Sinapaldehyde
Chemical compound
From Wikipedia, the free encyclopedia
Sinapaldehyde is an organic compound with the formula HO(CH3O)2C6H2CH=CHCHO. It is a derivative of cinnamaldehyde, featuring one hydroxy group and two methoxy groups as substituents. It is an intermediate in the formation of sinapyl alcohol, a lignol that is a major precursor to lignin.[3][4]
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| Names | |
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| Systematic IUPAC name
(E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)prop-2-enal[1] | |
Other names
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| Identifiers | |
3D model (JSmol) |
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| 2215799 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.156.065 |
| EC Number |
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| KEGG | |
| MeSH | Sinapaldehyde |
PubChem CID |
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CompTox Dashboard (EPA) |
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| 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 |
| Hazards | |
| GHS labelling:[2] | |
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| Warning | |
| H315, H319, H335 | |
| Related compounds | |
Related alkenals |
Cinnamaldehyde |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Biosynthetic role
In sweetgum (Liquidambar styraciflua), sinapaldehyde arises in two steps from coniferyl aldehyde beginning with hydroxylation mediated by coniferyl aldehyde 5-hydroxylase. The diphenol is then methylated at the 5-OH by the action of caffeate O-methyltransferase.[5]
Sinapaldehyde is reduced to the alcohol by the action of dehydrogenase enzymes.[4] In Arabidopsis thaliana, the enzyme dihydroflavonol 4-reductase uses NADP+ to reduce sinapaldehyde to sinapyl alcohol.[6]
It is found in Senra incana (Hibisceae). It is a low molecular weight phenol that is susceptible to extraction from cork stoppers into wine.[7]