Triolein: Difference between revisions
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{{chembox |
{{chembox |
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|verifiedrevid = 470616235 |
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|ImageFile = Triolein Structural Formula V1.svg |
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|ImageSize = 300px |
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|ImageAlt = Skeletal formula of triolein |
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| IUPACName = 2,3-Bis<nowiki>[[</nowiki>(''Z'')-octadec-9-enoyl]oxy]propyl (''Z'')-octadec-9-enoate |
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|SystematicName = Propane-1,2,3-triyl tri[(9''Z'')-octadec-9-enoate] |
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| OtherNames = |
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|OtherNames = Glyceryl trioleate |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}= {{chemspidercite|correct|chemspider}}= {{chemspidercite|correct|chemspider}} |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 4593733 |
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|ChemSpiderID = 4593733 |
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| 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- |
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|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- |
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| InChIKey = PHYFQTYBJUILEZ-IUPFWZBJBN |
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|InChIKey = PHYFQTYBJUILEZ-IUPFWZBJBN |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = O05EC62663 |
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|UNII = O05EC62663 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| 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- |
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|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- |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = PHYFQTYBJUILEZ-IUPFWZBJSA-N |
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|StdInChIKey = PHYFQTYBJUILEZ-IUPFWZBJSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 122-32-7 |
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|CASNo = 122-32-7 |
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| PubChem = 5497163 |
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|PubChem = 5497163 |
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| SMILES = O=C(OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC)CCCCCCC\C=C/CCCCCCCC |
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|ChEBI_Ref = {{ebicite|correct|EBI}} |
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| MeSHName = Triolein |
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|ChEBI = 53753 |
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}} |
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|SMILES = O=C(OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC)CCCCCCC\C=C/CCCCCCCC |
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| Section2 = {{Chembox Properties |
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|MeSHName = Triolein |
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| Formula = C<sub>57</sub>H<sub>104</sub>O<sub>6</sub> |
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| MolarMass = 885.432 g/mol |
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| Appearance = colourless viscous liquid |
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| Density =0.95 g/cm<sup>3</sup> |
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| MeltingPtK = 278 |
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| BoilingPtK = 827.4 |
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}} |
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| Section3 = {{Chembox Hazards |
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| Solubility = |
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| SolubleOther = chloroform 0.1g/ml |
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| MainHazards = |
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| FlashPt = 302.6°C |
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| Autoignition = |
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}} |
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<!-- This data needs to be formatted properly |
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| Section4 = {{Chembox Thermochemistry |
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| T<sub>c</sub> = 977.8 K |
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| P<sub>c</sub> = 3.34 bar |
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| V<sub>c</sub> = 3.250 m<sup>3</sup>/kmol |
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| G<sub>f</sub> = -1.8*10<sup>5</sup> kJ/kmol |
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| H<sub>f</sub> = 1.97*10<sup>5</sup> kJ/kmol |
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| H<sub>v</sub> = 3.02*10<sup>5</sup> kJ/kmol |
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}} --> |
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}} |
}} |
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|Section2={{Chembox Properties |
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|Formula = C<sub>57</sub>H<sub>104</sub>O<sub>6</sub> |
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|MolarMass = 885.432 g/mol |
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|Appearance = Colourless viscous liquid |
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|Density =0.9078 g/cm<sup>3</sup> at 25 °C |
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|MeltingPtK = 278 |
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|BoilingPtK = 827.4 |
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|Solubility = |
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|SolubleOther = Chloroform 0.1g/mL |
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}} |
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|Section3={{Chembox Hazards |
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|FlashPtC = 302.6 |
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|AutoignitionPtC = |
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}} |
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|Section4={{Chembox Thermochemistry |
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<!--| T<sub>c</sub> = 977.8 K |
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| P<sub>c</sub> = 3.34 bar |
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| V<sub>c</sub> = 3.250 m<sup>3</sup>/kmol |
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| H<sub>v</sub> = 3.02*10<sup>5</sup> kJ/kmol |
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--> |
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| DeltaGf = -1.8*10<sup>5</sup> kJ/kmol |
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| DeltaHf = 1.97*10<sup>5</sup> kJ/kmol |
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|DeltaHc ={{convert|8389|kcal|kJ|abbr=on}} /mole |
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}}}} |
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'''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> |
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'''Triolein''' is a [[triglyceride]] and [[unsaturated fat]] formed from [[oleic acid]]. Triolein is used in Semipermeable membrane devices (SPMD) to collect organic compounds in form of a passive sampling device in water analysis.<ref name="stuer-lauridsen">[http://www.sciencedirect.com/science?_ob=MImg&_imagekey=B6VB5-4FSCMG8-2-1&_cdi=5917&_user=644074&_pii=S0269749105000175&_origin=search&_coverDate=08%2F31%2F2005&_sk=998639996&view=c&wchp=dGLbVlW-zSkWA&md5=c8e826f1a60e88272a480331815bcdd3&ie=/sdarticle.pdf] F. Stuer-Lauridsen, Review of passive accumulation devices for monitoring organic micropollutants in the aquatic environment; Env. Poll. 136 (2005) 503-524</ref> the collecting compound triolein is placed in a tube and set up in a cage like container into the water system (such as streams, rivers and other water reservoirs). |
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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> |
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{{Glycerides}} |
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The oxidation of triolein is according to the formula: |
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:{{chem|C|57|H|104|O|6}} + 80 {{chem|O|2}} → 57 {{chem|CO|2}} + 52 {{chem|H|2|O}} |
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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}}. |
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==References== |
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<references /> |
<references /> |
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{{Glycerides}} |
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[[Category:Triglycerides]] |
[[Category:Triglycerides]] |
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{{ester-stub}} |
{{ester-stub}} |
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[[de:Triolein]] |
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[[fr:Oléine]] |
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[[pt:Trioleína]] |
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Latest revision as of 15:17, 27 March 2024
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| Names | |
|---|---|
| Systematic IUPAC name
Propane-1,2,3-triyl tri[(9Z)-octadec-9-enoate] | |
| Other names
Glyceryl trioleate
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.004.123 |
| MeSH | Triolein |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C57H104O6 | |
| Molar mass | 885.432 g/mol |
| Appearance | Colourless viscous liquid |
| Density | 0.9078 g/cm3 at 25 °C |
| Melting point | 5 °C; 41 °F; 278 K |
| Boiling point | 554.2 °C; 1,029.6 °F; 827.4 K |
| Solubility | Chloroform 0.1g/mL |
| Hazards | |
| Flash point | 302.6 °C (576.7 °F; 575.8 K) |
| Thermochemistry | |
Std enthalpy of
formation (ΔfH⦵298) |
1.97*105 kJ/kmol |
Gibbs free energy (ΔfG⦵)
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-1.8*105 kJ/kmol |
Std enthalpy of
combustion (ΔcH⦵298) |
8,389 kcal (35,100 kJ) /mole |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[1]
Triolein is also known as glyceryl trioleate and is one of the two components of Lorenzo's oil.[2]
The oxidation of triolein is according to the formula:
- C
57H
104O
6 + 80 O
2 → 57 CO
2 + 52 H
2O
This gives a respiratory quotient of 57/80 or 0.7125. The heat of combustion is 8,389 kcal (35,100 kJ) per mole or 9.474 kcal (39.64 kJ) per gram. Per mole of oxygen it is 104.9 kcal (439 kJ).
References
[edit]- ^ Alfred Thomas (2002). "Fats and Fatty Oils". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_173. ISBN 3-527-30673-0.
- ^ Lerner, Barron H (2009). "Complicated lessons: Lorenzo Odone and medical miracles". The Lancet. 373 (9667): 888–889. doi:10.1016/S0140-6736(09)60534-1. ISSN 0140-6736. PMID 19291841. S2CID 38174463.
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