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Erythritol information


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
CAS Number
  • 149-32-6 ☒N
3D model (JSmol)
  • Interactive image
  • Interactive image
Beilstein Reference
1719753
ChEBI
  • CHEBI:17113 checkY
ChEMBL
  • ChEMBL349605 checkY
ChemSpider
  • 192963 checkY
DrugBank
  • DB04481 checkY
ECHA InfoCard 100.005.217 Edit this at Wikidata
E number E968 (glazing agents, ...)
Gmelin Reference
82499
KEGG
  • D08915 checkY
PubChem CID
  • 222285
UNII
  • RA96B954X6 checkY
CompTox Dashboard (EPA)
  • DTXSID6043919 Edit this at Wikidata
InChI
  • 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
SMILES
  • OC[C@@H](O)[C@@H](O)CO
  • C([C@H]([C@H](CO)O)O)O
Properties
Chemical formula
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)
Solubility in water
61% w/w (25 °C)[1]
Magnetic susceptibility (χ)
−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 ?)
Infobox references

Erythritol (/ɪˈrɪθrɪtɒl/, US: /-tɔːl, -tl/)[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
4
H
10
O
4
, 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.

  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". CollinsDictionary.com. 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.
  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.
  6. ^ 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.

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HOCH2CH(OH)CH(OH)CH(OH)CH(OH)CHO + H2 → HOCH2CH(OH)CH(OH)CH(OH)CH(OH)CHHOH Erythritol is obtained by the fermentation of glucose and sucrose. Sugar alcohols...

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5-phosphate (DXP) and 2-C-methyl-D-erythritol 4-phosphate (MEP). 1-Deoxy-D-xylulose 5-phosphate 2-C-methyl-D-erythritol 4-phosphate It is classified under...

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In enzymology, an erythritol kinase (EC 2.7.1.27) is an enzyme that catalyzes the chemical reaction ATP + erythritol ⇌ {\displaystyle \rightleftharpoons...

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(June 2019). "Metabolic effects of the natural sweeteners xylitol and erythritol: A comprehensive review". Critical Reviews in Food Science and Nutrition...

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Truvia

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as well as a food ingredient. Truvia is made of stevia leaf extract, erythritol, and natural flavors. Because it comes from the stevia plant, Cargill...

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Sugar substitute

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sweeten them without adding calories. Additionally, sugar alcohols such as erythritol, xylitol, and sorbitol are derived from sugars. Approved artificial sweeteners...

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Remineralisation of teeth

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caries, malodorous breath, excessive plaque and gingivitis conditions. Erythritol may have greater protective action than xylitol and sorbitol. However...

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pentaerythritol is a blend of penta- in reference to its 5 carbon atoms and erythritol, which also possesses 4 alcohol groups. Pentaerythritol was first reported...

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C4H10O4

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may refer to: Erythritol, a sugar alcohol (or polyol) food additive Threitol, a four-carbon sugar alcohol; the diastereomer of erythritol This set index...

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or approximately 0.3% of that of sucrose. Similar to the sugar alcohol erythritol, allulose is minimally metabolized and is excreted largely unchanged....

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YgbB N terminal protein domain

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involved in terpenoid and isoprenoid biosynthesis. MECDP (2-C-methyl-D-erythritol 2,4-cyclodiphosphate) synthetase, an enzyme in the non-mevalonate pathway...

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Black Black

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[clarification needed] Ingredients include sugar, starch syrup, grape sugar, erythritol, oolong tea extract, ginkgo extract, chrysanthemum flower extract, gum...

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Bai Brands

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water, iced tea, and non-carbonated fruit-flavored drinks) sweetened with erythritol and rebaudioside A (stevia leaf extract), ascorbic acid, and extract from...

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Carotenoid

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erythritol (CDP-ME2P). The conversion to CDP-ME2P is catalyzed by CDP-ME kinase. Next, CDP-ME2P is converted to 2-C-methyl-D-erythritol 2,4-cyclodiphosphate...

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and lower). Pentaerythritol tetranitrate (PETN) Xylitol pentanitrate Erythritol tetranitrate (ETN) Ethylene glycol dinitrate Methyl nitrate Künzel, Martin;...

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John Stenhouse

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value; e.g., Stenhouse discovered betorcinol, a homologue of orcinol, and erythritol, both of which are found in lichens. He was the author of many ingenious...

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Isomalt

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solution), lower than many other sugar alcohols, in particular, xylitol and erythritol. Isomalt is manufactured in a two-stage process in which sucrose (typically...

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Isoprene

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macroscopic algae also produce isoprene. Isoprene is made through the methyl-erythritol 4-phosphate pathway (MEP pathway, also called the non-mevalonate pathway)...

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Maltitol

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in diabetes. Like other sugar alcohols (with the possible exception of erythritol), maltitol has a laxative effect, typically causing diarrhea at a daily...

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Sucralose

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those required to cause adverse effects to certain kinds of aquatic life. Erythritol and Xylitol Neotame, PureVia, Stevia, and Truvia Tagatose This is contrast...

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