Triolein
Skeletal formula of triolein
Names
Systematic IUPAC name
Propane-1,2,3-triyl tri[(9Z)-octadec-9-enoate]
Other names
Glyceryl trioleate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.004.123 Edit this at Wikidata
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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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

  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.


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