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1,2-DIPALMITOYL-SN-GLYCEROL

CAS No.
30334-71-5
Chemical Name:
1,2-DIPALMITOYL-SN-GLYCEROL
Synonyms
DPG;(S)-3-Hydroxypropane-1,2-diyl dipalmitate;1,2-DIPALMITIN;DG(16:0/16:0/0:0);16:0 DG;NSC 269964;Einecs 250-131-4;D-a,b-DipalMitin;sn-1,2-DipalMitin;(S)-1,2-DIPALMITIN
CBNumber:
CB4228240
Molecular Formula:
C35H68O5
Molecular Weight:
568.91
MDL Number:
MFCD00067471
MOL File:
30334-71-5.mol
MSDS File:
SDS
Last updated:2023-05-18 11:31:17

1,2-DIPALMITOYL-SN-GLYCEROL Properties

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)
BRN 1730209

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS06,GHS08
Signal word  Danger
Hazard statements  H302-H315-H319-H331-H336-H351-H361d-H372-H412
Precautionary statements  P201-P273-P301+P312+P330-P302+P352-P304+P340+P311-P308+P313
WGK Germany  1
10

1,2-DIPALMITOYL-SN-GLYCEROL price More Price(19)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich D9135 1,2-Dipalmitoyl-sn-glycerol ≥99% 30334-71-5 25mg $49.3 2024-03-01 Buy
Sigma-Aldrich D9135 1,2-Dipalmitoyl-sn-glycerol ≥99% 30334-71-5 100mg $78.6 2024-03-01 Buy
Cayman Chemical 10008648 1,2-Dipalmitoyl-sn-glycerol ≥95% 30334-71-5 25mg $32 2024-03-01 Buy
Cayman Chemical 10008648 1,2-Dipalmitoyl-sn-glycerol ≥95% 30334-71-5 50mg $55 2024-03-01 Buy
Cayman Chemical 10008648 1,2-Dipalmitoyl-sn-glycerol ≥95% 30334-71-5 100mg $81 2024-03-01 Buy
Product number Packaging Price Buy
D9135 25mg $49.3 Buy
D9135 100mg $78.6 Buy
10008648 25mg $32 Buy
10008648 50mg $55 Buy
10008648 100mg $81 Buy

1,2-DIPALMITOYL-SN-GLYCEROL Chemical Properties,Uses,Production

Uses

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.

Uses

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.

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.]

30403-51-1
30334-71-5
Synthesis of 1,2-DIPALMITOYL-SN-GLYCEROL from 1,2-di-O-hexacecanoyl-3-O-benzyl-sn-glycerol

1,2-DIPALMITOYL-SN-GLYCEROL Preparation Products And Raw materials

Raw materials

Preparation Products

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D-ALPHA,BETA-DIPALMITIN L-1,2-DIPALMITOYLGLYCEROL 16:0 DG 1,2-DIPALMITOYL-SN-GLYCEROL 1,2-DIPALMITOYL-SN-3-GLYCEROL 1,2-DIHEXADECANOYL-SN-GLYCEROL (S)-1,2-DIPALMITIN (S)-GLYCEROL 1,2-DIPALMITATE (S)-1-(hydroxymethyl)ethane-1,2-diyl dipalmitate 1,2-DIPALMITOYL-SN-GLYCEROL (C16:0) (S)-1-(Hydroxymethyl)ethan-1,2-diyldipalmitat L-1,2-DIPALMITOYLGLYCEROL synthetic Einecs 250-131-4 1,2-Di-O-palMitoyl-sn-glycerol Hexadecanoic Acid 1,1'-[(1S)-1-(HydroxyMethyl)-1,2-ethanediyl] Ester NSC 269964 sn-1,2-DipalMitin D-a,b-DipalMitin (S)-1,2-Dipalmitin, (S)-Glycerol 1,2-dipalmitate, 1,2-Dihexadecanoyl-sn-glycerol (-)-L-1,2-Dipalmitin (S)-Propane-1,2,3-triol 1,2-dipalmitate 1-O,2-O-Dipalmitoyl-L-glycerol Bishexadecanoic acid (S)-3-hydroxypropane-1,2-diyl ester Bispalmitic acid (S)-3-hydroxypropane-1,2-diyl ester (-)-1,2-di-O-hexadecanoyl-sn-glycerol DipalMitoyl-sn-glycerol L-0016 1,2-DIPALMITOYL-SN-GLYCEROL, >=99% 1,2-Dipalmitin-sn-glycerol DPG 1,2-DIPALMITIN DG(16:0/16:0/0:0) (S)-3-Hydroxypropane-1,2-diyl dipalmitate Endogenous Metabolite,1,2Dipalmitoylsnglycerol,1,2 Dipalmitoyl sn glycerol,inhibit,Inhibitor (2S)-2-hexadecanoyloxy-3-hydroxypropyl] hexadecanoate 30334-71-5 Neutral Glycerides Lipids Glycerides Diradylglycerols Biochemicals and Reagents BioChemical Fatty & Aliphatic Acids, Esters, Alcohols & Derivatives Aliphatics Fatty Acid Derivatives & Lipids Glycerols Protein Kinase Inhibitors and Activators