Biochemical Application
Glyceryl trioleate is derived from glycerol. It is composed of three oleic acid units and is an unsaturated triglyceride. Glyceryl trioleate has been used as an experimental diet along with fat-free basal mix and corn oil and then to access the dietary fat absorption among mice, as an interfering substance to test its effect on human serum in the approach to develop rapid enzyme immunoassay for the detection of retinol-binding protein, and as a standard in the determination of triglyceride concentration, colorimetrically using liver tissue sample from cows, and so on.
Industrial Uses
Triolein can be used as a textile finishing agent in textile industry, also used as additive in pigment grind. In pharm industry, it is used as an ointment, emulsifiable paste, suppository, lotion, emulsifier in air agent, stabilizing agent, lubricating agent, antifoaming agents. In food industry, it has the function as emulsify, disperse, defoaming, blister, antistaling of starch and control fat agglutination, usually used as an agent in candy, ice cream, cookie and bread. When triolein is used in beverage, could avoid ester to float, and avoid protein to sink, therefore to improve stability. When used in bread, cookie, could improve organization structure, increase volume, antistaling, prolongs warranty validity.
Applications in cosmetics
Triolen is widely used as the ingredients in cosmetics. Triolein has oleic acid in its structure, which is very beneficial for the skin. It is a skin-conditioning agent because it moisturizes the skin and forms a film over the skin. It can be used as a viscosity controlling agent, helps provide the desirable viscosity for a product, so it is used in body care, skin care and hair care products, toiletries, makeup products, and decorative cosmetics.
The Cosmetic Ingredient Review (CIR) Expert Panel found that dermal application of triolein was not associated with significant irritation, and no evidence of sensitization or photosensitization was observed. Ocular exposures were found to be only mildly irritating to eyes. Triolein has not been found to be genotoxic in a number of in vitro and in vitro assay systems.
Description
1,2,3-Trioleoyl glycerol is a triacylglycerol that contains oleic acid (Item Nos.
90260 |
24659) at the
sn-1,
sn-2, and
sn-3 positions. It inhibits oxidized LDL-induced decreases in cell viability and superoxide dismutase (SOD) and glutathione peroxidase (GPX) activities and increases in apoptosis in endothelial cells when used at a concentration of 10 μM. 1,2,3-Trioleoyl glycerol has been found in sunflower, corn, and extra virgin olive oils. It has been used as a standard for the quantification of triacylglycerols in extra virgin olive oil by high temperature gas chromatography-(ionic trap)mass spectrometry (HTGC-(IT)MS). 1,2,3-Trioleoyl glycerol is a major component of Lorenzo''s oil.
Chemical Properties
colourless viscous liquid
Chemical Properties
Triolein occurs as a clear, colorless to yellowish oily liquid, and is
tasteless and odorless.
Uses
Glycerol trioleate can be used as an emulsifier, also as creams, lotions and lipsticks matrix. Used as textile finishing agent in textile industry, also used as additive in pigment grind. In pharm industry, used as ointment, emulsifiable paste, suppository, lotion, emulsifier in air agent, stabilizing agent, lubricating agent, antifoaming agents. In food industry, it has the function as emulsify, disperse, defoaming, blister, antistaling of starch and control fat agglutination, usually used as agent in candy, ice cream, cookie and bread. When used in beverage, could avoid ester to float, and avoid protein to sink, therefore to improve stability. When used in bread, cookie , could improve organization structure, increase volume, antistaling, prolong warranty validity.
Uses
Glyceryl trioleate has been used:
- as an experimental diet along with fat-free basal mix and corn oil and then to access the dietary fat absorption among mice
- as an interfering substance to test its effect on human serum in the approach to develop rapid enzyme immunoassay for the detection of retinol-binding protein
- as a standard in the determination of triglyceride concentration, colorimetrically using liver tissue sample from cows
Definition
ChEBI: A triglyceride formed by esterification of the three hydroxy groups of glycerol with oleic acid. Triolein is one of the two components of Lorenzo's oil.
Production Methods
Triolein is manufactured by the esterification of fractionated fatty
acids, mainly oleic acid and glycerin.
General Description
Glyceryl trioleate is derived from glycerol. It is composed of three oleic acid units and is an unsaturated triglyceride.
Flammability and Explosibility
Non flammable
Pharmaceutical Applications
Triolein is used as a solubilizer and solvent in injectable preparations.
It has been used in marketed preparations of sustained-release
injections of cytarabine and multivesicular liposomal injections of
morphine sulfate. It has also been used in enteric coatings for oral
preparations in combination with other enteric coating excipients to
protect against degradation by pancreatic lipase.
Triolen is used in personal care products as a skin-conditioning
and viscosity-controlling agent.
Safety
Triolein is used in injectable preparations, in enteric coatings for
oral preparations, and in personal care products. Chronic exposure
may cause nausea and vomiting, and higher exposures may cause
unconsciousness.
The Cosmetic Ingredient Review (CIR) Expert Panel found that
dermal application of triolein was not associated with significant
irritation, and no evidence of sensitization or photosensitization
was observed. Ocular exposures were found to be only mildly
irritating to eyes. Triolein has not been found to be genotoxic in a
number of in vitro and in vitro assay systems. Subcutaneous
injections of triolein in rats showed no tumors at the injection site.
The CIR Expert Panel also noted that metabolism data indicated
that glyceryl triesters (including triolein) followed the same
metabolic pathways as fats in food. They were split into
monoglycerides, free fatty acids, and glycerol, all of which were
absorbed into the intestinal mucosa and metabolized further.
Therefore, oral exposure to these compounds was not found to be
a concern.
A triolein-based amphotericin emulsion showed better safety
with a higher LD50 in rats as compared with the conventional
amphotericin deoxycholate.
storage
Triolein is classified as a stable compound but is sensitive to air and
light. It should be stored in tightly sealed containers in a dry area at
2–8℃. Thermal decomposition of triolein may lead to release of
irritating gases and vapors such as carbon oxides. Exposure to air
and moisture over prolonged periods should be avoided.
Incompatibilities
Triolein is incompatible with strong oxidizing agents and spontaneously
flammable products. Being a triglyceride ester, triolein can
be hydrolyzed by strong acids, and particularly by strong bases. It is
possible for primary amines to form an adduct across the olefinic
double bonds (analogous to a Michael addition).
Regulatory Status
Included in the FDA Inactive Ingredients Database (liposomal
suspension for epidural injections). Included in parenteral medicines
(suspension for intrathecal injection) licensed in the UK.
Triolein is included in the CIR category as safe for use in
cosmetics and personal care products. Its use as an indirect food
additive has been approved by the FDA.
References
[1] TING LUO. Triolein and Trilinolein Ameliorate Oxidized Low-Density Lipoprotein-Induced Oxidative Stress in Endothelial Cells[J]. Lipids, 2014, 49 5: 495-504. DOI:
10.1007/s11745-014-3889-4[2] BOYAN GAO . Triacylglycerol compositions of sunflower, corn and soybean oils examined with supercritical CO2 ultra-performance convergence chromatography combined with quadrupole time-of-flight mass spectrometry[J]. Food Chemistry, 2017, 218: Pages 569-574. DOI:
10.1016/j.foodchem.2016.09.099[3] RUIZ-SAMBLáS C, CUADROS-RODRíGUEZ L, GONZáLEZ-CASADO A, et al. A straightforward quantification of triacylglycerols (and fatty acids) in monovarietal extra virgin olive oils by high-temperature GC[J]. Analytical Methods, 2012, 3: 753-758. DOI:
10.1039/c2ay05574k[4] HUGO W. MOSER. “Lorenzo’s Oil” Therapy for X-linked Adrenoleukodystrophy: Rationale and Current Assessment of Efficacy[J]. Journal of Molecular Neuroscience, 2007, 33 1: 105-113. DOI:
10.1007/s12031-007-0041-4[5] RUCHA PATEL. ATGL is a biosynthetic enzyme for fatty acid esters of hydroxy fatty acids[J]. Nature, 2022, 606 7916: 968-975. DOI:
10.1038/s41586-022-04787-x
