Chemistry:Sinapaldehyde

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Sinapaldehyde
Kekulé skeletal formula of sinapaldehyde (2E)-2-en with some implicit hydrogens shown and one explicit hydrogen added
Names
Systematic IUPAC name
3-(4-Hydroxy-3,5-dimethoxyphenyl)prop-2-enal[1]
Other names
3,5-Dimethoxy-4-hydroxycinnamaldehyde

Sinapic aldehyde
Sinapinaldehyde
Sinapoyl aldehyde

Sinapyl aldehyde
Identifiers
3D model (JSmol)
3DMet
2215799
ChEBI
ChEMBL
ChemSpider
KEGG
MeSH Sinapaldehyde
Properties
C11H12O4
Molar mass 208.213 g·mol−1
Melting point 104 to 106 °C (219 to 223 °F; 377 to 379 K)
log P 1.686
Acidity (pKa) 9.667
Basicity (pKb) 4.330
Hazards
Irritant Xi
R-phrases (outdated) R36/37/38
S-phrases (outdated) S26, S36
Related compounds
Related alkenals
Cinnamaldehyde

Coniferyl aldehyde
DMACA reagent
2-Nitrocinnamaldehyde

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Tracking categories (test):

Sinapaldehyde is an organic compound that is an intermediate in the formation of lignin.[2]

In Arabidopsis thaliana, this compound is part of the lignin biosynthesis pathway. The enzyme dihydroflavonol 4-reductase uses sinapaldehyde and NADPH to produce sinapyl alcohol and NADP+.[3]

It is found in Senra incana (Hibisceae). It is a low molecular weight phenol that is susceptible to be extracted from cork stoppers into wine.[4]

See also


References

  1. "AC1L3OEQ - Compound Summary". The PubChem Project. USA: National Center for Biotechnology Information. https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=119216. 
  2. 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
  3. Dihydroflavonol 4-reductase on arabidopsisreactome.org
  4. 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