Misplaced Pages

This is an old revision of this page, as edited by CheMoBot (talk | contribs) at 19:37, 3 March 2011 (Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Oleic acid

Names
IUPAC name (9Z)-Octadec-9-enoic acid
Other names (9Z)-Octadecenoic acid (Z)-Octadec-9-enoic acid cis-9-Octadecenoic acid cis-Δ-Octadecenoic acid Oleic acid 18:1 cis-9
Identifiers
CAS Number	112-80-1
3D model (JSmol)	Interactive image
ECHA InfoCard	100.003.643
CompTox Dashboard (EPA)	DTXSID1025809
SMILES CCCCCCCC\C=C/CCCCCCCC(O)=O
Properties
Chemical 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)
Solubility in water	Insoluble
Solubility in methanol	Soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is  ?) 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. It is an odorless, colourless oil. 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.

Occurrence

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

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

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 or ant is daubed with oleic acid, it is dragged off as if it were dead. The oleic acid smell indicates to living insects how to avoid others that have succumbed to disease or places where predators lurk.

Production and chemical behavior

Oleic acid exhibits many of 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 yields the saturated derivative called 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:

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

Esters of azelaic acid find applications in lubrication and plasticizers.

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 adrenoleukodystrophy (ALD), a fatal disease that affects the brain and adrenal glands. 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.

References

1. Oleic acid, Chemical Laboratory Information Profile, American Chemical Society
2. ^ Alfred Thomas (2002). "Fats and Fatty Oils". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_173.
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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
4. http://jhered.oxfordjournals.org/cgi/pdf_extract/80/3/252
5. Untoro J, Schultink W, West CE, Gross R, Hautvast JG (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
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 (eds.). Chemoecology of Insect Eggs and Egg Deposition. Blackwell, Berlin, 117-148.
10. Krulwich, Robert (2009). "Hey I'm Dead! The Story Of The Very Lively Ant" http://www.npr.org/templates/story/story.php?storyId=102601823
11. Walker, Matt (2009-09-09). "Ancient 'smell of death' revealed". BBC - Earth News. 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. {{cite book}}: Check |isbn= value: invalid character (help)
14. "Adrenoleukodystrophy: oleic acid lowers fibroblast saturated C22-26 fatty acids". National Center for Biotechnology Information. 1986-03-03. Retrieved 2008-10-07. {{cite web}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
15. 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. Retrieved 2008-11-30.{{cite journal}}: CS1 maint: multiple names: authors list (link)
16. Terés, S; Barceló-Coblijn, G; Benet, M; Alvarez, R; Bressani, R; Halver, Je; Escribá, Pv (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): 13811–6. doi:10.1073/pnas.0807500105. PMC 2544536. PMID 18772370. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)

External links

• NIST Chemistry Webbook

This biochemistry article is a stub. You can help Misplaced Pages by expanding it.

• v
• t
• e

• Fatty acids
• Excipients
• Pheromones
• Insect ecology
• Insect repellents
• Biochemistry stubs