Coniferyl aldehyde

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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16547;
ChEMBL	ChEMBL242529;
ChemSpider	4444167;
ECHA InfoCard	100.006.618
PubChem CID	5352904; 5280536;
UNII	06TPT01AD5 ;
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

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]

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]

References

^ Boerjan, Wout; Ralph, John; Baucher, Marie (2003). "Lignin Biosynthesis". Annual Review of Plant Biology. 54: 519–546. doi:10.1146/annurev.arplant.54.031902.134938. PMID 14503002.
^ ^a ^b Li, Laigeng; Cheng, Xiao Fei; Leshkevich, Jacqueline; Umezawa, Toshiaki; Harding, Scott A.; Chiang, Vincent L. (2001). "The Last Step of Syringyl Monolignol Biosynthesis in Angiosperms is Regulated by a Novel Gene Encoding Sinapyl Alcohol Dehydrogenase". The Plant Cell. 13 (7): 1567–1586. Bibcode:2001PlanC..13.1567L. doi:10.1105/tpc.010111. PMC 139549. PMID 11449052.
^ Osakabe, Keishi; Tsao, Cheng Chung; Li, Laigeng; Popko, Jacqueline L.; Umezawa, Toshiaki; Carraway, Daniel T.; Smeltzer, Richard H.; Joshi, Chandrashekhar P.; Chiang, Vincent L. (1999). "Coniferyl aldehyde 5-hydroxylation and methylation direct syringyl lignin biosynthesis in angiosperms". Proceedings of the National Academy of Sciences. 96 (16): 8955–8960. Bibcode:1999PNAS...96.8955O. doi:10.1073/pnas.96.16.8955. PMC 17714. PMID 10430877.
^ Conde, Elvira; Cadahía, Estrella; García-Vallejo, María Concepción; Fernández De Simón, Brígida (1998). "Polyphenolic Composition of Quercus suber Cork from Different Spanish Provenances". Journal of Agricultural and Food Chemistry. 46 (8): 3166–3171. Bibcode:1998JAFC...46.3166C. doi:10.1021/jf970863k.

[1] Boerjan, Wout; Ralph, John; Baucher, Marie (2003). "Lignin Biosynthesis". Annual Review of Plant Biology. 54: 519–546. doi:10.1146/annurev.arplant.54.031902.134938. PMID 14503002.

[PNAS-2] Li, Laigeng; Cheng, Xiao Fei; Leshkevich, Jacqueline; Umezawa, Toshiaki; Harding, Scott A.; Chiang, Vincent L. (2001). "The Last Step of Syringyl Monolignol Biosynthesis in Angiosperms is Regulated by a Novel Gene Encoding Sinapyl Alcohol Dehydrogenase". The Plant Cell. 13 (7): 1567–1586. Bibcode:2001PlanC..13.1567L. doi:10.1105/tpc.010111. PMC 139549. PMID 11449052.

[3] Osakabe, Keishi; Tsao, Cheng Chung; Li, Laigeng; Popko, Jacqueline L.; Umezawa, Toshiaki; Carraway, Daniel T.; Smeltzer, Richard H.; Joshi, Chandrashekhar P.; Chiang, Vincent L. (1999). "Coniferyl aldehyde 5-hydroxylation and methylation direct syringyl lignin biosynthesis in angiosperms". Proceedings of the National Academy of Sciences. 96 (16): 8955–8960. Bibcode:1999PNAS...96.8955O. doi:10.1073/pnas.96.16.8955. PMC 17714. PMID 10430877.

[4] Conde, Elvira; Cadahía, Estrella; García-Vallejo, María Concepción; Fernández De Simón, Brígida (1998). "Polyphenolic Composition of Quercus suber Cork from Different Spanish Provenances". Journal of Agricultural and Food Chemistry. 46 (8): 3166–3171. Bibcode:1998JAFC...46.3166C. doi:10.1021/jf970863k.

[1]

[2]

[3]

[4]

Biosynthetic role

See also

References