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Erythritol

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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 C
4H
10O
4, or HO(CH2)(CHOH)2(CH2)OH.

Erythritol
Skeletal formula of erythritol
Ball-and-stick model of the erythritol molecule
Crystals of erythritol
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
ECHA InfoCard 100.005.217 Edit this at Wikidata
E number E968 (glazing agents, ...)
82499
KEGG
UNII
  • InChI=1S/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2/t3-,4  checkY
    Key: UNXHWFMMPAWVPI-ZXZARUISSA-N checkY
  • InChI=1/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2/t3-,4
    Key: UNXHWFMMPAWVPI-ZXZARUISBN
  • OC[C@@H](O)[C@@H](O)CO
  • C([C@H]([C@H](CO)O)O)O
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)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Erythritol is 60–70% as sweet as 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

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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.[7]

History

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Erythritol was discovered in 1848 by the Scottish chemist John Stenhouse[8] and first isolated in 1852.

Starting from 1945,[9][10] 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.[11]

It was first approved and marketed as a sweetener in Japan in 1990, and in the US in 1997.[12]

Occurrence

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Erythritol occurs naturally in some fruit and fermented foods.[13]

Uses

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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.[14]

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.[14] 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.[15]

Absorption and excretion

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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.[14]

Safety

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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,[16] 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."[16]

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.[14] The upper limit of tolerance was 0.78 and 0.71 g/kg kg body weight in adults and children respectively.[14]

In the United States, erythritol is among several sugar alcohols that are generally recognized as safe (GRAS) for food manufacturing.[17][18][19]

Dietary and metabolic aspects

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Caloric value and labeling

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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.[20]

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).[citation needed]

Human digestion

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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.[21]

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).[22] 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.[21]

Large doses can cause nausea, stomach rumbling, and watery feces.[23] Doses greater than 0.66 g/kg body weight in males and greater than 0.8 g/kg body weight in females cause laxation,[24] and diarrhea in higher doses (over 50 grams (1.8 oz)).[23] Rarely, erythritol can cause allergic hives (urticaria).[25]

Blood sugar and insulin levels

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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.[26][27] 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.[28]

Oral bacteria

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Erythritol is tooth-friendly; since it cannot be metabolized by oral bacteria, it does not contribute to tooth decay.[6][27] In addition, erythritol, like xylitol, has antibacterial effects against streptococci bacteria, reduces dental plaque, and may be protective against tooth decay.[27]

Manufacturing

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Erythritol is manufactured by using enzymatic hydrolysis of the starch from corn to generate glucose.[29] 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%.[30]

Chemical properties

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Heat of solution

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Erythritol has a strong cooling effect (endothermic, or positive heat of solution)[31] 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.[32] Erythritol has a pKa of 13.903 at 18 °C.[33]

Biological properties

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According to a 2014 study,[34] 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.[35]

Synonyms

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In the 19th and the early 20th centuries, several synonyms were in use for erythritol: erythrol, erythrite, erythoglucin, eryglucin, erythromannite and phycite.[36] Zerose is a tradename for erythritol.[37]

See also

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References

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  1. ^ O'Neil M, ed. (2006). The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (14th ed.). Merck. p. 629. ISBN 978-0-911910-00-1.
  2. ^ "erythritol". Collins English Dictionary. HarperCollins. Retrieved 2023-06-29.
  3. ^ Rzechonek DA, Dobrowolski A, Rymowicz W, Mirończuk AM (June 2018). "Recent advances in biological production of erythritol". Critical Reviews in Biotechnology. 38 (4): 620–633. doi:10.1080/07388551.2017.1380598. PMID 28954540. S2CID 3075870.620-633&rft.date=2018-06&rft_id=https://api.semanticscholar.org/CorpusID:3075870#id-name=S2CID&rft_id=info:pmid/28954540&rft_id=info:doi/10.1080/07388551.2017.1380598&rft.aulast=Rzechonek&rft.aufirst=DA&rft.au=Dobrowolski, A&rft.au=Rymowicz, W&rft.au=Mirończuk, AM&rft_id=https://doi.org/10.1080%2F07388551.2017.1380598&rfr_id=info:sid/en.wikipedia.org:Erythritol" class="Z3988">
  4. ^ Vasudevan DM (2013). Textbook of biochemistry for medical students. New Delhi: Jaypee Brothers Medical Publishers (P) Ltd. p. 81. ISBN 978-93-5090-530-2.
  5. ^ Moon HJ, Jeya M, Kim IW, Lee JK (April 2010). "Biotechnological production of erythritol and its applications". Applied Microbiology and Biotechnology. 86 (4): 1017–1025. doi:10.1007/s00253-010-2496-4. PMID 20186409. S2CID 9560435.1017-1025&rft.date=2010-04&rft_id=https://api.semanticscholar.org/CorpusID:9560435#id-name=S2CID&rft_id=info:pmid/20186409&rft_id=info:doi/10.1007/s00253-010-2496-4&rft.aulast=Moon&rft.aufirst=HJ&rft.au=Jeya, M&rft.au=Kim, IW&rft.au=Lee, JK&rfr_id=info:sid/en.wikipedia.org:Erythritol" class="Z3988">
  6. ^ a b Kawanabe J, Hirasawa M, Takeuchi T, Oda T, Ikeda T (1992). "Noncariogenicity of erythritol as a substrate". Caries Research. 26 (5): 358–362. doi:10.1159/000261468. PMID 1468100.358-362&rft.date=1992&rft_id=info:doi/10.1159/000261468&rft_id=info:pmid/1468100&rft.aulast=Kawanabe&rft.aufirst=J&rft.au=Hirasawa, M&rft.au=Takeuchi, T&rft.au=Oda, T&rft.au=Ikeda, T&rfr_id=info:sid/en.wikipedia.org:Erythritol" class="Z3988">
  7. ^ Senning, Alexander (2019). The Etymology of Chemical Names in Chemical Nomenclature: Tradition and convenience vs. rationality. de Gruyter. p. 85. ISBN 9783110611069. Retrieved 9 March 2023.
  8. ^ The discovery of erythritol, which Stenhouse called "erythroglucin", was announced in Stenhouse J (January 1, 1848). "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. doi:10.1098/rstl.1848.0004. S2CID 83653513.63-89, see especially p. 76&rft.date=1848-01-01&rft_id=info:doi/10.1098/rstl.1848.0004&rft_id=https://api.semanticscholar.org/CorpusID:83653513#id-name=S2CID&rft.aulast=Stenhouse&rft.aufirst=J&rft_id=https://doi.org/10.1098%2Frstl.1848.0004&rfr_id=info:sid/en.wikipedia.org:Erythritol" class="Z3988">
  9. ^ Binkley, W. W.; Blair, Mary Grace; Wolfrom, M. L. (October 1945). "Isolation of Constituents of Cane Juice and Blackstrap Molasses by Chromatographic Methods". Journal of the American Chemical Society. 67 (10): 1789–1793. doi:10.1021/ja01226a051. ISSN 0002-7863.1789-1793&rft.date=1945-10&rft_id=info:doi/10.1021/ja01226a051&rft.issn=0002-7863&rft.aulast=Binkley&rft.aufirst=W. W.&rft.au=Blair, Mary Grace&rft.au=Wolfrom, M. L.&rft_id=https://pubs.acs.org/doi/abs/10.1021/ja01226a051&rfr_id=info:sid/en.wikipedia.org:Erythritol" class="Z3988">
  10. ^ Forces (U.S.), Quartermaster Food and Container Institute for the Armed (1953). Chromatography; Its Development and Various Applications. Library Branch, Quartermaster Food and Container Institute.
  11. ^ Binkley, W. W.; Wolfrom, M. L. (October 1950). "Chromatographic Fractionation of Cane Blackstrap Molasses and of Its Fermentation Residue 1". Journal of the American Chemical Society. 72 (10): 4778–4782. doi:10.1021/ja01166a122. ISSN 0002-7863.4778-4782&rft.date=1950-10&rft_id=info:doi/10.1021/ja01166a122&rft.issn=0002-7863&rft.aulast=Binkley&rft.aufirst=W. W.&rft.au=Wolfrom, M. L.&rft_id=https://pubs.acs.org/doi/abs/10.1021/ja01166a122&rfr_id=info:sid/en.wikipedia.org:Erythritol" class="Z3988">
  12. ^ O'Brien-Nabors, Lyn (2001-06-08). Alternative Sweeteners, Third Edition, Revised and Expanded. CRC Press. ISBN 978-0-8247-0437-7.
  13. ^ Shindou T, Sasaki, Y, Miki H, Eguchi T, Hagiwara K, Ichikawa T (1988). "Determination of erythritol in fermented foods by high performance liquid chromatography" (pdf). Shokuhin Eiseigaku Zasshi. 29 (6): 419–22. doi:10.3358/shokueishi.29.419.419-22&rft.date=1988&rft_id=info:doi/10.3358/shokueishi.29.419&rft.aulast=Shindou&rft.aufirst=T&rft.au=Sasaki&rft.au=Y&rft.au=Miki, H&rft.au=Eguchi, T&rft.au=Hagiwara, K&rft.au=Ichikawa, T&rft_id=https://www.jstage.jst.go.jp/article/shokueishi1960/29/6/29_6_419/_pdf&rfr_id=info:sid/en.wikipedia.org:Erythritol" class="Z3988">
  14. ^ a b c d e 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."
  15. ^ Regnat K, Mach RL, Mach-Aigner AR (January 2018). "Erythritol as sweetener-wherefrom and whereto?". Applied Microbiology and Biotechnology. 102 (2): 587–595. doi:10.1007/s00253-017-8654-1. PMC 5756564. PMID 29196787.587-595&rft.date=2018-01&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5756564#id-name=PMC&rft_id=info:pmid/29196787&rft_id=info:doi/10.1007/s00253-017-8654-1&rft.aulast=Regnat&rft.aufirst=K&rft.au=Mach, RL&rft.au=Mach-Aigner, AR&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5756564&rfr_id=info:sid/en.wikipedia.org:Erythritol" class="Z3988">
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  18. ^ "Aspartame and Other Sweeteners in Food". US Food and Drug Administration. 25 September 2024. Retrieved 15 December 2024.
  19. ^ "How Sweet It Is: All About Sweeteners". US Food and Drug Administration. 9 June 2023. Retrieved 16 December 2024.
  20. ^ (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."
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