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Erythritol is an
organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. T ...
, a four-carbon
sugar alcohol Sugar alcohols (also called polyhydric alcohols, polyalcohols, alditols or glycitols) are organic compounds, typically derived from sugars, containing one hydroxyl group (–OH) attached to each carbon atom. They are white, water-soluble solids ...
(or
polyol In organic chemistry, a polyol is an organic compound containing multiple hydroxyl groups (). The term "polyol" can have slightly different meanings depending on whether it is used in food science or polymer chemistry. Polyols containing two, thr ...
) with no optical activity, used as a food additive and sugar substitute. It is naturally occurring. It can be made from corn using enzymes and fermentation. Its formula is , or HO(CH2)(CHOH)2(CH2)OH; specifically, one particular
stereoisomer In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in ...
with that formula. Erythritol is 60–70% as sweet as sucrose (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.


History

Erythritol was discovered in 1848 by Scottish chemist
John Stenhouse John Stenhouse FRS FRSE FIC FCS (21 October 1809 – 31 December 1880) was a Scottish chemist. In 1854, he invented one of the first practical respirators. He was a co-founder of the Chemical Society in 1841. Life John Stenhouse was born ...
and first isolated in 1852. In 1950 it was found in
blackstrap molasses Molasses () is a viscous substance resulting from refining sugarcane or sugar beets into sugar. Molasses varies in the amount of sugar, method of extraction and age of the plant. Sugarcane molasses is primarily used to sweeten and flavour f ...
that was fermented by yeast, and it became commercialized as a sugar alcohol in the 1990s in Japan.


Natural occurrence and production

Erythritol occurs naturally in some fruit and fermented foods. It also occurs in human body fluids such as eye lens tissue, serum, plasma, fetal fluid, and urine. At the industrial level, it is produced from glucose by fermentation with a
yeast Yeasts are eukaryotic, single-celled microorganisms classified as members of the fungus kingdom. The first yeast originated hundreds of millions of years ago, and at least 1,500 species are currently recognized. They are estimated to constit ...
, ''Moniliella pollinis''.


Uses, absorption, and safety

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 of 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 Laxatives, purgatives, or aperients are substances that loosen stools and increase bowel movements. They are used to treat and prevent constipation. Laxatives vary as to how they work and the side effects they may have. Certain stimulant, lubri ...
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 Confectionery is the art of making confections, which are food items that are rich in sugar and carbohydrates. Exact definitions are difficult. In general, however, confectionery is divided into two broad and somewhat overlapping categories ...
, 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. 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 in many other animals. Urine flows from the kidneys through the ureters to the urinary bladder. Urination results in urine being excreted from the body through the urethra. Cellular ...
within 24 hours. As a test of safety, scientists assessed doses for erythritol where symptoms of mild
gastrointestinal The gastrointestinal tract (GI tract, digestive tract, alimentary canal) is the tract or passageway of the digestive system that leads from the mouth to the anus. The GI tract contains all the major organs of the digestive system, in humans and ...
upset occurred, such as nausea, excess
flatus Flatulence, in humans, is the expulsion of gas from the intestines via the anus, commonly referred to as farting. "Flatus" is the medical word for gas generated in the stomach or bowels. A proportion of intestinal gas may be swallowed environm ...
, abdominal bloating or pain, and stool frequency. At a content of 1.6% in beverages it is not considered to have a
laxative Laxatives, purgatives, or aperients are substances that loosen stools and increase bowel movements. They are used to treat and prevent constipation. Laxatives vary as to how they work and the side effects they may have. Certain stimulant, lubri ...
effect. The upper limit of tolerance was 0.78 and 0.71 grams per kg body weight in adults and children, respectively. For safe use in children, a scientific panel for the
European Food Safety Authority The European Food Safety Authority (EFSA) is the agency of the European Union (EU) that provides independent scientific advice and communicates on existing and emerging risks associated with the food chain. EFSA was established in February 2002, ...
recommended the upper limit content per food or beverage serving was 0.6 grams per kg body weight.


Dietary and metabolic aspects


Caloric value and labeling

Nutritional labeling of erythritol in food products varies from country to country. Some countries, such as Japan and the
European Union The European Union (EU) is a supranational political and economic union of member states that are located primarily in Europe. The union has a total area of and an estimated total population of about 447million. The EU has often been de ...
(EU), label it as zero- calorie. Under U.S.
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 respon ...
(FDA) labeling requirements, it has a caloric value of 0.2 calories per gram (95% less than sugar and other carbohydrates). The FDA has not made its own determination regarding the generally recognized as safe (GRAS) status of erythritol, but has accepted the conclusion that erythritol is GRAS as submitted to it by several food manufacturers.


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 in many other animals. Urine flows from the kidneys through the ureters to the urinary bladder. Urination results in urine being excreted from the body through the urethra. Cellular ...
. About 10% enters the colon. In small doses, erythritol does not normally cause
laxative Laxatives, purgatives, or aperients are substances that loosen stools and increase bowel movements. They are used to treat and prevent constipation. Laxatives vary as to how they work and the side effects they may have. Certain stimulant, lubri ...
effects and gas or bloating, as are often experienced after consumption of other sugar alcohols (such as
maltitol Maltitol is a sugar alcohol (a polyol) used as a sugar substitute. It has 75–90% of the sweetness of sucrose (table sugar) and nearly identical properties, except for browning. It is used to replace table sugar because it is half as energetic, ...
, sorbitol,
xylitol Xylitol is a chemical compound with the formula , or HO(CH2)(CHOH)3(CH2)OH; specifically, one particular stereoisomer with that structural formula. It is a colorless or white crystalline solid that is freely soluble in water. It can be classifi ...
, and
lactitol Lactitol is a sugar alcohol used as a replacement bulk sweetener for low calorie foods with 30–40% of the sweetness of sucrose. It is also used medically as a laxative. Lactitol is produced by two manufacturers, Danisco and Purac Biochem. ...
). About 90% is absorbed before it enters the
large intestine The large intestine, also known as the large bowel, is the last part of the gastrointestinal tract and of the digestive system in tetrapods. Water is absorbed here and the remaining waste material is stored in the rectum as feces before bein ...
, and since erythritol is not digested by intestinal bacteria, the remaining 10% is excreted in the feces. Large doses can cause
nausea Nausea is a diffuse sensation of unease and discomfort, sometimes perceived as an urge to vomit. While not painful, it can be a debilitating symptom if prolonged and has been described as placing discomfort on the chest, abdomen, or back of the ...
, stomach rumbling and watery feces. In males, doses greater than 0.66 g/kg body weight, and in females, doses greater than 0.8 g/kg body weight, will cause laxation, and diarrhea in higher doses (over ). Rarely, erythritol can cause allergic hives (
urticaria Hives, also known as urticaria, is a kind of skin rash with red, raised, itchy bumps. Hives may burn or sting. The patches of rash may appear on different body parts, with variable duration from minutes to days, and does not leave any long-last ...
).


Blood sugar and insulin levels

Erythritol has no effect on
blood sugar Glycaemia, also known as blood sugar level, blood sugar concentration, or blood glucose level is the measure of glucose concentrated in the blood of humans or other animals. Approximately 4 grams of glucose, a simple sugar, is present in the blo ...
or blood insulin levels and therefore may become an effective substitute for sugar for
diabetics Diabetes, also known as diabetes mellitus, is a group of metabolic disorders characterized by a high blood sugar level (hyperglycemia) over a prolonged period of time. Symptoms often include frequent urination, increased thirst and increased a ...
. The
glycemic index The glycemic (glycaemic) index (GI; ) is a number from 0 to 100 assigned to a food, with pure glucose arbitrarily given the value of 100, which represents the relative rise in the blood glucose level two hours after consuming that food. The GI of ...
(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 The tooth-friendly label distinguishes products which are non-cariogenic and non-erosive, i.e. safe for teeth. To replace sugar, toothfriendly products often contain sweeteners (polyols, intense sweeteners) that are not fermented by the microflora o ...
; it cannot be
metabolized Metabolism (, from el, μεταβολή ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cell ...
by oral
bacteria Bacteria (; singular: bacterium) are ubiquitous, mostly free-living organisms often consisting of one Cell (biology), biological cell. They constitute a large domain (biology), domain of prokaryotic microorganisms. Typically a few micrometr ...
, so it does not contribute to
tooth decay Tooth decay, also known as cavities or caries, is the breakdown of teeth due to acids produced by bacteria. The cavities may be a number of different colors from yellow to black. Symptoms may include pain and difficulty with eating. Complicatio ...
. In addition, erythritol, similarly to
xylitol Xylitol is a chemical compound with the formula , or HO(CH2)(CHOH)3(CH2)OH; specifically, one particular stereoisomer with that structural formula. It is a colorless or white crystalline solid that is freely soluble in water. It can be classifi ...
, has antibacterial effects against streptococci bacteria, reduces
dental plaque Dental plaque is a biofilm of microorganisms (mostly bacteria, but also fungi) that grows on surfaces within the mouth. It is a sticky colorless deposit at first, but when it forms tartar, it is often brown or pale yellow. It is commonly found be ...
, and may be protective against tooth decay.


Production

Erythritol is produced industrially beginning with enzymatic
hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolys ...
of the starch from corn to generate
glucose Glucose is a simple sugar with the molecular formula . Glucose is overall the most abundant monosaccharide, a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, u ...
. Glucose is then fermented with yeast or another fungus to produce erythritol. Other methods such as electrochemical synthesis are in development. A genetically engineered mutant form of ''
Yarrowia lipolytica ''Yarrowia'' is a fungal genus in the family Dipodascaceae. For a while the genus was monotypic, containing the single species ''Yarrowia lipolytica'', a yeast that can use unusual carbon sources, such as hydrocarbons. This has made it of interes ...
'', a yeast, has been optimized for erythritol production by fermentation, using
glycerol Glycerol (), also called glycerine in British English and glycerin in American English, is a simple triol compound. It is a colorless, odorless, viscous liquid that is sweet-tasting and non-toxic. The glycerol backbone is found in lipids known ...
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 In thermochemistry, an endothermic process () is any thermodynamic process with an increase in the enthalpy (or internal energy ) of the system.Oxtoby, D. W; Gillis, H.P., Butler, L. J. (2015).''Principle of Modern Chemistry'', Brooks Cole. ...
, or positive
heat of solution In thermochemistry, the enthalpy of solution ( heat of solution or enthalpy of solvation) is the enthalpy change associated with the dissolution of a substance in a solvent at constant pressure resulting in infinite dilution. The enthalpy of sol ...
) when it dissolves in water, which is often compared with the cooling effect of
mint MiNT is Now TOS (MiNT) is a free software alternative operating system kernel for the Atari ST system and its successors. It is a multi-tasking alternative to TOS and MagiC. Together with the free system components fVDI device drivers, XaA ...
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 Xylitol is a chemical compound with the formula , or HO(CH2)(CHOH)3(CH2)OH; specifically, one particular stereoisomer with that structural formula. It is a colorless or white crystalline solid that is freely soluble in water. It can be classifi ...
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 ''Drosophila melanogaster'' is a species of fly (the taxonomic order Diptera) in the family Drosophilidae. The species is often referred to as the fruit fly or lesser fruit fly, or less commonly the " vinegar fly" or "pomace fly". Starting with ...
'', 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 early 20th centuries, several synonyms were in use for erythritol: erythrol, erythrite, erythoglucin, eryglucin, erythromannite and phycite. Zerose is a
tradename A trade name, trading name, or business name, is a pseudonym used by companies that do not operate under their registered company name. The term for this type of alternative name is a "fictitious" business name. Registering the fictitious name w ...
for erythritol.


See also

*
Erythritol tetranitrate Erythritol tetranitrate (ETN) is an explosive compound chemically similar to PETN, though it is thought to be slightly more sensitive to friction and impact. Like many nitrate esters, ETN acts as a vasodilator, and was the active ingredient in ...
*
Pentaerythritol Pentaerythritol is an organic compound with the formula C(CH2OH)4. Classified as a polyol, it is a white solid. Pentaerythritol is a building block for the synthesis and production of explosives, plastics, paints, appliances, cosmetics, and many o ...
*
Threitol Threitol is a four-carbon sugar alcohol with the molecular formula C4H10O4. It is primarily used as an intermediate in the chemical synthesis of other compounds. It is the diastereomer of erythritol, which is used as a sugar substitute. In livin ...
, the diastereomer of erythritol


References


External links

* {{Alcohols, state=collapsed E-number additives Food additives Sugar alcohols Sugar substitutes Tetrols