{{Chembox |ImageFile = Butyloleat.svg |Section1={{Chembox Identifiers | CASNo = 142-77-8 | ChEBI = 82946 | ChEMBL = 3183174 | ChemSpiderID = 4510551 | EC_number = 205-559-6 | PubChem = 5354342 | UNII = 487I65419Q | StdInChI=1S/C22H42O2/c1-3-5-7-8-9-10-11-12-13-14-15-16-17-18-19-20-22(23)24-21-6-4-2/h12-13H,3-11,14-21H2,1-2H3/b13-12- | StdInChIKey = WIBFFTLQMKKBLZ-SEYXRHQNSA-N | SMILES = CCCCCCCC/C=C\CCCCCCCC(=O)OCCCC }} |Section2={{Chembox Properties | C=22|H=42|O=2 }} |Section7={{Chembox Hazards | GHS_ref=<ref>{{cite web |title=Butyl oleate |url=https://pubchem.ncbi.nlm.nih.gov/compound/5354342#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref> | GHSPictograms = {{GHS07}} | GHSSignalWord = Warning | HPhrases = {{H-phrases|315|319|335}} | PPhrases = {{P-phrases|261|264|264+265|271|280|302+352|304+340|305+351+338|319|321|332+317|337+317|362+364|403+233|405|501}} }} |Section8={{Chembox Related }} }}
'''Butyl oleate''' is a fatty acid ester and an organic chemical found in liquid form. It has the formula C<sub>22</sub>H<sub>42</sub>O<sub>2</sub> and the CAS Registry Number 142-77-8.<ref>{{Cite web |title=CAS Common Chemistry |url=https://commonchemistry.cas.org/detail?cas_rn=142-77-8 |access-date=2023-11-10 |website=commonchemistry.cas.org}}</ref> It is REACH registered and produced or imported into the European Union with the EC number of 205-559-6.
==Synthesis and reactions== It is formed by the condensation of oleic acid and butanol often using an enzyme as catalyst or other biobased catalysts.<ref>{{Cite journal |last1=Orrego |first1=Carlos Eduardo |last2=Valencia |first2=Jesús Sigifredo |last3=Zapata |first3=Catalina |date=2009-05-01 |title=Candida rugosa Lipase Supported on High Crystallinity Chitosan as Biocatalyst for the Synthesis of 1-Butyl Oleate |journal=Catalysis Letters |language=en |volume=129 |issue=3 |pages=312–322 |doi=10.1007/s10562-009-9857-6 |s2cid=86759909 |issn=1572-879X}}</ref><ref>{{Cite book |last1=Linko |first1=Y.-Y. |series=Progress in Biotechnology |chapter=Factors Affecting Lipase Catalyzed ''n''-Butyl Oleate Synthesis |date=1992-01-01 |volume=8 |pages=601–608 |editor-last=Tramper |editor-first=J. |title=Biocatalysis in Non-Conventional Media |publisher=Elsevier |doi=10.1016/b978-0-444-89046-7.50087-4 |last2=Rantanen |first2=O. |last3=Yu |first3=H. -C. |last4=Linko |first4=P. |isbn=978-0-444-89046-7 |editor2-last=Vermüe |editor2-first=M. H. |editor3-last=Beeftink |editor3-first=H. H. |editor4-last=von Stockar |editor4-first=U.}}</ref><ref>{{Cite journal |last1=Leitgeb |first1=M. |last2=Knez |first2=ž. |date=November 1990 |title=The influence of water on the synthesis of ''n''‐butyl oleate by immobilized ''Mucor miehei'' lipase |journal=Journal of the American Oil Chemists' Society |language=en |volume=67 |issue=11 |pages=775–778 |doi=10.1007/BF02540490 |s2cid=84864739 |issn=0003-021X}}</ref> Ionic liquids may also be used as the catalyst.<ref>{{Cite journal |last1=Zhou |first1=Ningning |last2=Yang |first2=Liancheng |last3=Wang |first3=Yuehan |last4=Ding |first4=Yunlong |date=2022-08-01 |title=''N''-butyl oleate catalyzed- synthesized by triethylamine citrate lonic liquid |journal=Journal of Physics: Conference Series |volume=2321 |issue=1 |article-number=012022 |doi=10.1088/1742-6596/2321/1/012022 |bibcode=2022JPhCS2321a2022Z |s2cid=251491831 |issn=1742-6588|doi-access=free }}</ref> It undergoes the Bouveault–Blanc reduction with oleyl alcohol and butanol as the products.<ref>{{cite book|chapter = 109. Bouveault–Blanc Reduction|title = Comprehensive Organic Name Reactions and Reagents|pages = 493–496|year = 2009|doi = 10.1002/9780470638859.conrr109|editor-first = Zerong|editor-last = Wang|isbn = 978-0-471-70450-8}}</ref>
==Alternative names== It is also known as Butyl ''cis''-9-octadecenoate, Oleic acid butyl ester, butyl 9-octadecenoate and 1-butyl oleate. The IUPAC name is butyl (''Z'')-octadec-9-enoate.<ref>{{Cite web |last=PubChem |title=Butyl oleate |url=https://pubchem.ncbi.nlm.nih.gov/compound/5354342 |access-date=2023-11-10 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref>
==Uses== It has approval for use as a food additive in Europe<ref>{{Cite web|title=EU Commission Implementing Regulation adopting the list of flavouring substances |date=2012-10-01 |url=http://data.europa.eu/eli/reg_impl/2012/872/oj/eng |access-date=2023-11-10 |language=en}}</ref> and also the US by the FDA.<ref>{{Cite web |title=Inventory of Food Contact Substances Listed in 21 CFR |url=https://www.hfpappexternal.fda.gov/scripts/fdcc/index.cfm?set=IndirectAdditives&id=BUTYLOLEATE |access-date=2023-11-10 |website=www.cfsanappsexternal.fda.gov |language=en-US}}</ref> Various other uses include as a lubricant and lubricant additive,<ref>{{Cite journal |last1=Dailey |first1=Oliver D. |last2=Prevost |first2=Nicolette T. |last3=Strahan |first3=Gary D. |date=July 2008 |title=Synthesis and Structural Analysis of Branched‐Chain Derivatives of Methyl Oleate |journal=Journal of the American Oil Chemists' Society |language=en |volume=85 |issue=7 |pages=647–653 |doi=10.1007/s11746-008-1235-9 |s2cid=84876707 |issn=0003-021X}}</ref> paints and coatings additive, and as a plasticizer especially for PVC.<ref>{{Cite journal |last1=Riser |first1=G. R. |last2=Bloom |first2=F. W. |last3=Witnauer |first3=L. P. |date=March 1964 |title=Evaluation of butyl stearate, butyl oleate, butyl ricinoleate, and methyl oleate as poly(vinyl chloride) plasticizers |journal=Journal of the American Oil Chemists' Society |language=en |volume=41 |issue=3 |pages=172–174 |doi=10.1007/BF03024639 |s2cid=101771799 |issn=0003-021X}}</ref><ref>{{Cite journal |last1=Ghamgui |first1=Hanen |last2=Karra-Chaâbouni |first2=Maha |last3=Gargouri |first3=Youssef |date=2004-09-01 |title=1-Butyl oleate synthesis by immobilized lipase from ''Rhizopus oryzae'': a comparative study between ''n''-hexane and solvent-free system |journal=Enzyme and Microbial Technology |volume=35 |issue=4 |pages=355–363 |doi=10.1016/j.enzmictec.2004.06.002 |issn=0141-0229}}</ref> Similar to other fatty acid esters, it has found use in biodiesel and as a fuel additive.<ref>{{Cite journal |last1=Lee |first1=Inmok |last2=Johnson |first2=Lawrence A. |last3=Hammond |first3=Earl G. |date=October 1995 |title=Use of branched‐chain esters to reduce the crystallization temperature of biodiesel |journal=Journal of the American Oil Chemists' Society |language=en |volume=72 |issue=10 |pages=1155–1160 |doi=10.1007/BF02540982 |s2cid=84340949 |issn=0003-021X}}</ref>
==See also== * Ethyl oleate * Oleate
==References== <references/>
Category:Food additives Category:Fatty acid esters