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Glycerol Trioleate (GTO) is a triacylglycerol that contains oleic acid at the sn-1, sn-2, and sn-3 positions.
Glycerol Trioleate (GTO) 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.
Glycerol Trioleate (GTO) 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).
CAS: 122-32-7
MF: C57H104O6
MW: 885.43
EINECS: 204-534-7
Synonyms
18:1TG;1,2,3-Propanetriyltri-((E)-9-octadecenoate);1,2,3-propanetriyltrioleate;9-octadecenoic;9-Octadecenoic acid (Z)-, 1,2,3-propanetriyl ester;9-Octadecenoic acid 1,2,3-propanetriyl ester;9-Octadecenoicacid(Z)-,1,2,3-propanetriylester;9-octadecenoicaci;(z)1,2,3-propanetriyl;Triolein;GLYCERYL TRIOLEATE;Glycerol trioleate;122-32-7;Glycerol triolein;Oleic triglyceride;Trioleoylglycerol;Oleic acid triglyceride;Olein;Trioleoylglyceride;Glycerin trioleate;Oleyl triglyceride;Raoline;Aldo TO;Glyceryl-1,2,3-trioleate;Olein, tri-;Emery 2423;Emery oleic acid ester 2230;Glycerol, tri(cis-9-octadecenoate);HSDB 5594;1,2,3-Propanetriyl trioleate;1,2,3-tri-(9Z-octadecenoyl)-glycerol;Triglyceride OOO;9-Octadecenoic acid (Z)-, 1,2,3-propanetriyl ester;EINECS 204-534-7;9-Octadecenoic acid (9Z)-, 1,2,3-propanetriyl ester;Edenor NHTi-G;Kaolube 190;CCRIS 8687;sn-Glyceryl trioleate;1,2,3-Tri(cis-9-octadecenoyl)glycerol;Actor LO 1;Kemester 1000;UNII-O05EC62663;CHEBI:53753;Emerest 2423;1,2,3-Propanetriol tri(9-octandecenoate);Estol 1433;Radia 7363;9-Octadecenoic acid, 1,2,3-propanetriyl ester;TG(18:1(9Z)/18:1(9Z)/18:1(9Z));O05EC62663;1,2,3-tri-oleoyl-glycerol;propane-1,2,3-triyl (9Z,9'Z,9''Z)tris-octadec-9-enoate;DTXSID3026988;2,3-bis[[(Z)-octadec-9-enoyl]oxy]propyl (Z)-octadec-9-enoate;EC 204-534-7;(9Z)9-Octadecenoic acid 1,2,3-propanetriyl ester;MFCD00137563;TRIOLEIN (USP-RS);TRIOLEIN [USP-RS];(Z)-9-Octadecenoic acid, 1,2,3-propanetriyl ester;GLYCERYL TRIOLEATE (II);GLYCERYL TRIOLEATE [II];GLYCERYL TRIOLEATE (MART.);GLYCERYL TRIOLEATE [MART.];Glycerine Trioleate (Technical Grade);Trioleyl Glycerol;TG 54:3;Trioleate Glycerin;Trioleate-Glycerin;Glycerol, Trioleyl;Trioleate, Glycerol;propane-1,2,3-triyl tris((9Z)-octadec-9-enoate);propane-1,2,3-triyl tris[(9Z)-octadec-9-enoate];tri-Olein;9-Octadecenoic-9,10-t2 acid, 1,2,3-propanetriyl ester, (Z,Z,Z)- (9CI);Glycerol trioleate;;triolein C18:1;Triolein, tech grade;GLYCERYLTRIOLEATE;reagent grade,60.0%;TRIOLEIN [MI];tri(cis-9-octadecenoate);Epitope ID:117714;TRIOLEIN [WHO-DD];1,2,3-propanetriyl ester;Glyceryl trioleate, ~65%;SCHEMBL23730;Glyceryl trioleate, >=99%;9-Octadecenoic acid (9Z)-, 1,1',1''-(1,2,3-propanetriyl) ester;DTXCID006988;1,3-bis[(9Z)-octadec-9-enoyloxy]propan-2-yl (9Z)-octadec-9-enoate;CHEMBL4297656;GLYCERYL TRIOLEATE [HSDB];GLYCERYL TRIOLEATE [VANDF];GLYCERYL TRIOLEATE [WHO-DD];HY-N1981;Triolein, [9,10-3H(N)]-;LMGL03010250;s3590;AKOS024437536;Triolein (mixture of Triacylglycerins);DB13038;Glyceryl trioleate, >=97.0% (TLC);1,2,3-tri-(9Z-octadecenoyl)-sn-glycerol;CS-0018302;G0089;NS00002311;Glyceryl trioleate, technical, >=60% (GC);(Z)-1,2,3-propanetriyl ester 9-Octadecenoate;(9Z)-1,2,3-propanetriyl ester 9-Octadecenoate;Glyceryl trioleate, analytical reference material;Q413929;(9Z)-1,2,3-propanetriyl ester 9-Octadecenoic acid;(Z)-1,2,3-propanetriyl ester 9-Octadecenoic acid;J-004788;AC7B54B8-0E34-455F-A1E0-442F3ECD69EA;Triolein, European Pharmacopoeia (EP) Reference Standard;TG(18:1(9Z)/18:1(9Z)/18:1(9Z))[iso];(9Z)-1,1',1''-(1,2,3-propanetriyl) ester 9-Octadecenoate;(9Z)-1,1',1''-(1,2,3-propanetriyl) ester 9-Octadecenoic acid;9-octadecenoic acid, 1,2,3-propanetriyl ester, (9Z,9'Z,9''Z)-
Glycerol Trioleate (GTO) is a major component of Lorenzo''s oil.
A triglyceride formed by esterification of the three hydroxy groups of glycerol with oleic acid.
Glycerol Trioleate (GTO) is one of the two components of Lorenzo's oil.
Glycerol Trioleate (GTO) is derived from glycerol.
Glycerol Trioleate (GTO) is composed of three oleic acid units and is an unsaturated triglyceride.
Glycerol Trioleate (GTO) 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.
Glycerol Trioleate (GTO) represents 4–30% of olive oil.
Glycerol Trioleate (GTO) is also known as glyceryl trioleate and is one of the two components of Lorenzo's oil.
The oxidation of Glycerol Trioleate (GTO) 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 Glycerol Trioleate (GTO) is 104.9 kcal (439 kJ).
Glycerol Trioleate (GTO) Chemical Properties
Melting point: -5,5°C
Boiling point: 235-240 °C18 mm Hg(lit.)
Density: 0.91 g/mL(lit.)
Pour Point: -16
Refractive index: n20/D 1.470
Fp: 330 °C
Storage temp.: -20°C
Solubility chloroform: 0.1 g/mL, clear, colorless
Form: Liquid
Color: Clear Pale Yellow
Merck: 14,9732
BRN: 1718692
Dielectric constant: 3.2（26℃）
Stability: Stability Stable, but air and light sensitive.
Incompatible with strong oxidizing agents.
LogP: 23.444 (est)
CAS DataBase Reference: 122-32-7(CAS DataBase Reference)
EPA Substance Registry System:Glycerol Trioleate (GTO) (122-32-7)
Glycerol Trioleate (GTO) occurs as a clear, colorless to yellowish oily liquid, and is tasteless and odorless.
Glycerol Trioleate (GTO) is colorless and tasteless liquid, boiling point 235~240 ℃, relative density (25 ℃)0.915, soluble in ether, chloroform, carbon tetrachloride, slightly soluble in alcohol, insoluble in water.
Uses
Glycerol Trioleate (GTO) 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, Glycerol Trioleate (GTO) 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.
Glycerol Trioleate (GTO) has been widely used in industry.
As a medicinal raw material, it is generally used as an emulsifier.
Glycerol Trioleate (GTO) can be used in the textile printing and dyeing industry and the pharmaceutical and food fermentation industry.
Glycerol Trioleate (GTO) can also be used as a lubricant in the textile industry; a smoothing agent for post-metal processing; used as an emulsifier and emulsion stabilizer, and wetting agent in food and cosmetics; in medicine, can produce penicillin inhibitor clavulanic acid.
Glycerol Trioleate (GTO) can be used as textile lubricant and cosmetic emulsifier.
Glycerol Trioleate (GTO) can also be used as a matrix for cream, lotion and lipstick.
Used as an industrial emulsifier and a lubricant in the textile industry.
Lubricants used in the textile industry, smoothing agents for metal post-processing
Determination of natural fat components.
Emulsifiers, opacifying agents, defoamers, finishing agents, lubricants, and pharmaceutical raw materials.
Glycerol Trioleate (GTO) 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.
Glycerol Trioleate (GTO) has been widely used in industry.
As a medicinal raw material, Glycerol Trioleate (GTO) is generally used as an emulsifier.
Glycerol Trioleate (GTO) can be used in the textile printing and dyeing industry and the pharmaceutical and food fermentation industry.
Glycerol Trioleate (GTO) can also be used as a lubricant in the textile industry; a smoothing agent for post-metal processing; used as an emulsifier and emulsion stabilizer, and wetting agent in food and cosmetics; in medicine, can produce penicillin inhibitor clavulanic acid.
Biochemical Application
Glycerol Trioleate (GTO) is derived from glycerol.
Glycerol Trioleate (GTO) is composed of three oleic acid units and is an unsaturated triglyceride.
Glycerol Trioleate (GTO) 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.
Pharmaceutical Applications
Glycerol Trioleate (GTO) is used as a solubilizer and solvent in injectable preparations.
Glycerol Trioleate (GTO) has been used in marketed preparations of sustained-release injections of cytarabine and multivesicular liposomal injections of morphine sulfate.
Glycerol Trioleate (GTO) has also been used in enteric coatings for oral preparations in combination with other enteric coating excipients to protect against degradation by pancreatic lipase.
Glycerol Trioleate (GTO) is used in personal care products as a skin-conditioning and viscosity-controlling agent.
Industrial Uses
Glycerol Trioleate (GTO) can be used as a textile finishing agent in textile industry, also used as additive in pigment grind.
In pharm industry, Glycerol Trioleate (GTO) is used as an ointment, emulsifiable paste, suppository, lotion, emulsifier in air agent, stabilizing agent, lubricating agent, antifoaming agents.
In food industry, Glycerol Trioleate (GTO) 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 Glycerol Trioleate (GTO) 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
Glycerol Trioleate (GTO) is widely used as the ingredients in cosmetics.
Glycerol Trioleate (GTO) has oleic acid in its structure, which is very beneficial for the skin.
Glycerol Trioleate (GTO) is a skin-conditioning agent because it moisturizes the skin and forms a film over the skin.
Glycerol Trioleate (GTO) 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 Glycerol Trioleate (GTO) 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.
Glycerol Trioleate (GTO) has not been found to be genotoxic in a number of in vitro and in vitro assay systems.
Production Methods
Glycerol Trioleate (GTO) is manufactured by the esterification of fractionated fatty acids, mainly oleic acid and glycerin.
Preparation
preparation steps are as follows:
1. take a certain proportion of glycerol and oleic acid, wherein the molar ratio of glycerol to oleic acid is 2.3-3.2:1, and the optimal ratio is 2.6-3:1;
2. take 0.1%-1% of the total amount of catalyst, the optimal dose is 0.3%-0.6%, the catalyst is p-toluenesulfonic acid, solid super strong acid, self-made catalyst, etc., among which the best is self-made catalyst;
3., the above-mentioned glycerol, oleic acid and catalyst are added to the reactor, the reactor is heated, and the reaction temperature is kept at 140-220 ℃, the optimal reaction temperature is 190-220 ℃, and the reaction time is 4-8 hours, and the optimal reaction time is 6-8 hours;
4. after the reaction is over, the reactant is dehydrated by vacuum dehydrator until the acid value reaches the standard.
The standard is as follows: the appearance is light yellow clear liquid; Acid value/(mgKOH/g):≤ 2; Hydroxyl value/(mgKOH/g):185-205; Saponification value/(mgKOH/g)≤ 25; Moisture: ≤ 1%.
