Oleic acid

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Occurrence

Triglyceride esters of oleic acid comprise the majority of olive oil, though there may be less than 2.0% as actual free acid in the virgin olive oil, while higher concentrations make the olive oil inedible. It also makes up 36-67% of peanut oil, 15-20% of grape seed oil, sea buckthorn oil, and sesame oil, and 14% of poppyseed oil.

Oleic acid is the most abundant fatty acid in human adipose tissue. chocolate fountain recipe

Smell of death mango pulp

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 or ant is daubed with oleic acid, it is dragged off as if it were dead. This is why oleic acid is also sometimes referred as "smell of death". The repellent smell indicates to living insects how to avoid others that have succumbed to disease or places where predators lurk. This "death recognition system" based on a simple fatty acid likely evolved over 400 million years ago.

Chemistry

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

Uses

As an excipient in pharmaceuticals, oleic acid is used as an emulsifying or solubilizing agent in aerosol products.

Health effects

Oleic acid may hinder the progression of ALD, or Adrenoleukodystrophy, a fatal disease that affects the brain and adrenal glands.

Oleic acid may help boost memory.

Oleic and monounsaturated fatty acid levels in the membranes of red blood cells have been associated with increased risk of breast cancer. Oleic acid may be responsible for the hypotensive (blood pressure reducing) effects of olive oil.

See also

Fatty acids

Linoleic acid

Pheromone

References

^ Oleic acid, Chemical Laboratory Information Profile, American Chemical Society

^ Bishop, Paul L. (2000). Pollution Prevention: Chapter 2 - Properties and Fates of Environmental Contaminants, instructional slides to accompany Pollution Prevention:Fundamentals and Practice, by Paul L. Bishop (ISBN 0-07-366147-3). Retrieved 2005-03-07.

^ http://jhered.oxfordjournals.org/cgi/pdf_extract/80/3/252

^ Alfred Thomas (2002). "Fats and Fatty Oils". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_173. 

^ 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): 120814. PMID 17093176. 

^ 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. PMID 495536. http://www.ajcn.org/cgi/content/abstract/32/11/2198. 

^ Anies Hannawati Purnamadjaja, R. Andrew Russell (2005). "Pheromone communication in a robot swarm: necrophoric bee behaviour and its replication". Robotica 23 (6): 731742. doi:10.1017/S0263574704001225. 

^ Ayasse, M, Paxton, R (2002) Brood protection in social insects. In: Hilker, M, Meiners, T (eds.). Chemoecology of Insect Eggs and Egg Deposition. Blackwell, Berlin, 117-148.

^ Krulwich, Robert (2009). "Hey I'm Dead! The Story Of The Very Lively Ant" http://www.npr.org/templates/story/story.php?storyId=102601823

^ 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. 

^ Smolinske, Susan C. (1992). Handbook of Food, Drug, and Cosmetic Excipients. pp. 247248. ISBN 084933585X, 9780849335853. 

^ "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. 

^ "Fatty foods 'offer memory boost'". BBC. 27 April 2009. http://news.bbc.co.uk/1/hi/health/8020218.stm. 

^ Valeria Pala, Vittorio Krogh, Paola Muti, Vronique Chajs, 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. doi:10.1093/jnci/93.14.1088. PMID 11459870. http://jnci.oxfordjournals.org/cgi/content/full/93/14/1088. Retrieved 2008-11-30. 

^ Ters, S; Barcel-Coblijn, G; Benet, M; Alvarez, R; Bressani, R; Halver, Je; Escrib, Pv (September 2008). "Oleic acid content is responsible for the reduction in blood pressure induced by olive oil". Proceedings of the National Academy of Sciences of the United States of America 105 (37): 13811. doi:10.1073/pnas.0807500105. PMID 18772370. 

External links

NIST Chemistry Webbook

v  d  e

Lipids: fatty acids

Saturated

Acetic (C2) Propionic (C3) Butyric (C4) Valeric (C5) Hexanoic (C6) Heptanoic (C7) Caprylic (C8) Nonanoic (C9) Capric (C10) Lauric (C12) Myristic (C14) Palmitic (C16) Heptadecanoic (C17) Stearic (C18) Arachidic (C20) Behenic (C22) Lignoceric (C24)

n3 Unsaturated

-Linolenic Stearidonic Eicosapentaenoic Docosahexaenoic

n6 Unsaturated

Linoleic -Linolenic Dihomo--linolenic Arachidonic

n9 Unsaturated

Oleic Elaidic Eicosenoic Erucic Nervonic

Categories: Fatty acids | Carboxylic acids | Excipients | Pheromones | Insect ecology | Insect repellents