POLYGLYCEROL ESTERS

What are Polyglycerol Esters?
Polyglycerol esters of fatty acids (PGEs) are used in food as an emulsifier.
PGEs are a class of synthetic, nonionic surfactant frequently used in food, pharmaceutical, and cosmetic industries on account of their amphiphilic properties.
The hydrophilic part of these amphiphiles consists of oligomeric esters of glycerol, and the hydrophobic part consists of alkyl chains of varying length and degree of unsaturation.

Polyglycerol Ester Commercial Production
PGEs are produced by polymerization of glycerol in the presence of an alkaline catalyst followed by esterification with fatty acids.
The fatty acids are from corn oil, cottonseed oil, lard, palm oil, peanut oil, sesame oil, sunflower oil, soybean oil, etc.
Besides esters, PGEs also contain impurities, like mono, di, and triglycerides, free fatty acids, free glycerol and polyglycerol, and sodium salts of fatty acids may be present.

Polyglycerol Ester Description
Polyglycerol esters of fatty acids belongs to the class of organic compounds known as 1-alkyl,3-acylglycerols.
These are glycerides consisting of two fatty acyl chains covalently bonded to a glycerol molecule at the 1- and 3-positions through an ether and an ester linkage, respectively.
Polyglycerol esters of fatty acids is an extremely weak basic (essentially neutral) compound (based on its pKa).

Polyglycerol Ester Functions
Components of bakery products, such as oil, water and flour, are not soluble in each other.
Interfaces are present between these substances, such as water and oil, gases (air bubbles) and solid substances (flour components), air and water.
PGEs, like other emulsifiers, have both a hydrophobic and hydrophilic nature so they can reduce interfacial tension between different phases.

PGEs’ hydrophilic-lipophilic balance (HLB) depends on the length of the polyglycerol chain and the degree of esterification.
The HLB can vary from 3 to 14, and the desired HLB value may be obtained by appropriate blending.
Depending upon their HLB, PGEs can act as water-in-oil (W/O) or oil-in-water (O/W) emulsifiers.

PGEs form highly stable alpha-gel in water.
The α-gel phase of PGEs is surface active and is able to stabilize foams when the temperature is lower than the melting temperature of the emulsifier.
The special structure of Polyglycerol Ester is also leads to better emulsification properties.

Polyglycerol Ester Applications
An important application of PGEs is in cake batters with little or no content of fat and oil (i.e. batters for sponge cakes, Swiss rolls and similar types of cake formulations that are based on egg, sugar and flour and/or starch).
PGEs enhance aeration and help stabilize foams.
The use of PGEs makes Polyglycerol Esters possible to produce sponge cakes by single stage mixing, and produce final products with a finer crumb structure and longer shelf life.

PGEs can be used in margarines.
The addition of PGEs improve the functional properties of the margarine (e.g. the organoleptic properties of spreads, stabilizing or aerating of food) in addition to the emulsification of the emulsion.
PGEs are reported to improve the organolepic properties of a margarine or low-fat spread by reducing the graininess of the lipid phase to yield a plasticity and elasticity of the margarine corresponding to natural butter.

Compared to alternative emulsifiers, such as monoglycerides, the polyglycerol ester is found to have an advantage in providing long-time stability of whipping properties, making the emulsifier an excellent choice for cake mixes.
PGEs can also be used as low fat shortening.
Polyglycerol Esters can also form emulsion systems with a high amount water, thus reducing the overall caloric content of a food product.
As the α-tending emulsifier, PGEs also have the crumb softening and anti-staling effects and they also help improve cake volume in baked products.
The reason is that emulsifiers can reduce the rate of starch retrogradation.

PGEs can be used in whippable emulsions and toppings.
Polyglycerol Esters can promote fat particle aggregation and water absorption, and help achieve increased viscosity and aeration, and reduced coalescence.
Different than monoglycerides (MGs), the α-gel structure formed by PGEs are thermodynamically more stable, which means the emulsion system formed by PGEs are more stable than that of MGs.
Blends of PGEs and MGs are known to improve sponge cake aeration and stability with less mixing time and improved foam and emulsion stability.

Polyglycerol esters are a class of food emulsifiers used extensively within the food industry because of their amphiphilic nature in various types of food.
The corresponding polyglycerol esters are produced from polyglycerol and fatty acids in a direct esterification of triglycerides and polyglycerol.
The emulsifiers are of the non-ionic type and exhibit a broad range of polarity or hydrophilic-lipophilic balance (HLB) values, ranging from 6 to 11, compared with many other food emulsifiers.
The broad range of HLB values of the polyglycerol esters makes them a versatile emulsifier for food applications.
The amphiphilic properties of the polyglycerol ester of the emulsifier in water exhibit mesomorphic activities forming liquid crystalline structures.
An important application of the polyglycerol esters is in cake batters with little or no content of fat and oil.
Polyglycerol esters have also found applications in the pharmaceutical and cosmetics industries.

High-functioning polyglycerol ester of fatty acid centered on food additives synthesized by our original manufacturing method are mild, safe surfactants with a wide range of functions such as emulsion, solubilization, cleaning, and antibacterial properties, used in a variety of cosmetics.
Molecular design of the wide-ranging HLB is possible, providing excellent salt resistance and acid resistance.
Polyglycerol Ester retains skin moisture which is vital for cosmetics, and has unique features from the aspect of feel, such as comfort when applying.
We suggest Polyglycerol Ester as an ingredient for various cosmetics.

Surfactant-based separations are attracting interest due to simple operations and viable economics.
The present work focuses on the synthesis of two nonionic surfactants, polyglycerol fatty acid esters of cotton seed oil and castor seed oil, Polyglycerol Esters characterization using Fourier transform infrared spectroscopy and liquid spectroscopy-mass spectroscopy.
The synthesized surfactant is used in breaking azeotropic composition of n-propanol–water mixture via cloud point separation.
The separation obtained from the synthesized surfactants is compared with the separation obtained from Tween 20 and Polyglycerol Ester is found that both the synthesized surfactants are capable of breaking the azeotrope of n-propanol–water mixture.

Polyglycerol Ester Origin
PGEs have been used as food additives in Europe and America since the 1940s and they were approved for food use in the U.S. in the 1960s.

POLYGLYCERYL ESTERS
These compounds are formed chemically by esterification of fatty acids, largely saturated or mono-unsaturated, to one or several hydroxyl groups of polyglycerol.
As glycerol is a trifunctional molecule, Polyglycerol Ester may condense with itself to give polymers.
These polyglycerols are hydroxy-containing ethers, diglycerol being the simplest example.
If the primary hydroxyls are the only ones concerned in the reaction, the products are linear, but if the secondary hydroxyl groups are also involved, branched chains are formed.
Thus, several diglycerol molecules can be formed (see figure below) but if the polymerization proceeds to tri-, tetra- and higher glycerols the number of possible isomers increases exponentially.
Polyglycerol Ester has been found that cyclic products can also result from intra-molecular reactions.

Polyglycerol esters obtained from edible oils are commonly used surfactants in the food industry.
Despite their widespread application, the composition and properties of these surfactants are still not well characterized.
This study reveals the presence of so far unknown tetra-, penta-antennary constituents in polyglycerol esters, which exhibit very strong sodium affinity.

Many Uses of Polyglycerol Esters
Polyglycerol Esters or PGE are a range of ingredients with a wide range of functional properties.

Polysorbate replacer in Flavors
Many consumers want to avoid foods with polysorbate 60.
Polysorbate is a proven safe ingredient with powerful functionality, sometimes Polyglycerol Esters must be replaced with a more consumer-friendly ingredient.
PGE is a perfect choice for this replacement

High HLB ratio polyglycerol esters can function as Polysorbate replacers.
Many liquid flavors use polysorbate 60 to emulsifier the fat-soluble flavor components in the high water flavor.
Polyglycerol esters are the perfect polysorbate replacer for use in flavors.
Typically a 10-1-o grade is used to replace polysorbate in flavors.

Whipped Toppings
PGE’s are perfect for use in whipped toppings.
The higher HLB ratio will provide fat particle aggregation in the high water environment of whipped toppings.
PGE will provide increased viscosity and reduced coalescence.

What is a 10-2 Polyglycerol Ester?
Polyglycerol esters, specifically deca-polyglycerol diester or 10-2 polyglycerol ester is a powerful water-binding emulsifier that will turn an ordinary dry cake into a rich tender moist cake.
The 10 stands for 10 moles or parts polyglycerol to 2 moles or parts of fatty acids.
Normal fats are 1 glycerol to 3 fatty acids or the term triglyceride.
This emulsifier has similar components as regular fat but in a different proportion.
A special form of glycerol is used which is a chain of 10 glycerides.
To this 2 fatty acids are connected to the chain of glycerols.

The chain of 10 glycerols is very water-loving and will bind a lot of water.
The 2 fatty acids will bind fat.
This creates a Water in oil emulsion where water is bound in the center of oil.
This complex is very resistant to evaporation in the oven resulting in an extra moist cake.
10-2 polyglycerol esters are allowed for use in food in the US.
Other countries need to check into the legal status of this emulsifier in their respective country.

When glycerol is heated with an alkaline catalyst to over 230 C, water is evolved and polymerization occurs to form a whole family of polyglycerols ranging from diglycerol with 3 hydroxy groups, to triacontaglycerol with 32 hydroxy groups.
The carboxylic acid esters of polyglycerols prepared by direct esterification or by interchange, may be solid or liquid; saturated or unsaturated; aliphatic or aromatic; mono, di- or polycarboxylic acid esters; mono-, di-, or polyesters of the polyglycerol; single or mixed acid esters; high or low molecular weight; water or oil soluble; and with an HLB from about 4 to about 13.
Polyglycerol esters find utility in a wide variety of food products including beverages, desserts, topping and baked goods.
They are thermally stable and find application in several industrial systems.

3-1 Polyglycerol Esters
3-1 polyglycerol ester tri-polyglycerol ester is not as powerful as 10-2 polyglycerol ester in its water-binding ability.
This emulsifier is a chain of 3 glycerols with 1 fatty acid.
The overall complex of fat and water is much smaller.
This does increase moistness, but not as much as 10-2 polyglycerol esters.

How to use 10-2 Polyglycerol Esters
10-2 polyglycerol is a very hard plastic-like product that needs to be melted into fat or water to be functional.
This process is a simple heating/melting of the Polyglycerol Ester into water or oil and allowing the mixture to cool for storage and future use.
Del-Val can pre-melt the polyglycerol esters on special orders.
Please contact us for more information on how to purchase this solution to your dry cake and stale cake complaints.

Low-Fat Applications
Low-fat foods frequently use water as a mass volume replacer of the fat content.
PGEs strongly bond to the water creating a strong emulsion that is viscous and fat like.
10-2-P is the perfect grade for replacing fat as 10-20% 10-2-p PGE forms a vicious fat like emulsion.

Polyglycerol fatty acid ester (PGFE), abbreviated as polyglycerol ester, is an ester formed from polyglycerol and fatty acid.
Polyglycerol Ester is a new type of polyhydroxy ester nonionic surfactant with high efficiency and excellent performance.

Use of Polyglycerol Ester
Polyglycerol Ester is fed simultaneously with other required raw materials, dissolved, stirred, and emulsified at a temperature of about 70°C or higher, and then various products are made according to law.
Since Polyglycerol Ester is soluble in grease, Polyglycerol Ester is heated to dissolve with grease, and then fed after mixing.

Add one part of PGFE to 3-4 parts of water, heat to 70°C or higher, stir to dissolve, and then cool under stirring to obtain a milky white paste.
Put this paste into the raw material for better effect.
Suggested dosage: 0.1%-0.5%
Storage method and shelf life: Store in a cool and dry place, 18 months.

Polyglycerol Esters Nature
As the polyglycerol ester in the glycerol fatty acid ester series, Polyglycerol Esters emulsification performance is much better than that of monoglyceride.
The reason is that polyglycerol ester has more hydrophilic hydroxyl groups; and its hydrophilicity increases with the increase of glycerin polymerization degree.
The lipophilicity varies with different fatty acid alkyl groups, so by changing the degree of polyglycerol polymerization, fatty acid type and esterification degree, a series of HLB values (hydrophilic-lipophilic balance) can be obtained from 1 to 20, from lipophilic to hydrophilic Polyglycerol ester products with different properties are suitable for various special purposes.

The appearance of polyglycerol esters ranges from light yellow oily liquid to waxy solid, which is related to the combination of different fatty acids.
Polyglycerol ester has both hydrophilic and lipophilic properties, and has multiple properties such as good emulsification, dispersion, wetting, stability, and foaming.
Polyglycerol Ester can be decomposed in the process of human metabolism, thereby participating in metabolism, and used by the human body.
Polyglycerol Ester has a high degree of safety.
Polyglycerol Ester is a high-efficiency and safe additive and is recommended by the Food and Agriculture Organization of the United Nations and the World Health Organization.
At the same time, polyglycerol esters are quite stable in acidic, alkaline and neutral environments, and have good emulsification properties when the salt content is high.
Polyglycerol ester is colorless, odorless, hard to hydrolyze, and has no adverse effects on product appearance and odor; Polyglycerol Ester can be compounded with other emulsifiers and has good synergistic effects, so Polyglycerol Ester is widely used in food, daily chemical, petroleum, textile, Coatings, plastics, pesticides, rubber, medicine and other fields.
Based on all these application, Polyglycerol esters have become a rapidly developing class of nonionic surfactants.

Improve Dry Cakes with Polyglycerol Esters
The number one complaint with cakes is dry or crumbly cakes.
These complaints are inter-related and sometimes are actually the same complaint.
The average cake customer does not like a dry cake, a crumbly cake, or a stale cake.
All three of these terms are used by customers to describe the same cake problem and require a similar solution.
Solve your #1 complaint with our 10-2P polyglycerol esters.

We studied the structure and mechanical properties of surface films resulting from the adsorption of a dispersed Lβ phase at the air−water interface.
This Lβ phase corresponds to multilamellar vesicles and is formed by a commercial polyglycerol fatty acid ester (PGE) in aqueous solution at temperatures below the main chain-melting temperature (Tm = 58 °C).
We measured the adsorption kinetics using the pendant drop technique and mechanical properties of PGE films using oscillatory surface shear and dilatational rheometric methods.
Though the adsorption kinetics are very slow, we show that the Lβ phase of PGE is surface-active and forms viscoelastic films at the air−water surface after sufficiently long adsorption times.
The rheological response functions to shear and dilatational deformation are reminiscent of those of temporary networks, indicating an intermolecular connectivity at the surface.
This temporary network is probably created by hydrophobic interactions of alkyl chains.

We obtained more detailed information about the properties of this network by comparing the rheological signature of an adsorbed PGE film (unknown structure) with a solvent-spread monolayer (known structure).
We characterized the structural features of spread PGE films by recording the Langmuir isotherm and Brewster angle micrographs (BAM).
We show that the rheological responses of the adsorbed film and the solvent-spread monolayer are very close to each other, indicating a structural similarity.
From this study, we conclude that a dispersed Lβ phase of PGE is able to adsorb at the air−water surface at T < Tm.
The structure of the resulting film is a composite consisting of a monomolecular layer at the surface and eventually further bimolecular sublayers in the bulk.
At T < Tm, the alkyl chains within the layers are noncovalently connected and provide mechanical film stability measured as a viscoelastic response under small-amplitude shear or dilatational deformation.

Liquid–liquid extraction was used to fractionate a polyglycerol ester ingredient in order to link physicochemical behavior to the polarity of the fractions.
The most polar fraction showed faster adsorption kinetics and higher elastic moduli than the full mixture, whereas the least polar fraction showed slower adsorption kinetics and lower elastic moduli as compared to the complex mixture.
The addition of Na⁺ was shown to accelerate the agglomeration of surfactant self-assemblies in bulk solutions and also to increase the elastic modulus at the air–water interface.
These observations suggest that the composition of natural polyglycerol esters is more diverse than so far assumed and the overall behavior of these mixtures is determined not only by the amphyphilic interactions between mono- and penta-antennary forms, but also by the endogenous salt content of the ingredient.

Classically, 30 to 50 % of the total amount of hydroxyl groups are esterified by fatty acids.
These fatty acids are formed either of one species (lauric, stearic or oleic acid) or a mixture from vegetal oils (cottonseed oil, castor oil) or from animal source (beeswax).
Chemically, polyglycerol esters may be formed by an alkaline catalyzed random polymerization of glycerol followed by an esterification with isolated fatty acids or triacylglycerols.
The obtained mixture varies in polymerization degree, kind and position of esterified fatty acid (monoesters diglycerol or triglycerol or tetraglycerol, diesters diglycerol or triglycerol).

Polyglyceryl esters are important non-ionic surfactants with various applications in cosmetic, in food, pharmaceutical and other industries.
Their amphiphilic character enables their use in the stabilization of various suspensions.
In cosmetics they are used to emulsify, control viscosity, disperse and stabilize the final mixture.
They are incorporated into hair styling gels, skin treatment gels, skin cleansers, baby creams, long-acting hand creams, moisturizing sunscreens, and sun-protective sticks.
The most powerful emulsifiers are diglyceryl diisostearate in foundation creams, diglyceryl monolaurate in makeup-removing skin cleansers, and diglyceryl monooleate in baby creams.
In foods they are used as emulsifying agents in the production of fine bakery, chewing gum, and in replacement of fats.
Thus, polyglycerol polyricinoleate (E476), is an emulsifier made from castor beans (rich in ricinoleic acid) which reduces the viscosity of chocolate and similar coatings and compounds.
Polyglycerol Ester is used at low levels (fractions of percents).
By using E476), the chocolate recipe has lower costs in terms of less cocoa butter but also gives the benefit of having less fat.

Polyglycerol esters have been touted as replacements for fats to reduce human calorie consumption.
This replacement may be intended since the fatty acid esters were found to resist hydrolysis by digestive enzymes.

Polyglycerol Esters Functionalities Include:
-Improves texture, mouthfeel and consistency
-Emulsification
-Solubilization
-Emollient & refatting agents
-Improve flow properties
-Reduces interfacial tension

Polyglycerol Esters Features Include:
-Non-toxic, Natural
-Vegetable-based
-100% biodegradable
-Non-irritating to skin
-GRAS/food-grade
-Wide range of HLBs

Polyglycerol fatty acid ester nonionic surfactants have been used for a long time in foods and have been suggested as an alternative to the safety problems of PEG based nonionic surfactants.
The polyglycerol fatty acid ester surfactants are synthesized by combining a hydrophilic polyglycerin and a lipophilic fatty acid.
The hydrophilic polyglycerin is polymerized using glycerin, glycidol, epichlorohydrin, etc.
The main issues of the polyglycerol polymerization reaction are to increase the content of the polyglycerol in the form of linear rather than branched or cyclic forms and to narrow the distribution of the degree of polymerization.
The method of binding a lipophilic fatty acid group to a hydrophilic polyglycerin includes chemical synthesis such as esterification reaction and enzyme synthesis using lipase enzyme.
The main issues of polyglycerin fatty acid ester synthesis are to increase the yield and to control the degree of esterification while reducing side reactions.

Cake bakers have fought this issue for years.
In the past, gums, starches, and corn syrups were used to combat dry cake, stale cake, and crumbly cake.
None of these solutions made a significant difference to the dry or stale cake problem.
Commercial cake mixes make can make great moist cakes, but the cost is sometimes too high for the scratch baker to tolerate.

PGE will function in low-fat content cakes providing great aeration in cakes that contain little to no fat.
We have a solution to this problem with an innovative emulsifier that truly binds the water to make a great ultra moist cake.

Mixed partial esters formed by reacting polymerized glycerols with edible fats, oils, or fatty acids; minor amounts of mono-, di-, and triglycerides, free glycerol and polyglycerols, free fatty acids, and sodium salts of fatty acids may be present; degree of polymerization varies, and is specified by a number (such as tri-) that is related to the average number of glycerol residues per polyglycerol molecule.
A specified polyglycerol consists of a distribution of molecular species characteristic of Polyglycerol Esters nominal degree of polymerization.
By varying the proportions as well as the nature of the fats or fatty acids to be reacted with the polyglycerols, a large and diverse class of products may be obtained.

POLYGLYCEROL ESTERS

POLYGLYCEROL ESTERS

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