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Showing Compound Glycerol trioleate (FDB002910)

Record Information
Version1.0
Creation date2010-04-08 22:05:34 UTC
Update date2019-11-26 02:58:08 UTC
Primary IDFDB002910
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGlycerol trioleate
DescriptionConstituent of olive oil and other vegetable oils TG(18:1(9Z)/18:1(9Z)/18:1(9Z)) or Triolein is a monoacid triglyceride. Triglycerides (TGs) are also known as triacylglycerols or triacylglycerides. TGs are fatty acid triesters of glycerol and may be divided into three general types with respect to their acyl substituents. They are simple or monoacid if they contain only one type of fatty acid, diacid if they contain two types of fatty acids and triacid if three different acyl groups. Chain lengths of the fatty acids in naturally occurring triglycerides can be of varying lengths and saturations but 16, 18 and 20 carbons are the most common. TGs are the main constituent of vegetable oil and animal fats. TGs are major components of very low density lipoprotein (VLDL) and chylomicrons, play an important role in metabolism as energy sources and transporters of dietary fat. They contain more than twice the energy (9 kcal/g) of carbohydrates and proteins. In the intestine, triglycerides are split into glycerol and fatty acids (this process is called lipolysis) (with the help of lipases and bile secretions), which can then move into blood vessels. The triglycerides are rebuilt in the blood from their fragments and become constituents of lipoproteins, which deliver the fatty acids to and from fat cells among other functions. Various tissues can release the free fatty acids and take them up as a source of energy. Fat cells can synthesize and store triglycerides. When the body requires fatty acids as an energy source, the hormone glucagon signals the breakdown of the triglycerides by hormone-sensitive lipase to release free fatty acids. As the brain cannot utilize fatty acids as an energy source, the glycerol component of triglycerides can be converted into glucose for brain fuel when it is broken down. (www.cyberlipid.org, www.wikipedia.org); ; TAGs can serve as fatty acid stores in all cells, but primarily in adipocytes of adipose tissue. The major building block for the synthesis of triacylglycerides, in non-adipose tissue, is glycerol. Adipocytes lack glycerol kinase and so must use another route to TAG synthesis. Specifically, dihydroxyacetone phosphate (DHAP), which is produced during glycolysis, is the precursor for TAG synthesis in adipose tissue. DHAP can also serve as a TAG precursor in non-adipose tissues, but does so to a much lesser extent than glycerol. The use of DHAP for the TAG backbone depends on whether the synthesis of the TAGs occurs in the mitochondria and ER or the ER and the peroxisomes. The ER/mitochondria pathway requires the action of glycerol-3-phosphate dehydrogenase to convert DHAP to glycerol-3-phosphate. Glycerol-3-phosphate acyltransferase then esterifies a fatty acid to glycerol-3-phosphate thereby generating lysophosphatidic acid. The ER/peroxisome reaction pathway uses the peroxisomal enzyme DHAP acyltransferase to acylate DHAP to acyl-DHAP which is then reduced by acyl-DHAP reductase. The fatty acids that are incorporated into TAGs are activated to acyl-CoAs through the action of acyl-CoA synthetases. Two molecules of acyl-CoA are esterified to glycerol-3-phosphate to yield 1,2-diacylglycerol phosphate (also known as phosphatidic acid). The phosphate is then removed by phosphatidic acid phosphatase (PAP1), to generate 1,2-diacylglycerol. This diacylglycerol serves as the substrate for addition of the third fatty acid to make TAG. Intestinal monoacylglycerols, derived from dietary fats, can also serve as substrates for the synthesis of 1,2-diacylglycerols.; Triolein is a triglyceride and unsaturated fat formed from oleic acid. Glycerol trioleate is found in fats and oils, almond, and peach.
CAS Number122-32-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Glycerol trioleic acidGenerator
(9Z)-1,1',1''-(1,2,3-propanetriyl) ester 9-Octadecenoatebiospider
(9Z)-1,1',1''-(1,2,3-propanetriyl) ester 9-octadecenoic acidHMDB
(9Z)-1,2,3-propanetriyl ester 9-Octadecenoatebiospider
(9Z)-1,2,3-propanetriyl ester 9-Octadecenoic acidbiospider
(Z)-1,2,3-propanetriyl ester 9-Octadecenoatebiospider
(Z)-1,2,3-propanetriyl ester 9-Octadecenoic acidbiospider
(Z)-9-Octadecenoate, 1,2,3-propanetriyl esterGenerator
(Z)-9-Octadecenoic acid, 1,2,3-propanetriyl esterChEBI
1,2,3-Propanetriol tri(9-octandecenoate)biospider
1,2,3-Propanetriyl trioleatebiospider
1,2,3-Tri-(9Z-octadecenoyl)-glycerolChEBI
1,2,3-tri-(9Z-octadecenoyl)-sn-glycerolbiospider
1,2,3-Tri(cis-9-octadecenoyl)glycerolbiospider
2,3-Bis[(9E)-9-octadecenoyloxy]propyl (9E)-9-octadecenoatebiospider
9-Octadecenoic acid (9Z)-, 1,2,3-propanetriyl esterbiospider
9-Octadecenoic acid (Z)-, 1,2,3-propanetriyl esterbiospider
9-Octadecenoic acid 1,2,3-propanetriyl esterbiospider
9-Octadecenoic acid, 1,2,3-propanetriyl esterbiospider
Actor LO 1biospider
Aldo tobiospider
Edenor nhti-gbiospider
Emerest 2423biospider
Emery 2423HMDB
Emery oleic acid ester 2230biospider
Estol 1433HMDB
Glycerin trioleatebiospider
Glycerin trioleic acidGenerator
Glycerol trioleatedb_source
Glycerol trioleinbiospider
Glycerol, tri(cis-9-octadecenoate)biospider
Glycerol, tri(cis-9-octadecenoic acid)Generator
Glyceryl trioleatebiospider
Glyceryl trioleic acidGenerator
Glyceryl-1,2,3-trioleatebiospider
Glyceryl-1,2,3-trioleic acidGenerator
Kaolube 190biospider
Kemester 1000biospider
Oleate triglycerideGenerator
Oleic acid triglyceridebiospider
Oleic triglyceridebiospider
Oleindb_source
Olein, tri-biospider
Oleyl triglyceridebiospider
Priolube 1435biospider
propane-1,2,3-triyl (9Z,9'Z,9''Z)tris-octadec-9-enoatebiospider
Propane-1,2,3-triyl (9Z,9'z,9''z)tris-octadec-9-enoic acidGenerator
Radia 7363HMDB
Raolinebiospider
SN-glyceryl trioleatebiospider
TG(18:1(9Z)/18:1(9Z)/18:1(9Z))HMDB
TG(18:1(9Z)/18:1(9Z)/18:1(9Z))[iso]ChEBI
Tri-oleinbiospider
Triglyceride ooobiospider
Trioleindb_source
triolein C18:1biospider
Triolein glyceryl trioleatebiospider
Triolein, [9,10-3H(N)]-biospider
Trioleoylglyceridebiospider
Trioleoylglycerolbiospider
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
Polarizability118.51 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC57H104O6
IUPAC name3-[(9E)-octadec-9-enoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propyl (9E)-octadec-9-enoate
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-BSCDBXJPSA-N
Isomeric SMILESCCCCCCCC\C=C\CCCCCCCC(=O)OCC(COC(=O)CCCCCCC\C=C\CCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC
Average Molecular Weight885.4321
Monoisotopic Molecular Weight884.78329106
Classification
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 DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 77.32%; H 11.84%; O 10.84%DFC
Melting PointMp 5°DFC
Boiling PointBp18 235-240° part. dec.DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID4593733
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5497163
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB05453
CRC / DFC (Dictionary of Food Compounds) IDCPD57-F:CPD60-B
EAFUS IDNot Available
Dr. Duke IDTRIOLEIN
BIGG IDNot Available
KNApSAcK IDC00032423
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDTriolein
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti aggregantDUKE
Enzymes
NameGene NameUniProt ID
Liver carboxylesterase 1CES1P23141
Pancreatic triacylglycerol lipasePNLIPP16233
Hepatic triacylglycerol lipaseLIPCP11150
Inactive pancreatic lipase-related protein 1PNLIPRP1P54315
Patatin-like phospholipase domain-containing protein 3PNPLA3Q9NST1
Gastric triacylglycerol lipaseLIPFP07098
Endothelial lipaseLIPGQ9Y5X9
Diacylglycerol O-acyltransferase 1DGAT1O75907
Pancreatic lipase-related protein 2PNLIPRP2P54317
Lipoprotein lipaseLPLP06858
Monoglyceride lipaseMGLLQ99685
Protein disulfide-isomeraseP4HBP07237
2-acylglycerol O-acyltransferase 2MOGAT2Q3SYC2
Patatin-like phospholipase domain-containing protein 4PNPLA4P41247
Diacylglycerol O-acyltransferase 2DGAT2Q96PD7
2-acylglycerol O-acyltransferase 1MOGAT1Q96PD6
2-acylglycerol O-acyltransferase 3MOGAT3Q86VF5
Glycerol-3-phosphate acyltransferase 3AGPAT9Q53EU6
Patatin-like phospholipase domain-containing protein 2PNPLA2Q96AD5
Pancreatic lipase-related protein 3PNLIPRP3Q17RR3
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).