Erythritol

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 (/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 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.

  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.