Coniferyl aldehyde

Coniferyl aldehyde is an organic compound with the formula HO(CH₃O)C₆H₃CH=CHCHO. It is a derivative of cinnamaldehyde, featuring 4-hydroxy and 3-methoxy substituents. It is a major precursor to lignin.^[1][2]

Coniferyl aldehyde

Chemical structure of trans-coniferyl aldehyde
Names
IUPAC names (Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enal (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enal
Other names coniferaldehyde cis-coniferyl aldehyde trans-coniferyl aldehyde
Identifiers
CAS Number	458-36-6 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16547
ChEMBL	ChEMBL242529
ChemSpider	4444167
ECHA InfoCard	100.006.618
PubChem CID	5352904 5280536
UNII	06TPT01AD5 Y
CompTox Dashboard (EPA)	DTXSID8075047
InChI InChI=1S/C10H10O3/c1-13-10-7-8(3-2-6-11)4-5-9(10)12/h2-7,12H,1H3/b3-2+
SMILES COC1=C(C=CC(=C1)C=CC=O)O
Properties
Chemical formula	C10H10O3
Molar mass	178.187 g·mol−1
Density	1.186 g/mL
Melting point	80 °C (176 °F; 353 K)
Boiling point	338.8 °C (641.8 °F; 612.0 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Biosynthetic role

In sweetgum (Liquidambar styraciflua), coniferyl aldehyde is a precursor to sinapaldehyde via hydroxylation mediated by coniferyl aldehyde 5-hydroxylase.^[3]

Coniferyl aldehyde is reduced to coniferyl alcohol by the action of dehydrogenase enzymes.^[2]

It is found in Senra incana (Hibisceae). It is a low molecular weight phenol that is susceptible to extraction from cork stoppers into wine.^[4]

See also

• Phenolic compounds in wine