5-Hydroxyferulic acid

• CAT Number: R074691
• CAS Number: 1782-55-4
• Molecular Formula: C10H10O5
• Molecular Weight: 210.18
• Purity: ≥95%
• Synonyms: (E)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoic acid
• InChI: 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+
• InChIKey: YFXWTVLDSKSYLW-NSCUHMNNSA-N
• SMILES: COC1=CC(=CC(=C1O)O)C=CC(=O)O

5-Hydroxyferulic acid is a hydroxycinnamic acid and is a metabolite of the phenylpropanoid pathway. 5-Hydroxyferulic acid is a precursor in the biosynthesis of sinapic acid and is also a COMT non-esterifed substrate[1][2][3].
The product of the alfalfa Caffeic acid/5-hydroxyferulic acid 3/5-O-methyltransferase (COMT) catalyzed methylation of 5-Hydroxyferulic acid is sinapic acid. 5-Hydroxyferulic acid O-methyltransferase activities (pkat mg-1 protein) in stem material from COMT downregulates transgenic alfalfa[1].

Reference

[1]. K Parvathi, et al. Substrate Preferences of O-methyltransferases in Alfalfa Suggest New Pathways for 3-O-methylation of Monolignols. Plant J. 2001 Jan;25(2):193-202.
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[2]. S Maury, et al. Tobacco O-methyltransferases Involved in Phenylpropanoid Metabolism. The Different Caffeoyl-Coenzyme A/5-hydroxyferuloyl-coenzyme A 3/5-O-methyltransferase and Caffeic acid/5-hydroxyferulic Acid 3/5-O-methyltransferase Classes Have Distinct Substrate Specificities and Expression Patterns. Plant Physiol. 1999 Sep;121(1):215-24.
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[3]. Inoue, et al. Substrate Preferences of Caffeic acid/5-hydroxyferulic Acid 3/5-O-methyltransferases in Developing Stems of Alfalfa (Medicago Sativa L.). Arch Biochem Biophys. 2000 Mar 1;375(1):175-82.
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