Chemistry:Erythritol

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Erythritol (/ɪˈrɪθrɪtɒl/, US: /-tɔːl, -toʊl/)[1] is an organic compound, the naturally occurring achiral meso four-carbon sugar alcohol (or polyol).[2] 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 and sugar substitute. It is synthesized from corn using enzymes and fermentation. Its formula is C4H10O4, or HO(CH2)(CHOH)2(CH2)OH.

Erythritol is 60–70% as sweet as table sugar. However, erythritol is almost completely noncaloric[3] and does not affect blood sugar[4] or cause tooth decay.[5] 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 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.[6]

History

Erythritol was discovered in 1848 by the Scottish chemist John Stenhouse[7] and first isolated in 1852.

Starting from 1945,[8][9] 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.[10]

It was first approved and marketed as a sweetener in Japan in 1990, and in the US in 1997.[11] In February 1997, Cerestar Holding Co., Mitsubishi Chemical Co., and Nikken Chemicals Co. submitted a formal generally recognized as safe (GRAS) affirmation petition with the US FDA.[12] However, in April 1997 the FDA replaced the GRAS affirmation petition process with the current GRAS notification process, a notice was first filed by Cerestar in April 2001, and the FDA responded with "no questions" in September 2001.[13][14]

Occurrence

Erythritol occurs naturally in some fruits (watermelons, pears, and grapes in minimal amounts),[15] and in fungus-fermented foods.[16]

Uses

Sulá-brand sugar-free liquorice, 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.[17]

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.[17] 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.[18]

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 within 24 hours.[17]

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,[19] 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."[19]

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.[17] The upper limit of tolerance was 0.78 and 0.71 g/kg body weight in adults and children respectively.[17]

In the United States, erythritol is among several sugar alcohols that are generally recognized as safe (GRAS) for food manufacturing.[20][21][22]

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 and the European Union (EU), label it as zero-calorie.[23]

Under Food and Drug Administration (FDA) labeling requirements in the United States, erythritol has a caloric value of zero.[24]

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. About 10% enters the colon.[25]

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).[26] 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.[25]

Large doses can cause nausea, stomach rumbling, and watery feces.[27] Doses greater than 0.66 g/kg body weight in males and greater than 0.8 g/kg body weight in females cause laxation,[28] and doses over 50 grams (1.8 oz) cause diarrhea.[27] Rarely, erythritol can cause allergic hives (urticaria).[29]

Blood sugar and insulin levels

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.[30][31] 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.[32]

Oral bacteria

Erythritol is tooth-friendly; since it cannot be metabolized by oral bacteria, it does not contribute to tooth decay.[5][31] In addition, erythritol, like xylitol, has antibacterial effects against streptococci bacteria, reduces dental plaque, and may be protective against tooth decay.[31]

Manufacturing

Erythritol is manufactured by using enzymatic hydrolysis of the starch from corn to generate glucose.[33] 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%.[34]

Chemical properties

Heat of solution

Erythritol has a strong cooling effect (endothermic, or positive heat of solution)[35] 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.[36] Erythritol has a pKa of 13.903 at 18 °C.[37]

Biological properties

According to a 2014 study,[38] 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.[39]

Synonyms

In the 19th and the early 20th centuries, several synonyms were in use for erythritol: erythrol, erythrite, erythroglucin, eryglucin, erythromannite and phycite.[40] Zerose is a tradename for erythritol.[41]

See also

References

  1. ↑ "erythritol". CollinsDictionary.com. HarperCollins. https://www.collinsdictionary.com/dictionary/english/erythritol. 
  2. ↑ "Recent advances in biological production of erythritol". Critical Reviews in Biotechnology 38 (4): 620–633. June 2018. doi:10.1080/07388551.2017.1380598. PMID 28954540. 
  3. ↑ Textbook of biochemistry for medical students. New Delhi: Jaypee Brothers Medical Publishers (P) Ltd. 2013. p. 81. ISBN 978-93-5090-530-2. 
  4. ↑ "Biotechnological production of erythritol and its applications". Applied Microbiology and Biotechnology 86 (4): 1017–1025. April 2010. doi:10.1007/s00253-010-2496-4. PMID 20186409. 
  5. ↑ 5.0 5.1 "Noncariogenicity of erythritol as a substrate". Caries Research 26 (5): 358–362. 1992. doi:10.1159/000261468. PMID 1468100. 
  6. ↑ Senning, Alexander (2019). The Etymology of Chemical Names in Chemical Nomenclature: Tradition and convenience vs. rationality. de Gruyter. p. 85. ISBN 978-3-11-061106-9. https://books.google.com/books?id=6z3EDwAAQBAJ&pg=PA85. Retrieved 9 March 2023. 
  7. ↑ The discovery of erythritol, which Stenhouse called "erythroglucin", was announced in "Examination of the proximate principles of some of the lichens". Philosophical Transactions of the Royal Society of London 138: 63–89; see especially p. 76. January 1, 1848. doi:10.1098/rstl.1848.0004. 
  8. ↑ Binkley, W. W.; Blair, Mary Grace; Wolfrom, M. L. (October 1945). "Isolation of Constituents of Cane Juice and Blackstrap Molasses by Chromatographic Methods" (in en). Journal of the American Chemical Society 67 (10): 1789–1793. doi:10.1021/ja01226a051. ISSN 0002-7863. Bibcode: 1945JAChS..67.1789B. https://pubs.acs.org/doi/abs/10.1021/ja01226a051. 
  9. ↑ Forces (U.S.), Quartermaster Food and Container Institute for the Armed (1953) (in en). Chromatography; Its Development and Various Applications. Library Branch, Quartermaster Food and Container Institute. https://books.google.com/books?id=tMwvAAAAYAAJ&pg=PA19. 
  10. ↑ Binkley, W. W.; Wolfrom, M. L. (October 1950). "Chromatographic Fractionation of Cane Blackstrap Molasses and of Its Fermentation Residue 1" (in en). Journal of the American Chemical Society 72 (10): 4778–4782. doi:10.1021/ja01166a122. ISSN 0002-7863. Bibcode: 1950JAChS..72.4778B. https://pubs.acs.org/doi/abs/10.1021/ja01166a122. 
  11. ↑ O'Brien-Nabors, Lyn (2001-06-08) (in en). Alternative Sweeteners, Third Edition, Revised and Expanded. CRC Press. ISBN 978-0-8247-0437-7. https://books.google.com/books?id=aeMH0F5Z4q4C&pg=PA252. 
  12. ↑ 62 FR 10285, 6 March 1997.
  13. ↑ Ostfeld, Gregory E.; Prochnow, Justin J.; Halat, Angelica (7 March 2023). "New Erythritol Study Creates Potential Litigation Exposure for Makers, Sellers of Erythritol-Containing Products". Greenberg Traurig. https://www.gtlaw.com/en/insights/2023/3/new-erythritol-study-creates-potential-litigation-exposure-for-makers. 
  14. ↑ Gaynor, Paulette (1 December 2005). "How U.S. FDA's GRAS Notification Program Works". Food Safety Magazine (Food and Drug Administration). https://www.fda.gov/food/generally-recognized-safe-gras/how-us-fdas-gras-notification-program-works. Retrieved 10 August 2025. 
  15. ↑ Shindou, Tatsuji; Sasaki, Yoshiyuki; Eguchi, Toru; Euguchi, Toru; Hagiwara, Kiyokazu; Ichikawa, Tomio (1 November 1989). "Identification of erythritol by HPLC and GC-MS and quantitative measurement in pulps of various fruits" (in en). Journal of Agricultural and Food Chemistry 37 (6): 1474–76. doi:10.1021/jf00090a004. ISSN 0021-8561. Bibcode: 1989JAFC...37.1474S. https://pubs.acs.org/doi/abs/10.1021/jf00090a004. 
  16. ↑ "Determination of erythritol in fermented foods by high performance liquid chromatography" (pdf). Shokuhin Eiseigaku Zasshi 29 (6): 419–22. 1 December 1988. doi:10.3358/shokueishi.29.419. https://www.jstage.jst.go.jp/article/shokueishi1960/29/6/29_6_419/_pdf. 
  17. ↑ 17.0 17.1 17.2 17.3 17.4 Scientific Panel on Food Additives and Nutrient Sources Added to Food, European Food Safety Authority (2015). "Scientific Opinion on the safety of the proposed extension of use of erythritol (E 968) as a food additive". EFSA Journal 13 (3): 4033. doi:10.2903/j.efsa.2015.4033. ISSN 1831-4732. PMID 40061618. , 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."
  18. ↑ "Erythritol as sweetener-wherefrom and whereto?". Applied Microbiology and Biotechnology 102 (2): 587–595. January 2018. doi:10.1007/s00253-017-8654-1. PMID 29196787. 
  19. ↑ 19.0 19.1 "Europe: Erythritol Laxative Effect, Lead Levels Concerning". 2023-11-22. https://www.medscape.com/viewarticle/erythritol-laxative-effect-and-lead-levels-concerning-europe-2023a1000wga. 
  20. ↑ "Erythritol, GRN No. 789". GRAS Notice Inventory, US Food and Drug Administration. 20 February 2019. https://www.hfpappexternal.fda.gov/scripts/fdcc/index.cfm?set=GRASNotices&id=789. 
  21. ↑ "Aspartame and Other Sweeteners in Food". US Food and Drug Administration. 25 September 2024. https://www.fda.gov/food/food-additives-petitions/aspartame-and-other-sweeteners-food. 
  22. ↑ "How Sweet It Is: All About Sweeteners". US Food and Drug Administration. 9 June 2023. https://www.fda.gov/consumers/consumer-updates/how-sweet-it-all-about-sweeteners. 
  23. ↑ (2008) 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."
  24. ↑ "Nutrition labeling of food. Title 21, Chapter I, Subchapter B, Part 101.9, Section 12, (c) (F)". US Federal Register: Code of Federal Regulations. 17 July 2025. https://www.ecfr.gov/current/title-21/chapter-I/subchapter-B/part-101/subpart-A/section-101.9. 
  25. ↑ 25.0 25.1 "Human gut microbiota does not ferment erythritol". The British Journal of Nutrition 94 (5): 643–646. November 2005. doi:10.1079/BJN20051546. PMID 16277764. 
  26. ↑ "Erythritol: an interpretive summary of biochemical, metabolic, toxicological and clinical data". Food and Chemical Toxicology 36 (12): 1139–1174. December 1998. doi:10.1016/S0278-6915(98)00091-X. PMID 9862657. 
  27. ↑ 27.0 27.1 "Gastrointestinal tolerance of erythritol and xylitol ingested in a liquid". European Journal of Clinical Nutrition 61 (3): 349–354. March 2007. doi:10.1038/sj.ejcn.1602532. PMID 16988647. 
  28. ↑ "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". International Journal of Dentistry 2016. 2016. doi:10.1155/2016/5967907. PMID 27840639. 
  29. ↑ "A case of allergic urticaria caused by erythritol". The Journal of Dermatology 27 (3): 163–165. March 2000. doi:10.1111/j.1346-8138.2000.tb02143.x. PMID 10774141. 
  30. ↑ "Erythritol: an interpretive summary of biochemical, metabolic, toxicological and clinical data". Food and Chemical Toxicology 36 (12): 1139–1174. December 1998. doi:10.1016/S0278-6915(98)00091-X. PMID 9862657. 
  31. ↑ 31.0 31.1 31.2 "Erythritol". Sweeteners and Sugar Alternatives in Food Technology. 2012. pp. 213–41. doi:10.1002/9781118373941.ch10. ISBN 978-1-118-37394-1. 
  32. ↑ "Health potential of polyols as sugar replacers, with emphasis on low glycaemic properties". Nutrition Research Reviews 16 (2): 163–191. December 2003. doi:10.1079/NRR200371. PMID 19087388. 
  33. ↑ "How Is Erythritol Made? Manufacture of a Low-Calorie Sugar Substitute". Decoded Science. January 28, 2014. http://www.decodedscience.org/erythritol-made-manufacture-low-calorie-sugar-substitute/42248. 
  34. ↑ "Erythritol production by yeasts: a snapshot of current knowledge". Yeast 35 (7): 455–463. July 2018. doi:10.1002/yea.3306. PMID 29322598. 
  35. ↑ CRC handbook of enthalpy data of polymer-solvent systems. CRC / Taylor & Francis. 2006. p. 3. ISBN 978-0-8493-9361-7. https://books.google.com/books?id=e2XyFi-bMY8C&pg=PA3. 
  36. ↑ "Enthalpies of Solution, Partial Molal Heat Capacities and Apparent Molal Volumes of Sugars and Polyols in Water". Journal of Solution Chemistry 11 (5): 325–38. 1982. doi:10.1007/BF00649291. ISSN 1572-8927. 
  37. ↑ "Erythritol". The Merck Index – an Encyclopedia of Chemicals, Drugs, and Biologicals: 629. 2006. 
  38. ↑ "Erythritol, a non-nutritive sugar alcohol sweetener and the main component of truvia®, is a palatable ingested insecticide". PLOS ONE 9 (6). 2014. doi:10.1371/journal.pone.0098949. PMID 24896294. Bibcode: 2014PLoSO...998949B. 
  39. ↑ "Erythritol triggers expression of virulence traits in Brucella melitensis". Microbes and Infection 15 (6–7): 440–449. June 2013. doi:10.1016/j.micinf.2013.02.002. PMID 23421980. 
  40. ↑ "A list of words whose use should be avoided in favor of the accompanying synonyms". Journal of Analytical and Applied Chemistry 6: 160. 1892. https://books.google.com/books?id=RogMAQAAIAAJ&pg=PA160. 
  41. ↑ "Cargill unveils new products featuring Zerose natural sweetener". New Hope Network. 9 March 2010. https://www.newhope.com/sweeteners/cargill-unveils-new-products-featuring-zerose-natural-sweetener. 




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