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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
ECHA InfoCard 100.156.065 Edit this at Wikidata
KEGG
MeSH Sinapaldehyde
  • InChI=1S/C11H12O4/c1-14-9-6-8(4-3-5-12)7-10(15-2)11(9)13/h3-7,13H,1-2H3
    Key: CDICDSOGTRCHMG-UHFFFAOYSA-N
  • COc1cc(C=CC=O)cc(OC)c1O
  • COC1=CC(C=CC=O)=CC(OC)=C1O
  • COC1=CC(=CC(=C1O)OC)C=CC=O
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
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).

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.
  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