Chemistry:Erythritol

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Erythritol
Skeletal formula of erythritol
Ball-and-stick model of the erythritol molecule
Names
IUPAC name
meso-Erythritol
Systematic IUPAC name
(2R,3S)-Butane-1,2,3,4-tetrol
Other names
(2R,3S)-Butane-1,2,3,4-tetraol (not recommended)
Identifiers
3D model (JSmol)
1719753
ChEBI
ChEMBL
ChemSpider
DrugBank
82499
KEGG
UNII
Properties
C4H10O4
Molar mass 122.120 g·mol−1
Density 1.45 g/cm3
Melting point 121 °C (250 °F; 394 K)
Boiling point 329 to 331 °C (624 to 628 °F; 602 to 604 K)
61% w/w (25 °C)[1]
−73.80·10−6 cm3/mol
Hazards
NFPA 704 (fire diamond)
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
1
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Tracking categories (test):

Erythritol (/ɪˈrɪθrɪtɒl/, US: /-tɔːl, -toʊl/)[2] is an organic compound, the naturally occurring achiral meso four-carbon sugar alcohol (or polyol).[3] 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 sucrose (table sugar). However, erythritol is almost completely noncaloric,[4] and does not affect blood sugar[5] or cause tooth decay.[6] 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). This is the case even though erythritol is almost always found in the form of white crystals or powder and it does not turn red as a result of chemical reactions. The name "erythritol" comes from erythrin, a closely related compound, which turns red upon oxidation.[7]

History

Erythritol was discovered in 1848 by Scottish chemist John Stenhouse[8] and first isolated in 1852. In 1950 it was found in blackstrap molasses that was fermented by yeast, and it became commercialized as a sugar alcohol in the 1990s in Japan.[9]

Crystals of erythritol

Occurrence

Erythritol occurs naturally in some fruit and fermented foods.[10] It also occurs in human body fluids, such as eye lens tissue, serum, plasma, fetal fluid, and urine.[11]

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 of more than 60 countries.[12] 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.[12] 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.[13]

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.[12]

Safety

In 2023, European Food Safety Authority reassessed the safety of erythritol and lowered the recommended daily intake limit to 0.5 grams per kg body weight,[14] which equates to 35 g for an average adult (70 kg). This 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."[14]

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.[12] The upper limit of tolerance was 0.78 and 0.71 grams per kg body weight in adults and children, respectively.[12]

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 (EU), label it as zero-calorie.[15]

Under U.S. Food and Drug Administration (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.[16]

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.[17]

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).[18] 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.[17]

Large doses can cause nausea, stomach rumbling and watery feces.[19] 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,[20] and diarrhea in higher doses (over 50 grams (1.8 oz)).[19] Rarely, erythritol can cause allergic hives (urticaria).[21]

Blood sugar and insulin levels

Erythritol has no effect on blood sugar or blood insulin levels[22][23] and therefore may become an effective substitute for sugar for diabetics.[9] 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.[24]

Oral bacteria

Erythritol is tooth-friendly; it cannot be metabolized by oral bacteria, so it does not contribute to tooth decay.[6][23] In addition, erythritol, similarly to xylitol, has antibacterial effects against streptococci bacteria, reduces dental plaque, and may be protective against tooth decay.[23]

Manufacturing

Erythritol is manufactured using enzymatic hydrolysis of the starch from corn to generate glucose.[25] Glucose is then fermented with yeast or another fungus to produce erythritol. A genetically engineered mutant form of Yarrowia lipolytica, a yeast, has been optimized for erythritol production by fermentation, using glycerol as a carbon source and high osmotic pressure to increase yields up to 62%.[11]

Chemical properties

Heat of solution

Erythritol has a strong cooling effect (endothermic, or positive heat of solution)[26] 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.[27] Erythritol has a pKa of 13.903 at 18 °C.[28]

Biological properties

According to a 2014 study,[29] 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.[30]

Synonyms

In the 19th and early 20th centuries, several synonyms were in use for erythritol: erythrol, erythrite, erythoglucin, eryglucin, erythromannite and phycite.[31] Zerose is a tradename for erythritol.[32]

See also

References

  1. ↑ The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (14th ed.). Merck. 2006. p. 629. ISBN 978-0-911910-00-1. 
  2. ↑ "erythritol". CollinsDictionary.com. HarperCollins. https://www.collinsdictionary.com/dictionary/english/erythritol. 
  3. ↑ "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. 
  4. ↑ Textbook of biochemistry for medical students. New Delhi: Jaypee Brothers Medical Publishers (P) Ltd. 2013. p. 81. ISBN 978-93-5090-530-2. 
  5. ↑ "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. 
  6. ↑ 6.0 6.1 "Noncariogenicity of erythritol as a substrate". Caries Research 26 (5): 358–362. 1992. doi:10.1159/000261468. PMID 1468100. 
  7. ↑ Senning, Alexander (2019). The Etymology of Chemical Names in Chemical Nomenclature: Tradition and Convenience vs. Rationality. De Gruyter. p. 85. ISBN 9783110611069. https://books.google.com/books?id=6z3EDwAAQBAJ&pg=PA85. Retrieved 9 March 2023. 
  8. ↑ 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. 
  9. ↑ 9.0 9.1 "Health effects of erythritol". Nutrafoods 14 (3): 3–9. 2015. doi:10.1007/s13749-014-0067-5. 
  10. ↑ "Determination of erythritol in fermented foods by high performance liquid chromatography" (pdf). Shokuhin Eiseigaku Zasshi 29 (6): 419–22. 1988. doi:10.3358/shokueishi.29.419. https://www.jstage.jst.go.jp/article/shokueishi1960/29/6/29_6_419/_pdf. 
  11. ↑ 11.0 11.1 "Erythritol production by yeasts: a snapshot of current knowledge". Yeast 35 (7): 455–463. July 2018. doi:10.1002/yea.3306. PMID 29322598. 
  12. ↑ 12.0 12.1 12.2 12.3 12.4 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. , 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."
  13. ↑ "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. 
  14. ↑ 14.0 14.1 "Europe: Erythritol Laxative Effect, Lead Levels Concerning". 2023-11-22. https://www.medscape.com/viewarticle/erythritol-laxative-effect-and-lead-levels-concerning-europe-2023a1000wga. 
  15. ↑ (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."
  16. ↑ "GRAS notices: erythritol". US Food and Drug Administration. 16 November 2018. https://www.accessdata.fda.gov/scripts/fdcc/?set=GRASNotices&sort=GRN_No&order=DESC&startrow=1&type=basic&search=erythritol. 
  17. ↑ 17.0 17.1 "Human gut microbiota does not ferment erythritol". The British Journal of Nutrition 94 (5): 643–646. November 2005. doi:10.1079/BJN20051546. PMID 16277764. 
  18. ↑ "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. 
  19. ↑ 19.0 19.1 "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. 
  20. ↑ "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: 5967907. 2016. doi:10.1155/2016/5967907. PMID 27840639. 
  21. ↑ "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. 
  22. ↑ "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. 
  23. ↑ 23.0 23.1 23.2 "Erythritol". Sweeteners and Sugar Alternatives in Food Technology. 2012. pp. 213–41. doi:10.1002/9781118373941.ch10. ISBN 9781118373941. 
  24. ↑ "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. 
  25. ↑ "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. 
  26. ↑ 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. 
  27. ↑ "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. 
  28. ↑ "Erythritol". The Merck Index – an Encyclopedia of Chemicals, Drugs, and Biologicals: 629. 2006. 
  29. ↑ "Erythritol, a non-nutritive sugar alcohol sweetener and the main component of truvia®, is a palatable ingested insecticide". PLOS ONE 9 (6): e98949. 2014. doi:10.1371/journal.pone.0098949. PMID 24896294. Bibcode: 2014PLoSO...998949B. 
  30. ↑ "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. 
  31. ↑ "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. 
  32. ↑ "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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