Furoin

Furoin
Names
	IUPAC name 1,2-bis(2-furyl)-2-hydroxy-ethanone
Identifiers
CAS Number	552-86-3 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL364893 ;
ChemSpider	10629 ;
ECHA InfoCard	100.008.205
EC Number	209-024-8;
PubChem CID	11100;
UNII	FP41RNB020 ;
CompTox Dashboard (EPA)	DTXSID60862181 ;
	InChI InChI=1S/C10H8O4/c11-9(7-3-1-5-13-7)10(12)8-4-2-6-14-8/h1-6,9,11H Key: MIJRFWVFNKQQDK-UHFFFAOYSA-N ;
	SMILES O=C(c1occc1)C(O)c2occc2;
Properties
Chemical formula	C10H8O4
Molar mass	192.170 g·mol−1
	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

Furoin or 1,2-di(furan-2-yl)-2-hydroxyethanone is an organic compound with formula C₁₀H₈O₄. It can be produced from furfural by a benzoin condensation reaction catalyzed by cyanide ions.^[1]

Reactions

Furoin synthesis from furfural is also catalyzed by vitamin B₁ (thiamine). In 1957, Ronald Breslow proposed that this reaction involves a relatively stable carbene form of thiamine.^[2]^[3] In the catalytic cycle shown below two molecules of furfural react to give furoin, via a thiazol-2-ylidene catalyst, resulting from loss of one proton at carbon 2 of the thiazolium cation of vitamin B₁:

Furoin formation from furfural, catalysed by thiamine

This was the first evidence for the existence of persistent carbenes.

Uses

Furoin has been used as a plasticizer.^[1]

References

^ ^a ^b Denis Lorient (1999), New ingredients in food processing: biochemistry and agriculture. Woodhead Publishing ISBN 1-85573-443-5 366 pages
^ Ronald Breslow (1957). "Mechanism of Thiamine Action: Participation of a Thiazolium Zwitterion". Chemistry and Industry. 26: 893.
^ R. Breslow (1957). "Rapid Deuterium Exchange in Thiazolium Salts". Journal of the American Chemical Society. 79 (7): 1762–1763. doi:10.1021/ja01564a064.

[Lorient-1] Denis Lorient (1999), New ingredients in food processing: biochemistry and agriculture. Woodhead Publishing ISBN 1-85573-443-5 366 pages

[2] Ronald Breslow (1957). "Mechanism of Thiamine Action: Participation of a Thiazolium Zwitterion". Chemistry and Industry. 26: 893.

[3] R. Breslow (1957). "Rapid Deuterium Exchange in Thiazolium Salts". Journal of the American Chemical Society. 79 (7): 1762–1763. doi:10.1021/ja01564a064.

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