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Sinapaldehyde

  • (trans)-3,5-Dimethoxy-4-hydroxycinnamaldehyde
  • Sinapic aldehyde
  • Sinapinaldehyde
  • Sinapoyl aldehyde
  • Sinapyl aldehyde

Coniferyl aldehyde

DMACA reagent

2-Nitrocinnamaldehyde

Sinapaldehyde is an organic compound with the formula HO(CH3O)2C6H2CH=CHCHO. It is a derivative of cinnamaldehyde, featuring one hydroxy group and two methoxy groups as substituents. It is an intermediate in the formation of sinapyl alcohol, a lignol that is a major precursor to lignin.

Biosynthetic role

In sweetgum (Liquidambar styraciflua), sinapaldehyde arises in two steps from coniferyl aldehyde beginning with hydroxylation mediated by coniferyl aldehyde 5-hydroxylase. The diphenol is then methylated at the 5-OH by the action of caffeate O-methyltransferase.

Sinapaldehyde is reduced to the alcohol by the action of dehydrogenase enzymes.

It is found in Senra incana (Hibisceae). It is a low molecular weight phenol that is susceptible to extraction from cork stoppers into wine.

References

References

  1. "AC1L3OEQ - Compound Summary". National Center for Biotechnology Information.
  2. "C&L Inventory".
  3. Wout Boerjan, John Ralph, Marie Baucher "Lignin Biosynthesis" Annu. Rev. Plant Biol. 2003, vol. 54, pp. 519–46. {{doi. 10.1146/annurev.arplant.54.031902.134938
  4. (2001). "The Last Step of Syringyl Monolignol Biosynthesis in Angiosperms is Regulated by a Novel Gene Encoding Sinapyl Alcohol Dehydrogenase". The Plant Cell.
  5. (1999). "Coniferyl aldehyde 5-hydroxylation and methylation direct syringyl lignin biosynthesis in angiosperms". Proceedings of the National Academy of Sciences.
  6. "Dihydroflavonol 4-reductase on arabidopsisreactome.org".
  7. Polyphenolic Composition of ''Quercus suber'' Cork from Different Spanish Provenances. Elvira Conde, Estrella Cadahía, María Concepción García-Vallejo and Brígida Fernández de Simón, J. Agric. Food Chem., 1998, volume 46, pp 3166–3171 {{doi. 10.1021/jf970863k
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natural-phenols aldehydes o-methylated-phenylpropanoids
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