Sinapaldehyde

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

Sinapaldehyde
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
CAS Number
3D model (JSmol)
3DMet
Beilstein Reference
 2215799
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.156.065
KEGG
MeSH Sinapaldehyde
PubChem CID
Properties
Chemical formula
 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
EU classification (DSD) (outdated)
 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R-phrases (outdated) R36/37/38
S-phrases (outdated) S26, S36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

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.
  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
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