Erythritol

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
CAS Number	149-32-6 ;
3D model (JSmol)	Interactive image; Interactive image;
Beilstein Reference	1719753
ChEBI	CHEBI:17113 ;
ChEMBL	ChEMBL349605 ;
ChemSpider	192963 ;
DrugBank	DB04481 ;
ECHA InfoCard	100.005.217
E number	E968 (glazing agents, ...)
Gmelin Reference	82499
KEGG	D08915 ;
PubChem CID	222285;
UNII	RA96B954X6 ;
CompTox Dashboard (EPA)	DTXSID6043919 ;
	InChI InChI=1S/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2/t3-,4+ Key: UNXHWFMMPAWVPI-ZXZARUISSA-N ; 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)
Magnetic susceptibility (χ)	−73.80·10−6 cm3/mol
Hazards
NFPA 704 (fire diamond)	1 1 0
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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.

^ 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.
^ "erythritol". Collins English Dictionary. HarperCollins. Retrieved 2023-06-29.
^ 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.
^ 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.
^ 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.
^ 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.

[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.

[Vasudevan2013-4] 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.

[Kawanabe_April_1994-6] 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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