TRIOLEIN Chemical Properties

Melting point:

-5,5°C

Boiling point:

235-240 °C18 mm Hg(lit.)

Density 

0.91 g/mL(lit.)

refractive index 

n20/D 1.470

Flash point:

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

9-Octadecenoic acid (9Z)-, 1,1',1''-(1,2,3-propanetriyl) ester (122-32-7)

Safety Information

Hazard Codes 

F,Xn

Risk Statements 

11-20/21/22-53

Safety Statements 

24/25-39-26

RIDADR 

UN 1282 3/PG 2

WGK Germany 

-

RTECS 

RG1936500

F 

10-23

TSCA 

Yes

HS Code 

29161500

Hazardous Substances Data

122-32-7(Hazardous Substances Data)

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

TRIOLEIN Usage And Synthesis

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

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

Production Methods

Triolein is manufactured by the esterification of fractionated fatty acids, mainly oleic acid and glycerin.

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.

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.

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