ContaminantDB: Glycerol tritridecanoate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 22:08:35 UTC

Update Date

2016-11-09 01:18:01 UTC

Accession Number

CHEM025104

Identification

Common Name

Glycerol tritridecanoate

Class

Small Molecule

Description

Glycerol tritridecanoate is a probable constituent of fats. 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

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Glycerol tritridecanoic acid	Generator
1,2,3-Propanetriyl tritridecanoate, 9ci	HMDB
Tritridecanoin, 8ci	HMDB

Chemical Formula

C₄₂H₈₀O₆

Average Molecular Mass

681.081 g/mol

Monoisotopic Mass

680.595 g/mol

CAS Registry Number

26536-12-9

IUPAC Name

1,3-bis(tridecanoyloxy)propan-2-yl tridecanoate

Traditional Name

1,3-bis(tridecanoyloxy)propan-2-yl tridecanoate

SMILES

CCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCCC)OC(=O)CCCCCCCCCCCC

InChI Identifier

InChI=1S/C42H80O6/c1-4-7-10-13-16-19-22-25-28-31-34-40(43)46-37-39(48-42(45)36-33-30-27-24-21-18-15-12-9-6-3)38-47-41(44)35-32-29-26-23-20-17-14-11-8-5-2/h39H,4-38H2,1-3H3

InChI Key

UDXANBFMQUOKTQ-UHFFFAOYSA-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerolipids

Sub Class

Triradylcglycerols

Direct Parent

Triacylglycerols

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 Framework

Aliphatic acyclic compounds

External Descriptors

Triacylglycerols (LMGL03012619 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.3e-05 g/L	ALOGPS
logP	10.07	ALOGPS
logP	14.92	ChemAxon
logS	-7.7	ALOGPS
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.9 Å²	ChemAxon
Rotatable Bond Count	41	ChemAxon
Refractivity	199.88 m³·mol⁻¹	ChemAxon
Polarizability	91.07 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0000009000-a44bb5f42de5a1ae200e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0000009000-a44bb5f42de5a1ae200e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0159-0000907000-7583eb1a166c9e9b4b46	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000000900-695da9e0d66dd1f66a59	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0000000900-695da9e0d66dd1f66a59	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0000000900-695da9e0d66dd1f66a59	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0100109000-5a76b64ac03f82d9efb1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06rt-2910328000-9b565062a7546e84dc08	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0535-9320000000-280e7f7f318dff9d938c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000009000-63ad216e53297c6978a6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0000009000-63ad216e53297c6978a6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dr-0090909000-c0d611659287ec92097e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0000009000-9396795dbc2df771836f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0000009000-9396795dbc2df771836f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0159-0100907000-607bc789ee1208a482b2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0060709000-85b8caf668e0968a7a7c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0090202000-2f02257a20a93e6f2a2c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-0090110000-837af8d9ba6f782d14c8	Spectrum