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
CAS Number	3598-26-3 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:86071 N
ChEMBL	ChEMBL1321891 N
ChemSpider	4445310 N
PubChem CID	5282096
UNII	P5Y9E2Q5EQ Y
CompTox Dashboard (EPA)	DTXSID801027142
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+ N Key: ZCKDCRKBURQZPT-OWOJBTEDSA-N 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 [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]

Related compounds

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