Caffeyl alcohol
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.
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| Names | |
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| IUPAC name
4-(3-hydroxy-1-propen-1-yl)-1,2-benzenediol, | |
| Other names
Caffeyl alcohol, Caffeoyl alcohol, 3,4-Dihydroxycinnamyl alcohol | |
| Identifiers | |
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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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| Infobox references | |
Preparation and occurrence
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
Two related compounds are caffeyl aldehyde and caffeic acid, the latter also being a minor component of coffee.[3]
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References
- 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.
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