5-Hydroxyferulic acid
5-Hydroxyferulic acid
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| Names |
| IUPAC name
(E)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoic acid |
| Identifiers |
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1782-55-4 |
| ChemSpider |
394087 |
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 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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| Jmol-3D images |
Image |
| PubChem |
446834 |
O=C(O)\C=C\c1cc(O)c(O)c(OC)c1
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| Properties |
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C10H10O5 |
| Molar mass |
210.18 g/mol |
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) |
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| Infobox references |
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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).
References
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| | Aglycones | Precursor | |
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| Monohydroxycinnamic acids
(Coumaric acids) | |
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| Trihydroxycinnamic acids |
- 3,4,5-Trihydroxycinnamic acid
- 3,4,6-Trihydroxycinnamic acid
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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 | esters of
quinic acid |
- Chlorogenic acid (3-caffeoylquinic acid)
- Cryptochlorogenic acid (4-O-caffeoylquinic acid)
- Neochlorogenic acid (5-O-Caffeoylquinic acid)
- Cynarine (1,5-dicaffeoylquinic acid)
- 3,4-dicaffeoylquinic acid
- 3,5-dicaffeoylquinic acid
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| esters of
shikimic acid | |
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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 and F
- Chiritoside A, B and C
- Cistanoside A, B, C, D, E, F, G an 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 | |
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