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Diglycerol is a clear viscous liquid very similar to glycerol.
Diglycerol has a higher molecular weight than glycerol and is less volatile.
Diglycerol is water soluble and can be combined with aqueous systems.
CAS: 627-82-7
MF: C6H14O5
MW: 166.17
EINECS: 211-013-8
Synonyms
;bis-(2,3-dihydroxy-propyl)-ether;bis-2,3-dihydroxy-propyl-ether;Diglycerol (mixture of isomers) ;Di(2,3-dihydroxypropyl)ether;Diglycerine;glycerinether;Glycerine;Ether;Diglycerol=Bis-(2,3-dihydroxypropyl)-ether;Diglycerol;627-82-7;Diglycerine;alpha,alpha'-Diglycerol;3-(2,3-dihydroxypropoxy)propane-1,2-diol;Diglycerin;Propanediol, oxybis-;1,2-Propanediol, 3,3'-oxybis-;59113-36-9;3,3'-Oxybis(propane-1,2-diol);.alpha.,.alpha.'-Diglycerol;UC0A740LR3;3,3'-oxydipropane-1,2-diol;4-Oxaheptane-1,2,6,7-tetrol;3,3'-Oxydi(propane-1,2-diol);NSC-8689;MFCD00049316;glyceryl ether;UNII-UC0A740LR3;diglyceryl ether;3,3'-Oxydi(propylene glycol);3,2-propanediol;NSC8689;1,2-Propanediol, 3,3'-oxydi-;Oxydi(propanediol);3,3'-Oxydi-1,2-propanediol; 4-Oxaheptane-1,2,6,7-tetrol; Bis(2,3-dihydroxypropyl) Ether; NSC 8689;EINECS 211-013-8;OXYBISPROPANEDIOL;Tetrahydroxydipropyl Ether;1, 3,3'-oxybis-;1, 3,3'-oxydi-;Diglycerol (isomers mixture);SCHEMBL30754;4-Oxaheptane-1,6,7-tetrol;3-glyceryloxypropane-1,2-diol;3,3'-Oxydi-1,2-propanediol;UNII-3YC120743U;GPLRAVKSCUXZTP-UHFFFAOYSA-;DTXSID90872273;CHEBI:140430;DIGLYCERIN, ALPHA,ALPHA'-;bis-(2,3-dihydroxy-propyl)-ether;NSC 8689;EINECS 261-605-5;.ALPHA.,.ALPHA.'-DIGLYCERIN;AKOS015915864;3YC120743U;DIGLYCERIN, .ALPHA.,.ALPHA.'-;SY053494;DB-053322;CS-0197339;NS00009635;T0119;EC 261-605-5;F71162;.ALPHA.,.ALPHA.'-DIGLYCEROL, (+/-)-;EN300-7701666;Q27291013;InChI=1/C6H14O5/c7-1-5(9)3-11-4-6(10)2-8/h5-10H,1-4H2;51493-70-0
Diglycerol is an alkylglycerol.
Diglycerol has been reported in Triticum aestivum and Stelletta with data available.
Diglycerol is a glyceride that has antimicrobial properties.
Diglycerol is a surface-active agent, which inhibits bacterial growth and biofilm formation by disrupting the lipid bilayer of the cell membrane.
Diglycerol is also used in the production of glycerin and glycol esters, which are used in the manufacture of soaps, lotions, and other cosmetics.
Diglycerol shows anti-atherosclerotic effects at low doses in laboratory animals by inhibiting inflammation and breakdown of blood vessels.
The reaction mechanism for this effect is not fully understood; however, Diglycerol may be due to its ability to inhibit the release of reactive oxygen species from macrophages or cardiac muscle cells.
Diglycerol, also known as diglycerine or glycerinether, is an organic compound with the molecular formula C6H14O5.
Diglycerol is a colorless to light yellow viscous liquid that is soluble in water and ethanol but insoluble in ether.
Diglycerol is primarily used in the preparation of fatty acid esters, emulsifiers, and defoamers.
Diglycerol is also utilized as an intermediate in organic synthesis due to its multiple hydroxyl groups.
DIGLYCEROL Chemical Properties
Melting point: 319 °C
Boiling point: 214.38°C (rough estimate)
Density: 1.280 g/mL at 20 °C(lit.)
Refractive index: n20/D 1.489
Fp: 240°C
Storage temp.: Room Temperature
Solubility: Chloroform, DMSO, Methanol (Slightly), Water (Soluble)
Form: Oil
pka: 13.31±0.20(Predicted)
Color: Colourless to Light Yellow
Specific Gravity: 1.285 (20/4℃)
Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
CAS DataBase Reference: 627-82-7(CAS DataBase Reference)
Uses
Diglycerol can increase the water content in the top layers of the skin.
Formulators may select Diglycerol for its humectant properties, and also when needing a skin-conditioning agent or a solvent.
Diglycerol is synthetically manufactured.
Diglycerol was used in cosmetic deodorants.
Diglycerol is also a component in thickening and gelatation agents.
Diglyceride molecule contains 4 hydroxyl groups, is a kind of esterified, etherification and other reaction possibilities of organic synthesis intermediates.
Mainly used for the preparation of fatty acid esters, used as emulsifiers and Defoamers.
The main derivatives of diglycerols and diglyceryl tetramethyl acrylate: monomers of adhesives.
Diglyceryl oleate: antifoaming agent, lubricating oil rust inhibitor, non-drop polyvinyl chloride packaging material, food, margarine and butter emulsifier.
Diglyceryl ricinoleate: brake oil raw material, emulsifier and Defoamer.
Diglyceryl stearate: food emulsifier, paint and detergent additives, anti-fogging agent, detergent containing solvent, shoe polish, wax and other anti-evaporation agent.
Diglyceryl laurate: emulsifier, additive to detergents.
Ethylene oxide adduct of diglycerol: demulsifier, antistatic agent, release agent.
Diglycerin propylene oxide adduct: raw material of polyurethane, mold release agent.
Triallyl ether of diglycerol: softener for synthetic rubber.
mainly used for the preparation of fatty acid esters, as emulsifiers and Defoamers, and instead of glycerol for printing
Diglycerol has a wide range of applications in scientific research and industry:
Chemistry: Used as an intermediate in the synthesis of various compounds, including fatty acid esters and polyglycerols.
Biology: Functions as a second messenger in biochemical signaling, particularly in the activation of protein kinase C (PKC) and Munc13, which are involved in intracellular calcium release and vesicle release, respectively.
Medicine: Investigated for its potential as a fat substitute due to its ability to suppress body fat accumulation.
Industry: Utilized in the production of emulsifiers, defoamers, and as a solvent in cosmetic formulations.
Preparation Methods
Synthetic Routes and Reaction Conditions: Diglycerol can be synthesized through the etherification of glycerol.
This process involves the condensation of two glycerol molecules to form Diglycerol, which can occur in the presence of either homogeneous or heterogeneous catalysts.
Common catalysts include acid and base types, with microwave irradiation being an advanced technology that offers advantages over conventional heating .
Industrial Production Methods: Industrial production of Diglycerol typically involves the partial reaction of glycerol in the presence of an alkaline catalyst.
The reaction mixture, containing 10-15% this compound, undergoes separation of unreacted glycerol through distillation at reduced pressure to obtain a product with at least 90% Diglycerol.
