Triolein

Names

Systematic IUPAC name Propane-1,2,3-triyl tri[(9Z)-octadec-9-enoate]

Other names Glyceryl trioleate

Identifiers

CAS NumberY

3D model (JSmol)

ChEBIY

ChemSpiderY

ECHA InfoCard

MeSH

PubChem CID

UNIIY

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-YKey: PHYFQTYBJUILEZ-IUPFWZBJSA-NYInChI=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 formulaC57H104O6

Molar mass885.432 g/mol

AppearanceColourless viscous liquid

Density0.9078 g/cm3 at 25 °C

Melting point5 °C; 41 °F; 278 K

Boiling point554.2 °C; 1,029.6 °F; 827.4 K

SolubilityChloroform 0.1g/mL

Hazards

Flash point302.6 °C (576.7 °F; 575.8 K)

Thermochemistry

Std enthalpy of formation (Δ f H ⦵ 298 )1.97·105 kJ/kmol

Gibbs free energy (Δ f G ⦵ )−1.8·105 kJ/kmol

Std enthalpy of combustion (Δ c H ⦵ 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 (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:

C57H104O6 + 80 O2 → 57 CO2 + 52 H2O

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).