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
3DMet B00807
2215799
4206-58-0 (2E)-2-en
ChEBI CHEBI:27949
ChEMBL ChEMBL225067 YesY
ChemSpider 106501 YesY
4509719 (2Z)-2-en YesY
Jmol-3D images Image
Image
Image
KEGG C05610
MeSH Sinapaldehyde
PubChem 119216
5352903 (2Z)-2-en
5280802 (2E)-2-en
Properties
C11H12O4
Molar mass 208.21 g·mol−1
Melting point 104 °C (219 °F; 377 K)
log P 1.686
Acidity (pKa) 9.667
Basicity (pKb) 4.330
Hazards
EU classification Irritant Xi
R-phrases R36/37/38
S-phrases S26, S36
Related compounds
Related alkenals
Cinnamaldehyde

Coniferyl aldehyde
DMACA reagent
2-Nitrocinnamaldehyde

Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Sinapaldehyde is a chemical compound.

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+.[2]

It is found in Senra incana (Hibisceae). It is a low molecular weight phenolic compound susceptible to be extracted from cork stoppers into wine.[3]

See also[edit]

References[edit]

  1. ^ "AC1L3OEQ - Compound Summary". The PubChem Project. USA: National Center for Biotechnology Information. 
  2. ^ Dihydroflavonol 4-reductase on arabidopsisreactome.org
  3. ^ 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, 46 (8), pp 3166–3171 doi:10.1021/jf970863k