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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-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
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.

Additional recommended knowledge

Essential Laboratory Skills Guide

Daily Sensitivity Test

What is the Sensitivity of my Balance?

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]

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^[4] or ant^[5] is daubed with oleic acid, it is dragged off as if it were dead.

References

^ http://membership.acs.org/c/ccs/pubs/CLIPS/JCE20020024.pdf
^ 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.
^ 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.