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Triolein

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Triolein
Skeletal formula of triolein
Names
Systematic IUPAC name Propane-1,2,3-triyl tri
Other names Glyceryl trioleate
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.004.123 Edit this at Wikidata
MeSH Triolein
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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-Key: PHYFQTYBJUILEZ-IUPFWZBJSA-N
  • 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
SMILES
  • O=C(OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC)CCCCCCC\C=C/CCCCCCCC
Properties
Chemical formula C57H104O6
Molar mass 885.432 g/mol
Appearance Colourless viscous liquid
Density 0.9078 g/cm 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 (ΔfH298) 		1.97*10 kJ/kmol
Gibbs free energy (ΔfG) -1.8*10 kJ/kmol
Std enthalpy of
combustion (ΔcH298) 		8,389 kcal (35,100 kJ) /mole
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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.

Triolein is also known as glyceryl trioleate and is one of the two components of Lorenzo's oil.

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.
Types of lipids
General
Geometry
Eicosanoids
Fatty acids
Glycerides
Phospholipids
Sphingolipids
Steroids


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