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Showing Compound Glycerol tridecanoate (FDB003134)

Record Information
Version1.0
Creation date2010-04-08 22:05:40 UTC
Update date2019-11-26 02:58:31 UTC
Primary IDFDB003134
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGlycerol tridecanoate
DescriptionIt is used in dietary food products TG(10:0/10:0/10:0) or tricapric glyceride is a tridecanoic acid triglyceride or medium chain triglyceride. Triglycerides (TGs) are also known as triacylglycerols or triacylglycerides, meaning that they are glycerides in which the glycerol is esterified with three fatty acid groups (i.e. fatty acid tri-esters of glycerol). TGs 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. TG(10:0/10:0/10:0), in particular, consists of one chain of decanoic acid at the C-1 position, one chain of decanoic acid at the C-2 position and one chain of decanoic acid acid at the C-3 position. 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.
CAS Number621-71-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
1,2,3-Propanol tridecanoateChEBI
1,2,3-TridecanoylglycerolChEBI
Capric acid triglycerideChEBI
Capric triglycerideChEBI
CaprinChEBI
Decanoic acid, 1,2,3-propanetriyl esterChEBI
Glycerin tridecanoateChEBI
Glycerol tricaprateChEBI
Glycerol tridecanoateChEBI
Glyceryl tricaprateChEBI
Glyceryl tridecanoateChEBI
TG 10:0/10:0/10:0ChEBI
Tri-N-caprinChEBI
Tricapric glycerideChEBI
TridecanoinChEBI
TridecanoylglycerolChEBI
1,2,3-Propanol tridecanoic acidGenerator
Caprate triglycerideGenerator
Decanoate, 1,2,3-propanetriyl esterGenerator
Glycerin tridecanoic acidGenerator
Glycerol tricapric acidGenerator
Glycerol tridecanoic acidGenerator
Glyceryl tricapric acidGenerator
Glyceryl tridecanoic acidGenerator
1-Animal fats-2-animal fats-3-animal fats-glycerolHMDB
1-Decanoic acid-2-decanoic acid-3-decanoic acid-glycerolHMDB
TAG(10:0/10:0/10:0)HMDB
TriacylglycerolHMDB
Tracylglycerol(30:0)HMDB
TriglycerideHMDB
Tracylglycerol(10:0/10:0/10:0)HMDB
TAG(30:0)HMDB
TG(30:0)HMDB
1,2, 3-Propanetriyl-decanoateHMDB
1,2, 3-Propanetriyl-decanoic acidHMDB
2,3-Bis(decanoyloxy)propyl decanoateHMDB
2,3-Bis(decanoyloxy)propyl decanoate (acd/name 4.0)HMDB
2,3-Bis(decanoyloxy)propyl decanoic acidHMDB
Glycerol tricaprinHMDB
Tri-decanoinHMDB
TricaprinHMDB
TG(10:0/10:0/10:0)Lipid Annotator, ChEBI
1,2,3-Propanetriyl decanoate, 9CIdb_source
Decanoic acid, 1,2, 3-propanetriyl esterbiospider
Dynasanâ 110db_source
Predicted Properties
PropertyValueSource
Water Solubility1.6e-05 g/LALOGPS
logP8.78ALOGPS
logP10.92ChemAxon
logS-7.5ALOGPS
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.9 ŲChemAxon
Rotatable Bond Count32ChemAxon
Refractivity158.47 m³·mol⁻¹ChemAxon
Polarizability70.75 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC33H62O6
IUPAC name1,3-bis(decanoyloxy)propan-2-yl decanoate
InChI IdentifierInChI=1S/C33H62O6/c1-4-7-10-13-16-19-22-25-31(34)37-28-30(39-33(36)27-24-21-18-15-12-9-6-3)29-38-32(35)26-23-20-17-14-11-8-5-2/h30H,4-29H2,1-3H3
InChI KeyLADGBHLMCUINGV-UHFFFAOYSA-N
Isomeric SMILES[H]C(COC(=O)CCCCCCCCC)(COC(=O)CCCCCCCCC)OC(=O)CCCCCCCCC
Average Molecular Weight554.853
Monoisotopic Molecular Weight554.454639716
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 Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 71.44%; H 11.26%; O 17.30%DFC
Melting PointMp 32°DFC
Boiling PointNot Available
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSGlycerol tridecanoate, non-derivatized, GC-MS Spectrumsplash10-0a59-3958000000-f57192615ab610f32defSpectrum
GC-MSGlycerol tridecanoate, non-derivatized, GC-MS Spectrumsplash10-0a59-3958000000-f57192615ab610f32defSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-0000190000-62ceec1552f50a5d78862012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-0175090000-8c7de03a1649bbcb94822012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0089-9010000000-4e7483739c7dcb61b0bc2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0a59-3958000000-f57192615ab610f32def2012-08-31View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000090000-ce340e48f0c1c82582ea2017-10-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000090000-ce340e48f0c1c82582ea2017-10-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-0009070000-2c86bfc78962fbd6aa8d2017-10-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000090000-2a5a4f209f02f40b110f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000090000-2a5a4f209f02f40b110f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03ii-0909090000-c6a9641978779d1182b02021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ue9-0527090000-00cdfe845f15d4b6a6612021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000t-0933010000-de250ac1d1f0d8fcdca22021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dj-0912000000-3aa31014b1eb3b307c922021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000090000-add7d9098153c7a00e9a2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000090000-add7d9098153c7a00e9a2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0000090000-add7d9098153c7a00e9a2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0102090000-747370baaa832594f1b22021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-5727790000-91d904d103a37903b33b2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bu0-3591100000-2da6107e763a64b2df762021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000090000-d6cd7cf63c9fb0b8a2662021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000090000-d6cd7cf63c9fb0b8a2662021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-0109070000-6b4138a13a27d3e873082021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Spectrum
ChemSpider ID62521
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID69310
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00548
CRC / DFC (Dictionary of Food Compounds) IDCRK83-H:CRK83-H
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
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