Triolein

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Triolein is a naturally occurring triglyceride made from three molecules of oleic acid bound to a glycerol backbone. It is one of the primary lipid components found in many plant-derived oils, including olive oil, avocado oil, and sunflower oil. In its pure form, triolein is a clear to pale yellow oil with a smooth, non-volatile texture.

In skincare, triolein functions as an emollient and skin-conditioning agent. Because it is rich in oleic acid, it helps reinforce the skin’s lipid barrier, reducing transepidermal water loss and improving softness and flexibility. Its molecular structure closely resembles lipids already present in the skin, which allows it to spread easily and integrate well without creating a heavy or occlusive feel when used at appropriate levels.

Triolein also plays an important role in formulation performance. It improves slip, enhances sensory feel, and helps dissolve or evenly distribute oil-soluble ingredients such as antioxidants or botanical extracts. While it does not act as an active ingredient on its own, triolein supports overall skin comfort and formula stability, making it a valuable component in creams, lotions, facial oils, and treatment products designed for dry, compromised, or mature skin.

Triolein (Wikipedia)

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
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).
checkY verify (what is checkY☒N ?)

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
57
H
104
O
6
+ 80 O
2
→ 57 CO
2
+ 52 H
2
O

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).

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