Triolein

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

Names
Systematic IUPAC name Propane-1,2,3-triyl tri[(9Z)-octadec-9-enoate]
Other names Glyceryl trioleate
Identifiers
CAS Number	122-32-7 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:53753 Y
ChemSpider	4593733 Y
ECHA InfoCard	100.004.123
MeSH	Triolein
PubChem CID	5497163
UNII	O05EC62663 Y
CompTox Dashboard (EPA)	DTXSID3026988
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- Y Key: PHYFQTYBJUILEZ-IUPFWZBJSA-N Y 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/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⦵)	-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). Y verify (what is YN ?) 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

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.