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;
	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).
	(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.

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