Oleic acid: Difference between revisions

{{Short description|Monounsaturated omega-9 fatty acid}}

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|Name=Oleic acid

|=Oleic-acid-.

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|=Oleicacid

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|ImageName=Oleic acid

|PIN=(9''Z'')-Octadec-9-enoic acid <!-- Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) -->

|SystematicName=

|OtherNames=Oleic acid<br />(9''Z'')-Octadecenoic acid<br />(''Z'')-Octadec-9-enoic acid<br />''cis''-9-Octadecenoic acid<br />''cis''-Δ⁹-Octadecenoic acid<br />18:1 cis-9

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|Section1={{Chembox Identifiers

| IUPHAR_ligand = 1054

| SMILES = CCCCCCCC\C=C/CCCCCCCC(O)=O

| CASNo_Ref = {{cascite|correct|CAS}}

| PubChem = 445639

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 8659

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 2UMI9U37CP

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 393217

| DrugBank = DB04224

| InChI = 1/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9-

| InChIKey = ZQPPMHVWECSIRJ-KTKRTIGZBB

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9-

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = ZQPPMHVWECSIRJ-KTKRTIGZSA-N

| RTECS =

|Section2={{Chembox Properties

| C=18|H=34|O=2

| Appearance = colorless oily liquid with lard-like odor

| Density = 0.895 g/mL

| Solubility = Insoluble

| SolubleOther = Soluble

| Solvent = [[Ethanol]]

| MeltingPtC = 13 to 14

| BoilingPtC = 360

| BoilingPt_ref = <ref>{{Cite journal |last=Young |first=Jay A. |year=2002 |title=Chemical Laboratory Information Profile: Oleic Acid |journal=Journal of Chemical Education |volume=79 |issue=1 |pages=24 |bibcode=2002JChEd..79...24Y |doi=10.1021/ed079p24}}</ref>

| pKa =

| pKb =

| Viscosity =

| MagSus = -208.5·10⁻⁶ cm³/mol

|Section3={{Chembox Structure

| MolShape =

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| CrystalStruct =

| Dipole =

|Section7={{Chembox Hazards

| = [http://.com/msds//o3596.htm JT Baker]

| MainHazards =

| FlashPt =

| =

| =

| NFPA-R = 0

|Section8={{Chembox Related

| OtherAnions =

| OtherCations =

| OtherCompounds = [[Elaidic acid]]

'''Oleic acid''' is a [[fatty acid]] that occurs naturally in various [[animal fat|animal]] and [[vegetable oil|vegetable fats and oils]]. It is an odorless, colorless oil, although commercial samples may be yellowish due to the presence of impurities. In chemical terms, oleic acid is classified as a [[monounsaturated fat|monounsaturated]] [[omega-9 fatty acid]], abbreviated with a [[lipid number]] of 18:1 [[cis–trans isomerism|''cis'']]-9, and a main product of [[Stearoyl-CoA 9-desaturase|Δ9-desaturase]].<ref>{{Cite journal |last1=Nakamura |first1=Manabu T. |last2=Nara |first2=Takayuki Y. |date=2004 |title=Structure, function, and dietary regulation of Δ6, Δ5, and Δ9 desaturases |url=https://www.annualreviews.org/doi/10.1146/annurev.nutr.24.121803.063211 |journal=[[Annual Review of Nutrition]] |volume=24 |pages=345–376 |doi=10.1146/annurev.nutr.24.121803.063211 |pmid=15189125 |url-access=subscription}}</ref> It has the formula {{chem2|CH3\s(CH2)7\sCH\dCH\s(CH2)7\sCOOH}}.<ref name=Ullmann />{{Page needed|date=February 2023}} The name derives from the Latin word ''[[wikt:oleum|oleum]]'', which means oil.<ref>{{Cite journal |last=Bailey and Bailey |first=Dorothy and Kenneth |year=1929 |title=An Etymological Dictionary of Chemistry and Mineralogy |journal=Nature |volume=124 |issue=3134 |pages=789–790 |bibcode=1929Natur.124..789V |doi=10.1038/124789b0|s2cid=4024133 }}</ref> It is the most common fatty acid in nature.<ref>{{Cite web |url=https://pubchem.ncbi.nlm.nih.gov/compound/965#section=Top |title=9-Octadecenoic acid |date=14 July 2018 |publisher=PubChem, National Center for Biotechnology Information, US National Library of Medicine |access-date=19 July 2018}}</ref> The salts and esters of oleic acid are called '''oleates'''. It is a common component of oils, and thus occurs in many types of food, as well as in soap.

==Occurrence==

Fatty acids (or their salts) often do not occur as such in biological systems. Instead fatty acids such as oleic acid occur as their [[ester]]s, commonly [[triglyceride]]s, which are the greasy materials in many natural oils. Oleic acid is the most common monounsaturated fatty acid in nature. It is found in fats (triglycerides), the phospholipids that make membranes, [[cholesterol ester|cholesteryl ester]]s, and [[wax ester]]s.<ref name=Ntambi />

[[Triglyceride]]s of oleic acid comprise the majority of [[olive oil]] (about 70%).<ref name=oleic>{{Cite web |url=http://www.ams.usda.gov/grades-standards/olive-oil-and-olive-pomace-oil-grades-and-standards |title=Olive Oil and Olive-Pomace Oil Grades and Standards {{!}} Agricultural Marketing Service |website=www.ams.usda.gov |access-date=2016-01-20}}</ref> It also makes up 59–75% of [[pecan oil]],<ref>{{Cite journal |last1=Villarreal-Lozoya |first1=Jose E. |last2=Lombardini |first2=Leonardo |last3=Cisneros-Zevallos |first3=Luis |year=2007 |title=Phytochemical constituents and antioxidant capacity of different pecan Carya illinoinensis (Wangenh.) K. Koch cultivars |journal=Food Chemistry |volume=102 |issue=4 |pages=1241–1249 |doi=10.1016/j.foodchem.2006.07.024}}{{closed access}}</ref> 61% of [[canola]] oil,<ref name="ccc">{{Cite web |url=http://www.canola-council.org/canola_resources/product45.aspx |title=Comparison of Dietary Fats Chart |publisher=Canola Council of Canada |url-status=dead |archive-url=https://web.archive.org/web/20080606083831/http://www.canola-council.org/canola_resources/product45.aspx |archive-date=2008-06-06 |access-date=2008-09-03}}</ref> 36–67% of [[peanut oil]],<ref name="hopeanut">{{Cite journal |last1=Moore |first1=K. M. |last2=Knauft |first2=D. A. |year=1989 |title=The Inheritance of High Oleic Acid in Peanut |journal=The Journal of Heredity |volume=80 |issue=3 |pages=252–3 |doi=10.1093/oxfordjournals.jhered.a110845}}{{closed access}}</ref> 60% of [[macadamia oil]], 20–80% of [[sunflower oil]],<ref name="USDA">{{Cite web |url=https://fdc.nal.usda.gov |title=Nutrient database, Release 25 |publisher=United States Department of Agriculture}}(NDB ID: 04678, 04584)</ref> 15–20% of [[grape seed oil]], [[sea buckthorn oil]], 40% of [[sesame oil]],<ref name="Ullmann">{{Cite book |last=Thomas |first=Alfred |url=https://onlinelibrary.wiley.com/doi/10.1002/14356007.a10_173 |title=Ullmann's Encyclopedia of Industrial Chemistry |year=2000 |isbn=978-3-527-30673-2 |chapter=Fats and Fatty Oils |doi=10.1002/14356007.a10_173 |url-access=subscription}}</ref> and 14% of [[poppyseed oil]]. High oleic variants of plant sources such as sunflower (~80%) and canola oil (70%) also have been developed.<ref name="USDA" /> [[Karuka]] contains 52.39% oleic acid.<ref name="Purwanto">{{Cite journal |last1=Purwanto |first1=Y. |last2=Munawaroh |first2=Esti |date=2010 |title=Etnobotani Jenis-Jenis Pandanaceae Sebagai Bahan Pangan di Indonesia |trans-title=Ethnobotany Types of Pandanaceae as Foodstuffs in Indonesia |url=https://rin.lipi.go.id/file.xhtml;jsessionid=ccb24f0a337710227d6d5cecae10?fileId=1258&version=RELEASED&version=.1 |url-status=dead |format=PDF |journal=Berkala Penelitian Hayati |language=id |volume=5A |pages=97–108 |doi=10.5072/FK2/Z6P0OQ |issn=2337-389X |oclc=981032990 |archive-url=https://web.archive.org/web/20181029232426/https://rin.lipi.go.id/file.xhtml;jsessionid=ccb24f0a337710227d6d5cecae10?fileId=1258&version=RELEASED&version=.1 |archive-date=29 October 2018 |access-date=25 October 2018}}</ref> It is abundantly present in many animal fats, constituting 37 to 56% of chicken and turkey fat,<ref>{{Cite journal |last1=Nutter |first1=Mary K. |last2=Lockhart |first2=Ernest E. |last3=Harris |first3=Robert S. |year=1943 |title=The chemical composition of depot fats in chickens and turkeys |journal=Oil & Soap |volume=20 |issue=11 |pages=231–4 |doi=10.1007/BF02630880|s2cid=84893770 }}{{closed access}}</ref> and 44 to 47% of [[lard]].

Free oleic acid occurs in oils and fats as a product of the breakdown of triglycerides. Olive oil exceeding 2% [[Olive oil acidity|free oleic acid]] is graded unfit for human consumption. See {{section link|Fatty acid|Free fatty acids}}.<ref name=oleic/>

Oleic acid is the most abundant fatty acid in human [[adipose tissue]],<ref>{{Cite journal |last1=Kokatnur |first1=MG |last2=Oalmann |first2=MC |last3=Johnson |first3=WD |last4=Malcom |first4=GT |last5=Strong |first5=JP |year=1979 |title=Fatty acid composition of human adipose tissue from two anatomical sites in a biracial community |journal=The American Journal of Clinical Nutrition |volume=32 |issue=11 |pages=2198–205 |doi=10.1093/ajcn/32.11.2198 |pmid=495536}}{{open access}}</ref> and second in abundance in human tissues overall, following [[palmitic acid]].

== Production and chemical behavior ==

The [[biosynthesis]] of oleic acid involves the action of the enzyme [[stearoyl-CoA 9-desaturase]] acting on [[stearoyl-CoA]]. In effect, [[stearic acid]] is [[Dehydrogenation|dehydrogenated]] to give the monounsaturated derivative, oleic acid.<ref name="Ntambi">{{Cite journal |author=Ntambi, James M. |author2=Miyazaki, Makoto |year=2003 |title=Recent insights into stearoyl-CoA desaturase-1 |journal=Current Opinion in Lipidology |volume=14 |issue=3 |pages=255–61 |doi=10.1097/00041433-200306000-00005 |pmid=12840656|s2cid=45954457 }}</ref>

Oleic acid undergoes the typical reactions of carboxylic acids and [[alkene]]s. It is soluble in [[Base (chemistry)|aqueous base]] to give [[soap]]s called oleates. Iodine adds across the double bond. Hydrogenation of the double bond yields the [[Saturated and unsaturated compounds|saturated]] derivative [[stearic acid]]. [[Redox|Oxidation]] at the [[double bond]] occurs slowly in air, and is known as [[rancidification]] in foodstuffs and as [[drying oil|drying]] in coatings.

[[Redox|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:<ref>{{Cite book |last1=Cornils |first1=Boy |title=Ullmann's Encyclopedia of Industrial Chemistry |last2=Lappe |first2=Peter |year=2000 |isbn=978-3-527-30673-2 |chapter=Dicarboxylic Acids, Aliphatic |doi=10.1002/14356007.a08_523}}</ref>

:{{chem2|H17C8CH\dCHC7H14CO2H + 4"O" → HO2CC7H14CO2H + H17C8CO2H}}

Neutralizing oleic acid with [[ethanolamine]]s gives the [[protic ionic liquid]] [[monoethanolamine oleate]].<ref>{{cite journal |doi=10.1021/acs.jpcb.7b01384 |title=Phase Behavior and Physical Properties of New Biobased Ionic Liquid Crystals |date=2017 |last1=Toledo Hijo |first1=Ariel A. C. |last2=Maximo |first2=Guilherme J. |last3=Costa |first3=Mariana C. |last4=Cunha |first4=Rosiane L. |last5=Pereira |first5=Jorge F. B. |last6=Kurnia |first6=Kiki A. |last7=Batista |first7=Eduardo A. C. |last8=Meirelles |first8=Antonio J. A. |journal=The Journal of Physical Chemistry B |volume=121 |issue=14 |pages=3177–3189 |pmid=28332847 }}</ref>

== Related compounds ==

The [[Cis–trans isomerism|trans isomer]] of oleic acid is called [[elaidic acid]] or ''trans''-9-octadecenoic acid. These isomers have distinct physical properties and biochemical properties. Elaidic acid, the most abundant trans fatty acid in diet, appears to have an adverse effect on health.<ref>{{cite journal | last1 = Tardy | first1 = Anne-Laure | last2 = Morio | first2 = Beatrice | last3 = Chardigny | first3 = Jean-Michel | last4 = Malpuech-Brugere | first4 = Corinne | year = 2011 | title = Ruminant and industrial sources of trans-fat and cardiovascular and diabetic diseases | journal = Nutrition Research Reviews | volume = 24 | issue = 1| pages = 111–117 | doi = 10.1017/S0954422411000011 | pmid = 21320382 | doi-access = free }}</ref> A reaction that converts oleic acid to elaidic acid is called [[elaidinization]].

Another naturally occurring isomer of oleic acid is [[petroselinic acid]].

In chemical analysis, fatty acids are separated by gas chromatography of their methyl ester derivatives. Alternatively, separation of unsaturated isomers is possible by [[Argentation chromatography|argentation thin-layer chromatography]].<ref>{{Cite journal |last1=Breuer |first1=B. |last2=Fock |first2=H. P. |year=1987 |title=Separation of fatty acids or methyl esters including positional and geometric isomers by alumina argentation thin-layer chromatography |journal=J. Chromatogr. Sci. |volume=25 |issue=7 |pages=302–306 |doi=10.1093/chromsci/25.7.302 |pmid=3611285}}</ref>

In [[ethenolysis]], '''methyl oleate''', the ''methyl ester'' of the acid, converts to [[1-decene]] and methyl 9-[[Decenoic acid|decenoate]]:<ref>{{ cite journal | last1 = Marinescu | first1 = Smaranda C. | last2 = Schrock | first2 = Richard R. | last3 = Müller | first3 = Peter | last4 = Hoveyda | first4 = Amir H. | title = Ethenolysis Reactions Catalyzed by Imido Alkylidene Monoaryloxide Monopyrrolide (MAP) Complexes of Molybdenum | journal = J. Am. Chem. Soc. | year = 2009 | volume = 131 | issue = 31 | pages = 10840–10841 | doi = 10.1021/ja904786y | pmid=19618951}}</ref>

:{{chem2|CH3(CH2)7CH\dCH(CH2)7CO2Me + '''CH2\dCH2''' -> CH3(CH2)7CH\d'''CH2''' + MeO2C(CH2)7CH\d'''CH2'''}}

==Dietary sources==

{{Vegetable oils, composition}}

== Uses ==

[[File:Comparison of dietary fat composition.svg|thumb|Safflower and olive oil have one of the highest levels of oleic acid among dietary fats]]

Oleic acid is used as a component in many foods, in the form of its triglycerides. It is a component of the normal human diet, being a part of animal fats and vegetable oils.

Oleic acid as its sodium salt is a major component of soap as an [[Emulsion|emulsifying agent]]. It is also used as an [[Moisturizer|emollient]].<ref name="Carrasco">{{Cite book |last=Carrasco |first=F. |title=Diccionario de Ingredientes |year=2009 |isbn=978-84-613-4979-1 |edition=4th |page=428 |chapter=Ingredientes Cosméticos|publisher=Francisco Carrasco Otero }}</ref> Small amounts of oleic acid are used as an [[excipient]] in pharmaceuticals, and it is used as an emulsifying or solubilizing agent in aerosol products.<ref>{{Cite book |last=Smolinske |first=Susan C. |title=Handbook of Food, Drug, and Cosmetic Excipients |year=1992 |isbn=978-0-8493-3585-3 |pages=247–8|publisher=CRC Press }}</ref>

[[E.O. Wilson]] found that oleic acid is used by ants; when a dead ant's corpse begins to emit oleic acid, other ants in the [[Ant colony|colony]] transport it away to the ant refuse pile.<ref>{{Cite journal |last1=Wilson |first1=E. O. |last2=Durlach |first2=N. I. |last3=Roth |first3=L. M. |date=December 1958 |title=Chemical Releasers of Necrophoric Behavior in Ants |journal=Psyche: A Journal of Entomology |language=en |volume=65 |issue=4 |pages=108–114 |doi=10.1155/1958/69391 |issn=0033-2615 |doi-access=free}}</ref><ref>{{Cite web |title='Hey I'm Dead!' The Story Of The Very Lively Ant |website=[[NPR]] |url=https://www.npr.org/sections/krulwich/2009/04/01/102601823/hey-im-dead-the-story-of-the-very-lively-ant}}</ref><ref>{{Cite web |title=How ants determine the death of another ant {{!}} Britannica |url=https://www.britannica.com/video/193428/Edward-O-Wilson-ants-research-ant |access-date=2023-07-03 |website=www.britannica.com |language=en}}</ref><ref>{{Cite journal |last1=Diez |first1=Lise |last2=Moquet |first2=Laura |last3=Detrain |first3=Claire |date=2013-12-01 |title=Post-mortem Changes in Chemical Profile and their Influence on Corpse Removal in Ants |url=https://doi.org/10.1007/s10886-013-0365-1 |journal=Journal of Chemical Ecology |language=en |volume=39 |issue=11 |pages=1424–1432 |doi=10.1007/s10886-013-0365-1 |pmid=24242873 |bibcode=2013JCEco..39.1424D |s2cid=254654298 |issn=1573-1561}}</ref>

=== Niche uses ===

Oleic acid is used to induce lung damage in certain types of animals for the purpose of testing new drugs and other means to treat lung diseases. Specifically in sheep, intravenous administration of oleic acid causes acute lung injury with corresponding [[pulmonary edema]].<ref name="sheep">{{Cite journal |last1=Julien |first1=M |last2=Hoeffel |first2=JM |last3=Flick |first3=MR |year=1986 |title=Oleic acid lung injury in sheep |journal=Journal of Applied Physiology |volume=60 |issue=2 |pages=433–40 |doi=10.1152/jappl.1986.60.2.433 |pmid=3949648}}</ref>

Oleic acid is used as a soldering flux in stained glass work for joining [[Came glasswork#Lead|lead came]].<ref>{{Cite book |last=Duncan |first=Alastair |title=The Technique of Leaded Glass |year=2003 |isbn=978-0-486-42607-5 |pages=77|publisher=Dover Publications }}</ref>

== Health effects ==

Oleic acid is the most common [[monounsaturated fat]] in the human diet (~90% of all monounsaturated fats).<ref>{{cite journal|vauthors=Schwingshackl L, Hoffmann G|year=2014|title=Monounsaturated fatty acids, olive oil and health status: a systematic review and meta-analysis of cohort studies|journal=Lipids in Health and Disease|volume=13|issue=|pages=154|pmid=25274026|doi=10.1186/1476-511X-13-154|pmc=4198773 |doi-access=free }}</ref> Monounsaturated fat consumption has been associated with decreased [[low-density lipoprotein]] (LDL) cholesterol, and possibly with increased [[high-density lipoprotein]] (HDL) cholesterol.<ref>{{Cite web |url=http://www.mercksource.com/pp/us/cns/cns_krames_template.jspzQzpgzEzzSzppdocszSzuszSzcnszSzcontentzSzkrameszSz1292_01zPzhtm |title=You Can Control Your Cholesterol: A Guide to Low-Cholesterol Living |publisher=[[Merck & Co.]] Inc. |url-status=dead |archive-url=https://web.archive.org/web/20090303124418/http://www.mercksource.com/pp/us/cns/cns_krames_template.jspzQzpgzEzzSzppdocszSzuszSzcnszSzcontentzSzkrameszSz1292_12zPzhtm |archive-date=2009-03-03 |access-date=2009-03-14}}</ref> Oleic acid may be responsible for the [[antihypertensive drug|hypotensive]] ([[blood pressure]] reducing) effects of [[olive oil]] that is considered a health benefit.<ref>{{Cite journal |last1=Teres |first1=S. |last2=Barcelo-Coblijn |first2=G. |last3=Benet |first3=M. |last4=Alvarez |first4=R. |last5=Bressani |first5=R. |last6=Halver |first6=J. E. |last7=Escriba |first7=P. V. |year=2008 |title=Oleic acid content is responsible for the reduction in blood pressure induced by olive oil |journal=Proceedings of the National Academy of Sciences |volume=105 |issue=37 |pages=13811–6 |bibcode=2008PNAS..10513811T |doi=10.1073/pnas.0807500105 |jstor=25464133 |pmc=2544536 |pmid=18772370|doi-access=free }}</ref> A 2017 review found that diets enriched in oleic acid are beneficial for regulating body weight.<ref>{{cite journal|last1=Tutunchi|first1=Helda|last2=Ostadrahimi|first2=Alireza|last3=Saghafi-Asl|first3=Maryam|year=2020|title=The Effects of Diets Enriched in Monounsaturated Oleic Acid on the Management and Prevention of Obesity: a Systematic Review of Human Intervention Studies|journal=Advances in Nutrition|url=https://academic.oup.com/advances/article/11/4/864/5782385|volume=11|issue=4|pages=864–877|pmid=32135008|doi=10.1093/advances/nmaa013|pmc=7360458}}</ref>

The United States [[FDA]] has approved a health claim on reduced risk of coronary heart disease for high oleic (> 70% oleic acid) oils.<ref>{{cite web |last1=Nutrition |first1=Center for Food Safety and Applied |title=FDA Completes Review of Qualified Health Claim Petition for Oleic Acid and the Risk of Coronary Heart Disease |url=https://www.fda.gov/food/cfsan-constituent-updates/fda-completes-review-qualified-health-claim-petition-oleic-acid-and-risk-coronary-heart-disease |website=FDA |language=en |date=20 December 2019}}</ref> Some oil plants have cultivars bred to increase the amount of oleic acid in the oils. In addition to providing a health claim, the heat stability and shelf life may also be improved, but only if the increase in monounsaturated oleic acid levels correspond to a substantial reduction in polyunsaturated fatty acid (especially [[α-Linolenic acid|α-linolenic acid]]) content.<ref>{{cite journal |last1=Aladedunye |first1=Felix |last2=Przybylski |first2=Roman |title=Frying stability of high oleic sunflower oils as affected by composition of tocopherol isomers and linoleic acid content |journal=Food Chemistry |date=December 2013 |volume=141 |issue=3 |pages=2373–2378 |doi=10.1016/j.foodchem.2013.05.061|pmid=23870970 }}</ref><ref>{{cite web |title=Properties of High Oleic Seed Oils |url=https://extension.okstate.edu/fact-sheets/properties-of-high-oleic-seed-oils.html |website=Oklahoma State University Extension |language=en |date=19 November 2020}}</ref> When the saturated fat or trans fat in a [[frying|fried food]] is replaced with a stable high oleic oil, consumers may be able to avoid certain [[Saturated fat#Association with diseases|health risks associated with consuming saturated fat]] and [[trans fat]].<ref>{{cite web |title=High-oleic canola oils and their food applications |url=https://www.aocs.org/stay-informed/inform-magazine/featured-articles/high-oleic-canola-oils-and-their-food-applications-september-2012 |website=The American Oil Chemists' Society}}</ref><ref name=Canada>{{cite book|isbn=0-662-43689-X|author=Trans Fat Task Force|title=TRANSforming the Food Supply|date=June 2006|publisher=Trans Fat Task Force |url=http://www.hc-sc.gc.ca/fn-an/nutrition/gras-trans-fats/tf-ge/tf-gt_rep-rap_e.html|access-date=7 January 2007}}</ref>

== See also ==

* [[Oleylamine]] – the corresponding amine

* [[Oleamide]] – the corresponding amide

== References ==

{{Reflist|30em}}

== External links ==

*[https://web.archive.org/web/20111003004433/http://lipidlibrary.aocs.org/Lipids/fa_mono/index.htm FATTY ACIDS: STRAIGHT-CHAIN MONOENOIC] (The AOCS Lipid Library)

*[http://webbook.nist.gov/cgi/cbook.cgi?ID=C2027476&Units=SI 9-octadecenoic acid] (NIST Chemistry Webbook)

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