Caffeyl alcohol

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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:86071 ;
ChEMBL	ChEMBL1321891 ;
ChemSpider	4445310 ;
PubChem CID	5282096;
UNII	P5Y9E2Q5EQ ;
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+ 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 [77 °F], 100 kPa). verify (what is ?) Infobox references

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.^[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]

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.

[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.

[1]

[2]

[3]