:5-Hydroxyferulic acid

{{Chembox

| ImageFile = 5-hydroxyferulic acid.svg

| ImageSize = 250px

| ImageAlt = Chemical structure of 5-hydroxyferulic acid.

| PIN = (2E)-3-(3,4-Dihydroxy-5-methoxyphenyl)prop-2-enoic acid

| OtherNames =

|Section1={{Chembox Identifiers

| CASNo = 110642-42-7

| CASNo_Ref = {{Cascite|changed|CAS}}

| index_label=trans (2E)

| index1_label=cis&trans

| index2_label=cis

| CASNo1=1782-55-4

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = R3LZY3E4HE

| EC_number1=803-254-8

| PubChem = 446834

| ChEBI = 20582

| ChemSpiderID = 394087

| SMILES = O=C(O)\C=C\c1cc(O)c(O)c(OC)c1

| SMILES1 = O=C(O)C=Cc1cc(O)c(O)c(OC)c1

| SMILES2 = O=C(O)\C=C/c1cc(O)c(O)c(OC)c1

| 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+

| InChIKey = YFXWTVLDSKSYLW-NSCUHMNNBP

| StdInChI = 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+

| StdInChIKey = YFXWTVLDSKSYLW-NSCUHMNNSA-N

}}

|Section2={{Chembox Properties

| Formula = C₁₀H₁₀O₅

| MolarMass = 210.18 g/mol

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility =

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|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

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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).