic acid is used as an emulsifying or solubilizing agent in aerosol products.[13] 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.[14] This sort of research has been of particular benefit to premature newborns, for whom treatment for underdeveloped lungs (and associated complications) often is a matter of life and death.

Health effects

Positive health effects of the substance have been documented. Oleic acid may hinder the progression of adrenoleukodystrophy (ALD), a fatal disease that affects the brain and adrenal glands.[15] Oleic acid may be responsible for the hypotensive (blood pressure reducing) effects of olive oil.[16] 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.[17]


  1. ^ Oleic acid, Chemical Laboratory Information Profile, American Chemical Society
  2. ^ a b Alfred Thomas (2002). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_173. ISBN 3527306730. 
  3. ^ Villarreal, J.E., L. Lombardini, and L. Cisneros-Zevallos (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. http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6T6R-4M1DB79-2&_user=952835&_coverDate=12%2F31%2F2007&_rdoc=1&_fmt=high&_orig=search&_sort=d&_docanchor=&view=c&_searchStrId=1412335994&_rerunOrigin=google&_acct=C000049198&_version=1&_urlVersion=0&_userid=952835&md5=589de1e394ce2412a09767a3b5f542be. 
  4. ^ http://jhered.oxfordjournals.org/cgi/pdf_extract/80/3/252
  5. ^ Untoro J, Schultink W, West CE, Gross R, Hautvast JG (November 2006). "Efficacy of oral iodized peanut oil is greater than that of iodized poppy seed oil among Indonesian schoolchildren". The American Journal of Clinical Nutrition 84 (5): 1208–14. PMID 17093176. 
  6. ^ http://www.springerlink.com/content/0837289583682243/
  7. ^ MG Kokatnur, MC Oalmann, WD Johnson, GT Malcom and JP Strong (November 1, 1979). "Fatty acid composition of human adipose tissue from two anatomical sites in a biracial community". American Journal of Clinical Nutrition 32 (11): 2198–205. PMID 495536. http://www.ajcn.org/cgi/content/abstract/32/11/2198. 
  8. ^ Anies Hannawati Purnamadjaja, R. Andrew Russell (2005). "Pheromone communication in a robot swarm: necrophoric bee behaviour and its replication". Robotica 23 (6): 731–742. doi:10.1017/S0263574704001225. 
  9. ^ 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. 117–148. ISBN 1405106948. 
  10. ^ Krulwich, Robert (2009). "Hey I'm Dead! The Story Of The Very Lively Ant". NPR. http://www.npr.org/templates/story/story.php?storyId=102601823. 
  11. ^ Walker, Matt (2009-09-09). "Ancient 'smell of death' revealed". BBC - Earth News. http://news.bbc.co.uk/earth/hi/earth_news/newsid_8232000/8232607.stm. Retrieved 2009-09-13. 
  12. ^ Boy Cornils, Peter Lappe "Dicarboxylic Acids, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a08_523
  13. ^ Smolinske, Susan C. (1992). Handbook of Food, Drug, and Cosmetic Excipients. pp. 247–248. ISBN 084933585X, 9780849335853. 
  14. ^ Julien M, Hoeffel JM, Flick MR (February, 1986). "Oleic acid lung injury in sheep". Journal of Applied Physiology. http://www.ncbi.nlm.nih.gov/pubmed/3949648. 
  15. ^ "Adrenoleukodystrophy: oleic acid lowers fibroblast saturated C22-26 fatty acids". National Center for Biotechnology Information. 1986-03-03. http://www.ncbi.nlm.nih.gov/pubmed/3951702. Retrieved 2008-10-07. 
  16. ^ Terés, S; Barceló-Coblijn, G; Benet, M; Alvarez, R; Bressani, R; Halver, Je; Escribá, Pv (September 2008). "Oleic acid content is responsible for the reduction in blood pressure induced by olive oil". PNAS 105 (37): 13811–6. doi:10.1073/pnas.0807500105. PMC 2544536. PMID 18772370. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2544536. 
  17. ^ Valeria Pala, Vittorio Krogh, Paola Muti, Véronique Chajès, Elio Riboli, Andrea Micheli, Mitra Saadatian, Sabina Sieri, Franco Berrino (July 18, 2001). "Erythrocyte Membrane Fatty Acids and Subsequent Breast Cancer: a Prospective Italian Study". JNCL 93 (14): 1088–95. doi:10.1093/jnci/93.14.1088. PMID 11459870. http://jnci.oxfordjournals.org/cgi/content/full/93/14/1088. Retrieved 2008-11-30. 

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  • oleic acid — Chem. a colorless, odorless, liquid, water insoluble, unsaturated acid, C18H34O2, obtained from animal tallow and natural vegetable oils, in which it occurs as the glycerol ester: used chiefly in the manufacture of soap, commercial oleates, and… …   Universalium

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  • oleic acid — ole′ic ac′id n. chem. a colorless, odorless, liquid unsaturated acid, C18H34O2, used esp. in the manufacture of soap …   From formal English to slang

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