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555-44-2 Usage

Description

1,2,3-Tripalmitoyl glycerol 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

Different sources of media describe the Uses of 555-44-2 differently. You can refer to the following data:
1. 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.
2. Soap, leather dressing.
3. Glyceryl tripalmitate has been used as a reference standardfor the generation of calibration curve generation for the quantification of lipids from Azospirillum brasilensefor the quantification of silk worm embryos and extraembryonic yolk lipids using thin layer chromatographyfor the quantification of triacylglycerol in Neochloris minuta microalgal cells

Definition

ChEBI: A triglyceride obtained by formal acylation of the three hydroxy groups of glycerol by palmitic (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.]

Check Digit Verification of cas no

The CAS Registry Mumber 555-44-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,5 and 5 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 555-44:
(5*5)+(4*5)+(3*5)+(2*4)+(1*4)=72
72 % 10 = 2
So 555-44-2 is a valid CAS Registry Number.
InChI:InChI=1/C54H104O6/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-43-46-52(55)58-49-51(60-54(57)48-45-42-39-36-33-30-27-24-21-18-15-12-9-6-3)50-59-53(56)47-44-41-38-35-32-29-26-23-20-17-14-11-8-5-2/h51H,4-50H2,1-3H3/i52+1,53+1,54+1

555-44-2 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
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  • Detail
  • TCI America

  • (G0091)  Tripalmitin  

  • 555-44-2

  • 25g

  • 403.00CNY

  • Detail
  • TCI America

  • (G0213)  Tripalmitin  >85.0%(GC)

  • 555-44-2

  • 25g

  • 725.00CNY

  • Detail
  • TCI America

  • (G0213)  Tripalmitin  >85.0%(GC)

  • 555-44-2

  • 250g

  • 2,970.00CNY

  • Detail
  • TCI America

  • (T3096)  Tripalmitin  >80.0%(GC)

  • 555-44-2

  • 25g

  • 490.00CNY

  • Detail
  • TCI America

  • (T3096)  Tripalmitin  >80.0%(GC)

  • 555-44-2

  • 100g

  • 1,990.00CNY

  • Detail
  • Alfa Aesar

  • (A10922)  Glycerol tripalmitate, 98%   

  • 555-44-2

  • 1g

  • 297.0CNY

  • Detail
  • Alfa Aesar

  • (A10922)  Glycerol tripalmitate, 98%   

  • 555-44-2

  • 5g

  • 1003.0CNY

  • Detail
  • Alfa Aesar

  • (A10922)  Glycerol tripalmitate, 98%   

  • 555-44-2

  • 25g

  • 3713.0CNY

  • Detail
  • Sigma

  • (T8127)  Glyceryl tripalmitate  ≥85%

  • 555-44-2

  • T8127-100G

  • 2,721.42CNY

  • Detail
  • Sigma

  • (T5888)  Glyceryl tripalmitate  ≥99%

  • 555-44-2

  • T5888-100MG

  • 453.96CNY

  • Detail
  • Sigma

  • (T5888)  Glyceryl tripalmitate  ≥99%

  • 555-44-2

  • T5888-500MG

  • 888.03CNY

  • Detail
  • Sigma

  • (T5888)  Glyceryl tripalmitate  ≥99%

  • 555-44-2

  • T5888-1G

  • 983.97CNY

  • Detail

555-44-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name tripalmitin

1.2 Other means of identification

Product number -
Other names Hexadecanoic acid, 1,2,3-propanetriyl ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:555-44-2 SDS

555-44-2Synthetic route

1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

glycerol
56-81-5

glycerol

glyceroltripalmitate
555-44-2

glyceroltripalmitate

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 115℃; for 5h;85%
With toluene-4-sulfonic acid at 115℃;61%
Stage #1: 1-hexadecylcarboxylic acid; glycerol With sulfuric acid at 119.84℃; for 3h;
Stage #2: In chloroform at 69.84℃; for 0.5h;
53%
1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

glycerol
56-81-5

glycerol

A

1,2-dipalmitoylglycerol bromohydrid
34607-52-8

1,2-dipalmitoylglycerol bromohydrid

B

glyceroltripalmitate
555-44-2

glyceroltripalmitate

Conditions
ConditionsYield
With bromine; sodium hydrogencarbonate; triphenylphosphine In dichloromethane for 0.5h;A n/a
B 65.2%
1,2,3-tribromopropane
96-11-7

1,2,3-tribromopropane

sodium palmitate
408-35-5

sodium palmitate

glyceroltripalmitate
555-44-2

glyceroltripalmitate

1,2,3-tribromopropane
96-11-7

1,2,3-tribromopropane

silver palmitate
3508-01-8

silver palmitate

glyceroltripalmitate
555-44-2

glyceroltripalmitate

Conditions
ConditionsYield
With xylene
glycerol
56-81-5

glycerol

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

glyceroltripalmitate
555-44-2

glyceroltripalmitate

Conditions
ConditionsYield
With pyridine; chloroform
With quinoline; chloroform
2-Oleodipalmitin
2190-25-2

2-Oleodipalmitin

glyceroltripalmitate
555-44-2

glyceroltripalmitate

Conditions
ConditionsYield
With water In hexane at 30℃; for 48h; Mechanism; Candida rugosa lipase; other lipases; var. time;
1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

α.α'-dipalmityne

α.α'-dipalmityne

glyceroltripalmitate
555-44-2

glyceroltripalmitate

Conditions
ConditionsYield
at 200 - 220℃; unter stark vermindertem Druck im trocknen Luftstrom;
1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

monopalmityne

monopalmityne

glyceroltripalmitate
555-44-2

glyceroltripalmitate

Conditions
ConditionsYield
at 250℃;
hexadecanoic acid ethyl ester
628-97-7

hexadecanoic acid ethyl ester

glycerol
56-81-5

glycerol

glyceroltripalmitate
555-44-2

glyceroltripalmitate

Conditions
ConditionsYield
With Novozym 435 at 60℃; under 40 Torr; for 36h;
1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

glycerol
56-81-5

glycerol

A

rac-1-monopalmitoylglycerol
305847-08-9

rac-1-monopalmitoylglycerol

B

rac-1,2-dipalmitoylglycerol
1042289-75-7

rac-1,2-dipalmitoylglycerol

C

hexadecanoic acid, 2-hydroxy-1,3-propanediyl ester
502-52-3

hexadecanoic acid, 2-hydroxy-1,3-propanediyl ester

D

glyceroltripalmitate
555-44-2

glyceroltripalmitate

Conditions
ConditionsYield
With lipozyme RM IM at 60℃; Enzymatic reaction; neat (no solvent); regioselective reaction;
methanol
67-56-1

methanol

glyceroltripalmitate
555-44-2

glyceroltripalmitate

A

hexadecanoic acid methyl ester
112-39-0

hexadecanoic acid methyl ester

B

glycerol
56-81-5

glycerol

Conditions
ConditionsYield
With [quaternary CH3I ammonizated co(divinylbenzene-N-vinylimidazolate)polymer][SO3CF3] at 65℃; for 16h;A 99.9%
B n/a
With lithium perchlorate 1) electrolyzis; 2) reflux, 3h;A 98%
B n/a
methanol
67-56-1

methanol

glyceroltripalmitate
555-44-2

glyceroltripalmitate

hexadecanoic acid methyl ester
112-39-0

hexadecanoic acid methyl ester

Conditions
ConditionsYield
With PDVB-VI-0.33 at 65℃; for 3h;99.9%
With nanoporous polydivinylbenzene treated with trifluoromethanesulfonic acid at 65℃; for 12h; Reagent/catalyst;99.3%
With sulphonated polymerized aniline in-between montmorillonite layers for 14h; Reagent/catalyst;99.1%
ethanol
64-17-5

ethanol

glyceroltripalmitate
555-44-2

glyceroltripalmitate

A

hexadecanoic acid ethyl ester
628-97-7

hexadecanoic acid ethyl ester

B

glycerol
56-81-5

glycerol

Conditions
ConditionsYield
With lithium perchlorate 1) electrolyzis; 2) reflux, 7h;A 96%
B n/a
glyceroltripalmitate
555-44-2

glyceroltripalmitate

ethanolamine
141-43-5

ethanolamine

2-(palmitoylamino)ethanol
544-31-0

2-(palmitoylamino)ethanol

Conditions
ConditionsYield
at 50 - 60℃; for 8h;95.4%
propan-1-ol
71-23-8

propan-1-ol

glyceroltripalmitate
555-44-2

glyceroltripalmitate

A

propyl palmitate
2239-78-3

propyl palmitate

B

glycerol
56-81-5

glycerol

Conditions
ConditionsYield
With lithium perchlorate 1) electrolyzis; 2) reflux, 7h;A 95%
B n/a
glyceroltripalmitate
555-44-2

glyceroltripalmitate

benzylamine
100-46-9

benzylamine

hexadecanoic acid benzylamide
74058-71-2

hexadecanoic acid benzylamide

Conditions
ConditionsYield
at 50 - 60℃; for 16h;94%
glyceroltripalmitate
555-44-2

glyceroltripalmitate

palmitonitrile
629-79-8

palmitonitrile

Conditions
ConditionsYield
With ammonia at 220℃; for 40h; Autoclave;94%
glyceroltripalmitate
555-44-2

glyceroltripalmitate

1,5-diamino-3-azapentane
111-40-0

1,5-diamino-3-azapentane

di-(palmitamidoethyl)amine

di-(palmitamidoethyl)amine

Conditions
ConditionsYield
at 50 - 60℃; for 3h;93%
bis(3-aminopropyl)amine
56-18-8

bis(3-aminopropyl)amine

glyceroltripalmitate
555-44-2

glyceroltripalmitate

di-(palmitamidopropyl)amine

di-(palmitamidopropyl)amine

Conditions
ConditionsYield
at 50 - 60℃; for 3h;86%
glyceroltripalmitate
555-44-2

glyceroltripalmitate

ethylenediamine
107-15-3

ethylenediamine

N,N'-ethylene-bis-(palmitamide)
5518-18-3

N,N'-ethylene-bis-(palmitamide)

Conditions
ConditionsYield
at 50 - 60℃; for 3h;85%
glyceroltripalmitate
555-44-2

glyceroltripalmitate

2-palmitoylglycerol
23470-00-0

2-palmitoylglycerol

Conditions
ConditionsYield
With Lipozyme TL-IM lipase In ethanol; tert-butyl methyl ether at 20℃; for 0.25h;84.4%
With sodium hydroxide In glycerol at 240℃;43.5%
With Thermomyces lanuginosa lipase In ethanol at 34.84℃; for 24h;8%
glyceroltripalmitate
555-44-2

glyceroltripalmitate

1-Hexadecanol
36653-82-4

1-Hexadecanol

Conditions
ConditionsYield
With 5 wt% Re/TiO2; hydrogen In neat (no solvent) at 230℃; under 37503.8 Torr; for 30h; Autoclave;84%
With ethanol; ruthenium(bis[2‐(ethylsulfanyl)ethyl]amine)(dichloro)(triphenylphosphine); potassium tert-butylate In toluene at 80℃; for 16h;57%
glyceroltripalmitate
555-44-2

glyceroltripalmitate

tetradecane
629-59-4

tetradecane

Conditions
ConditionsYield
With tris(pentafluorophenyl)borate In cyclohexane at 20℃; for 6h; Schlenk technique; Inert atmosphere; Green chemistry;70%
ethanol
64-17-5

ethanol

glyceroltripalmitate
555-44-2

glyceroltripalmitate

hexadecanoic acid ethyl ester
628-97-7

hexadecanoic acid ethyl ester

Conditions
ConditionsYield
With PDVB-VI-0.5 at 78℃; for 3h;64.3%
glyceroltripalmitate
555-44-2

glyceroltripalmitate

butan-1-ol
71-36-3

butan-1-ol

butyl palmitate
111-06-8

butyl palmitate

Conditions
ConditionsYield
With PDVB-VI-0.5 at 115℃; for 3h;55.1%
glyceroltripalmitate
555-44-2

glyceroltripalmitate

ascorbic acid
50-81-7

ascorbic acid

6-O-oleoyl L-ascorbate

6-O-oleoyl L-ascorbate

Conditions
ConditionsYield
With Lipozyme TL IM In tert-Amyl alcohol at 40℃; Enzymatic reaction;50%
glyceroltripalmitate
555-44-2

glyceroltripalmitate

glycerol
56-81-5

glycerol

A

rac-1-monopalmitoylglycerol
305847-08-9

rac-1-monopalmitoylglycerol

B

hexadecanoic acid, 2-hydroxy-1,3-propanediyl ester
502-52-3

hexadecanoic acid, 2-hydroxy-1,3-propanediyl ester

Conditions
ConditionsYield
With sodium methylate at 115℃; for 24h;A n/a
B 40%
glyceroltripalmitate
555-44-2

glyceroltripalmitate

Propyl gallate
121-79-9

Propyl gallate

A

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

B

3-((3',4',5'-trihydroxybenzoyl)oxy)propane-1,2-diyl dipalmitate

3-((3',4',5'-trihydroxybenzoyl)oxy)propane-1,2-diyl dipalmitate

Conditions
ConditionsYield
With recombinant lipase B from Candida antarctica, expressed in Aspergillus niger, and immobilized on a macroporous hydrophobic resin In neat (no solvent) at 70℃; for 120h; Catalytic behavior; Time; Enzymatic reaction;A n/a
B 33.02%
2-hydroxyethyl vinyl ether
764-48-7

2-hydroxyethyl vinyl ether

glyceroltripalmitate
555-44-2

glyceroltripalmitate

C20H38O3

C20H38O3

Conditions
ConditionsYield
With potassium hydroxide11%
glyceroltripalmitate
555-44-2

glyceroltripalmitate

aniline
62-53-3

aniline

palmitanilide
6832-98-0

palmitanilide

Conditions
ConditionsYield
at 50 - 60℃; for 16h;7.5%
triacetylglycerol
102-76-1

triacetylglycerol

glyceroltripalmitate
555-44-2

glyceroltripalmitate

hexadecanoic acid, 2-hydroxy-1,3-propanediyl ester
502-52-3

hexadecanoic acid, 2-hydroxy-1,3-propanediyl ester

Conditions
ConditionsYield
With sodium methylate; xylene und Behandeln des Reaktionsgemisches mit Glycerin;
glyceroltripalmitate
555-44-2

glyceroltripalmitate

cholesterol
57-88-5

cholesterol

cholesterol palmitate
601-34-3

cholesterol palmitate

Conditions
ConditionsYield
With enzyme-substances from liver; enzyme-substances from pancreas

555-44-2Related news

Morphology and functions of astrocytes cultured on water-repellent fractal TRIPALMITIN (cas 555-44-2) surfaces07/19/2019

In the brain, astrocytes play an essential role with their multiple functions and sophisticated structure, as surrounded by a fractal environment which has not been available in our traditional cell culture. Water-repellent fractal tripalmitin (PPP) surfaces can imitate the fractal environment i...detailed

TRIPALMITIN (cas 555-44-2) and monoacylglycerols as modifiers in the crystallisation of palm oil07/18/2019

An exhaustive analysis of the crystallisation behaviour of palm oil was performed using low-resolution magnetic pulsed nuclear resonance, differential scanning calorimetry, polarised light microscopy and X-ray diffraction. The aim of this study was to characterise the changes induced in the crys...detailed

Microscopic approach of the crystallization of TRIPALMITIN (cas 555-44-2) and tristearin by microscopy07/17/2019

The crystallization behavior of lipids has important implications in industrial processing of food products, whose physical characteristics depend largely on crystallized fats. The study of the crystallization behavior and polymorphism of a pure lipid system is of great scientific importance as ...detailed

Solid-liquid phase equilibrium diagrams of binary mixtures containing fatty acids, fatty alcohol compounds and TRIPALMITIN (cas 555-44-2) using differential scanning calorimetry07/16/2019

Fatty acids, fatty alcohol compounds and triacylglycerols (TAGs) present a significant role in industrial applications, mainly in food, cosmetics and pharmaceutical industries. In this study, eight solid-liquid phase diagrams composed by tripalmitin plus fatty acids (capric acid, lauric acid, my...detailed

Neutron diffraction of deuterated TRIPALMITIN (cas 555-44-2) and the influence of shear on its crystallisation07/15/2019

This neutron diffraction study of deuterated tripalmitin has provided further insight into a forensic observation of the crystallisation of lipids under high-shear conditions. To achieve this, an experimental set up was designed to enable simultaneous rheological data from a Couette cell to be r...detailed

555-44-2Relevant articles and documents

Enzymatic transesterification of palm olein with nonspecific and 1,3-specific lipases

Ghazali,Hamidah,Che Man

, p. 633 - 639 (1995)

The enzymatic transesterification of palm olein was conducted in a low-moisture medium with nonspecific and 1,3-specific lipases from microbial sources. The enzymes were first immobilized on Celite, lyophilized for 4 h and then added to a reaction medium that consisted of 10% (wt/vol) palm olein in water-saturated hexane. The catalytic performance of the enzymes was evaluated by determining the changes in triglyceride (TC) composition and concentrations by reverse-phase high-performance liquid chromatography (HPLC) and the formation of free fatty acids by titration. Studies with lipase from Candida rugosa showed that the degree of hydrolysis was reduced by drying the immobilized preparation and that the best drying time was 4 h. In all cases, the transesterification process resulted in the formation of PPP, a TG initially undetected in the oil, and increases in the concentrations of OOO (1.3-2.1 -fold), OOL (1.7-4.5-fold), and OLL (1.7-4.3-fold), where P, O, and L are palmitic, oleic, and linoleic acids, respectively. SOS (where S is stearic acid), another TC not detected in the oil, was synthesized by Rhizomucor miehei and Pseudomonas lipases, with the latter producing more of this TG. There was a corresponding decrease in the concentrations of POP, PLP, POO, and POL. PPP concentration ranged from 1.9% (w/w) for Mucor javanicus lipase to 6.2% (w/w) for Pseudomonas lipase after 24 h. The greatest degree and fastest rate of change were caused by Pseudomonas lipase, followed by the enzymes from R. miehei and Aspergillus niger. The effects of transesterification and hydrolysis of palm olein by the various lipases resulted in changes in the overall degree of saturation of the triglyceride components. There seems to be no clear correlation between the enzyme positional specificity and the products formed. Possible mechanisms for the formation of PPP, OOL, OLL, OOO, and SOS are discussed. Copyright

Monomyristin and monopalmitin derivatives: Synthesis and evaluation as potential antibacterial and antifungal agents

Jumina,Nurmala, Asma,Fitria, Anggit,Pranowo, Deni,Sholikhah, Eti Nurwening,Kurniawan, Yehezkiel Steven,Kuswandi, Bambang

, (2018/12/11)

In the present work, monoacylglycerol derivatives, i.e., 1-monomyristin, 2-monomyristin, and 2-monopalmitin were successfully prepared from commercially available myristic acid and palmitic acid. The 1-monomyristin compound was prepared through a transesterification reaction between ethyl myristate and 1,2-O-isopropylidene glycerol, which was obtained from the protection of glycerol with acetone, then followed by deprotection using Amberlyst-15. On the other hand, 2-monoacylglycerol derivatives were prepared through enzymatic hydrolysis of triglycerides in the presence of Thermomyces lanuginosa lipase enzymes. The synthesized products were analyzed using fourier transform infrared (FTIR) spectrophotometer, gas or liquid chromatography-mass spectrometer (GC-MS or LC-MS), and proton and carbon nuclear magnetic resonance (1H- and13C-NMR) spectrometers. It was found that monomyristin showed high antibacterial and antifungal activities, while 2-monopalmitin did not show any activity at all. The 1-monomyristin compound showed higher antibacterial activity against Staphylococcus aureus and Aggregatibacter actinomycetemcomitans and also higher antifungal activity against Candida albicans compared to the positive control. Meanwhile, 2-monomyristin showed high antibacterial activity against Escherichia coli. The effect of the acyl position and carbon chains towards antibacterial and antifungal activities was discussed.

MALLEABLE, BIODEGRADABLE HEMOSTATIC AGENT

-

, (2012/10/18)

A malleable, biodegradable hemostatic agent is provided that can be used for mechanical sealing of bleeding bone tissue, as well as a method for forming a malleable, biodegradable hemostatic agent of this type, and a medical implant having a coating that includes a malleable, biodegradable hemostatic agent of this type. The malleable, biodegradable hemostatic agent contains (a) at least one saturated glycerol-1,2,3-tri-fatty acid ester having a melting temperature above 37° C., (b) at least one filling agent present in particulate form, at least in part, and having a melting temperature above 37° C., and (c) at least one compound having a melting temperature not above 37° C. and a solubility at a temperature of 25° C. of less than 50 grams per liter of water.

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