Triolein

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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:53753 ;
ChemSpider	4593733 ;
ECHA InfoCard	100.004.123
MeSH	Triolein
PubChem CID	5497163;
UNII	O05EC62663 ;
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- 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/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). verify (what is ?) 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.^[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

^ 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.
^ 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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[Ullmann-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.

[Lerner2009-2] 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.

[1]

[2]

v t e Types of lipids
General	Saturation: Saturated fat Unsaturated fat Monounsaturated fatty acid Polyunsaturated fatty acid Essential fatty acid Other: Fat Oil
Geometry	Trans fat Omega−3 fatty acid Omega−6 fatty acid Omega−9 fatty acid
Eicosanoids	Arachidonic acid Prostaglandins Prostacyclin Thromboxane Leukotrienes
Fatty acids	Caprylic acid Capric acid Lauric acid Myristic acid Palmitic acid Stearic acid Arachidic acid Behenic acid Lignoceric acid
Glycerides	Monoglyceride Diglyceride Triglyceride Triheptanoin Trimyristin Tripalmitin Tristearin Trilinolein Triolein
Phospholipids	Phosphatidylserine Phosphatidylinositol Phosphatidyl ethanolamine Cardiolipin Dipalmitoylphosphatidylcholine
Sphingolipids	Ceramide
Steroids	Cholesterol Corticosteroids Sex steroids Secosteroids

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 (Δ_fH^⦵₂₉₈)	1.97*10⁵ kJ/kmol
Gibbs free energy (Δ_fG^⦵)	-1.8*10⁵ kJ/kmol
Std enthalpy of combustion (Δ_cH^⦵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