Furoin

Furoin
IUPAC name

1,2-bis(2-furyl)-2-hydroxy-ethanone
Identifiers
PubChem 11100
ChemSpider 10629 Y
ChEMBL CHEMBL364893 Y
Jmol-3D images Image 1
Properties
Molecular formula C10H8O4
Molar mass 192.17 g mol−1
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 the catalytic action of cyanide ions.[1]

Reactions

Furoin synthesis from furfural is also catalyzed by vitamin B1 (thiamine). In 1957, R. 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:

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

Uses

Furoin has been used as a plasticizer.[1]

References

  1. ^ a b 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.