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CAS Number: 122-32-7
EC Number: 204-534-7
Molecular Weight: 885.43

Glyceryl trioleate is derived from glycerol. 
Glyceryl trioleate is composed of three oleic acid units and is an unsaturated triglyceride.

Glyceryl trioleate, known widely as triolein, is an oily liquid that is a main constituent of some nondrying oils and fats. 
Triolein occurs in many natural fats and oils, including sunflower oil, palm oil, cacao butter, and, most notably, olive oil.

In 1941, Thomas P. Hilditch and L. Maddison at the University of Liverpool (UK) crystallized olive oils from Italy and Palestine at temperatures down to –30 °C to resolve them into several components. 
They found that olive oil from Palestine contained ≈30% triolein, whereas the Italian oil contained only ≈5%.

Eight years later, M. L. Meara, also at Liverpool, resolved cacao butter into 11 fractions “by exhaustive crystallization”. 
For his efforts, only 1.1% of the fat turned out to be glyceryl trioleate. 
From 1940 to 1961, several chemists devised syntheses of triolein by esterifying glycerol and oleic acid.

Sacramental uses of olive oil are strongly connected to Christian and Jewish traditions, especially Hanukkah.

During the period of the Hanukkah story (168 BCE), only pure olive oil blessed by the high priest could be used to light the Temple menorah, which had to be lit continuously. 
After their victorious battle over the Syrian Greeks, the Maccabees could find only enough holy oil to last for one day. 
The Hanukkah miracle is that the oil lasted eight days, enough time for more oil to be prepared and sanctified.

Olive oil was the major component of anointing oils and lamp fuel that date to biblical times. 
Kings were anointed with oil as a mark of their official status; and one title for Jesus is the Anointed One. 
References are found throughout the Hebrew and Christian scriptures about the use of oil as part of fasting and healing rituals.

Triolein 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 Glyceryl trioleate is 104.9 kcal (439 kJ).

Glyceryl trioleate is derived from glycerol. 
Glyceryl trioleate is composed of three oleic acid units and is an unsaturated triglyceride.

Glyceryl trielaidate (glycerol trielaidate, or trielaidin) is a triglyceride formed by esterification of the three hydroxy groups of glycerol with elaidic acid.

Glycerol trioleate or Triolein is a triglyceride formed by esterification of the three hydroxy groups of glycerol with oleic acid. 
Glycerol trioleate is one of the two components of Lorenzo's oil. 

Glyceryl trioleate has a role as a plant metabolite. 
Glyceryl trioleate derives from an oleic acid.

Constituent of olive oil and other vegetable oils TG(18:1(9Z)/18:1(9Z)/18:1(9Z)) or Triolein is a monoacid triglyceride. 
Triglycerides (TGs) are also known as triacylglycerols or triacylglycerides. 

TGs are fatty acid triesters of glycerol and may be divided into three general types with respect to their acyl substituents. 
They are simple or monoacid if they contain only one type of fatty acid, diacid if they contain two types of fatty acids and triacid if three different acyl groups. 

Chain lengths of the fatty acids in naturally occurring triglycerides can be of varying lengths and saturations but 16, 18 and 20 carbons are the most common. 
TGs are the main constituent of vegetable oil and animal fats. 

TGs are major components of very low density lipoprotein (VLDL) and chylomicrons, play an important role in metabolism as energy sources and transporters of dietary fat. 
They contain more than twice the energy (9 kcal/g) of carbohydrates and proteins. 

In the intestine, triglycerides are split into glycerol and fatty acids (this process is called lipolysis) (with the help of lipases and bile secretions), which can then move into blood vessels. 
The triglycerides are rebuilt in the blood from their fragments and become constituents of lipoproteins, which deliver the fatty acids to and from fat cells among other functions. 

Various tissues can release the free fatty acids and take them up as a source of energy. 
Fat cells can synthesize and store triglycerides. 

When the body requires fatty acids as an energy source, the hormone glucagon signals the breakdown of the triglycerides by hormone-sensitive lipase to release free fatty acids. 
As the brain cannot utilize fatty acids as an energy source, the glycerol component of triglycerides can be converted into glucose for brain fuel when Glyceryl trioleate is broken down. 

TAGs can serve as fatty acid stores in all cells, but primarily in adipocytes of adipose tissue. 
The major building block for the synthesis of triacylglycerides, in non-adipose tissue, is glycerol. 

Adipocytes lack glycerol kinase and so must use another route to TAG synthesis. 
Specifically, dihydroxyacetone phosphate (DHAP), which is produced during glycolysis, is the precursor for TAG synthesis in adipose tissue. DHAP can also serve as a TAG precursor in non-adipose tissues, but does so to a much lesser extent than glycerol. 

The use of DHAP for the TAG backbone depends on whether the synthesis of the TAGs occurs in the mitochondria and ER or the ER and the peroxisomes. 
The ER/mitochondria pathway requires the action of glycerol-3-phosphate dehydrogenase to convert DHAP to glycerol-3-phosphate. Glycerol-3-phosphate acyltransferase then esterifies a fatty acid to glycerol-3-phosphate thereby generating lysophosphatidic acid. 

The ER/peroxisome reaction pathway uses the peroxisomal enzyme DHAP acyltransferase to acylate DHAP to acyl-DHAP which is then reduced by acyl-DHAP reductase. 
The fatty acids that are incorporated into TAGs are activated to acyl-CoAs through the action of acyl-CoA synthetases. 

Two molecules of acyl-CoA are esterified to glycerol-3-phosphate to yield 1,2-diacylglycerol phosphate (also known as phosphatidic acid). The phosphate is then removed by phosphatidic acid phosphatase (PAP1), to generate 1,2-diacylglycerol. 
This diacylglycerol serves as the substrate for addition of the third fatty acid to make TAG. 

Intestinal monoacylglycerols, derived from dietary fats, can also serve as substrates for the synthesis of 1,2-diacylglycerols.
Triolein is a triglyceride and unsaturated fat formed from oleic acid. Glycerol trioleate is found in fats and oils, almond, and peach.

Physical description of Glyceryl trioleate:
Colorless to yellowish odorless liquid
Glyceryl trioleate can be found as a clear colorless liquid.

Application of Glyceryl trioleate:
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 Glyceryl trioleate 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

Uses of Glyceryl trioleate:
A major component of oils and fats, e.g., olive oil.
Used as lubricant (e.g. for cosmetics, drugs, and textiles), emulsifier (e.g. for water/oil mixtures), intermediate for radioactive iodine derivatives, and plasticizer.
Used in sweet almond oil for medicines and cosmetics.

Industry Uses of Glyceryl trioleate:
Lubricants and lubricant additives

Consumer Uses of Glyceryl trioleate:
Lubricants and greases
Non-TSCA use

Therapeutic Uses of Glyceryl trioleate:
The aim of this study was to identify asymptomatic boys with X-linked adrenoleukodystrophy who have a normal magnetic resonance image (MRI), and to assess the effect of 4:1 glyceryl trioleate-glyceryl trierucate (Lorenzo's oil) on disease progression. 
Eighty-nine boys (mean +/- SD baseline age, 4.7 +/- 4.1 years; range, 0.2-15 years) were identified by a plasma very long-chain fatty acids assay used to screen at-risk boys. 

All were treated with Lorenzo's oil and moderate fat restriction. 
Plasma fatty acids and clinical status were followed for 6.9 +/- 2.7 years. 

Changes in plasma hexacosanoic acid levels were assessed by measuring the length-adjusted area under the curve, and a proportional hazards model was used to evaluate association with the development of abnormal MRI results and neurological abnormalities. 
Of the 89 boys, 24% developed MRI abnormalities and 11% developed both neurological and MRI abnormalities. 

Abnormalities occurred only in the 64 patients who were aged 7 years or younger at the time therapy was started. 
There was significant association between the development of MRI abnormalities and a plasma hexacosanoic acid increase. 

(For a 0.1-ug/mL increase in the length-adjusted area under the curve for the hexacosanoic acid level, the hazard ratio for incident MRI abnormalities in the whole group was 1.36; P = .01; 95% confidence interval, 1.07-1.72.) 
Results for patients aged 7 years or younger were similar (P = .04). 

In this single-arm study, hexacosanoic acid reduction by Lorenzo's oil was associated with reduced risk of developing MRI abnormalities. 
We recommend Lorenzo's oil therapy in asymptomatic boys with X-linked adrenoleukodystophy who have normal brain MRI results.

X-linked adrenoleukodystrophy (X-ALD) is an inherited disorder of peroxisomal metabolism, biochemically characterized by deficient beta-oxidation of saturated very long chain fatty acids (VLCFA). 
The consequent accumulation of these fatty acids in different tissues and in biological fluids is associated with a progressive central and peripheral demyelination, as well as with adrenocortical insufficiency and hypogonadism. 

Seven variants of this disease have been described, cerebral childhood being the most frequent. 
The recommended therapy consists of the use of the glyceroltrioleate/glyceroltrierucate mixture known as Lorenzo's Oil (LO), combined with a VLCFA-poor diet, but only in asymptomatic patients will this treatment prevent the progression of the symptomatology. 

In the present study we evaluated the biochemical course of patients with cerebral childhood (CCER) and asymptomatic clinical forms of X-ALD treated with LO associated with a VLCFA-restricted diet. 
We observed that hexacosanoic acid plasma concentrations and hexacosanoic/docosanoic ratio were significantly reduced in CCER patients during treatment when compared with diagnosis. 

Hexacosanoic acid plasma level was significantly reduced when compared with that at diagnosis and achieved the normal levels only in asymptomatic patients under LO treatment. 
In asymptomatic patients the magnitude of hexacosanoic acid decrease was higher than that of the CCER patients. 

These results show the good biochemical response of LO treatment in asymptomatic X-ALD patients. 
Glyceryl trioleate is possible to suppose that this could be correlated with the prevention of the appearance of neurological signals in this group of patients treated with LO.

Investigated the possible therapeutic effect of decreasing plasma levels of very-long-chain fatty acids (C26:0) with a synthetic oil containing trioleate and trielucate (Lorenzo's oil) as well as increasing docosahexaenoic acid (DHA) in red blood cells (RBC) with DHA ethyl ester in four patients with Zellweger syndrome.
Investigated serial changes of plasma C26:0 levels and DHA levels in RBC membranes by gas-liquid chromatography/mass spectrometry (GC/MS). After death, the fatty acid composition of each patient's cerebrum and liver was studied. 

Dietary administration of Lorenzo's oil diminished plasma C26:0 levels. 
Earlier administration of Lorenzo's oil was more effective and the response did not depend on the duration of administration. 

DHA was incorporated into RBC membrane lipids when administrated orally, and Glyceryl trioleate level increased for several months. 
The final DHA level was correlated with the duration of administration and was not related to the timing of initiation of treatment. 

DHA levels in the brains and livers of treated patients were higher than in untreated patients. 
Early initiation of Lorenzo's oil and the long-term administration of DHA may be useful for patients with Zellweger syndrome.

Pharmacology and Biochemistry of Glyceryl trioleate:

Absorption, Distribution and Excretion of Glyceryl trioleate:
In the small intestine, most triglycerides are split into monoglycerides, free fatty acids, and glycerol, which are absorbed by the intestinal mucosa. 
Within the epithelial cells, resynthesized triglycerides collect into globules along with cholesterol and phospholipids and are encased in a protein coat as chylomicrons. 

Chylomicrons are transported in the lymph to the thoracic duct and eventually to the venous system. 
The chylomicrons are removed from the blood as they pass through the capillaries of adipose tissue. 
Fat is stored in adipose cells until Glyceryl trioleate is transported to other tissues as free fatty acids which are used for cellular energy or incorporated into cell membranes.

When (14)C-labeled long-chain triglycerides are administered intravenously, 25% to 30% of the radiolabel is found in the liver within 30 to 60 minutes, with less than 5% remaining after 24 hours. 
Lesser amounts of radiolabel are found in the spleen and lungs. 

After 24 hours, nearly 50% of the radiolabel has been expired in carbon dioxide, with 1% of the carbon label remaining in the brown fat. 
The concentration of radioactivity in the epididymal fat is less than half that of the brown fat.

Human Metabolite Information of Glyceryl trioleate:

Cellular Locations:

Methods of Manufacturing of Glyceryl trioleate:
Preparation by esterification of oleic acid.

Glyceryl trioleate is the predominating constituent in expressed almond oil, in lard oil, & in many of the more fluid animal oils & those of vegetable origin. 
Glyceryl trioleate is separated & purified by cold expression, the other constituents being retained by their lack of fluidity at low temp.

The triglyceride of oleic acid, occurring in most fats and oils. 
Glyceryl trioleate constitutes 70-80% of olive oil

Reaction of refined oil, eg, olive oil, with glycerol followed by fractional distillation; reaction of oleic acid with glycerol; separation & purification from fats & oils as liquid phase by cold expression.

General Manufacturing Information of Glyceryl trioleate:

Industry Processing Sectors:
Textiles, apparel, and leather manufacturing
Transportation equipment manufacturing

Stable water-in-oil emulsions (with a high water content) for cosmetics are prepared by dissolving the neutral oil & 5-50% lecithin emulsifier at less than or equal to 70 °C, cooling to 0-12 °C, & adding water to a concentration of 50-83%. 
The neutral oil can be a glycerol, such as glyceryl trioleate, or propylene glycol ester of a carbon 8-12 fatty acid or isopropyl myristate.

Ecological Information of Glyceryl trioleate:

Environmental Fate/Exposure Summary of Glyceryl trioleate:
Triolein's production and use as textile lubricant and plasticizer may result in Glyceryl trioleate release to the environment through various waste streams. 
Triolein is found in cacao butter and accounts for 70-80% of olive oil. 

If released to air, an estimated vapor pressure range of 5X10-5 mm Hg to 1.1X10-9 mm Hg at 25 °C indicates triolein may exist in both the vapor and particulate phases in the atmosphere. 
Vapor-phase triolein will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 1.7 hours. 

Vapor-phase triolein will also be degraded in the atmosphere by reaction with ozone; the half-life for this reaction in air is estimated to be 0.7 hours. 
Particulate-phase triolein will be removed from the atmosphere by wet or dry deposition. 

If released to soil, triolein is expected to have no mobility based upon an estimated Koc of 1X10+10.
Volatilization from moist soil surfaces may be an important fate process based upon an estimated Henry's Law constant of 9.6X10-4 atm-cu m/mole; however, soil adsorption will attenuate the importance of volatilization. 

14C-Labeled triolein biodegraded to CO2 at a rate of 63.5% to 84% over 140 days in a sewage sludge-amended soil, suggesting that biodegradation may occur in the soil environment. 
If released into water, triolein is expected to adsorb to suspended solids and sediment based upon the estimated Koc. 

Volatilization from water surfaces is expected to be an important fate process based upon this compound's estimated Henry's Law constant. 
Estimated volatilization half-lives for a model river and model lake are 11 hours and 13 days, respectively. 

However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. 
The estimated volatilization half-life from a model pond is 5.1X10+5 years if adsorption is considered. 

An estimated BCF of 3.2 suggests the potential for bioconcentration in aquatic organisms is low. 
An estimated base-catalyzed second-order hydrolysis rate constant of 0.15 L/mole-sec corresponds to half-lives of 1.5 years and 55 days at pH values of 7 and 8, respectively. 

In respirometry tests, triolein had a biodegradation rate constant of 0.0025 per hour which corresponds to a half-life of 11.6 days; bioavailability was restricted due to the presence of double bonds and an autoxidation process occurring in the allylic chains resulting in the production of hydroperoxides, but the non-oxidized fractions were readily mineralized. 
Occupational exposure to triolein may occur through dermal contact with this compound at workplaces where triolein is produced or used. Monitoring data indicate that the general population may be exposed to triolein via ingestion of food products containing triolein as well as via dermal contact with consumer products containing triolein.

Stability and Reactivity of Glyceryl trioleate:

Hazardous Reactivities and Incompatibilities of Glyceryl trioleate:
Triolein (major skin lipid) was irradiated with 300-nm ultraviolet (UV) light, and the conditions for exposure approximated those at the skin surface exposed to sunlight. 
Using gas chromatography, the irradiated samples were analyzed for the presence of acrolein, formaldehyde, and acetaldehyde. 

The maximum amount of acrolein (1.05 nmol/mg Triolein) was formed after 6 hours of irradiation. 
Maximum amounts of formaldehyde (6 nmol/mg Triolein) and acetaldehyde (2.71 nmol/mg Triolein) were formed after 12 hours of irradiation.

Disposal Methods of Glyceryl trioleate:
The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for Glyceryl trioleate approved use or return Glyceryl trioleate to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Antidote and Emergency Treatment of Glyceryl trioleate:
Immediate first aid: Ensure that adequate decontamination has been carried out. 
If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. 

Perform CPR if necessary. 
Immediately flush contaminated eyes with gently flowing water. 

Do not induce vomiting. 
If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. 

Keep patient quiet and maintain normal body temperature. 
Obtain medical attention.

Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). 
Suction if necessary. 
Watch for signs of respiratory insufficiency and assist ventilations if needed. 

Administer oxygen by nonrebreather mask at 10 to 15 L/min. 
Monitor for pulmonary edema and treat if necessary.

Monitor for shock and treat if necessary.
Anticipate seizures and treat if necessary.

For eye contamination, flush eyes immediately with water. 
Irrigate each eye continuously with 0.9% saline (NS) during transport.

Do not use emetics. 
For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool.
Cover skin burns with dry sterile dressings after decontamination.

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. 
Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema.

Consider administering a beta agonist such as albuterol for severe bronchospasm.
Monitor cardiac rhythm and treat arrhythmias as necessary.

Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. 
For hypotension with signs of hypovolemia, administer fluid cautiously. 

Watch for signs of fluid overload.
Treat seizures with diazepam or lorazepam.
Use proparacaine hydrochloride to assist eye irrigation.

Identifiers of Glyceryl trioleate:
CAS Number: 122-32-7
ChEBI: CHEBI:53753
ChemSpider: 4593733
ECHA InfoCard: 100.004.123
MeSH: Triolein
PubChem CID: 5497163
UNII: O05EC62663 
CompTox Dashboard (EPA): DTXSID3026988 
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- check

Properties of Glyceryl trioleate:
Biological source: plant (sunflower)
Quality Level: 200
Assay: ≥99%
Form: oil
bp: 235-240 °C/18 mmHg (lit.)
Density: 0.91 g/mL (lit.)
Functional group: ester
Shipped in: ambient
Storage temp.: −20°C
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-

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

Molecular Weight: 885.4
XLogP3-AA: 22.4    
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 6
Rotatable Bond Count: 53
Exact Mass: 884.78329103
Monoisotopic Mass: 884.78329103
Topological Polar Surface Area: 78.9 Ų
Heavy Atom Count: 63
Complexity: 1010
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 3
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Hazards of Glyceryl trioleate:
Flash point: 302.6 °C (576.7 °F; 575.8 K)

Thermochemistry of Glyceryl trioleate: 
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

Specifications of Glyceryl trioleate:
Density: 0.9130g/mL
Color: Colorless to Yellow
Boiling Point: 235.0°C to 240.0°C (18.0mmHg)
Assay Percent Range: 98.5% min. (GC)
Infrared Spectrum: Authentic
Linear Formula: (C17H33COOCH2)2CHOCOC17H33
Beilstein: 02,IV,1664
Packaging: Glass bottle
Merck Index: 15,9904
Refractive Index: 1.4680 to 1.4700
Quantity: 1mL
Solubility Information: Solubility in water: insoluble in water. Other solubilities: soluble in chloroform, ether, ccl4, slightly soluble in alcohol
Specific Gravity: 0.913
Formula Weight: 885.45
Physical Form: Liquid
Percent Purity: 99%
Chemical Name or Material: Glycerine trioleate

Names of Glyceryl trioleate:

Preferred IUPAC name of Glyceryl trioleate:
Propane-1,2,3-triyl tri[(9Z)-octadec-9-enoate]

Synonyms of Glyceryl trioleate:
(9Z)9-Octadecenoic acid 1,2,3-propanetriyl ester
Glycerol trioleate
Glycerol triolein
Oleic acid triglyceride
Oleic triglyceride
Glycerol trioleate
Oleic triglyceride
Glycerol triolein
Oleic acid triglyceride
Glycerin trioleate
Oleyl triglyceride
Aldo TO
Emery 2423
Olein, tri-
Emery oleic acid ester 2230
Glycerol, tri(cis-9-octadecenoate)
1,2,3-Propanetriyl trioleate
HSDB 5594
Triglyceride OOO
Edenor NHTi-G
Kaolube 190
sn-Glyceryl trioleate
Actor LO 1
Kemester 1000
Emerest 2423
9-Octadecenoic acid (Z)-, 1,2,3-propanetriyl ester
9-Octadecenoic acid (9Z)-, 1,2,3-propanetriyl ester
Estol 1433
Radia 7363
1,2,3-Propanetriol tri(9-octandecenoate)
2,3-bis[[(Z)-octadec-9-enoyl]oxy]propyl (Z)-octadec-9-enoate
9-Octadecenoic acid, 1,2,3-propanetriyl ester
propane-1,2,3-triyl (9Z,9'Z,9''Z)tris-octadec-9-enoate
glycerine trioleate
1,3-bis[(9Z)-octadec-9-enoyloxy]propan-2-yl (9Z)-octadec-9-enoate
TG 54:3
(9Z)9-Octadecenoic acid 1,2,3-propanetriyl ester
EINECS 204-534-7
CCRIS 8687
9-Octadecenoic-9,10-t2 acid, 1,2,3-propanetriyl ester, (Z,Z,Z)- (9CI)
triolein C18:1
Triolein, tech grade
Epitope ID:117714
1,2,3-propanetriyl ester
EC 204-534-7
Glyceryl trioleate, ~65%
Glyceryl trioleate, >=99%
9-Octadecenoic acid (9Z)-, 1,1',1''-(1,2,3-propanetriyl) ester
Triolein, [9,10-3H(N)]-
Glyceryl trioleate, >=97.0% (TLC)
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
(9Z)-1,2,3-propanetriyl ester 9-Octadecenoic acid
(Z)-1,2,3-propanetriyl ester 9-Octadecenoic acid
(Z)-9-Octadecenoic acid, 1,2,3-propanetriyl ester
propane-1,2,3-triyl tris[(9Z)-octadec-9-enoate]
Triolein, European Pharmacopoeia (EP) Reference Standard
(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)-
Triolein (18:1 TG), 1,2,3-tri-(9Z-octadecenoyl)-glycerol, neat oil
(9Z)9-Octadecenoic acid 1,2,3-propanetriyl ester
(9Z,9'Z,9''Z)Tris(-9-octadécénoate) de 1,2,3-propanetriyle
1,2,3-Propanetriyl (9Z,9'Z,9''Z)tris(-9-octadecenoate)
1,2,3-Trioleoyl Glycerol
9-Octadecenoic acid (9Z)-, 1,2,3-propanetriyl ester
9-Octadecenoic acid (Z)-, 1,2,3-propanetriyl ester
9-Octadecenoic acid, 1,2,3-propanetriyl ester, (9Z,9'Z,9''Z)- 
Glycerin trioleate
Glycerine trioleate
Glycerol trioleate
Glycerol triolein
Glycerol, tri(cis-9-octadecenoate)
glyceryl trioleate
Oleic acid triglyceride
Oleic triglyceride
Olein, tri-
Propane-1,2,3-triyl (9Z,9'Z,9''Z)tris-octadec-9-enoate
(9Z)-1,1',1''-(1,2,3-propanetriyl) ester 9-Octadecenoate
(9Z)-1,1',1''-(1,2,3-propanetriyl) ester 9-Octadecenoic acid
(9Z)-1,2,3-propanetriyl ester 9-Octadecenoate
(9Z)-1,2,3-propanetriyl ester 9-Octadecenoic acid
(9Z)-9-Octadecenoic acid 1,2,3-propanetriyl ester
(Z)-1,2,3-propanetriyl ester 9-Octadecenoate
(Z)-1,2,3-propanetriyl ester 9-Octadecenoic acid
(Z)-9-Octadecenoic acid, 1,2,3-propanetriyl ester
1,2,3-Propanetriol tri(9-octandecenoate)
1,2,3-Propanetriyl trioleate
1,3-bis[(9Z)-octadec-9-enoyloxy]propan-2-yl (9Z)-octadec-9-enoate
2,3-bis[[(Z)-octadec-9-enoyl]oxy]propyl (Z)-octadec-9-enoate
9-Octadecenoic acid, 1,2,3-propanetriyl ester
Aldo TO
Edenor NHTi-G
Kaolube 190
Oleyl triglyceride
propane-1,2,3-triyl trioleate
propane-1,2,3-triyl tris[(9Z)-octadec-9-enoate]
sn-Glyceryl trioleate
Triolein (18:1 TG)
Triolein, [9,10-3H(N)]-

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