Caffeyl alcohol

Chemical compound From Wikipedia, the free encyclopedia

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.

Quick facts Names, Identifiers ...
Caffeyl alcohol
Names
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)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C9H10O3/c10-5-1-2-7-3-4-8(11)9(12)6-7/h1-4,6,10-12H,5H2/b2-1+ ☒N
    Key: ZCKDCRKBURQZPT-OWOJBTEDSA-N ☒N
  • OC\C=C\c1ccc(O)c(O)c1
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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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]

Two related compounds are caffeyl aldehyde and caffeic acid, the latter also being a minor component of coffee.[3]

References

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