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.

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).
N verify (what is YN ?)
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]

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

References
  1. Karl Herrmann “Caffeyl Alcohol” Pharmazie 1953, volume 8, 303.
  2. 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
  3. Rinantonio Viani, Marino Petracco “Coffee” in Ullmann’s Encyclopedia of Industrial Chemistry” Wiley-VCH, 2007, Weinheim.
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