Tripalmitin Chemical Properties

Melting point:

66-68 °C

Boiling point:

bp 310-320°

Density 

0.8752 g/cm³ (70 ºC)

refractive index 

nD80 1.43807

storage temp. 

-20°C

solubility 

Chloroform (Sparingly), Ethyl Acetate (Slightly), Hexanes (Very Slightly)

form 

Fine Crystalline Powder

color 

White to almost white

biological source

synthetic (organic)

Merck 

14,9736

BRN 

1811188

Cosmetics Ingredients Functions

SKIN CONDITIONING
VISCOSITY CONTROLLING

InChIKey

PVNIQBQSYATKKL-UHFFFAOYSA-N

SMILES

CCCCCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC

LogP

21.615 (est)

CAS DataBase Reference

555-44-2(CAS DataBase Reference)

EPA Substance Registry System

Tripalmitin (555-44-2)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/22

Safety Statements 

22-24/25

WGK Germany 

-

RTECS 

RT4953500

TSCA 

TSCA listed

HS Code 

29157090

Storage Class

11 - Combustible Solids

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Tripalmitin Usage And Synthesis

Description

Tripalmitin, also known as Palmitin or 1,2,3-Tripalmitoyl glycerol, comes from the fatty acid palmitic acid and is a triacylglycerol that contains palmitic acid at the sn-1, sn-2, and sn-3 positions and has been found in palm oil. It inhibits glucose-stimulated insulin secretion and reduces viability of INS1 cells in a concentration-dependent manner. Myocardial levels of 1,2,3-tripalmitoyl glycerol are elevated by greater than 5-fold in a rat model of diabetes induced by streptozotocin . 1,2,3-Tripalmitoyl glycerol has been used to form the lipid matrices of etoposide-incorporated nanoparticles. Formulations containing 1,2,3-tripalmitoyl glycerol have been used in cosmetic products as thickening and skin-conditioning agents.

Chemical Properties

White, crystalline powder. Soluble in ether and chloroform; insoluble in water. Combustible.

Uses

Tripalmitin is a triglyceride derived from Palmitic Acid (P144500), a common fatty acid found in plants and animals. Tripalmitin is used in the preparation of solid lipid particles for oral delivery of drugs.

Uses

Soap, leather dressing.

Uses

Glyceryl tripalmitate has been used as a reference standard

• for the generation of calibration curve generation for the quantification of lipids from Azospirillum brasilense
• for the quantification of silk worm embryos and extraembryonic yolk lipids using thin layer chromatography
• for the quantification of triacylglycerol in Neochloris minuta microalgal cells

Definition

ChEBI: Tripalmitin is a triglyceride obtained by formal acylation of the three hydroxy groups of glycerol by palmitic (hexadecanoic) acid. It is functionally related to a hexadecanoic acid.

General Description

SRM 1595_cert SRM 1595 _SDS

Biochem/physiol Actions

Glyceryl tripalmitate is a carrier molecule for effective drug delivery and is used solid lipid nanoparticle formulations.

Purification Methods

Crystallise it from acetone, diethyl ether or EtOH. It exists in an -form (m 56.0o), a ’-form (m 63.5o) and a -form (m 65.5o). [Beilstein 2 H 373, 2 I 167, 2 II 340, 2 III 971.]

References

[1] MIROSLAV LíSA  Michal H. Triacylglycerols profiling in plant oils important in food industry, dietetics and cosmetics using high-performance liquid chromatography-atmospheric pressure chemical ionization mass spectrometry.[J]. Journal of Chromatography A, 2008, 1198-1199: 115-130. DOI: 10.1016/j.chroma.2008.05.037
[2] J H MOFFITT. Adverse physicochemical properties of tripalmitin in beta cells lead to morphological changes and lipotoxicity in vitro.[J]. Diabetologia, 2005: 1819-1829. DOI: 10.1007/s00125-005-1861-9
[3] LAKKIREDDY HARIVARDHAN REDDY. Etoposide-incorporated tripalmitin nanoparticles with different surface charge: formulation, characterization, radiolabeling, and biodistribution studies.[J]. AAPS Journal, 2004, 6 3: e23. DOI: 10.1208/aapsj060323

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