5-Hydroxyferulic acid

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5-Hydroxyferulic acid
Chemical structure of 5-hydroxyferulic acid.
IUPAC name
(E)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoic acid
3D model (JSmol)
ECHA InfoCard 100.230.072
Molar mass 210.18 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

5-Hydroxyferulic acid is a hydroxycinnamic acid.

It is a precursor in the biosynthesis of sinapic acid. Phenylalanine is first converted to cinnamic acid by the action of the enzyme phenylalanine ammonia-lyase (PAL). A series of enzymatic hydroxylations and methylations leads to coumaric acid, caffeic acid, ferulic acid, 5-hydroxyferulic acid and sinapic acid.

Thus 5-hydroxyferulic acid is formed from ferulic acid by the action of the specific enzyme ferulate 5-hydroxylase (F5H).