Paracoumaryl alcohol

Paracoumaryl alcohol is a phytochemical, one of the monolignols. It is a white solid. p-Coumaryl alcohol is a major precursor to lignin or lignans.[1]

Paracoumaryl alcohol
Names
Preferred IUPAC name
4-[(1E)-3-Hydroxyprop-1-en-1-yl]phenol
Other names
p-coumaryl alcohol, 4-coumaryl alcohol, 4-hydroxycinnamyl alcohol, 4-(3-hydroxy-1-propenyl)phenol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
  • InChI=1S/C9H10O2/c10-7-1-2-8-3-5-9(11)6-4-8/h1-6,10-11H,7H2/b2-1+ ☒N
    Key: PTNLHDGQWUGONS-OWOJBTEDSA-N ☒N
  • InChI=1/C9H10O2/c10-7-1-2-8-3-5-9(11)6-4-8/h1-6,10-11H,7H2/b2-1+
    Key: PTNLHDGQWUGONS-OWOJBTEDBL
  • OC/C=C/c1ccc(O)cc1
Properties
C9H10O2
Molar mass 150.1745
Appearance White solid
Melting point 114–116 °C (237–241 °F; 387–389 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Biosynthesis and occurrence

It is synthesized via the phenylpropanoid biochemical pathway.

Esters of p-coumaryl alcohol and fatty acids are the basis of epicuticular waxes covering the surfaces of apples.

p-Coumaryl alcohol is an intermediate in biosynthesis of chavicol, stilbenoids, and coumarin.

References
  1. Withers, Saunia; Lu, Fachuang; Kim, Hoon; Zhu, Yimin; Ralph, John; Wilkerson, Curtis G. (2012). "Identification of Grass-specific Enzyme That Acylates Monolignols with p-Coumarate". Journal of Biological Chemistry. 287 (11): 8347–8355. doi:10.1074/jbc.M111.284497. PMID 22267741. S2CID 24998478.
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