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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 of GLYCERYL TRIELAIDATE

SMILES

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

InChI

InChIKey=PHYFQTYBJUILEZ-WUOFIQDXSA-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
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

PubMed

TitleDatePubMed
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 Apr
Production of the mycelial phase of Malassezia in vitro.
2001 Dec
Identification, purification, and characterization of a thermally stable lipase from rice bran. A new member of the (phospho) lipase family.
2001 Dec
Conversion of Bacillus thermocatenulatus lipase into an efficient phospholipase with increased activity towards long-chain fatty acyl substrates by directed evolution and rational design.
2001 Nov
Effect of palm olein oil in a moderate-fat diet on plasma lipoprotein profile and aortic atherosclerosis in non-human primates.
2002
Effect of dietary cholesterol, trans and saturated fatty acids on serum lipoproteins in non-human primates.
2002
Utilisation of fatty acid and triacylglycerol by rat macrophages: the effect of endotoxin.
2002
Dual parallel electrospray ionization and atmospheric pressure chemical ionization mass spectrometry (MS), MS/MS and MS/MS/MS for the analysis of triacylglycerols and triacylglycerol oxidation products.
2002
Organotin compounds in a Norwegian fjord. A comparison of concentration levels in semipermeable membrane devices (SPMDs), blue mussels (Mytilus edulis) and water samples.
2002 Apr
LDL concentration is correlated with the removal from the plasma of a chylomicron-like emulsion in subjects with coronary artery disease.
2002 Apr
Microwave-assisted rapid characterization of lipase selectivities.
2002 Apr 18
Role of adipocyte differentiation-related protein in surfactant phospholipid synthesis by type II cells.
2002 Aug
Effect of a tumour-derived lipid-mobilising factor on glucose and lipid metabolism in vivo.
2002 Aug 27
Biofouling confounds the uptake of trace organic contaminants by semi-permeable membrane devices (SPMDs).
2002 Dec
Esterolytic and lipolytic activities of lactic acid bacteria isolated from ewe's milk and cheese.
2002 Dec
Lower calcium absorption in infants fed casein hydrolysate- and soy protein-based infant formulas containing palm olein versus formulas without palm olein.
2002 Dec
Analysis of lipoprotein lipase activity using high-performance liquid chromatography.
2002 Dec
Maldigestion and malabsorption of dietary lipid during severe childhood malnutrition.
2002 Dec
Glutamine promotes triglyceride absorption in a dose-dependent manner.
2002 Feb
Influence of phytostanol phosphoryl ascorbate, FM-VP4, on pancreatic lipase activity and cholesterol accumulation within Caco-2 cells.
2002 Jan-Apr
Edible arabinoxylan-based films. 1. Effects of lipid type on water vapor permeability, film structure, and other physical characteristics.
2002 Jul 3
Rapid method for determining malondialdehyde as secondary oxidation product in palm olein system by Fourier transform infrared spectroscopy.
2002 Jul-Aug
Lipoprotein lipase mRNA expression in abdominal adipose tissue is little modified by age and nutritional state in broiler chickens.
2002 Jun
Uptake of a cholesterol-rich emulsion by breast cancer.
2002 Jun
Regioselectivity of new bacterial lipases determined by hydrolysis of triolein.
2002 May
Cholesterol esterase accelerates intestinal cholesterol absorption.
2002 May 10
Application of infrared spectroscopy (attenuated total reflection) for monitoring enzymatic activity on substrate films.
2002 May 9
Purification and characterization of a novel cholesterol esterase from Pseudomonas aeruginosa, with its application to cleaning lipid-stained contact lenses.
2002 Nov
Use of triolein-semipermeable membrane devices to assess the bioconcentration and sediment sorption of hydrophobic organic contaminants in the Huaihe River, China.
2002 Nov
Effects of dietary lipids on cell proliferation of murine oral mucosa.
2002 Nov 20
Experimental cerebral fat embolism: embolic effects of triolein and oleic acid depicted by MR imaging and electron microscopy.
2002 Oct
Fat malabsorption in essential fatty acid-deficient mice is not due to impaired bile formation.
2002 Oct
Evidence that phospholipids play a key role in pre-beta apoA-I formation and high-density lipoprotein remodeling.
2002 Oct 15
Purification and structural characterization of the central hydrophobic domain of oleosin.
2002 Oct 4
Production, isolation and characterization of a sterol esterase from Ophiostoma piceae.
2002 Sep 23
Structure and properties of triolein-based polyurethane networks.
2002 Sep-Oct
Evidence of a relationship between autolysis of starter bacteria and lipolysis in cheddar cheese during ripening.
2003 Feb
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 Feb
A single-step procedure for the synthesis of photoreactive and radioactive glycerolipids.
2003 Feb 1
Behavior of flavor compounds in model food systems: a thermodynamic study.
2003 Feb 26
Fat and carbohydrate use in posthatch chicks.
2003 Jan
Solubilization of acyl heterogeneous triacylglycerol in phosphatidylcholine vesicles.
2003 Jan 15
Gas chromatography-mass spectrometry profile of urinary organic acids of Wistar rats orally treated with ozonized unsaturated triglycerides and ozonized sunflower oil.
2003 Jan 15
Enhancing quality and oxidative stability of aged fried food with gamma-tocopherol.
2003 Jan 29
Contribution of fatty acids released from lipolysis of plasma triglycerides to total plasma fatty acid flux and tissue-specific fatty acid uptake.
2003 Mar
Improvement of central motor conduction after bone marrow transplantation in adrenoleukodystrophy.
2003 Mar
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 Mar 12
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 Jun 11
Fat mobilization in adipose tissue is promoted by adipose triglyceride lipase.
2004 Nov 19
A cholesterol-free, high-fat diet suppresses gene expression of cholesterol transporters in murine small intestine.
2008 May
Patents
Name Type Language
GLYCERYL TRIELAIDATE
Systematic Name English
TRIELAIDIN
Common Name English
TRIELAIDOYLGLYCEROL
Systematic Name English
9-OCTADECENOIC ACID, 1,1',1''-(1,2,3-PROPANETRIYL) ESTER, (9E,9'E,9''E)-
Common Name English
GLYCEROL TRIELAIDATE
Systematic Name English
9-OCTADECENOIC ACID, 1,2,3-PROPANETRIYL ESTER, (9E,9'E,9''E)-
Common Name English
9-OCTADECENOIC ACID, 1,2,3-PROPANETRIYL ESTER, (E,E,E)-
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID101318457
Created by admin on Sat Dec 16 01:52:19 GMT 2023 , Edited by admin on Sat Dec 16 01:52:19 GMT 2023
PRIMARY
PUBCHEM
5364673
Created by admin on Sat Dec 16 01:52:19 GMT 2023 , Edited by admin on Sat Dec 16 01:52:19 GMT 2023
PRIMARY
CAS
537-39-3
Created by admin on Sat Dec 16 01:52:19 GMT 2023 , Edited by admin on Sat Dec 16 01:52:19 GMT 2023
PRIMARY
CHEBI
53759
Created by admin on Sat Dec 16 01:52:19 GMT 2023 , Edited by admin on Sat Dec 16 01:52:19 GMT 2023
PRIMARY
ECHA (EC/EINECS)
208-665-0
Created by admin on Sat Dec 16 01:52:19 GMT 2023 , Edited by admin on Sat Dec 16 01:52:19 GMT 2023
PRIMARY
FDA UNII
352S6U20HL
Created by admin on Sat Dec 16 01:52:19 GMT 2023 , Edited by admin on Sat Dec 16 01:52:19 GMT 2023
PRIMARY