Oleic Acid

Oleic acid
IUPAC name
(9Z)-Octadec-9-enoic acid
other names
(9Z)-Octadecenoic acid
(Z)-Octadec-9-enoic acid
cis-9-Octadecenoic acid
cis-Δ9-Octadecenoic acid
Oleic acid
18:1 cis-9
Identifiers
CAS number 112-80-1 Yes check.svgY
SMILES
Properties
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
Hazards
MSDS ScienceLab.com
 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Oleic acid is a mono-unsaturated omega-9 fatty acid found in various animal and vegetable sources. It has the formula CH3(CH2)7CH=CH(CH2)7COOH.2 The trans-isomer of oleic acid is called elaidic acid.

The term Oleic means related to, or derived from, oil or olive.

Contents

  • 1 Occurrence
  • 2 Smell of death
  • 3 Chemistry
  • 4 Uses
  • 5 Health effects
  • 6 See also
  • 7 References
  • 8 External links

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,3 15-20% of grape seed oil, sea buckthorn oil, and sesame oil, 4 and 14% of poppyseed oil.5

Oleic acid is the most abundant fatty acid in human adipose tissue.6

Smell of death

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 bee7 or ant89 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.10

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.11

Health effects

Oleic acid may hinder the progression of ALD, or Adrenoleukodystrophy, a fatal disease that affects the brain and adrenal glands.12

Oleic acid may help boost memory.13

Oleic and monounsaturated fatty acid levels in the membranes of red blood cells have been associated with increased risk of breast cancer.14 Oleic acid may be responsible for the hypotensive (blood pressure reducing) effects of olive oil.15

See also

  • Fatty acids
  • Linoleic acid
  • Pheromone

References

  1. ^ Oleic acid, Chemical Laboratory Information Profile, American Chemical Society
  2. ^ 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.
  3. ^ http://jhered.oxfordjournals.org/cgi/pdf_extract/80/3/252
  4. ^ Alfred Thomas (2002). "Fats and Fatty Oils". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_173. 
  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. ^ 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. 
  7. ^ 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. 
  8. ^ 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.
  9. ^ Krulwich, Robert (2009). "Hey I'm Dead! The Story Of The Very Lively Ant" http://www.npr.org/templates/story/story.php?storyId=102601823
  10. ^ 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. 
  11. ^ Smolinske, Susan C. (1992). Handbook of Food, Drug, and Cosmetic Excipients. pp. 247–248. ISBN 084933585X, 9780849335853. 
  12. ^ "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. 
  13. ^ "Fatty foods 'offer memory boost'". BBC. 27 April 2009. http://news.bbc.co.uk/1/hi/health/8020218.stm. 
  14. ^ 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. doi:10.1093/jnci/93.14.1088. PMID 11459870. http://jnci.oxfordjournals.org/cgi/content/full/93/14/1088. Retrieved 2008-11-30. 
  15. ^ 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". 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)
n−3 Unsaturated
α-Linolenic • Stearidonic • Eicosapentaenoic • Docosahexaenoic
n−6 Unsaturated
Linoleic • γ-Linolenic • Dihomo-γ-linolenic • Arachidonic
n−9 Unsaturated
Oleic • Elaidic • Eicosenoic • Erucic • Nervonic

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This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article http://en.wikipedia.org/wiki/Oleic_Acid. Additionally, in some cases elements from this article might be licensed under a different license. Please refer to the original article to check the license status http://en.wikipedia.org/wiki/Oleic_Acid.