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Erythritol (, ) is an
organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
, the naturally occurring achiral meso four-carbon sugar alcohol (or polyol). It is the reduced form of either D- or L- erythrose and one of the two reduced forms of erythrulose. It is used as a
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 ...
and sugar substitute. It is synthesized from corn using
enzyme An enzyme () is a protein that acts as a biological catalyst by accelerating chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, and the enzyme converts the substrates into different mol ...
s and fermentation. Its formula is , or HO(CH2)(CHOH)2(CH2)OH. Erythritol is 60–70% as sweet as table sugar. However, erythritol is almost completely noncaloric and does not affect blood sugar or cause tooth decay. Japanese companies pioneered the commercial development of erythritol as a sweetener in the 1990s.


Etymology

The name "erythritol" derives from the Greek word for the color red (''erythros'' or ). That is the case even though erythritol is almost always found in the form of white crystals or powder, and chemical reactions do not turn it red. The name "erythritol" is adapted from a closely-related compound, erythrin, which turns red upon oxidation.


History

Erythritol was discovered in 1848 by the Scottish chemist John Stenhouse and first isolated in 1852. Starting from 1945, American chemists applied newly-developed techniques of
chromatography In chemical analysis, chromatography is a laboratory technique for the Separation process, separation of a mixture into its components. The mixture is dissolved in a fluid solvent (gas or liquid) called the ''mobile phase'', which carries it ...
to sugarcane juice and blackstrap molasses, finding in 1950 that erythritol was present in molasses fermented by yeast. It was first approved and marketed as a sweetener in Japan in 1990, and in the US in 1997.


Occurrence

Erythritol occurs naturally in some fruit and fermented foods.


Uses

Since 1990, erythritol has had a history of safe use as a sweetener and flavor-enhancer in food and beverage products and is approved for use by government regulatory agencies in more than 60 countries., Quote: "In 2003, the European Union (EU) Scientific Committee on Food (SCF) concluded that erythritol is safe for use in foods. ..the SCF opinion stated that the laxative threshold may be exceeded, especially by young consumers, ..the ANS Panel concluded that the acute bolus consumption of erythritol via non-alcoholic beverages at a maximum level of 1.6 % would not raise concerns for laxation." Beverage categories for its use are coffee and tea, liquid dietary supplements, juice blends, soft drinks, and flavored water product variations, with foods including confections, biscuits and cookies, tabletop sweeteners, and sugar-free chewing gum. The mild sweetness of erythritol allows for a volume-for-volume replacement of sugar, whereas sweeter sugar substitutes need fillers that result in a noticeably different texture in baked products.


Absorption and excretion

Erythritol is absorbed rapidly into the blood, with peak amounts occurring in under two hours; the majority of an oral dose (80 to 90%) is excreted unchanged in the
urine Urine is a liquid by-product of metabolism in humans and many other animals. In placental mammals, urine flows from the Kidney (vertebrates), kidneys through the ureters to the urinary bladder and exits the urethra through the penile meatus (mal ...
within 24 hours.


Safety

In 2023, the European Food Safety Authority reassessed the safety of erythritol and lowered the recommended daily intake limit to 0.5 grams per kg body weight, which equates to 35 g for an average adult (70 kg). The lower limit was set to "safeguard against its laxative effect and to mitigate against long-term effects, such as electrolyte imbalance arising from prolonged exposure to erythritol-induced diarrhea." Previously, in 2015, scientists assessed doses for erythritol where symptoms of mild gastrointestinal upset occurred, such as nausea, excess flatus, abdominal bloating or pain, and stool frequency. At a content of 1.6% in beverages, it was not considered to have a laxative effect. The upper limit of tolerance was 0.78 and 0.71g/kg body weight in adults and children respectively. In the United States, erythritol is among several sugar alcohols that are generally recognized as safe (GRAS) for food manufacturing.


Dietary and metabolic aspects


Caloric value and labeling

Nutritional labeling of erythritol in food products varies from country to country. Some places, such as
Japan Japan is an island country in East Asia. Located in the Pacific Ocean off the northeast coast of the Asia, Asian mainland, it is bordered on the west by the Sea of Japan and extends from the Sea of Okhotsk in the north to the East China Sea ...
and the
European Union The European Union (EU) is a supranational union, supranational political union, political and economic union of Member state of the European Union, member states that are Geography of the European Union, located primarily in Europe. The u ...
(EU), label it as zero-calorie. Under
Food and Drug Administration The United States Food and Drug Administration (FDA or US FDA) is a List of United States federal agencies, federal agency of the United States Department of Health and Human Services, Department of Health and Human Services. The FDA is respo ...
(FDA) labeling requirements in the United States, erythritol has a caloric value of 0.2 calories per gram (95% less than sugar and other carbohydrates).


Human digestion

In the body, most erythritol is absorbed into the bloodstream in the small intestine and then for the most part excreted unchanged in the
urine Urine is a liquid by-product of metabolism in humans and many other animals. In placental mammals, urine flows from the Kidney (vertebrates), kidneys through the ureters to the urinary bladder and exits the urethra through the penile meatus (mal ...
. About 10% enters the colon. In small doses, erythritol does not normally cause laxative effects and gas or bloating, as are often experienced after consumption of other sugar alcohols (such as maltitol, sorbitol, xylitol, and lactitol). About 90% is absorbed before it enters the large intestine, and since erythritol is not digested by intestinal bacteria, the remaining 10% is excreted in the feces. Large doses can cause nausea, stomach rumbling, and watery feces. Doses greater than 0.66 g/kg body weight in males and greater than 0.8 g/kg body weight in females cause laxation, and doses over cause diarrhea. Rarely, erythritol can cause allergic hives ( urticaria).


Blood sugar and insulin levels

Erythritol has no effect on blood sugar or blood
insulin Insulin (, from Latin ''insula'', 'island') is a peptide hormone produced by beta cells of the pancreatic islets encoded in humans by the insulin (''INS)'' gene. It is the main Anabolism, anabolic hormone of the body. It regulates the metabol ...
levels, and therefore may be used as a sugar substitute by people with type 2 diabetes. The glycemic index (GI) of erythritol is 0% of the GI for glucose and the insulin index (II) is 2% of the II for glucose.


Oral bacteria

Erythritol is tooth-friendly; since it cannot be metabolized by oral
bacteria Bacteria (; : bacterium) are ubiquitous, mostly free-living organisms often consisting of one Cell (biology), biological cell. They constitute a large domain (biology), domain of Prokaryote, prokaryotic microorganisms. Typically a few micr ...
, it does not contribute to tooth decay. In addition, erythritol, like xylitol, has antibacterial effects against streptococci bacteria, reduces dental plaque, and may be protective against tooth decay.


Manufacturing

Erythritol is manufactured by using enzymatic hydrolysis of the starch from corn to generate
glucose Glucose is a sugar with the Chemical formula#Molecular formula, molecular formula , which is often abbreviated as Glc. It is overall the most abundant monosaccharide, a subcategory of carbohydrates. It is mainly made by plants and most algae d ...
. Glucose is then fermented with yeast or another fungus to produce erythritol. A genetically-engineered form of the yeast '' Yarrowia lipolytica'' has been optimized for erythritol production by fermentation by using
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 ...
as a carbon source and high osmotic pressure to increase yields up to 62%.


Chemical properties


Heat of solution

Erythritol has a strong cooling effect ( endothermic, or positive heat of solution) when it dissolves in water, which is often compared with the cooling effect of mint flavors. The cooling effect is present only when erythritol is not already dissolved in water, a situation that might be experienced in an erythritol-sweetened frosting, chocolate bar, chewing gum, or hard candy. The cooling effect of erythritol is very similar to that of xylitol and among the strongest cooling effects of all sugar alcohols. Erythritol has a p''K''a of 13.903 at 18 °C.


Biological properties

According to a 2014 study, erythritol functions as an insecticide toxic to the fruit fly '' Drosophila melanogaster'', impairing motor ability and reducing longevity even when nutritive sugars were available. Erythritol is preferentially used by the ''Brucella'' spp. The presence of erythritol in the placentas of goats, cattle, and pigs has been proposed as an explanation for the accumulation of ''Brucella'' bacteria found at these sites.


Synonyms

In the 19th and the early 20th centuries, several synonyms were in use for erythritol: erythrol, erythrite, erythoglucin, eryglucin, erythromannite and phycite. Zerose is a tradename for erythritol.


See also

* Erythritol tetranitrate * Pentaerythritol * Threitol, the diastereomer of erythritol


References


External links


"Erythritol and cardiovascular events"
National Institutes of Health The National Institutes of Health (NIH) is the primary agency of the United States government responsible for biomedical and public health research. It was founded in 1887 and is part of the United States Department of Health and Human Service ...
(14 Mar 2023) {{Alcohols, state=collapsed E-number additives Food additives Sugar alcohols Sugar substitutes Tetrols Substances discovered in the 19th century