Sinapaldehyde
Basic information
- CAS
4206-58-0- Standard SMILES
COc1cc(/C=C/C=O)cc(OC)c1O- InChIKey
CDICDSOGTRCHMG-ONEGZZNKSA-N- Molecular formula
- C11H12O4
- Average molar mass
- 208.21 g/mol
- Monoisotopic mass
- 208.07355886
Overview
(E)-sinapaldehyde is a member of the class of cinnamaldehydes that is cinnamaldehyde substituted by a hydroxy group at position 4 and methoxy groups at positions 3 and 5. It has a role as an antifungal agent and a plant metabolite. It is a member of cinnamaldehydes, a member of phenols and a dimethoxybenzene. It is functionally related to an (E)-cinnamaldehyde.
Names & identifiers
- Preferred name
- Sinapaldehyde
- IUPAC
- (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enal
- English name
- SINAPINALDEHYDE
- Molecular formula
- C11H12O4
- Molecular weight
- 208.21
Names & synonyms
Sinapaldehyde4206-58-0trans-Sinapaldehyde2-Propenal, 3-(4-hydroxy-3,5-dimethoxyphenyl)-, (2E)-(E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)-2-propenal(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enal4VB87UV6WG2-Propenal, 3-(4-hydroxy-3,5-dimethoxyphenyl)-, (E)-DTXSID10863340RefChem:886347DTXCID60909287Sinapinaldehyde
Show more names
C05610SINAPALEHYDE(E)-sinapinaldehyde
Sinapyl aldehydeSinapoyl aldehyde(E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)acrylaldehydetrans-3,5-Dimethoxy-4-hydroxycinnamaldehydeSinapic aldehyde3,5-Dimethoxy-4-hydroxycinnamaldehyde(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enalTrans-3,5-Dimethoxy-4-Hydroxy Cinnamaldehyde
Database identifiers
- CAS
4206-58-0- PubChem CID
- 5280802
- DTXSID
DTXSID10863340- ChEMBL
CHEMBL225067- ChEBI
Properties
Computed structural properties
- XLogP
- 1.4
- Topological polar surface area
- 55.8 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 213
Experimental & physicochemical properties
Flavoring AgentsEU Flavoring substances
Physicochemical properties
- Melting point
- 104 · 104-106 °C(lit.)
- Boiling point
- 372.3 · 372.3±37.0 °C(Predicted)
- Density
- 1.195 · 1.195±0.06 g/cm3(Predicted)
- FLAVIS Number
- 5.154 · 05.154 | (E)-4-Hydroxy-3,5-dimethoxycinnamaldehyde
- storage temp.
- 2 · 2-8°C
- solubility
- Acetone (Slightly), Chloroform (Slightly), Methanol (Slightly)
- pka
- 9.67 · 9.67±0.36(Predicted)
- form
- Solid
- color
- Light Yellow to Yellow
- Henry's Law Constant
- 3.1 · 3.1×106 mol/(m3Pa) at 25℃, McFall et al. (2020)
- Stability
- Air Sensitive, Light Sensitive
- InChI
- 1S/C11H12O4/c1-14-9-6-8(4-3-5-12)7-10(15-2)11(9)13/h3-7,13H,1-2H3/b4-3+
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
2-Propenal, 3-(4-hydroxy-3,5-dimethoxyphenyl)-, (2E)-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- hs_code
- 2912490090
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationCompounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes.
Applications
Usestrans-3,5-Dimethoxy-4-hydroxycinnamaldehyde (Sinapinaldehyde) is suitable for use in the determination of phenolic compounds by HPLC with multiple wavelength detector in grape marc distillates aged in Quercus petraea, Quercus robur and Quercus alba wooden barrels. It is suitable for use in the GC/MS positive ion chemical ionization (PICI) characterization of volatile phenols and benzene aldehydes in various woods.
Additional notes
DefinitionChEBI: A member of the class of cinnamaldehydes that is cinnamaldehyde substituted by a hydroxy group at position 4 and methoxy groups at positions 3 and 5.
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