Structure Database (LMSD)

Common Name
Trilauroyl-glycerol
Systematic Name
1,2,3-tridodecanoyl-sn-sn-glycerol
Synonyms
  • 1,2,3-tridodecanoyl-glycerol
  • 1,2,3-tridodecanoyl-sn-glycerol
LM ID
LMGL03012618
Formula
C39H74O6
Exact Mass
Calculate m/z
638.548541
Sum Composition
TG 36:0
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View MassBank spectra

Classification

Category
Main Class
Sub Class
Glycerolipids [GL]
Triradylglycerols [GL03]
Triacylglycerols [GL0301]

Biological Context

1,2,3-Trilauroyl glycerol is a triacylglycerol that contains lauric acid (Item No. 10006626) at the sn-1, sn-2, and sn-3 positions and is a component of coconut and seed oils.1,2 It increases the activity of HMG-CoA reductase in rat intestine and the production of cholesterol in the rat jejunal and ileal epithelium when administered at a dose of 10% (w/w) in the diet.3 A nanoemulsion of 1,2,3-trilauroyl glycerol (0.2%, w/v) is virucidal against severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) and H1N1 influenza A virus in infected MDCK cells.4 1,2,3-Trilauroyl glycerol has been used in the formation of solid lipid nanoparticles (SLNs) for the delivery of paclitaxel (Item No. 10461) in SKOV3 ovarian cancer cells.5 Formulations containing 1,2,3-trilauroyl glycerol have been used in cosmetics as skin conditioners and thickening agents.

This information has been provided by Cayman Chemical

References

1. Komaram, A.C., Anjaneyulu, E., Goswami, K., et al. Detection and quantification of palmolein and palm kernel oil added as adulterant in coconut oil based on triacylglycerol profile. J. Food Sci. Technol. 58(11), 4420-4428 (2021).
2. Litchfield, C., Miller, E., Harlow, R.D., et al. The triglyceride composition of 17 seed fats rich in octanoic, decanoic, or lauric acid. Lipids 2(4), 345-350 (1967).
3. Oku, H., and Sugano, M. Dietary fat dependence of intestinal 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase activity in rats. J. Nutr. 115(7), 880-889 (1985).
4. Weerapol, Y., Manmuan, S., Limmatvapirat, S., et al. Enhancing the efficacy of monolaurin against SARS-CoV-2 and influenza A (H1N1) with a nanoemulsion formulation. OpenNano 17, 100207 (2024).
5. Xu, W., Lim, S.-J., and Lee, M.-K. Cellular uptake and antitumour activity of paclitaxel incorporated into trilaurin-based solid lipid nanoparticles in ovarian cancer. J. Microencapsul. 30(8), 755-761 (2013).

Reactions

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Reactions graph legend

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Umbellularia californica (#3438)
Magnoliopsida (#3398)
Lauric acid-containing triglycerides in seeds of umbellularia californica nutt. (Lauraceae),
J Am Oil Chem Soc, 1991

String Representations

InChiKey (Click to copy)
VMPHSYLJUKZBJJ-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C39H74O6/c1-4-7-10-13-16-19-22-25-28-31-37(40)43-34-36(45-39(42)33-30-27-24-21-18-15-12-9-6-3)35-44-38(41)32-29-26-23-20-17-14-11-8-5-2/h36H,4-35H2,1-3H3
SMILES (Click to copy)
C(OC(=O)CCCCCCCCCCC)[C@]([H])(OC(CCCCCCCCCCC)=O)COC(CCCCCCCCCCC)=O

Other Databases

HMDB ID
HMDB0011188
CHEBI ID
77389
PubChem CID
10851
SwissLipids ID
SLM:000121575
Cayman ID
23336

Calculated Physicochemical Properties

Heavy Atoms 45
Rings 0
Aromatic Rings 0
Rotatable Bonds 38
Van der Waals Molecular Volume 728.08
Topological Polar Surface Area 78.90
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 6
logP 12.60
Molar Refractivity 188.82

Admin

Created at
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Updated at
30th Jan 2023
LIPID MAPS® abbreviations for glycerolipids (GL)

The LIPID MAPS® glycerolipid abbreviations (MG,DG,TG) are used here to refer to species with one, two or three radyl side-chains, respectively, where the structures of the side chains are indicated within parentheses in the 'Prefix(sn1/sn2/sn3)' format (e.g. TG(16:0/18:1(9Z)/18:0). Acyl chains are assumed by default. The alkyl ether linkage is represented by the 'O-' prefix, e.g. DG(O-16:0/18:1(9Z)/0:0), whereas the 1Z-alkenyl ether (Plasmalogen) linkage is represented by the 'P-' prefix, e.g. and DG(P-14:0/18:1(9Z)/0:0).

For Diradylglycerols and Triradylglycerols, it is not always possible to experimentally determine the exact position of radyl groups on the glycerol group. For Diradylglycerols with two different radyl groups, two different structural isomers exist. For Triradylglycerols with three different radyl groups, six different isomers exist.

Instead of drawing all possible structural isomers explicitly for Diradylglycerols and Triradylglycerols, the LIPID MAPS® abbreviation scheme supports the isomeric specification. A suffix containing 'iso' along with the number of possible isomers is appended to the abbreviation (e.g. [iso2],[iso6]) and a single unique LM_ID is assigned. The structure assigned to the LM_ID corresponds to the radyl substitution shown in the abbreviation. An option is provided to display the other isomers in the group.

The [rac] designation refers to racemic mixtures due to substitution at the sn1 and sn3 positions of glycerol.