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Oleic acid
   
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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-?9-Octadecenoic acid
Oleic acid
18:1 cis-9
Identifiers
CAS number [112-80-1]
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
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 sources. It has the formula C18H34O2 (or CH3(CH2)7CH=CH(CH2)7COOH).[2] The saturated form of this acid is stearic acid.

Contents

Occurrence

Oleic acid makes up 55-80% of olive oil, though there may be only 0.5-2.5% or so as actual free acid, and 15-20% of grape seed oil and sea buckthorn oil.[3] The Brazilian palmberry, açaí, contains one of the highest contents known for oleic acid in the pulp of a fruit (56%).[4]

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[5] or ant[6] is daubed with oleic acid, it is dragged off as if it were dead.

Chemistry

Reduction of oleic acid at the carboxyl end yields oleyl alcohol.

Salts of oleic acid are called oleates.

If dropped onto water, oleic acid spreads out into a very thin layer, only a molecule thick if allowed.[citation needed]

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. ^ Li, Thomas S. C. (1999). Sea buckthorn: New crop opportunity, from Perspectives on new crops and new uses by J. Janeck (ed.) Retrieved 2006-10-28.
  4. ^ Schauss AG, Wu X, Prior RL, Ou B, Patel D, Huang D, Kababick JP. Phytochemical and nutrient composition of the freeze-dried amazonian palm berry, Euterpe oleraceae Mart. (acai). J Agric Food Chem. 2006 Nov 1;54(22):8598-603. [1]
  5. ^ 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. 
  6. ^ 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.

External links



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