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Caffeyl alcohol

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Caffeyl alcohol
Names
Preferred IUPAC name 4-benzene-1,2-diol
Other names Caffeyl alcohol, Caffeoyl alcohol, 3,4-Dihydroxycinnamyl alcohol
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C9H10O3/c10-5-1-2-7-3-4-8(11)9(12)6-7/h1-4,6,10-12H,5H2/b2-1+Key: ZCKDCRKBURQZPT-OWOJBTEDSA-N
SMILES
  • OC\C=C\c1ccc(O)c(O)c1
Properties
Chemical formula C9H10O3
Appearance White solid
Melting point 144 to 145 °C (291 to 293 °F; 417 to 418 K)
Solubility in water moderate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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

In the laboratory, caffeyl alcohol can be synthesized from 3,4-dihydroxybenzaldehyde. It is an intermediate in the biosynthesis of coniferyl alcohol, the conversion being effected by caffeate O-methyltransferase.

Related compounds

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

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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