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Triolein

Summary

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
Skeletal formula of triolein
Names
Systematic IUPAC name
Propane-1,2,3-triyl tri[(9Z)-octadec-9-enoate]
Other names
Glyceryl trioleate
Identifiers
  • 122-32-7 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:53753 checkY
ChemSpider
  • 4593733 checkY
ECHA InfoCard 100.004.123 Edit this at Wikidata
MeSH Triolein
  • 5497163
UNII
  • O05EC62663 checkY
  • DTXSID3026988 Edit this at Wikidata
  • InChI=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- checkY
    Key: PHYFQTYBJUILEZ-IUPFWZBJSA-N checkY
  • 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-
    Key: PHYFQTYBJUILEZ-IUPFWZBJBN
  • O=C(OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC)CCCCCCC\C=C/CCCCCCCC
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
1.97*105 kJ/kmol
-1.8*105 kJ/kmol
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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Infobox references

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

  1. ^ 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.
  2. ^ 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.