Furoin
From Infogalactic: the planetary knowledge core
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| Names | |
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| IUPAC name
1,2-bis(2-furyl)-2-hydroxy-ethanone
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| Identifiers | |
| ChEMBL | ChEMBL364893  |
| ChemSpider | 10629 |
| Jmol 3D model | Interactive image |
| PubChem | 11100 |
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| Properties | |
| C10H8O4 | |
| Molar mass | 192.17 g·mol−1 |
| Vapor pressure | {{{value}}} |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| 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:
File:Breslow1.png
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
- ↑ 1.0 1.1 Denis Lorient (1999), New ingredients in food processing: biochemistry and agriculture. Woodhead Publishing. ISBN 1-85573-443-5. 366 pages
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