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HomeProduct name list1,2-DIPALMITOYL-SN-GLYCEROL

1,2-DIPALMITOYL-SN-GLYCEROL

  • CAS NO.:30334-71-5
  • Empirical Formula: C35H68O5
  • Molecular Weight: 568.91
  • MDL number: MFCD00067471
  • EINECS: 250-131-4
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-19 23:02:33
1,2-DIPALMITOYL-SN-GLYCEROL Structural

What is 1,2-DIPALMITOYL-SN-GLYCEROL?

The Uses of 1,2-DIPALMITOYL-SN-GLYCEROL

1,2-Dipalmitoyl-sn-glycerol (1,2-DPG) is an analog of the protein kinase C (PKC)-activating second messenger diacylglycerol. 1,2-Dipalmitoyl-sn-glycerol is a weak activator of PKC.

The Uses of 1,2-DIPALMITOYL-SN-GLYCEROL

16:0 DG has been used to spike brain samples for mass spectrometric analysis. It may be used as diacyl-glycerol source in diacylglycerol O-acyltransferase 1 (DGAT1) enzyme assay in human leukemic?K562 cells and in Golgi-like liposomes reconstitution.

What are the applications of Application

1,2-Dipalmitoyl-sn-glycerol is a DAG analog and weak PKC activator

Definition

ChEBI: A 1,2-diacyl-sn-glycerol in which both acyl groups are specified as palmitoyl (hexadecanoyl).

General Description

In biochemical signaling, diacylglycerol (DAG) functions as a second messenger signaling lipid, and is a product of the hydrolysis of the phospholipid PIP2 (phosphatidylinositolbisphosphate) by the enzyme phospholipase C (PLC) (a membrane-bound enzyme) that, through the same reaction, produces inositol trisphosphate (IP3). Although inositol trisphosphate (IP3) diffuses into the cytosol, DAG remains within the plasma membrane due to its hydrophobic properties. IP3 stimulates the release of calcium ions from the smooth endoplasmic reticulum, whereas DAG is a physiological activator of protein kinase C (PKC). The production of DAG in the membrane facilitates translocation of PKC from the cytosol to the plasma membrane.
Diacylglycerol mimicks the effects of the tumor-promoting compounds phorbol esters.

Biochem/physiol Actions

16:0 DG (1,2-dipalmitoyl-sn-glycerol) fails to prevent the late fission events in Golgi membrane. Supplementation of 16:0 DG promotes bacterial growth by preventing sporangia.

Purification Methods

Crystallise S(-)-1,2-dipalmitin from chloroform/pet ether (b 40-60o) ~1:1.5. [S(-)-isomer: Baer & Kates J Am Chem Soc 72 942 1950, Hanahan & Vercamer J Am Chem Soc 7 6 1804 1954, R(+)-isomer: Tattrie et al. Arch Biochem 78 319 1958, Beilstein 2 IV 1173.] The racemate [40290-32-2] is polymorphic with different IR spectra. When crystallised from hexane, or other solvents, the higher melting form with m 71.5-72.5o is obtained. The melt then solidifies to give the lower melting -form with m 49.7-50o. The -form has m 61o (65-66o is also reported). When the lower melting forms are kept at their melting temperatures for a while, they are converted to the higher melting form. [Howe & Malkin J Chem Soc 2663 1951, Baer & Kates J Am Chem Soc 72 942 1950, Beilstein 2 IV 1173.]

Properties of 1,2-DIPALMITOYL-SN-GLYCEROL

Melting point: 66-69 °C
Boiling point: 620.8±22.0 °C(Predicted)
Density  0.930±0.06 g/cm3(Predicted)
storage temp.  -20°C
solubility  DMF: 20 mg/ml; DMSO: 5 mg/ml; Ethanol: 30 mg/ml; PBS (pH 7.2): .25 mg/ml
form  A crystalline solid
pka 13.69±0.10(Predicted)
color  White to off-white
BRN  1730209

Safety information for 1,2-DIPALMITOYL-SN-GLYCEROL

Signal word Danger
Pictogram(s)
ghs
Skull and Crossbones
Acute Toxicity
GHS06
ghs
Health Hazard
GHS08
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H331:Acute toxicity,inhalation
H336:Specific target organ toxicity,single exposure; Narcotic effects
H351:Carcinogenicity
H372:Specific target organ toxicity, repeated exposure
H412:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes P201:Obtain special instructions before use.
P273:Avoid release to the environment.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P308+P313:IF exposed or concerned: Get medical advice/attention.

Computed Descriptors for 1,2-DIPALMITOYL-SN-GLYCEROL

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