Triolein

Triolein 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]
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.004.123
MeSH Triolein
UNII
  • 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 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
  1. Alfred Thomas (2002). "Fats and Fatty Oils". Ullmann's Encyclopedia of Industrial Chemistry. Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_173. ISBN 3527306730.
  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.


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