Structure via PubChem · Public domain (PubChem)
sinapaldehyde
Sign in to saveAlso known as Sinapic aldehyde, Sinapyl aldehyde, 3,5-dimethoxy-4-hydroxyphenylpropenaldehyde, (E/Z)-sinapaldehyde
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.
Chemical data
- Formula
- C11H12O4
- Molecular weight
- 208.21 g/mol
- IUPAC name
- 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enal
- SMILES
- COC1=CC(=CC(=C1O)OC)C=CC=O
- InChIKey
- CDICDSOGTRCHMG-UHFFFAOYSA-N
- XLogP
- 1.4
- Polar surface area
- 55.8 Ų
- H-bond donors
- 1
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
112 papers- Anti-Inflammatory Activity and ROS Regulation Effect of Sinapaldehyde in LPS-Stimulated RAW 264.7 Macrophages.Molecules (Basel, Switzerland) · 2020
- Different Routes for Conifer- and Sinapaldehyde and Higher Saccharification upon Deficiency in the Dehydrogenase CAD1.Plant physiology · 2017
- Integrated metabolomics and serum pharmacochemistry reveal Q-markers of Zhigancao decoction for antiarrhythmic efficacy.Journal of ethnopharmacology · 2025
- Nasal and other tumours in rats given 3,4,5-trimethoxy-cinnamaldehyde, a derivative of sinapaldehyde and of other alpha,beta-unsaturated aldehydic wood lignin constituents.British journal of cancer · 1972
- Signatures of cinnamyl alcohol dehydrogenase deficiency in poplar lignins.Phytochemistry · 2004
via PubMed
Wikidata facts
- Subclass of
- aldehydes
- Mass
- 208.073558864
Show 3 more facts
- found in taxon
- Talipariti tiliaceum
- chemical formula
- C₁₁H₁₂O₄
- canonical SMILES
- COc1cc(C=CC=O)cc(OC)c1O
Sources (1)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Biosynthetic role
- See also
- References
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.
==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.
Excerpted from Wikipedia’s “sinapaldehyde” article, available under the CC BY-SA 4.0 licence.