Mono- And Diglycerides
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Mono- and diglycerides of fatty acids ( E471) are a naturally occurring class of
food additive Food additives are substances added to food to preserve flavor or enhance taste, appearance, or other sensory qualities. Some additives, such as vinegar ( pickling), salt ( salting), smoke ( smoking) and sugar ( crystallization), have been used f ...
composed of
diglycerides 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 na ...
and
monoglycerides Monoglycerides (also: acylglycerols or monoacylglycerols) 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 differe ...
used as an
emulsifier An emulsion is a mixture of two or more liquids that are normally immiscible (unmixable or unblendable) owing to liquid-liquid phase separation. Emulsions are part of a more general class of two-phase systems of matter called colloids. Althou ...
in foods such as infant formula, fresh pasta, jams and jellies, chocolate, creams, baked goods, and more. It is also used as a fruit coating agent. This mixture is also sometimes referred to as partial glycerides.


Synthesis

Monoglyceride Monoglycerides (also: acylglycerols or monoacylglycerols) 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 differe ...
s and
diglyceride 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 ...
s are types of
glycerides Glycerides, also known as acylglycerols, are esters formed from glycerol and fatty acids, and are generally very hydrophobic. Glycerol has three hydroxyl functional groups, which can be esterified with one, two, or three fatty acids to form mo ...
both naturally present in food fats, including various
seed oil Vegetable oils, or vegetable fats, are oils extracted from seeds or from other parts of edible plants. Like animal fats, vegetable fats are ''mixtures'' of triglycerides. Soybean oil, grape seed oil, and cocoa butter are examples of seed oi ...
s; however, their concentration is usually low and industrial production is primarily achieved by a
glycerolysis 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 mi ...
reaction between
triglyceride A triglyceride (from '' tri-'' and '' glyceride''; also TG, triacylglycerol, TAG, or triacylglyceride) is an ester derived from glycerol and three fatty acids. Triglycerides are the main constituents of body fat in humans and other vertebrates ...
s (fats/oils) and
glycerol Glycerol () is a simple triol compound. It is a colorless, odorless, sweet-tasting, viscous liquid. The glycerol backbone is found in lipids known as glycerides. It is also widely used as a sweetener in the food industry and as a humectant in pha ...
, followed by purification via solvent-free
molecular distillation Molecular distillation is a type of short-path vacuum distillation, characterized by an extremely low vacuum pressure, 0.01 torr or below, which is performed using a molecular still. It is a process of separation, purification and concentration of ...
. The raw materials of mono- and diglycerides may be either
vegetable Vegetables are edible parts of plants that are consumed by humans or other animals as food. This original meaning is still commonly used, and is applied to plants collectively to refer to all edible plant matter, including edible flower, flo ...
or
animal Animals are multicellular, eukaryotic organisms in the Biology, biological Kingdom (biology), kingdom Animalia (). With few exceptions, animals heterotroph, consume organic material, Cellular respiration#Aerobic respiration, breathe oxygen, ...
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), although animal fats are sometimes used and cannot be completely excluded as being present in the product. The fatty acids from each source are chemically identical.
The Vegan Society The Vegan Society is a registered charity and the oldest vegan organization in the world, founded in the United Kingdom in 1944 by Donald Watson, Elsie Shrigley, George Henderson and his wife Fay Henderson among others. History In Novembe ...
, which discourages eating animal-based foods, flags E471 as potentially animal based. The
World Health Organization The World Health Organization (WHO) is a list of specialized agencies of the United Nations, specialized agency of the United Nations which coordinates responses to international public health issues and emergencies. It is headquartered in Gen ...
’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.” Mono- and diglycerides may contain small amounts of
trans fat Trans fat is a type of unsaturated fat that occurs in foods. Small amounts of trans fats occur naturally, but large amounts are found in some processed foods made with partially hydrogenated oils. Because consumption of trans fats is associated ...
.


Metabolism

Mono- and diglycerides are naturally digested as part of normal
lipid metabolism Lipid metabolism is the synthesis and degradation of lipids in cells, involving the breakdown and storage of fats for energy and the synthesis of structural and functional lipids, such as those involved in the construction of cell membranes. In ani ...
(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. 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. Additionally, the
Center for Science in the Public Interest The Center for Science in the Public Interest (CSPI) is a Washington, D.C.–based non-profit watchdog and consumer advocacy group. History and funding CSPI is a consumer advocacy organization. Its focus is nutrition and health, food safety ...
, 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. 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%). 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 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, anre ...
entered the market in parts of
South America South America is a continent entirely in the Western Hemisphere and mostly in the Southern Hemisphere, with a considerably smaller portion in the Northern Hemisphere. It can also be described as the southern Subregion#Americas, subregion o ...
, China, and Japan with monoacylglycerols as an alternative to fruit waxing and
plastic film Plastic film is a thin continuous polymeric material. Thicker plastic material is often called a "sheet". These thin plastic membranes are used to separate areas or volumes, to hold items, to act as barriers, or as printable surfaces. Plast ...
s to prevent withering and conserving fruit and vegetables for transport and storage.


See also

*
Polyglycerol polyricinoleate 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 subst ...
*
Monoglyceride Monoglycerides (also: acylglycerols or monoacylglycerols) 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 differe ...
*
Diglyceride 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 ...


References


External links


Food-Info.net: E-numbers: E471
{{Use dmy dates, date=October 2019 Food additives Fatty acid esters E-number additives Glycerol esters