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	4206-58-0 (2E)-2-en
3D model (JSmol)	Interactive image Interactive image Interactive image
3DMet	B00807
Beilstein Reference	2215799
ChEBI	CHEBI:27949
ChEMBL	ChEMBL225067
ChemSpider	106501 4509719 (2Z)-2-en
ECHA InfoCard	100.156.065
KEGG	C05610
MeSH	Sinapaldehyde
PubChem CID	119216 5352903 (2Z)-2-en 5280802 (2E)-2-en
InChI 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
SMILES COc1cc(C=CC=O)cc(OC)c1O COC1=CC(C=CC=O)=CC(OC)=C1O COC1=CC(=CC(=C1O)OC)C=CC=O
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EU classification (DSD) (outdated)	Xi
R-phrases (outdated)	R36/37/38
S-phrases (outdated)	S26, S36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

• Phenolic content in wine
• Syringaldehyde
• Syringol
• Syringic acid
• Acetosyringone
• Sinapyl alcohol
• Sinapinic acid
• Sinapine
• Canolol

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