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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)
|
|
3DMet | |
2215799 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.156.065 |
EC Number |
|
KEGG | |
MeSH | Sinapaldehyde |
PubChem
CID
|
|
CompTox Dashboard (
EPA)
|
|
| |
| |
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] | |
![]() | |
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).
|
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]
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]
![]() | |
Names | |
---|---|
Systematic IUPAC name
(E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)prop-2-enal
[1] | |
Other names
| |
Identifiers | |
3D model (
JSmol)
|
|
3DMet | |
2215799 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.156.065 |
EC Number |
|
KEGG | |
MeSH | Sinapaldehyde |
PubChem
CID
|
|
CompTox Dashboard (
EPA)
|
|
| |
| |
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] | |
![]() | |
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).
|
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]
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]