Sinapaldehyde
 | |
| Names | |
|---|---|
| Systematic IUPAC name
3-(4-Hydroxy-3,5-dimethoxyphenyl)prop-2-enal[1] | |
| Other names
3,5-Dimethoxy-4-hydroxycinnamaldehyde Sinapic aldehyde | |
| Identifiers | |
| 4206-58-0 (2E)-2-en | |
| 3D model (Jmol) | Interactive image Interactive image Interactive image |
| 3DMet | B00807 |
| 2215799 | |
| ChEBI | CHEBI:27949 |
| ChEMBL | ChEMBL225067  |
| ChemSpider | 106501 4509719 (2Z)-2-en |
| ECHA InfoCard | 100.156.065 |
| 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 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) |
 Xi |
| R-phrases | R36/37/38 |
| S-phrases | S26, S36 |
| Related compounds | |
| Related alkenals |
Cinnamaldehyde |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
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
- ↑ "AC1L3OEQ - Compound Summary". The PubChem Project. USA: National Center for Biotechnology Information.
- ↑ 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
- ↑ Dihydroflavonol 4-reductase on arabidopsisreactome.org
- ↑ 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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