Caffeyl alcohol
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| Names | |
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| Preferred IUPAC name
4-[(1E)-3-Hydroxyprop-1-en-1-yl]benzene-1,2-diol | |
| Other names
Caffeyl alcohol, Caffeoyl alcohol, 3,4-Dihydroxycinnamyl alcohol | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C9H10O3 | |
| Appearance | White solid |
| Melting point | 144 to 145 °C (291 to 293 °F; 417 to 418 K) |
| moderate | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Caffeyl alcohol is the organic compound with the formula (HO)2C6H3-4-CHCHCH2OH. This colourless solid is related to catechol by attachment to allyl alcohol. It is the precursor to one of the three principal lignols.
Preparation and occurrence
[edit]In the laboratory, caffeyl alcohol can be synthesized from 3,4-dihydroxybenzaldehyde.[1] It is an intermediate in the biosynthesis of coniferyl alcohol, the conversion being effected by caffeate O-methyltransferase.[2]
Related compounds
[edit]Two related compounds are caffeyl aldehyde and caffeic acid, the latter also being a minor component of coffee.[3]
References
[edit]- ↑ Karl Herrmann “Caffeyl Alcohol” Pharmazie 1953, volume 8, 303.
- ↑ John M Humphreys, Clint Chapple “Rewriting the Lignin Roadmap” Current Opinion in Plant Biology 2002, volume 5, 224–229. doi:10.1016/S1369-5266(02)00257-1
- ↑ Rinantonio Viani, Marino Petracco “Coffee” in Ullmann’s Encyclopedia of Industrial Chemistry” Wiley-VCH, 2007, Weinheim.