Erythritol

The name "erythritol" derives from the Greek word for the color red (erythros or {{math|ἐρυθρός}}). 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.{{cite book |last=Senning |first=Alexander |year=2019 |title=The Etymology of Chemical Names in Chemical Nomenclature: Tradition and convenience vs. rationality |publisher=de Gruyter |isbn=9783110611069 |page=85 |url=https://books.google.com/books?id=6z3EDwAAQBAJ&pg=PA85 |access-date=9 March 2023}}

Erythritol was discovered in 1848 by the Scottish chemist John Stenhouse The discovery of erythritol, which Stenhouse called "erythroglucin", was announced in {{ cite journal | vauthors = Stenhouse J | title = Examination of the proximate principles of some of the lichens | journal = Philosophical Transactions of the Royal Society of London | volume = 138 | pages = 63–89; see especially p. 76 | date = January 1, 1848 | doi = 10.1098/rstl.1848.0004 | s2cid = 83653513 | doi-access = free }} and first isolated in 1852.

Starting from 1945,{{Cite journal |last1=Binkley |first1=W. W. |last2=Blair |first2=Mary Grace |last3=Wolfrom |first3=M. L. |date=October 1945 |title=Isolation of Constituents of Cane Juice and Blackstrap Molasses by Chromatographic Methods |url=https://pubs.acs.org/doi/abs/10.1021/ja01226a051 |journal=Journal of the American Chemical Society |language=en |volume=67 |issue=10 |pages=1789–1793 |doi=10.1021/ja01226a051 |bibcode=1945JAChS..67.1789B |issn=0002-7863|url-access=subscription }}{{Cite book |last=Forces (U.S.) |first=Quartermaster Food and Container Institute for the Armed |url=https://books.google.com/books?id=tMwvAAAAYAAJ&pg=PA19 |title=Chromatography; Its Development and Various Applications |date=1953 |publisher=Library Branch, Quartermaster Food and Container Institute |language=en}} American chemists applied newly-developed techniques of chromatography to sugarcane juice and blackstrap molasses, finding in 1950 that erythritol was present in molasses fermented by yeast.{{Cite journal |last1=Binkley |first1=W. W. |last2=Wolfrom |first2=M. L. |date=October 1950 |title=Chromatographic Fractionation of Cane Blackstrap Molasses and of Its Fermentation Residue 1 |url=https://pubs.acs.org/doi/abs/10.1021/ja01166a122 |journal=Journal of the American Chemical Society |language=en |volume=72 |issue=10 |pages=4778–4782 |doi=10.1021/ja01166a122 |bibcode=1950JAChS..72.4778B |issn=0002-7863|url-access=subscription }}

It was first approved and marketed as a sweetener in Japan in 1990, and in the US in 1997.{{Cite book |last=O'Brien-Nabors |first=Lyn |url=https://books.google.com/books?id=aeMH0F5Z4q4C&pg=PA252 |title=Alternative Sweeteners, Third Edition, Revised and Expanded |date=2001-06-08 |publisher=CRC Press |isbn=978-0-8247-0437-7 |language=en}}

Erythritol occurs naturally in some fruit and fermented foods.{{cite journal | vauthors = Shindou T, Sasaki, Y, Miki H, Eguchi T, Hagiwara K, Ichikawa T | title = Determination of erythritol in fermented foods by high performance liquid chromatography | journal = Shokuhin Eiseigaku Zasshi | volume = 29 | issue = 6 | pages = 419–22 | year = 1988 | doi = 10.3358/shokueishi.29.419 | url = https://www.jstage.jst.go.jp/article/shokueishi1960/29/6/29_6_419/_pdf | format = pdf | doi-access = free | url-access = subscription }}

File:Sulá Salty liquorice.png, sweetened with erythritol]]

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.{{cite journal | title=Scientific Opinion on the safety of the proposed extension of use of erythritol (E 968) as a food additive | journal=EFSA Journal |author=Scientific Panel on Food Additives and Nutrient Sources Added to Food, European Food Safety Authority | volume=13 | issue=3 | year=2015 | issn=1831-4732 | doi=10.2903/j.efsa.2015.4033 | page=4033| doi-access=free | pmid=40061618 | pmc=11883093 }}, 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.{{cite journal | vauthors = Regnat K, Mach RL, Mach-Aigner AR | title = Erythritol as sweetener-wherefrom and whereto? | journal = Applied Microbiology and Biotechnology | volume = 102 | issue = 2 | pages = 587–595 | date = January 2018 | pmid = 29196787 | pmc = 5756564 | doi = 10.1007/s00253-017-8654-1 }}

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 within 24 hours.

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,{{cite web | title=Europe: Erythritol Laxative Effect, Lead Levels Concerning | website=Medscape | date=2023-11-22 | url=https://www.medscape.com/viewarticle/erythritol-laxative-effect-and-lead-levels-concerning-europe-2023a1000wga | access-date=2024-01-01}} 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 0.71{{nbs}}g/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.{{cite web |title=Recently Published GRAS Notices and FDA Letters (search "erythritol") |url=https://www.fda.gov/food/gras-notice-inventory/recently-published-gras-notices-and-fda-letters |publisher=GRAS Notice Inventory, US Food and Drug Administration |access-date=16 December 2024 |date=2 December 2024}}{{dead link|date=May 2025|bot=medic}}{{cbignore|bot=medic}}{{cite web |date=25 September 2024 |title=Aspartame and Other Sweeteners in Food |url=https://www.fda.gov/food/food-additives-petitions/aspartame-and-other-sweeteners-food |archive-url=https://web.archive.org/web/20230601065858/https://www.fda.gov/food/food-additives-petitions/aspartame-and-other-sweeteners-food |url-status=dead |archive-date=June 1, 2023 |access-date=15 December 2024 |publisher=US Food and Drug Administration }}{{cite web |title=How Sweet It Is: All About Sweeteners |url=https://www.fda.gov/consumers/consumer-updates/how-sweet-it-all-about-sweeteners |archive-url=https://web.archive.org/web/20230610152217/https://www.fda.gov/consumers/consumer-updates/how-sweet-it-all-about-sweeteners |url-status=dead |archive-date=June 10, 2023 |publisher=US Food and Drug Administration |access-date=16 December 2024 |date=9 June 2023}}

Nutritional labeling of erythritol in food products varies from country to country. Some places, such as Japan and the European Union (EU), label it as zero-calorie.(2008) [http://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=OJ:L:2008:285:0009:0012:EN:PDF European Commission Directive 2008/100/EC]. Quote: "Erythritol is a polyol, and according to the current rules as provided for in Article 5(1) of Directive 90/496/EEC, its energy would be calculated using the conversion factor for polyols, namely 10 kJ/g (2,4 kcal/g). Using this energy conversion factor would not fully inform the consumer about the reduced energy value of a product achieved by the use of erythritol in its manufacture. The Scientific Committee on Food in its opinion on erythritol, expressed on March 5, 2003, noted that the energy provided by erythritol was less than 0,9 kJ/g (less than 0,2 kcal/g). Therefore it is appropriate to adopt a suitable energy conversion factor for erythritol. Current regulations (Reg. (EC) 1169/2011) preserve this conversion factor at 0 kcal/g for energy value calculation purposes."

Under Food and Drug Administration (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).{{cn|date=December 2024}}

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. 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).{{cite journal | vauthors = Munro IC, Berndt WO, Borzelleca JF, Flamm G, Lynch BS, Kennepohl E, Bär EA, Modderman J, Bernt WO | display-authors = 6 | title = Erythritol: an interpretive summary of biochemical, metabolic, toxicological and clinical data | journal = Food and Chemical Toxicology | volume = 36 | issue = 12 | pages = 1139–1174 | date = December 1998 | pmid = 9862657 | doi = 10.1016/S0278-6915(98)00091-X }} 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.{{cite journal | vauthors = Arrigoni E, Brouns F, Amadò R | title = Human gut microbiota does not ferment erythritol | journal = The British Journal of Nutrition | volume = 94 | issue = 5 | pages = 643–646 | date = November 2005 | pmid = 16277764 | doi = 10.1079/BJN20051546 | doi-access = free | hdl = 20.500.11850/31086 | hdl-access = free }}

Large doses can cause nausea, stomach rumbling, and watery feces.{{cite journal | vauthors = Storey D, Lee A, Bornet F, Brouns F | title = Gastrointestinal tolerance of erythritol and xylitol ingested in a liquid | journal = European Journal of Clinical Nutrition | volume = 61 | issue = 3 | pages = 349–354 | date = March 2007 | pmid = 16988647 | doi = 10.1038/sj.ejcn.1602532 | s2cid = 10228622 | doi-access = free }} Doses greater than 0.66 g/kg body weight in males and greater than 0.8 g/kg body weight in females cause laxation,{{cite journal | vauthors = Mäkinen KK | title = Gastrointestinal Disturbances Associated with the Consumption of Sugar Alcohols with Special Consideration of Xylitol: Scientific Review and Instructions for Dentists and Other Health-Care Professionals | journal = International Journal of Dentistry | volume = 2016 | pages = 5967907 | date = 2016 | pmid = 27840639 | pmc = 5093271 | doi = 10.1155/2016/5967907 | doi-access = free }} and doses over {{convert|50|g|oz}} cause diarrhea. Rarely, erythritol can cause allergic hives (urticaria).{{cite journal | vauthors = Hino H, Kasai S, Hattori N, Kenjo K | title = A case of allergic urticaria caused by erythritol | journal = The Journal of Dermatology | volume = 27 | issue = 3 | pages = 163–165 | date = March 2000 | pmid = 10774141 | doi = 10.1111/j.1346-8138.2000.tb02143.x | s2cid = 40328472 }}

Erythritol has no effect on blood sugar or blood insulin levels, and therefore may be used as a sugar substitute by people with type 2 diabetes.{{cite journal | vauthors = Munro IC, Berndt WO, Borzelleca JF, Flamm G, Lynch BS, Kennepohl E, Bär EA, Modderman J, Bernt WO | display-authors = 6 | title = Erythritol: an interpretive summary of biochemical, metabolic, toxicological and clinical data | journal = Food and Chemical Toxicology | volume = 36 | issue = 12 | pages = 1139–1174 | date = December 1998 | pmid = 9862657 | doi = 10.1016/S0278-6915(98)00091-X }}{{cite book| vauthors = de Cock P |title=Sweeteners and Sugar Alternatives in Food Technology|chapter=Erythritol|year=2012|pages=213–41|doi=10.1002/9781118373941.ch10|isbn=9781118373941}} 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.{{cite journal | vauthors = Livesey G | title = Health potential of polyols as sugar replacers, with emphasis on low glycaemic properties | journal = Nutrition Research Reviews | volume = 16 | issue = 2 | pages = 163–191 | date = December 2003 | pmid = 19087388 | doi = 10.1079/NRR200371 | s2cid = 4541994 | doi-access = free }}

Erythritol is tooth-friendly; since it cannot be metabolized by oral bacteria, 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.

Erythritol is manufactured by using enzymatic hydrolysis of the starch from corn to generate glucose.{{cite web | url = http://www.decodedscience.org/erythritol-made-manufacture-low-calorie-sugar-substitute/42248 | publisher = Decoded Science | title = How Is Erythritol Made? Manufacture of a Low-Calorie Sugar Substitute | date = January 28, 2014 | vauthors = Piccirillo C | access-date = July 18, 2016 | archive-date = October 30, 2016 | archive-url = https://web.archive.org/web/20161030174650/http://www.decodedscience.org/erythritol-made-manufacture-low-calorie-sugar-substitute/42248 | url-status = dead }} 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 as a carbon source and high osmotic pressure to increase yields up to 62%.{{cite journal | vauthors = Carly F, Fickers P | title = Erythritol production by yeasts: a snapshot of current knowledge | journal = Yeast | volume = 35 | issue = 7 | pages = 455–463 | date = July 2018 | pmid = 29322598 | doi = 10.1002/yea.3306 | doi-access = free }}

Erythritol has a strong cooling effect (endothermic, or positive heat of solution){{cite book | vauthors = Wohlfarth C | title = CRC handbook of enthalpy data of polymer-solvent systems | url = https://books.google.com/books?id=e2XyFi-bMY8C&pg=PA3 | year = 2006 | publisher = CRC / Taylor & Francis | isbn = 978-0-8493-9361-7 | page = 3 }} 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.{{cite journal | vauthors = Jasra RV, Ahluwalia JC | title = Enthalpies of Solution, Partial Molal Heat Capacities and Apparent Molal Volumes of Sugars and Polyols in Water | journal = Journal of Solution Chemistry | year = 1982 | volume = 11 | issue = 5 | pages = 325–38 | doi = 10.1007/BF00649291 |s2cid=93845620 | issn = 1572-8927 }} Erythritol has a pK_a of 13.903 at 18 °C.{{cite journal | vauthors = O'Neil MJ | title = Erythritol | journal = The Merck Index – an Encyclopedia of Chemicals, Drugs, and Biologicals | year = 2006 | page = 629 }}

According to a 2014 study,{{cite journal | vauthors = Baudier KM, Kaschock-Marenda SD, Patel N, Diangelus KL, O'Donnell S, Marenda DR | title = Erythritol, a non-nutritive sugar alcohol sweetener and the main component of truvia®, is a palatable ingested insecticide | journal = PLOS ONE | volume = 9 | issue = 6 | pages = e98949 | date = 2014 | pmid = 24896294 | pmc = 4045977 | doi = 10.1371/journal.pone.0098949 | doi-access = free | bibcode = 2014PLoSO...998949B }} 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.{{cite journal | vauthors = Petersen E, Rajashekara G, Sanakkayala N, Eskra L, Harms J, Splitter G | title = Erythritol triggers expression of virulence traits in Brucella melitensis | journal = Microbes and Infection | volume = 15 | issue = 6–7 | pages = 440–449 | date = June 2013 | pmid = 23421980 | pmc = 3686989 | doi = 10.1016/j.micinf.2013.02.002 }}

In the 19th and the early 20th centuries, several synonyms were in use for erythritol: erythrol, erythrite, erythoglucin, eryglucin, erythromannite and phycite.{{cite journal|journal=Journal of Analytical and Applied Chemistry |title=A list of words whose use should be avoided in favor of the accompanying synonyms |volume=6 |page=160 |year=1892 |url=https://books.google.com/books?id=RogMAQAAIAAJ&pg=PA160 | vauthors = Hart E }} Zerose is a tradename for erythritol.{{cite web |title=Cargill unveils new products featuring Zerose natural sweetener |url=https://www.newhope.com/sweeteners/cargill-unveils-new-products-featuring-zerose-natural-sweetener |publisher=New Hope Network |access-date=13 November 2018 |date=9 March 2010}}

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

{{Reflist}}

{{Commonscat}}

• [https://www.nih.gov/news-events/nih-research-matters/erythritol-cardiovascular-events "Erythritol and cardiovascular events"], National Institutes of Health (14 Mar 2023)

{{Alcohols|state=collapsed}}

Category:E-number additives

Category:Food additives

Category:Sugar alcohols

Category:Sugar substitutes

Category:Tetrols

Category:Substances discovered in the 19th century