Mono- and diglycerides of fatty acids

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Monoglyceride of a fatty acid, in this example with a saturated fatty acid residue (blue marked). Monoglyceride Structural Formula V.1.png
Monoglyceride of a fatty acid, in this example with a saturated fatty acid residue (blue marked).
Diglyceride, in this example with a saturated fatty acid residue (highlighted blue) and an unsaturated fatty acid residue (highlighted green). Diglyceride Structural Formula V.1.png
Diglyceride, in this example with a saturated fatty acid residue (highlighted blue) and an unsaturated fatty acid residue (highlighted green).

Mono- and diglycerides of fatty acids ( E471) refers to a naturally occurring class of food additive composed of diglycerides and monoglycerides used as an emulsifier in foods such as infant formula, fresh pasta, jams and jellies, chocolate, creams, baked goods, and more. [1] It is also used as a fruit coating agent. This mixture is also sometimes referred to as partial glycerides.

Contents

Synthesis

Monoglycerides and diglycerides are types of glycerides both naturally present in food fats, [2] including various seed oils; [3] however, their concentration is usually low and industrial production is primarily achieved by a glycerolysis reaction between triglycerides (fats/oils) and glycerol, [4] followed by purification via solvent-free molecular distillation. The raw materials of mono- and diglycerides may be either vegetable or animal fats and oils.

Dietary aspects

E471 is mainly produced from vegetable oils (such as soybean, grapeseed, canola, sunflower, cottonseed, coconut, and palm oil) and plant pomace such as grape pomace or tomato pomace [5] ), although animal fats are sometimes used and cannot be completely excluded as being present in the product. [6] The fatty acids from each source are chemically identical. [7] The Vegan Society, which discourages eating animal-based foods, flags E471 as potentially animal based. [8]

The World Health Organization’s (WHO) report on the toxicological evaluation of mono- and diglycerides states that, “Food fats are in the main triglycerides. However, many of them have been shown to contain small amounts of diglycerides and monoglycerides. The amount present is commonly in the region of 1%. There is some evidence also that further amounts of these partial glycerides may be formed during the preparation of certain foods. Therefore, apart from any addition of these substances to food for technological purposes, they will always be present in the food as consumed.” [9] Mono- and diglycerides may contain small amounts of trans fat. [10] [11]

Metabolism

Mono- and diglycerides are naturally digested as part of normal lipid metabolism (i.e., the natural digestion of dietary fats and oils).


Effects on health

The safety of mono- and diglycerides of fatty acids has been assessed by several regulatory authorities. The Joint FAO/WHO Expert Committee on Food Additives (JECFA) has set an “acceptable daily intake” (ADI) as “not limited” due to the safety of these ingredients. [12] In 2017, the European Food Safety Authority (EFSA) re-evaluated the safety of mono- and diglycerides and concluded that there is no need to establish a numerical ADI and there is no safety concern for the reported food uses. [13]

Additionally, the Center for Science in the Public Interest, a consumer interest group that previously campaigned for the elimination of sulfite preservatives in fresh foods, as well as campaigned to label -- and eventually eliminate -- artificial trans fat found in partially hydrogenated oils) ranks mono- and diglycerides as “safe” in their Chemical Cuisine Ratings. [14]

A French observational study of several food additives published in 2024 suggested a correlation but not a causation between a higher intake of E471 in highly processed foods and increased risk of cancer by 15%, particularly breast cancer (24%) and prostate cancer (46%). [15] The study also notes, that “Cancer is a multifactorial pathology, thus as expected, one specific nutritional factor (here, exposure to an emulsifier) does not drastically increase absolute risks per se.”

Other uses

In the late 2010s, the company Apeel Sciences entered the market in parts of South America, China, and Japan with monoacylglycerols as an alternative to fruit waxing and plastic films to prevent withering and conserving fruit and vegetables for transport and storage. [16] [17]

See also

Related Research Articles

<span class="mw-page-title-main">Food additive</span> Substances added to food

Food additives are substances added to food to preserve flavor or enhance taste, appearance, or other sensory qualities. Some additives have been used for centuries as part of an effort to preserve food, for example vinegar (pickling), salt (salting), smoke (smoking), sugar (crystallization), etc. This allows for longer-lasting foods such as bacon, sweets or wines. With the advent of ultra-processed foods in the second half of the twentieth century, many additives have been introduced, of both natural and artificial origin. Food additives also include substances that may be introduced to food indirectly in the manufacturing process, through packaging, or during storage or transport.

<span class="mw-page-title-main">Triglyceride</span> Any ester of glycerol having all three hydroxyl groups esterified with fatty acids

A triglyceride is an ester derived from glycerol and three fatty acids. Triglycerides are the main constituents of body fat in humans and other vertebrates, as well as vegetable fat. They are also present in the blood to enable the bidirectional transference of adipose fat and blood glucose from the liver, and are a major component of human skin oils.

Essential fatty acids, or EFAs, are fatty acids that are required by humans and other animals for normal physiological function that cannot be synthesized in the body.⁠ As they are not synthesized in the body, the essential fatty acids – alpha-linolenic acid (ALA) and linoleic acid – must be obtained from food or from a dietary supplement. Essential fatty acids are needed for various cellular metabolic processes and for the maintenance and function of tissues and organs. These fatty acids also are precursors to vitamins, cofactors, and derivatives, including prostaglandins, leukotrienes, thromboxanes, lipoxins, and others.

<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">Glyceride</span> Chemical esters commonly found in fats and oils

Glycerides, also known as acylglycerols, are esters formed from glycerol and fatty acids, and are generally very hydrophobic.

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

DATEM is an emulsifier primarily used in baking to strengthen the gluten network in dough. It is added to crusty breads, such as rye, to impart a springy, chewy texture. It is also used in the production of biscuits, coffee whiteners, salsa con queso, ice cream, and salad dressings.

<span class="mw-page-title-main">Saponification value</span> Milligrams of a base required to saponify 1g of fat

Saponification value or saponification number represents the number of milligrams of potassium hydroxide (KOH) or sodium hydroxide (NaOH) required to saponify one gram of fat under the conditions specified. It is a measure of the average molecular weight of all the fatty acids present in the sample in form of triglycerides. The higher the saponification value, the lower the fatty acids average length, the lighter the mean molecular weight of triglycerides and vice versa. Practically, fats or oils with high saponification value are more suitable for soap making.

<span class="mw-page-title-main">Sunflower oil</span> Oil pressed from the seed of Helianthus annuus

Sunflower oil is the non-volatile oil pressed from the seeds of the sunflower. Sunflower oil is commonly used in food as a frying oil, and in cosmetic formulations as an emollient.

<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.

<i>tert</i>-Butylhydroquinone Chemical compound

tert-Butylhydroquinone is a synthetic aromatic organic compound which is a type of phenol. It is a derivative of hydroquinone, substituted with a tert-butyl group.

<span class="mw-page-title-main">Polyglycerol polyricinoleate</span> Emulsion used in food production

Polyglycerol polyricinoleate (PGPR), E476, is an emulsifier made from glycerol and fatty acids. In chocolate, compound chocolate and similar coatings, PGPR is mainly used with another substance like lecithin to reduce viscosity. It is used at low levels, and works by decreasing the friction between the solid particles in molten chocolate, reducing the yield stress so that it flows more easily, approaching the behaviour of a Newtonian fluid. It can also be used as an emulsifier in spreads and in salad dressings, or to improve the texture of baked goods. It is made up of a short chain of glycerol molecules connected by ether bonds, with ricinoleic acid side chains connected by ester bonds.

<span class="mw-page-title-main">Glycerolysis</span>

In organic chemistry glycerolysis refers to any process in which chemical bonds are broken via a reaction with glycerol. The term refers almost exclusively to the transesterification reaction of glycerol with triglycerides (fats/oils) to form mixtures of monoglycerides and diglycerides. These find a variety of uses; as food emulsifiers, 'low fat' cooking oils and surfactants.

Glycerol monostearate, commonly known as GMS, is a monoglyceride commonly used as an emulsifier in foods. It takes the form of a white, odorless, and sweet-tasting flaky powder that is hygroscopic. Chemically it is the glycerol ester of stearic acid. It is also used as hydration powder in exercise formulas

Lactylates are organic compounds that are FDA approved for use as food additives and cosmetic ingredients, e.g. as food-grade emulsifiers. These additives are non-toxic, biodegradable, and typically manufactured using biorenewable feedstocks. Owing to their safety and versatile functionality, lactylates are used in a wide variety of food and non-food applications. In the United States, the Food Chemicals Codex specifies the labeling requirements for food ingredients including lactylates. In the European Union, lactylates must be labelled in accordance with the requirements of the applicable EU regulation. Lactylates may be labelled as calcium stearoyl lactylate (CSL), sodium stearoyl lactylate (SSL), or lactylic esters of fatty acids (LEFA).

<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.

<span class="mw-page-title-main">Apeel Sciences</span> Company

Apeel Sciences is an American food technology company based in Goleta, California. Its edible coating product Apeel or Edipeel can make avocados, citrus and other types of fruit last twice as long as usual by using a tasteless edible coating, and reduces food loss and waste as well as reliance on single-use plastic packaging.

<span class="mw-page-title-main">Trans fat</span> Type of unsaturated fat

Trans fat, also called trans-unsaturated fatty acids, or trans fatty acids, is a type of unsaturated fat that occurs in foods. Trace concentrations of trans fats occur naturally, but large amounts are found in some processed foods. Since consumption of trans fats is unhealthy, artificial trans fats are highly regulated or banned in many nations. However, they are still widely consumed in developing nations, resulting in hundreds of thousands of deaths each year. The World Health Organization (WHO) had set a goal to make the world free from industrially produced trans fat by the end of 2023. The goal was not met, and the WHO announced another goal "for accelerated action till 2025 to complete this effort" along with associated support on 1 February 2024.

<span class="mw-page-title-main">Fat hydrogenation</span> Addition of hydrogen atoms to fat molecules

Fat hydrogenation is the process of combining unsaturated fat with hydrogen in order to partially or completely convert it into saturated fat. Typically this hydrogenation is done with liquid vegetable oils resulting in solid or semi-solid fats.

References

  1. "Food and Feed Information Portal Database | FIP". ec.europa.eu. Retrieved 11 July 2024.
  2. "Toxicological evaluation of some food additives including anticaking agents, antimicrobials, antioxidants, emulsifiers and thickening agents". World Health Organization.
  3. Flickinger, Brent D.; Matsuo, Noboru (February 2003). "Nutritional characteristics of DAG oil". Lipids. 38 (2): 129–132. doi:10.1007/s11745-003-1042-8. PMID   12733744. S2CID   4061326.
  4. Sonntag, Norman O. V. (1982). "Glycerolysis of fats and methyl esters — Status, review and critique". Journal of the American Oil Chemists' Society. 59 (10): 795A–802A. doi:10.1007/BF02634442. ISSN   0003-021X. S2CID   84808531.
  5. "Sources of Food Ingredients: Mono- and Diglycerides". Food Ingredient Facts. Retrieved 11 July 2024.
  6. Clarke, Chris (2012). The Science of Ice Cream. Royal Society of Chemistry. p. 55. ISBN   9781849731270. Mono-/diglycerides are made by partially hydrolysing vegetable fats, such as soybean oil, and palm oil. (Animal-fat-based emulsifiers are not commonly used because they are not suitable for vegetarian and certain religious diets).
  7. "Which E-numbers and additives are from animal origin ?". Food-Info.net. Netherlands: Wageningen University. Retrieved 4 September 2015. Chemically the fatty acids from animal or plant origin are identical. Therefore the origin is of no importance for the function in the food. Producers thus normally choose the cheapest oils to make these fats. This is generally some vegetable oil. However, animal fats can not be excluded.
  8. "Vegan Catering For All" (PDF). The Vegan Society. p. 12. Archived (PDF) from the original on 4 September 2015. Retrieved 4 September 2015.
  9. "301. Mono- and diglycerides (WHO Food Additives Series 5)". www.inchem.org. Retrieved 5 August 2024.
  10. "You May Be Getting More Mono- and Diglycerides Than You Should". Livestrong.com. Retrieved 11 July 2024.
  11. "Monoglycerides: What are they, risks, and who should avoid them". www.medicalnewstoday.com. 25 May 2018. Retrieved 5 August 2024.
  12. "Toxicological evaluation of certain food additives with a review of general principles and of specifications : seventeenth report of the Joint FAO/WHO Expert Committee on Food Additives". www.who.int. Retrieved 11 July 2024.
  13. "Re-evaluation of mono- and di-glycerides of fatty acids (E 471) as food additives | EFSA". www.efsa.europa.eu. 10 November 2017. Retrieved 11 July 2024.
  14. "Mono- and diglycerides". Center for Science in the Public Interest. Retrieved 11 July 2024.
  15. Sellem, L; Srour, B; Javaux, G; Chazelas, E; Chassaing, B; Viennois, E; Debras, C; Druesne-Pecollo, N; Esseddik, Y; Szabo de Edelenyi, F; Arnault, N; Agaësse, C; De Sa, A; Lutchia, R; Huybrechts, I; Scalbert, A; Pierre, F; Coumoul, X; Julia, C; Kesse-Guyot, E; Allès, B; Galan, P; Hercberg, S; Deschasaux-Tanguy, M; Touvier, M (February 2024). "Food additive emulsifiers and cancer risk: Results from the French prospective NutriNet-Santé cohort". PLOS Medicine. 21 (2): e1004338. doi: 10.1371/journal.pmed.1004338 . PMC   10863884 . PMID   38349899.
  16. https://www.fda.gov/media/99218/download [ bare URL PDF ]
  17. McGrath, Maggie (6 September 2018). "Fruit's Fountain Of Youth: Apeel's Edible Produce Coating Could Slay Food Waste And Save Supermarkets Billions". Forbes. Retrieved 24 July 2019.