5-Hydroxyferulic acid

5-Hydroxyferulic acid
Chemical structure of 5-hydroxyferulic acid.
Names
Preferred IUPAC name
(2E)-3-(3,4-Dihydroxy-5-methoxyphenyl)prop-2-enoic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.230.072 Edit this at Wikidata
EC Number
  • cis&trans: 803-254-8
UNII
  • InChI=1S/C10H10O5/c1-15-8-5-6(2-3-9(12)13)4-7(11)10(8)14/h2-5,11,14H,1H3,(H,12,13)/b3-2+
    Key: YFXWTVLDSKSYLW-NSCUHMNNSA-N
  • trans (2E): InChI=1/C10H10O5/c1-15-8-5-6(2-3-9(12)13)4-7(11)10(8)14/h2-5,11,14H,1H3,(H,12,13)/b3-2+
    Key: YFXWTVLDSKSYLW-NSCUHMNNBP
  • trans (2E): O=C(O)\C=C\c1cc(O)c(O)c(OC)c1
  • cis&trans: O=C(O)C=Cc1cc(O)c(O)c(OC)c1
  • cis: O=C(O)\C=C/c1cc(O)c(O)c(OC)c1
Properties
C10H10O5
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).

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).

References

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