Glyceryl Trioleate

Base Information

• Chemical Name: Glyceryl Trioleate
• CAS No.: 122-32-7
• Deprecated CAS: 124330-00-3,24016-60-2,41755-78-6,1352879-45-8,2679783-79-8,1352879-45-8,41755-78-6
• Molecular Formula: C57H104O6
• Molecular Weight: 885.449
• Hs Code.: 29161500
• European Community (EC) Number: 204-534-7
• UNII: O05EC62663
• DSSTox Substance ID: DTXSID3026988
• Nikkaji Number: J5.353H
• Wikipedia: Triolein
• Wikidata: Q413929
• NCI Thesaurus Code: C77513
• Metabolomics Workbench ID: 6605
• ChEMBL ID: CHEMBL4297656
• Mol file: 122-32-7.mol

Synonyms:Glycerol Trioleate;Glycerol, Trioleyl;Trielaidin;Trioleate Glycerin;Trioleate, Glycerol;Trioleate-Glycerin;Triolein;Trioleoylglycerol;Trioleyl Glycerol

Chemical Property of Glyceryl Trioleate

Chemical Property:

• Appearance/Colour: colourless viscous liquid
• Vapor Pressure: 6.66E-27mmHg at 25°C
• Melting Point: -5.5°C
• Refractive Index: n20/D 1.470
• Boiling Point: 818.7 °C at 760 mmHg
• Flash Point: 302.6 °C
• PSA: 78.90000
• Density: 0.921 g/cm³
• LogP: 18.09710
• Storage Temp.: 2-8°C
• Solubility.: chloroform: 0.1 g/mL, clear, colorless
• XLogP3: 22.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 53
• Exact Mass: 884.78329103
• Heavy Atom Count: 63
• Complexity: 1010

Purity/Quality:

99% ^*data from raw suppliers

GlycerineTrioleate(TechnicalGrade) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xn
• Hazard Codes: F,Xn
• Statements: 11-20/21/22-53
• Safety Statements: 24/25-39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Fatty Acids and Fats
• Canonical SMILES: CCCCCCCCC=CCCCCCCCC(=O)OCC(COC(=O)CCCCCCCC=CCCCCCCCC)OC(=O)CCCCCCCC=CCCCCCCCC
• Isomeric SMILES: CCCCCCCC/C=C\CCCCCCCC(=O)OCC(OC(=O)CCCCCCC/C=C\CCCCCCCC)COC(=O)CCCCCCC/C=C\CCCCCCCC
• Recent ClinicalTrials: Randomized Study of Beta Interferon and Thalidomide in Patients With Adrenoleukodystrophy
• 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.
• 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. 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 miceas an interfering substance to test its effect on human serum in the approach to develop rapid enzyme immunoassay for the detection of retinol-binding proteinas a standard in the determination of triglyceride concentration, colorimetrically using liver tissue sample from cows

Technology Process of Glyceryl Trioleate

There total 19 articles about Glyceryl Trioleate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

cis-Octadecenoic acid (112-80-1,2027-47-6) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → trioleoylglycerol (122-32-7)

Guidance literature:

With 2,2-dimethylpropanoic anhydride; dmap; at 50 ℃; for 24h;

DOI:10.1021/ja075824w

Reference yield: 93.0%

oleic anhydride (6085-36-5,55726-25-5,24909-72-6) + 1,2-dioleoyl-3-O-triisopropylsilyl-sn-glycerol (1001440-59-0) → trioleoylglycerol (122-32-7)

Guidance literature:

With trimethylsilyl bromide; tetrabutylammomium bromide; In chloroform; for 2h; Heating;

DOI:10.1039/b713246h

Reference yield:

cis-Octadecenoic acid (112-80-1,2027-47-6) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → trioleoylglycerol (122-32-7) + 1-monooleoyl glycerol (111-03-5,2716-53-2,30836-40-9,34487-30-4,69483-90-5,99297-71-9,129784-87-8,33978-07-3,925-14-4) + 1,2-dioleoylglycerol (2442-61-7,3738-74-7,22202-42-2,24529-88-2,26540-69-2,33735-55-6,38738-56-6,98719-67-6)

Guidance literature:

With 1.05HO₃P*0.95C₆H₅O₃P^(2-)*0.1H₂O*Zr⁽²⁺⁾; at 180 ℃; for 1h; Reagent/catalyst;

DOI:10.1016/j.apcata.2013.04.043

upstream raw materials:

(Z)-9-octadecenoyl chloride

glycerol

cis-Octadecenoic acid

Methyl oleate

Downstream raw materials:

1-monooleoyl glycerol

1,3-diolein

trielaidin

1,3-distearoyl-2-oleoylglycerol

Refernces

• 1、 Jeenpadiphat, Sirima,Bj?rk, Emma M.,Odén, Magnus,Tungasmita, Duangamol Nuntasri. "Propylsulfonic acid functionalized mesoporous silica catalysts for esterification of fatty acids". . p. 253 - 259. Retrieved 2015.
• 2、 Schreiberová, Olga,Krulikovská, Tereza,Sigler, Karel,?ejková, Alena,?ezanka, Tomá?. "RP-HPLC/MS-APCI analysis of branched chain TAG prepared by precursor-directed biosynthesis with rhodococcus erythropolis". . p. 743 - 756. Retrieved 2010.
• 3、 Zhao, Yanjun,Liu, Junfeng,Deng, Li,Wang, Fang,Tan, Tianwei. "Optimization of Candida sp. 99-125 lipase catalyzed esterification for synthesis of monoglyceride and diglyceride in solvent-free system". . p. 157 - 162. Retrieved 2011.
• 4、 -. "FUNCTIONALISED MATERIALS, PROCESS FOR THE PRODUCTION AND USES THEREOF". Paragraph 0041; 0055. . Retrieved 2015/04/22.
• 5、 -. "PALM OIL ENRICHED IN UNSATURATED FATTY ACIDS". Paragraph 0067; 0068. . Retrieved 2013/06/06.