Glyceryl trioleate (CHEM009649)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 03:08:43 UTC
Update Date2016-10-28 10:02:33 UTC
Accession NumberCHEM009649
Identification
Common NameGlyceryl trioleate
ClassSmall Molecule
DescriptionA TG(18:1(9Z)/18:1(9Z)/18:1(9Z)) formed by esterification of the three hydroxy groups of glycerol with oleic acid. TriTG(18:1(9Z)/18:1(9Z)/18:1(9Z)) is one of the two components of Lorenzo's oil.
Contaminant Sources
  • Cosmetic Chemicals
  • FooDB Chemicals
  • HPV EPA Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(Z)-9-Octadecenoic acid, 1,2,3-propanetriyl esterChEBI
1,2,3-Tri-(9Z-octadecenoyl)-glycerolChEBI
Glycerin trioleateChEBI
Glycerol trioleateChEBI
Glycerol trioleinChEBI
Glycerol, tri(cis-9-octadecenoate)ChEBI
Glyceryl trioleateChEBI
Glyceryl-1,2,3-trioleateChEBI
Oleic acid triglycerideChEBI
Oleic triglycerideChEBI
OleinChEBI
Oleyl triglycerideChEBI
Propane-1,2,3-triyl (9Z,9'z,9''z)tris-octadec-9-enoateChEBI
TG(18:1(9Z)/18:1(9Z)/18:1(9Z))[iso]ChEBI
TrioleoylglycerideChEBI
TrioleoylglycerolChEBI
(Z)-9-Octadecenoate, 1,2,3-propanetriyl esterGenerator
Glycerin trioleic acidGenerator
Glycerol trioleic acidGenerator
Glycerol, tri(cis-9-octadecenoic acid)Generator
Glyceryl trioleic acidGenerator
Glyceryl-1,2,3-trioleic acidGenerator
Oleate triglycerideGenerator
Propane-1,2,3-triyl (9Z,9'z,9''z)tris-octadec-9-enoic acidGenerator
TrielaidinHMDB
Trioleate glycerinHMDB
Trioleyl glycerolHMDB
Glycerol, trioleylHMDB
Trioleate, glycerolHMDB
Trioleate-glycerinHMDB
TriacylglycerolHMDB
TG(18:1/18:1/18:1)HMDB
TG(54:3)HMDB
Tracylglycerol(18:1/18:1/18:1)HMDB
TriglycerideHMDB
Tracylglycerol(54:3)HMDB
1-Oleoyl-2-oleoyl-3-oleoyl-glycerolHMDB
TAG(54:3)HMDB
1-(9Z-Octadecenoyl)-2-(9Z-octadecenoyl)-3-(9Z-octadecenoyl)-glycerolHMDB
TAG(18:1/18:1/18:1)HMDB
TG(18:1(9Z)/18:1(9Z)/18:1(9Z))Lipid Annotator
TrioleinMeSH
Chemical FormulaC57H104O6
Average Molecular Mass885.432 g/mol
Monoisotopic Mass884.783 g/mol
CAS Registry Number122-32-7
IUPAC Name1,3-bis[(9Z)-octadec-9-enoyloxy]propan-2-yl (9Z)-octadec-9-enoate
Traditional Nametriolein
SMILESCCCCCCCC\C=C/CCCCCCCC(=O)OCC(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC
InChI IdentifierInChI=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-
InChI KeyPHYFQTYBJUILEZ-IUPFWZBJSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as triacylglycerols. These are glycerides consisting of three fatty acid chains covalently bonded to a glycerol molecule through ester linkages.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerolipids
Sub ClassTriradylcglycerols
Direct ParentTriacylglycerols
Alternative Parents
Substituents
  • Triacyl-sn-glycerol
  • Tricarboxylic acid or derivatives
  • Fatty acid ester
  • Fatty acyl
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.1e-06 g/LALOGPS
logP10.82ALOGPS
logP20.51ChemAxon
logS-8.2ALOGPS
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.9 ŲChemAxon
Rotatable Bond Count53ChemAxon
Refractivity272.25 m³·mol⁻¹ChemAxon
Polarizability116.96 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 30V, positivesplash10-000i-0000000090-91d6e8bb3820a2b9ebdeSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 46V, positivesplash10-000i-0025004090-32e831ad9bb94e656965Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 61V, positivesplash10-00kr-4689024020-7527d97fb03536363c5bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 77V, positivesplash10-00lb-6942000000-37f17691e5732c6d232bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 93V, positivesplash10-000t-7920000000-8d53f79404c44a257cbcSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 109V, positivesplash10-0532-9800000000-5ddd79d8af2c416bab4dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 123V, positivesplash10-0532-9700000000-e96406e89785ef71e711Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 61V, positivesplash10-0udi-0000019030-5f72f64cb14b99025263Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 61V, positivesplash10-03di-0158960000-bad288273f5f0ef006e8Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 61V, positivesplash10-00or-0054190000-2d9cb5e1963a459c8830Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 61V, positivesplash10-0002-3940000000-daf7601cc0abe13d83faSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 31V, positivesplash10-0udi-0000009000-6d75632a4c7e9871410cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 42V, positivesplash10-0uxr-5671009000-a4a6beef3d7f47884d90Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 53V, positivesplash10-015a-9830001000-493c7832f4a4288ca519Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 63V, positivesplash10-00l2-9510000000-48886ae654cd58f8e05dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 74V, positivesplash10-05o1-9400000000-50d3f5f119ff86e93d72Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 84V, positivesplash10-05o1-9300000000-c9f83ff0d877bf07548bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 95V, positivesplash10-067j-9200000000-362946f8ec43e2da1de6Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 106V, positivesplash10-067j-9100000000-3cbc32304732b7cd617eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 127V, positivesplash10-067i-9100000000-975bad5ee71e2769d5a6Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 61V, positivesplash10-014i-0094041000-972891f073da867b3319Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 61V, positivesplash10-0072-2900000000-23da0caf841c568c5920Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000009-7ebc474373ce1c8c3388Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000000009-7ebc474373ce1c8c3388Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-0000009061-c361cdac983d0cdffd59Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB13038
HMDB IDHMDB0005453
FooDB IDFDB094046
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-11691
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTriolein
Chemspider IDNot Available
ChEBI ID53753
PubChem Compound ID5497163
Kegg Compound IDNot Available
YMDB IDYMDB01315
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11304127
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23475189
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24288099
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24362891
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24489110
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=24604600
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24810291
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24859695
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=25045169
10. A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)
11. Desnuelle, P.; Naudet, M. Isomerization of oleic acid during the synthesis of triolein. Bull. soc. chim. (1945), 12 998-1001. CAN 40:19192 AN 1946:19192 CAPLUS
12. Hollebeeck S, Borlon F, Schneider YJ, Larondelle Y, Rogez H: Development of a standardised human in vitro digestion protocol based on macronutrient digestion using response surface methodology. Food Chem. 2013 Jun 1;138(2-3):1936-44. doi: 10.1016/j.foodchem.2012.11.041. Epub 2012 Nov 17.
13. Wang Y, Wang YJ, Wang L, Fang GD, Cang L, Herath HM, Zhou DM: Reducing the bioavailability of PCBs in soil to plant by biochars assessed with triolein-embedded cellulose acetate membrane technique. Environ Pollut. 2013 Mar;174:250-6. doi: 10.1016/j.envpol.2012.12.004. Epub 2012 Dec 29.