Polyglycerol polyricinoleate

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Polyglycerol polyricinoleate
Polyglycerol polyricinoleate.svg
Names
IUPAC name
1,2,3-Propanetriol, homopolymer, (9Z,12R)-12-hydroxy-9-octadecenoate
Identifiers
ChemSpider
  • None
ECHA InfoCard 100.117.614 OOjs UI icon edit-ltr-progressive.svg
E number E476 (thickeners, ...)
PubChem CID
UNII
Properties
(C3H5O2)n(C18H32O2)m
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Polyglycerol polyricinoleate (PGPR), E476, is an emulsifier made from glycerol and fatty acids (usually from castor bean, but also from soybean oil). In chocolate, compound chocolate and similar coatings, PGPR is mainly used with another substance like lecithin [2] to reduce viscosity. It is used at low levels (below 0.5%), [3] [4] and works by decreasing the friction between the solid particles (e.g. cacao, sugar, milk) in molten chocolate, reducing the yield stress so that it flows more easily, approaching the behaviour of a Newtonian fluid. [4] It can also be used as an emulsifier in spreads and in salad dressings, [5] or to improve the texture of baked goods. [5] It is made up of a short chain of glycerol molecules connected by ether bonds, with ricinoleic acid side chains connected by ester bonds.

Contents

PGPR is a yellowish, viscous liquid, and is strongly lipophilic: it is soluble in fats and oils and insoluble in water and ethanol. [3]

Manufacture

Glycerol is heated to above 200 °C in a reactor in the presence of an alkaline catalyst to create polyglycerol. Castor oil fatty acids are separately heated to above 200 °C, to create interesterified ricinoleic fatty acids. The polyglycerol and the interesterified ricinoleic fatty acids are then mixed to create PGPR. [6]

Use in chocolate

Because PGPR improves the flow characteristics of chocolate and compound chocolate, especially near the melting point, it can improve the efficiency of chocolate coating processes: chocolate coatings with PGPR flow better around shapes of enrobed and dipped products, [7] [8] and it also improves the performance of equipment used to produce solid molded products: [8] the chocolate flows better into the mold, and surrounds inclusions and releases trapped air more easily. [2] PGPR can also be used to reduce the quantity of cocoa butter needed in chocolate formulations: the solid particles in chocolate are suspended in the cocoa butter, and by reducing the viscosity of the chocolate, less cocoa butter is required, [2] which saves costs, because cocoa butter is an expensive ingredient, and also leads to a lower-fat product. [9]

Safety

The FDA has deemed PGPR to be generally recognized as safe for human consumption, [1] and the Joint FAO/WHO Expert Committee on Food Additives (JECFA) has also deemed it safe. [3] Both of these organisations set the acceptable daily intake at 7.5 milligrams per kilogram of body weight. In 2017, a panel from the European Food Safety Authority recommended an increased acceptable daily intake of 25 milligrams per kilogram of body weight based on a new chronic toxicity and carcinogenicity study. [10] In Europe, PGPR is allowed in chocolate up to a level of 0.5%. [3]

In a 1998 review funded by Unilever of safety evaluations from the late 1950s and early 1960s, "PGPR was found to be 98% digested by rats and utilized as a source of energy superior to starch and nearly equivalent to peanut oil." [11] Additionally, no evidence was found of interference with normal fat metabolism, nor with growth, reproduction, and maintenance of tissue. Overall, it did not "constitute a human health hazard". [11]

A study published in the European Food Safety Authority in 2017 re-evaluated the safety of the additive and recommended to revise the acceptable daily intake and increase it to 25 milligrams per kilogram of body weight. [12]

Related Research Articles

<span class="mw-page-title-main">Aspartame</span> Artificial non-saccharide sweetener

Aspartame is an artificial non-saccharide sweetener 200 times sweeter than sucrose and is commonly used as a sugar substitute in foods and beverages. It is a methyl ester of the aspartic acid/phenylalanine dipeptide with brand names NutraSweet, Equal, and Canderel. Aspartame was approved by the US Food and Drug Administration (FDA) in 1974, and then again in 1981, after approval was revoked in 1980.

<span class="mw-page-title-main">Chocolate</span> Food produced from cacao seeds

Chocolate or cocoa is a food made from roasted and ground cacao seed kernels that is available as a liquid, solid, or paste, either on its own or as a flavoring agent in other foods. Cacao has been consumed in some form for at least 5,300 years starting with the Mayo-Chinchipe culture in what is present-day Ecuador and later Mesoamerican civilizations also consumed chocolate beverages before being introduced to Europe in the 16th century.

<span class="mw-page-title-main">Castor oil</span> Vegetable oil pressed from castor beans

Castor oil is a vegetable oil pressed from castor beans. It is a colourless or pale yellow liquid with a distinct taste and odor. Its boiling point is 313 °C (595 °F) and its density is 0.961 g/cm3. It includes a mixture of triglycerides in which about 90% of fatty acids are ricinoleates. Oleic acid and linoleic acid are the other significant components.

<span class="mw-page-title-main">Margarine</span> Semi-solid oily spread often used as a butter substitute

Margarine is a spread used for flavoring, baking, and cooking. It is most often used as a substitute for butter. Although originally made from animal fats, most margarine consumed today is made from vegetable oil. The spread was originally named oleomargarine from Latin for oleum and Greek margarite. The name was later shortened to margarine.

<span class="mw-page-title-main">Stearic acid</span> Eighteen-carbon straight-chain fatty acid

Stearic acid is a saturated fatty acid with an 18-carbon chain. The IUPAC name is octadecanoic acid. It is a soft waxy solid with the formula CH3(CH2)16CO2H. The triglyceride derived from three molecules of stearic acid is called stearin. Stearic acid is a prevalent fatty-acid in nature, found in many animal and vegetable fats, but is usually higher in animal fat than vegetable fat. It has a melting point of 69.4 °C and a pKa of 4.50.

<span class="mw-page-title-main">Lecithin</span> Generic term for amphiphilic substances of plant and animal origin

Lecithin is a generic term to designate any group of yellow-brownish fatty substances occurring in animal and plant tissues which are amphiphilic – they attract both water and fatty substances, and are used for smoothing food textures, emulsifying, homogenizing liquid mixtures, and repelling sticking materials.

<span class="mw-page-title-main">Xanthan gum</span> Polysaccharide gum used as a food additive and thickener

Xanthan gum is a polysaccharide with many industrial uses, including as a common food additive. It is an effective thickening agent and stabilizer that prevents ingredients from separating. It can be produced from simple sugars by fermentation and derives its name from the species of bacteria used, Xanthomonas campestris.

<span class="mw-page-title-main">Cocoa butter</span> Pale-yellow, edible fat extracted from the cocoa bean

Cocoa butter, also called theobroma oil, is a pale-yellow, edible fat extracted from the cocoa bean. It is used to make chocolate, as well as some ointments, toiletries, and pharmaceuticals. Cocoa butter has a cocoa flavor and aroma. Its melting point is slightly below human body temperature. It is an essential ingredient of chocolate and related confectionary products. Cocoa butter does not contain butter or other animal products; it is vegan.

<span class="mw-page-title-main">White chocolate</span> Confectionery made from milk solids without cocoa solids

White chocolate is a confectionery typically made of sugar, milk, and cocoa butter, but no cocoa solids. It is pale ivory in color, and lacks many of the compounds found in milk, dark, and other chocolates. It is solid at room temperature because the melting point of cocoa butter, the only white cocoa bean component, is 35 °C (95 °F).

<span class="mw-page-title-main">Monoglyceride</span> Class of glycerides

Monoglycerides are a class of glycerides which are composed of a molecule of glycerol linked to a fatty acid via an ester bond. As glycerol contains both primary and secondary alcohol groups two different types of monoglycerides may be formed; 1-monoacylglycerols where the fatty acid is attached to a primary alcohol, or a 2-monoacylglycerols where the fatty acid is attached to the secondary alcohol.

<span class="mw-page-title-main">Caramel color</span> Water soluble food coloring

Caramel color or caramel coloring is a water-soluble food coloring. It is made by heat treatment of carbohydrates (sugars), in general in the presence of acids, alkalis, or salts, in a process called caramelization. It is more fully oxidized than caramel candy, and has an odor of burnt sugar and a somewhat bitter taste. Its color ranges from pale yellow to amber to dark brown.

<span class="mw-page-title-main">Compound chocolate</span> Combination of cocoa, vegetable fat and sweeteners

Compound chocolate is a product made from a combination of cocoa, vegetable fat and sweeteners. It is used as a lower-cost alternative to pure chocolate, as it uses less-expensive hard vegetable fats such as coconut oil or palm kernel oil in place of the more expensive cocoa butter. It may also be known as "compound coating" or "chocolatey coating" when used as a coating for candy. It is often used in less expensive chocolate bars to replace enrobed chocolate on a product.

<span class="mw-page-title-main">Modified starch</span> Thickening agent

Modified starch, also called starch derivatives, is prepared by physically, enzymatically, or chemically treating native starch to change its properties. Modified starches are used in practically all starch applications, such as in food products as a thickening agent, stabilizer or emulsifier; in pharmaceuticals as a disintegrant; or as binder in coated paper. They are also used in many other applications.

<span class="mw-page-title-main">Ricinoleic acid</span> Chemical compound

Ricinoleic acid, formally called 12-hydroxy-9-cis-octadecenoic acid, is a fatty acid. It is an unsaturated omega-9 fatty acid and a hydroxy acid. It is a major component of the seed oil obtained from the seeds of castor plant, the plant that produces ricin. It is also found in the sclerotium of ergot. About 90% of the fatty acid content in castor oil is the ricinolein.

<span class="mw-page-title-main">Cocoa solids</span> Mixture remaining after cocoa butter is extracted from cocoa beans

Dry cocoa solids are the components of cocoa beans remaining after cocoa butter, the fatty component of the bean, is extracted from chocolate liquor, roasted cocoa beans that have been ground into a liquid state. Cocoa butter is 46% to 57% of the weight of cocoa beans and gives chocolate its characteristic melting properties. Cocoa powder is the powdered form of the dry solids with a small remaining amount of cocoa butter. Untreated cocoa powder is bitter and acidic. Dutch process cocoa has been treated with an alkali to neutralize the acid.

<span class="mw-page-title-main">Mono- and diglycerides of fatty acids</span> Emulsifier

Mono- and diglycerides of fatty acids (E471) refers to a naturally occurring class of food additive composed of diglycerides and monoglycerides which is used as an emulsifier. It is also used as a fruit coating agent. This mixture is also sometimes referred to as partial glycerides.

<span class="mw-page-title-main">Enrober</span> Machine to coat a food item

An enrober is a machine used in the confectionery industry to coat a food item with a coating medium, typically chocolate. Foods that are coated by enrobers include nuts, ice cream, toffee, chocolate bars, biscuits and cookies. Enrobing with chocolate extends a confection's shelf life.

<span class="mw-page-title-main">Diglyceride</span> Type of fat derived from glycerol and two fatty acids

A diglyceride, or diacylglycerol (DAG), is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Two possible forms exist, 1,2-diacylglycerols and 1,3-diacylglycerols. Diglycerides are natural components of food fats, though minor in comparison to triglycerides. DAGs can act as surfactants and are commonly used as emulsifiers in processed foods. DAG-enriched oil has been investigated extensively as a fat substitute due to its ability to suppress the accumulation of body fat; with total annual sales of approximately USD 200 million in Japan since its introduction in the late 1990s till 2009.

<span class="mw-page-title-main">Sucrose esters</span> Class of chemical compounds

Sucrose esters or sucrose fatty acid esters are a group of non-naturally occurring surfactants chemically synthesized from the esterification of sucrose and fatty acids. This group of substances is remarkable for the wide range of hydrophilic-lipophilic balance (HLB) that it covers. The polar sucrose moiety serves as a hydrophilic end of the molecule, while the long fatty acid chain serves as a lipophilic end of the molecule. Due to this amphipathic property, sucrose esters act as emulsifiers; i.e., they have the ability to bind both water and oil simultaneously. Depending on the HLB value, some can be used as water-in-oil emulsifiers, and some as oil-in-water emulsifiers. Sucrose esters are used in cosmetics, food preservatives, food additives, and other products. A class of sucrose esters with highly substituted hydroxyl groups, olestra, is also used as a fat replacer in food.

References

  1. 1 2 "GRAS Notice 000466: polyricinoleic acid" (PDF). Food and Drug Administration . Archived from the original (PDF) on 2017-10-31. Retrieved 2016-07-09.
  2. 1 2 3 Hasenhuettl, Gerard L; Hartel, Richard W, eds. (2008). Food Emulsifiers and Their Applications. Springer Science & Business Media. p. 294. ISBN   9780387752846.
  3. 1 2 3 4 Food Additives in Europe 2000. Nordic Council of Ministers. 2002. p. 482. ISBN   9789289308298.
  4. 1 2 Afoakwa, Emmanuel Ohene (2016). Chocolate Science and Technology. John Wiley & Sons. p. 248. ISBN   9781118913772.
  5. 1 2 Dunford, Nurhan Turgut (2012). Food and Industrial Bioproducts and Bioprocessing. John Wiley & Sons. p. 254. ISBN   9781119946069.
  6. "GRAS Notification for Polyglycerol Polyricinoleate" (PDF). FDA, (Palsgaard). 23 October 2008.
  7. Talbot, Geoff (2009). Science and Technology of Enrobed and Filled Chocolate, Confectionery and Bakery Products. Elsevier. p. 44. ISBN   9781845696436.
  8. 1 2 Gaonkar, Anilkumar G.; McPherson, Andrew (2016). Ingredient Interactions: Effects on Food Quality. CRC Press. p. 418. ISBN   9781420028133.
  9. "High grade PGPR in chocolate". Palsgaard. 2014. Archived from the original on 2007-08-03. Retrieved 2007-09-17.
  10. Mortensen, Alicja; Aguilar, Fernando; Crebelli, Riccardo; et al. (March 2017). "Re‐evaluation of polyglycerol polyricinoleate (E 476) as a food additive". EFSA Journal. 15 (3): e04743. doi:10.2903/J.EFSA.2017.4743. PMC   7010163 . PMID   32625446.
  11. 1 2 Wilson, R.; van Schie, B.J.; Howes, D. (1998). "Overview of the Preparation, Use and Biological Studies on Polyglycerol Polyricinoleate (PGPR)". Food and Chemical Toxicology. 36 (9–10): 711–8. doi:10.1016/S0278-6915(98)00057-X. PMID   9737417.
  12. "Re-evaluation of polyglycerol polyricinoleate (E 476) as a food additive". EFSA.