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5-Hydroxyferulic acid
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Names
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Preferred IUPAC name
(2E)-3-(3,4-Dihydroxy-5-methoxyphenyl)prop-2-enoic acid
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Identifiers
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ChEBI
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ChemSpider
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ECHA InfoCard
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100.230.072
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EC Number
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UNII
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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
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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
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Properties
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C10H10O5
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Molar mass
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210.18 g/mol
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
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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Aglycones | Precursor | |
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Monohydroxycinnamic acids (Coumaric acids) | |
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Dihydroxycinnamic acids | |
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Trihydroxycinnamic acids | |
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O-methylated forms | |
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others | |
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Esters | glycoside-likes | Esters of caffeic acid with cyclitols | |
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Glycosides | |
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Tartaric acid esters | |
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Other esters with caffeic acid | |
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Caffeoyl phenylethanoid glycoside (CPG) |
- Echinacoside
- Calceolarioside A, B, C, F
- Chiritoside A, B, C
- Cistanoside A, B, C, D, E, F, G, H
- Conandroside
- Myconoside
- Pauoifloside
- Plantainoside A
- Plantamajoside
- Tubuloside B
- Verbascoside (Isoverbascoside, 2′-Acetylverbascoside)
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Oligomeric forms | Dimers |
- Diferulic acids (DiFA) : 5,5′-Diferulic acid, 8-O-4′-Diferulic acid, 8,5′-Diferulic acid, 8,5′-DiFA (DC), 8,5′-DiFA (BF), 8,8′-Diferulic acid
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Trimers | |
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Tetramers | |
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Conjugates with coenzyme A (CoA) | |
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