Sinapaldehyde

Sinapaldehyde
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
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;
CompTox Dashboard (EPA)	DTXSID201016569 ;
	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
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

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]

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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