GLYCERYL TRIOLEATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C57H104O6
Molecular Weight	885.4321
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	3
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCCCC\C=C/CCCCCCCC(=O)OCC(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC

InChI

InChIKey=PHYFQTYBJUILEZ-IUPFWZBJSA-N

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-

HIDE SMILES / InChI

Molecular Formula	C57H104O6
Molecular Weight	885.4321
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	3
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8779968 | https://pubchem.ncbi.nlm.nih.gov/compound/Trielaidin

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

Approval Year

PubMed

Title	Date	PubMed
A cholesterol-free, high-fat diet suppresses gene expression of cholesterol transporters in murine small intestine.	2008-05	18356535
Fat mobilization in adipose tissue is promoted by adipose triglyceride lipase.	2004-11-19	15550674
Stearoyl-CoA desaturase 1 gene expression is necessary for fructose-mediated induction of lipogenic gene expression by sterol regulatory element-binding protein-1c-dependent and -independent mechanisms.	2004-06-11	15066988
Dynamics of competitive adsorption of alphas-casein and beta-casein at planar triolein-water interface: evidence for incompatibility of mixing in the interfacial film.	2003-03-12	12617601
Contribution of fatty acids released from lipolysis of plasma triglycerides to total plasma fatty acid flux and tissue-specific fatty acid uptake.	2003-03	12606500
Improvement of central motor conduction after bone marrow transplantation in adrenoleukodystrophy.	2003-03	12588932
Behavior of flavor compounds in model food systems: a thermodynamic study.	2003-02-26	12590487
A single-step procedure for the synthesis of photoreactive and radioactive glycerolipids.	2003-02-01	12576071
Evidence of a relationship between autolysis of starter bacteria and lipolysis in cheddar cheese during ripening.	2003-02	12617399
Atorvastatin enhances the plasma clearance of chylomicron-like emulsions in subjects with atherogenic dyslipidemia: relevance to the in vivo metabolism of triglyceride-rich lipoproteins.	2003-02	12535744
Enhancing quality and oxidative stability of aged fried food with gamma-tocopherol.	2003-01-29	12537432
Solubilization of acyl heterogeneous triacylglycerol in phosphatidylcholine vesicles.	2003-01-15	12517113
Gas chromatography-mass spectrometry profile of urinary organic acids of Wistar rats orally treated with ozonized unsaturated triglycerides and ozonized sunflower oil.	2003-01-15	12482495
Fat and carbohydrate use in posthatch chicks.	2003-01	12580253
Biofouling confounds the uptake of trace organic contaminants by semi-permeable membrane devices (SPMDs).	2002-12	12523542
Esterolytic and lipolytic activities of lactic acid bacteria isolated from ewe's milk and cheese.	2002-12	12495024
Lower calcium absorption in infants fed casein hydrolysate- and soy protein-based infant formulas containing palm olein versus formulas without palm olein.	2002-12	12480803
Analysis of lipoprotein lipase activity using high-performance liquid chromatography.	2002-12	12474211
Maldigestion and malabsorption of dietary lipid during severe childhood malnutrition.	2002-12	12456554
Effects of dietary lipids on cell proliferation of murine oral mucosa.	2002-11-20	12617749
Purification and characterization of a novel cholesterol esterase from Pseudomonas aeruginosa, with its application to cleaning lipid-stained contact lenses.	2002-11	12506971
Use of triolein-semipermeable membrane devices to assess the bioconcentration and sediment sorption of hydrophobic organic contaminants in the Huaihe River, China.	2002-11	12389917
Evidence that phospholipids play a key role in pre-beta apoA-I formation and high-density lipoprotein remodeling.	2002-10-15	12369845
Purification and structural characterization of the central hydrophobic domain of oleosin.	2002-10-04	12124381
Review of the background and application of triolein-containing semipermeable membrane devices in aquatic environmental study.	2002-10-02	12204593
Experimental cerebral fat embolism: embolic effects of triolein and oleic acid depicted by MR imaging and electron microscopy.	2002-10	12372741
Fat malabsorption in essential fatty acid-deficient mice is not due to impaired bile formation.	2002-10	12223350
Production, isolation and characterization of a sterol esterase from Ophiostoma piceae.	2002-09-23	12479402
Structure and properties of triolein-based polyurethane networks.	2002-09-10	12217052
Effect of a tumour-derived lipid-mobilising factor on glucose and lipid metabolism in vivo.	2002-08-27	12189560
Rapid method for determining malondialdehyde as secondary oxidation product in palm olein system by Fourier transform infrared spectroscopy.	2002-08-20	12184171
Role of adipocyte differentiation-related protein in surfactant phospholipid synthesis by type II cells.	2002-08	12114189
Expression and characterization of Ca(2+)-independent lipase from Bacillus pumilus B26.	2002-07-11	12117564
Edible arabinoxylan-based films. 1. Effects of lipid type on water vapor permeability, film structure, and other physical characteristics.	2002-07-03	12083869
Feeding of red palm oil-supplemented diets to rats may impact positively on vitamin A status.	2002-07	12090023
Influence of phytostanol phosphoryl ascorbate, FM-VP4, on pancreatic lipase activity and cholesterol accumulation within Caco-2 cells.	2002-06-04	12042117
[Changes in of plasma lipoproteins after the use of palm oil in the diet of a group healthy adults].	2002-06	12184147
Lipoprotein lipase mRNA expression in abdominal adipose tissue is little modified by age and nutritional state in broiler chickens.	2002-06	12079052
Uptake of a cholesterol-rich emulsion by breast cancer.	2002-06	12051880
Cholesterol esterase accelerates intestinal cholesterol absorption.	2002-05-10	12031288
Application of infrared spectroscopy (attenuated total reflection) for monitoring enzymatic activity on substrate films.	2002-05-09	11911924
Regioselectivity of new bacterial lipases determined by hydrolysis of triolein.	2002-05	11927984
Microwave-assisted rapid characterization of lipase selectivities.	2002-04-18	12062110
Organotin compounds in a Norwegian fjord. A comparison of concentration levels in semipermeable membrane devices (SPMDs), blue mussels (Mytilus edulis) and water samples.	2002-04	11993770
LDL concentration is correlated with the removal from the plasma of a chylomicron-like emulsion in subjects with coronary artery disease.	2002-04	11888530
Effect of palm olein oil in a moderate-fat diet on plasma lipoprotein profile and aortic atherosclerosis in non-human primates.	2002	12492629
Effect of palm olein oil in a moderate-fat diet on low-density lipoprotein composition in non-human primates.	2002	12492628
Effect of dietary cholesterol, trans and saturated fatty acids on serum lipoproteins in non-human primates.	2002	12492627
Utilisation of fatty acid and triacylglycerol by rat macrophages: the effect of endotoxin.	2002	12438765
T cells ignore aniline, a prohapten, but respond to its reactive metabolites generated by phagocytes: possible implications for the pathogenesis of toxic oil syndrome.	2001-04	11304127

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:26:20 GMT 2025` Edited by `admin` on `Mon Mar 31 21:26:20 GMT 2025`
Record UNII	O05EC62663
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

TRIOLEIN

Preferred Name

English

GLYCERYL TRIOLEATE

Systematic Name

English

Triolein [WHO-DD]

Common Name

English

GLYCEROL TRIOLEATE

Common Name

English

Glyceryl trioleate [WHO-DD]

Common Name

English

GLYCERYL TRIOLEATE [VANDF]

Common Name

English

GLYCEROL TRIOLEIN

Systematic Name

English

GLYCERYL TRIOLEATE [HSDB]

Common Name

English

GLYCERYL TRIOLEATE [MART.]

Common Name

English

GLYCERYL TRIOLEATE [II]

Common Name

English

TRIOLEIN [USP-RS]

Common Name

English

OLEIC ACID TRIGLYCERIDE

Common Name

English

TRIOLEIN [MI]

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

87594