{{chembox |verifiedrevid = 470616235 |ImageFile = Triolein Structural Formula V1.svg |ImageSize = 300px |ImageAlt = Skeletal formula of triolein |SystematicName = Propane-1,2,3-triyl tri[(9''Z'')-octadec-9-enoate] |OtherNames = Glyceryl trioleate |Section1={{Chembox Identifiers |ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |ChemSpiderID = 4593733 |InChI = 1/C57H104O6/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-43-46-49-55(58)61-52-54(63-57(60)51-48-45-42-39-36-33-30-27-24-21-18-15-12-9-6-3)53-62-56(59)50-47-44-41-38-35-32-29-26-23-20-17-14-11-8-5-2/h25-30,54H,4-24,31-53H2,1-3H3/b28-25-,29-26-,30-27- |InChIKey = PHYFQTYBJUILEZ-IUPFWZBJBN |UNII_Ref = {{fdacite|correct|FDA}} |UNII = O05EC62663 |StdInChI_Ref = {{stdinchicite|correct|chemspider}} |StdInChI = 1S/C57H104O6/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-43-46-49-55(58)61-52-54(63-57(60)51-48-45-42-39-36-33-30-27-24-21-18-15-12-9-6-3)53-62-56(59)50-47-44-41-38-35-32-29-26-23-20-17-14-11-8-5-2/h25-30,54H,4-24,31-53H2,1-3H3/b28-25-,29-26-,30-27- |StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |StdInChIKey = PHYFQTYBJUILEZ-IUPFWZBJSA-N |CASNo_Ref = {{cascite|correct|CAS}} |CASNo = 122-32-7 |PubChem = 5497163 |ChEBI_Ref = {{ebicite|correct|EBI}} |ChEBI = 53753 |SMILES = O=C(OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC)CCCCCCC\C=C/CCCCCCCC |MeSHName = Triolein }} |Section2={{Chembox Properties |Formula = C<sub>57</sub>H<sub>104</sub>O<sub>6</sub> |MolarMass = 885.432 g/mol |Appearance = Colourless viscous liquid |Density =0.9078 g/cm<sup>3</sup> at 25 °C |MeltingPtK = 278 |BoilingPtK = 827.4 |Solubility = |SolubleOther = Chloroform 0.1g/mL }} |Section3={{Chembox Hazards |FlashPtC = 302.6 |AutoignitionPtC = }} |Section4={{Chembox Thermochemistry <!--| T<sub>c</sub> = 977.8 K | P<sub>c</sub> = 3.34 bar | V<sub>c</sub> = 3.250 m<sup>3</sup>/kmol | H<sub>v</sub> = 3.02*10<sup>5</sup> kJ/kmol --> | DeltaGf = −1.8·10<sup>5</sup> kJ/kmol | DeltaHf = 1.97·10<sup>5</sup> kJ/kmol |DeltaHc ={{convert|8389|kcal|kJ|abbr=on}} /mole }}}}
'''Triolein''' ('''glyceryl trioleate''') is a symmetrical triglyceride derived from glycerol and three units of the unsaturated fatty acid oleic acid. Most triglycerides are unsymmetrical, being derived from mixtures of fatty acids. Triolein represents 4–30% of olive oil.<ref name=Ullmann>{{cite encyclopedia|author=Alfred Thomas |encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|publisher=Wiley-VCH|place=Weinheim|year=2002|doi=10.1002/14356007.a10_173|chapter=Fats and Fatty Oils|isbn=3-527-30673-0}}</ref>
Triolein is also known as glyceryl trioleate and is one of the two components of Lorenzo's oil.<ref name="Lerner2009">{{cite journal|last1=Lerner|first1=Barron H|title=Complicated lessons: Lorenzo Odone and medical miracles|journal=The Lancet|volume=373|issue=9667|year=2009|pages=888–889|issn=0140-6736|doi=10.1016/S0140-6736(09)60534-1|pmid=19291841 |s2cid=38174463 }}</ref>
The oxidation of triolein is according to the formula: :{{chem|C|57|H|104|O|6}} + 80 {{chem|O|2}} → 57 {{chem|CO|2}} + 52 {{chem|H|2|O}}
This gives a respiratory quotient of 57/80 or 0.7125. The heat of combustion is {{convert|8389|kcal|kJ|abbr=on}} per mole or {{convert|9.474|kcal|kJ|abbr=on}} per gram. Per mole of oxygen it is {{convert|104.9|kcal|kJ|abbr=on}}.
==References== <references />
{{Glycerides}}
Category:Triglycerides
{{ester-stub}}