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Sinapaldehyde

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
Other names
3,5-Dimethoxy-4-hydroxycinnamaldehyde

Sinapic aldehyde
Sinapinaldehyde
Sinapoyl aldehyde

Sinapyl aldehyde
Identifiers
3D model (Jmol)
3DMet B00807
2215799
ChEBI
ChemSpider
ECHA InfoCard 100.156.065
KEGG
MeSH Sinapaldehyde
PubChem CID
Properties
C11H12O4
Molar mass 208.21 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 R36/37/38
S-phrases 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

Sinapic aldehyde
Sinapinaldehyde
Sinapoyl aldehyde

Coniferyl aldehyde
DMACA reagent
2-Nitrocinnamaldehyde

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

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+.

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.


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Wikipedia

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