Oleic acid

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Categories: Fatty acids | Carboxylic acids

Oleic acid
Image:Oleic-acid-skeletal.svg
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]
SMILES	CCCCCCCC\C=C/CCCCCCC(OH)=O
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 in water; soluble in Methanol
Hazards
MSDS	ScienceLab.com
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and 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.

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].

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

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.

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.
^ 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.
^ 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]
^ 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.
^ 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

NIST Chemistry Webbook

v • d • e Lipids: fatty acids
Saturated	Butyric - Hexanoic - Caprylic - Decanoic - Lauric - Myristic - Palmitic - Stearic - Arachidic - Behenic - Lignoceric
Omega-3 fatty acid	Alpha-linolenic - Stearidonic acid - Eicosapentaenoic acid - Docosahexaenoic acid
Omega-6 fatty acid	Linoleic - Gamma-Linolenic acid - Dihomo-gamma-linolenic acid - Arachidonic
Omega-9 fatty acid	Oleic - Erucic