24529-88-2

Basic information

• Product Name: 1,2-DIOLEOYL-SN-GLYCEROL
• Synonyms: Olein, 1,2-di-, (S)-(-)-;(Z)-(S)-3-hydroxypropane-1,2-diyl dioleate;(9Z)-9-Octadecenoic acid 1,1′-[(1S)-1-(hydroxymethyl)-1,2-ethanediyl] ester;DG(18:1/18:1/0:0);1,2-DIOLEOYL-SN-GLYCEROL, >=97%;1,2-BIS(O-9Z-OCTADECENOYL)-SN-GLYCEROL;1,2-DIOLEOYL-SN-GLYCEROL;1,2-DI[CIS-9-OCTADECENOYL]-SN-GLYCEROL
• CAS NO: 24529-88-2
• Molecular Formula: C₃₉H₇₂O₅
• Molecular Weight: 620.99
• Mol File: 24529-88-2.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 670.8°Cat760mmHg
• Flash Point: 186.3°C
• Appearance: /
• Density: 0.934g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.477
• Storage Temp.: −20°C
• PKA: 13.69±0.10(Predicted)
• BRN: 1730457
• CAS DataBase Reference: 1,2-DIOLEOYL-SN-GLYCEROL(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-DIOLEOYL-SN-GLYCEROL(24529-88-2)
• EPA Substance Registry System: 1,2-DIOLEOYL-SN-GLYCEROL(24529-88-2)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: RK1250000
• F: 23
• Hazardous Substances Data: 24529-88-2(Hazardous Substances Data)

Usage

Description

1,2-Dioleoyl-sn-glycerol is an analog of the protein kinase C-activating second messenger DAG. 1,2-Dioleoyl-sn-glycerol and 1,2-dioctanoyl-sn-glycerol are nearly equipotent in induction of the acrosome reaction in human sperm.

Uses

Different sources of media describe the Uses of 24529-88-2 differently. You can refer to the following data:
1. 1,2-Dioleoyl-sn-glycerol is an analog of 1,3-Dioleoylglycerol (D4842100 which is used in the synthesis of amphiphilic gadolinium complexes as MRI contrast agents.
2. 18:1 DG may be used: in the lipid-protein overlay screen assay with Arabidopsis Rho-like GTPases recombinant protein and Arabidopsis plasma membrane H+-ATPasein the preparation of the Golgi-like liposomesin giant unilamellar vesicles (GUVs) preparation

Definition

ChEBI: A 1,2-diacyl-sn-glycerol in which the acyl groups at positions 1 and 2 are specified as oleoyl.

General Description

Diacylglycerol/diglyceride (DAG) is a glycerolipid, that is located at the plasma membrane. It is made up of two fatty acid chains that are covalently attached to a single glycerol molecule with the help of an ester linkage.

Biochem/physiol Actions

18:1 DG or 1,2-dioleoyl-sn-glycerol (DOG) fails to prevent the late fission events in the Golgi membrane. DOG is used in ferrihaem π–π tetramer aggregate preparation and β-haematin production.

InChI:InChI=1/C39H72O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(41)43-36-37(35-40)44-39(42)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h17-20,37,40H,3-16,21-36H2,1-2H3/b19-17-,20-18-/t37-/m0/s1

Upstream product

• 112-62-9 Methyl oleate 
• 56-81-5 glycerol 
• 112-80-1 cis-Octadecenoic acid 
• 122-32-7 trioleoylglycerol 
• 71-36-3 butan-1-ol 
• 24472-44-4 2-oxopropane-1,3-diyl dioleate 
• 50-81-7 ascorbic acid 
• 3896-58-0 vinyl oleate 
• 143997-01-7 (S)-3-((4-methoxybenzyl)oxy)propane-1,2-diyl dioleate 
• 112-79-8 Elaidic Acid 

Downstream Products

• 853996-13-1 phosphoric acid-((R)-2,3-bis-oleoyloxy-propyl ester)-((R)-2,3-dihydroxy-propyl ester) 
• 2465-32-9 1,3-diolein 
• 71260-67-8 (Z)-Octadec-9-enoic acid 1-((Z)-octadec-9-enoyloxymethyl)-2-[phenylamino-(2,2,2-trichloro-ethoxy)-phosphoryloxy]-ethyl ester 
• 71260-68-9 (Z)-Octadec-9-enoic acid 1-((Z)-octadec-9-enoyloxymethyl)-2-[phenylamino-(2,2,2-tribromo-ethoxy)-phosphoryloxy]-ethyl ester 
• 102916-98-3 (Z)-Octadec-9-enoic acid 2-[(2,4-dichloro-phenoxy)-hydroxy-phosphoryloxy]-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester; compound with triethyl-amine 
• 4004-05-1 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine 
• 876310-67-7 (Z)-Octadec-9-enoic acid (R)-2-{methoxy-[(1S,2R,3S,4S,5R,6R)-2,3,4,6-tetrakis-methoxymethoxy-5-(methoxy-methyl-phosphinoyloxy)-cyclohexyloxy]-phosphoryloxy}-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester 
• 876310-70-2 (Z)-Octadec-9-enoic acid (R)-2-{[(1S,2R,3R,4S,5S,6R)-3-(fluoromethyl-methoxy-phosphinoyloxy)-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyloxy]-methoxy-phosphoryloxy}-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester 
• 876310-82-6 (Z)-Octadec-9-enoic acid (R)-2-[{(1S,2S,3R,4S,5R,6R)-3-[bis-(2-cyano-ethoxy)-thiophosphoryloxy]-2,4,5,6-tetrakis-methoxymethoxy-cyclohexyloxy}-(2-cyano-ethoxy)-phosphoryloxy]-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester 
• 4235-95-4 dioleoylphosphatidylcholine 
• 197303-74-5 (Z)-Octadec-9-enoic acid (R)-2-{(2-chloro-phenoxy)-[(2R,3R,4S,5R)-5-[2-oxo-4-(4-oxo-pentanoylamino)-2H-pyrimidin-1-yl]-3,4-bis-(4-oxo-pentanoyloxy)-tetrahydro-furan-2-ylmethoxy]-phosphoryloxy}-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester 
• 2462-63-7 dioleoylphosphatidylethanolamine 
• 71260-21-4 (Z)-Octadec-9-enoic acid 1-((Z)-octadec-9-enoyloxymethyl)-2-{(2,2,2-tribromo-ethoxy)-[2-(trityl-amino)-ethoxy]-phosphoryloxy}-ethyl ester 
• 69747-56-4 (Z)-Octadec-9-enoic acid 2-{hydroxy-[2-(trityl-amino)-ethoxy]-phosphoryloxy}-1-((Z)-octadec-9-enoyloxymethyl)-ethyl ester 

Relevant articles and documents

Stereospecific synthesis of phosphatidylglycerol using a cyanoethyl phosphoramidite precursor

Phosphatidylglycerols (PG) are a family of naturally occurring phospholipids that are responsible for critical operations within cells. PG are characterized by an (R) configuration in the diacyl glycerol backbone and an (S) configuration in the phosphoglycerol head group. Herein, we report a synthetic route to provide control over the PG stereocenters as well as control of the acyl chain identity.

An insight into the solvent effect on the positional selectivity of the immobilized lipase from Burkholderia cepacia in 1,3-diolein synthesis

The solvent effect on the positional selectivity of the immobilized lipase from Burkholderia cepacia in 1,3-diolein synthesis was investigated for the first time. The results indicated that the preferential selectivity to sn-1 hydroxyl of the glycerol molecule over sn-2 hydroxyl was weaker in solvents with higher logP values.

Zirconium phenyl phosphonate phosphite as a highly active, reusable, solid acid catalyst for producing fatty acid polyol esters

The application of zirconium phenyl phosphonate phosphite (ZrPP) as a solid acid catalyst for producing polyol esters by esterification of glycerol or trimethylolpropane with a fatty acid (C8-C18.1) is reported for the first time. ZrPP exhibits high catalytic activity and in particular, (di + tri) esters selectivity (92.3 mol%). These esters of polyols are known for their application as biolubricants. The catalyst prepared using phosphorous acid to phenyl phosphonic acid molar ratio of 3:1 was found superior. The influence of process parameters on activity and selectivity of the catalyst was investigated. ZrPP was reusable in at least three recycling experiments. Hydrophobicity due to exposed phenyl groups on the surface is the possible cause for superior esterification activity of this novel, solid catalyst.