sinapaldehyde
2-propenal, 3-(4-hydroxy-3,5-dimethoxyphenyl)-, (2E)-
Identification
| Name | sinapaldehyde |
| IUPAC | (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enal |
| CAS Number | 4206-58-0 |
| FDA UNII | Search |
| Molecular Formula | C11 H12 O4 |
| Molecular Weight | 208.21344000 |
| MDL Number | MFCD00075980 |
| Nikkaji Number | J329.696B |
| Beilstein | 2215799 |
| CoE Number | 10341 |
Regulatory
| DG SANTE Food Flavourings | 05.154 (E)-4-hydroxy-3,5-dimethoxycinnamaldehyde |
Physical Properties
| Appearance | white to pale yellow solid (est) |
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 108.00 °C. @ 760.00 mm Hg |
| Boiling Point | 393.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.000004 mmHg @ 25.00 °C. (est) |
| Flash Point | 295.00 °F. TCC ( 146.11 °C. ) |
| logP (o/w) | 1.686 (est) |
| Soluble in | water, 5692 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | flavoring agents |
| Recommendation for sinapaldehyde usage levels up to | not for fragrance use. |
| Maximised Survey-derived Daily Intakes (MSDI-EU) | 0.085 (μg/capita/day) |
| Modified Theoretical Added Maximum Daily Intake (mTAMDI) | 1900 (μg/person/day) |
| Threshold of Concern | 1800 (μg/person/day) |
| Structure Class | I |
| Dairy products, excluding products of category 02.0 (01.0) | 3.00000 |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0) | 2.00000 |
| Edible ices, including sherbet and sorbet (03.0) | 3.00000 |
| Processed fruit (04.1) | 7.00000 |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2) | - |
| Confectionery (05.0) | 4.00000 |
| Chewing gum (05.3) | - |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0) | 2.00000 |
| Bakery wares (07.0) | 5.00000 |
| Meat and meat products, including poultry and game (08.0) | 1.00000 |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0) | 1.00000 |
| Eggs and egg products (10.0) | - |
| Sweeteners, including honey (11.0) | - |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0) | 2.00000 |
| Foodstuffs intended for particular nutritional uses (13.0) | 3.00000 |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1) | 2.00000 |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2) | 4.00000 |
| Ready-to-eat savouries (15.0) | 5.00000 |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0) | 2.00000 |
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Potential Uses
Natural Occurrence
Synonyms
trans-3,5-
dimethoxy-4-hydroxy cinnamaldehyde
(E)-3,5-
dimethoxy-4-hydroxycinnamaldehyde
trans-3,5-
dimethoxy-4-hydroxycinnamaldehyde
(E)-4-
hydroxy-3,5-dimethoxycinnamaldehyde
(2E)-3-(4-
hydroxy-3,5-dimethoxyphenyl)-2-propenal
(E)-3-(4-
hydroxy-3,5-dimethoxyphenyl)-2-propenal
(2E)-3-(4-
hydroxy-3,5-dimethoxyphenyl)acrylaldehyde
(E)-3-(4-
hydroxy-3,5-dimethoxyphenyl)acrylaldehyde
(2E)-3-(4-
hydroxy-3,5-dimethoxyphenyl)prop-2-enal
(E)-3-(4-
hydroxy-3,5-dimethoxyphenyl)prop-2-enal
2-
propenal, 3-(4-hydroxy-3,5-dimethoxyphenyl)-, (2E)-
2-
propenal, 3-(4-hydroxy-3,5-dimethoxyphenyl)-, (E)-
sinapinaldehyde
sinapoyl aldehyde
sinapyl aldehyde
PubMed:
[Chemical constituents of Jasminum giraldii and their antioxidant activity].
PubMed:
Structural Studies of Cinnamoyl-CoA Reductase and Cinnamyl-Alcohol Dehydrogenase, Key Enzymes of Monolignol Biosynthesis.
PubMed:
ISOLATION OF GLYCOSIDES FROM THE BARKS OF ILEX ROTUNDA BY HIGH-SPEED COUNTER-CURRENT CHROMATOGRAPHY.
PubMed:
Enrichment and purification of pedunculoside and syringin from the barks of Ilex rotunda with macroporous resins.
PubMed:
Molecular cloning and functional analysis of nine cinnamyl alcohol dehydrogenase family members in Populus tomentosa.
PubMed:
Determination of the Structure and Catalytic Mechanism of Sorghum bicolor Caffeic Acid O-Methyltransferase and the Structural Impact of Three brown midrib12 Mutations.
PubMed:
Flavonoids and other constituents from Aletris spicata and their chemotaxonomic significance.
PubMed:
Antimicrobial activities of some Thai traditional medical longevity formulations from plants and antibacterial compounds from Ficus foveolata.
PubMed:
Leucaena sp. recombinant cinnamyl alcohol dehydrogenase: purification and physicochemical characterization.
PubMed:
Loss of function of cinnamyl alcohol dehydrogenase 1 leads to unconventional lignin and a temperature-sensitive growth defect in Medicago truncatula.
PubMed:
Congeners in sugar cane spirits aged in casks of different woods.
PubMed:
Biochemical characterization of recombinant cinnamoyl CoA reductase 1 (Ll-CCRH1) from Leucaena leucocephala.
PubMed:
Reprogramming the phenylpropanoid metabolism in seeds of oilseed rape by suppressing the orthologs of reduced epidermal fluorescence1.
PubMed:
Whiskey congeners suppress LPS/IFNγ-induced NO production in murine macrophage RAW 264 cells by inducing heme oxygenase-1 expression.
PubMed:
Disrupting the cinnamyl alcohol dehydrogenase 1 gene (BdCAD1) leads to altered lignification and improved saccharification in Brachypodium distachyon.
PubMed:
Down-regulation of the caffeic acid O-methyltransferase gene in switchgrass reveals a novel monolignol analog.
PubMed:
Biochemical characterization and identification of a cinnamyl alcohol dehydrogenase from Artemisia annua.
PubMed:
[Chemical constituents of Halenia elliptica].
PubMed:
Environmental stresses of field growth allow cinnamyl alcohol dehydrogenase-deficient Nicotiana attenuata plants to compensate for their structural deficiencies.
PubMed:
Phenolic compounds from the aerial parts of Diplomorpha canescens.
PubMed:
Investigating the structure-effect relationships of various natural phenols used as laccase mediators in the biobleaching of kenaf and sisal pulps.
PubMed:
Changes in cinnamyl alcohol dehydrogenase activities from sugarcane cultivars inoculated with Sporisorium scitamineum sporidia.
PubMed:
Synthesis and structural characterization of oaklin-catechins.
PubMed:
Syringyl lignin is unaltered by severe sinapyl alcohol dehydrogenase suppression in tobacco.
PubMed:
Influences of cinnamic aldehydes on H⺠extrusion activity and ultrastructure of Candida.
PubMed:
[Study on chemical constituents from ethyl acetate extract of Myricaria bracteata].
PubMed:
A rapid sample screening method for authenticity control of whiskey using capillary electrophoresis with online preconcentration.
PubMed:
Antimutagenic constituents of adlay (Coix lachryma-jobi L. var. ma-yuen Stapf) with potential cancer chemopreventive activity.
PubMed:
Antinociceptive, free radical-scavenging, and cytotoxic activities of Acanthus hirsutus Boiss.
PubMed:
[Chemical constituents of Swertia macrosperma].
PubMed:
Downregulation of cinnamyl-alcohol dehydrogenase in switchgrass by RNA silencing results in enhanced glucose release after cellulase treatment.
PubMed:
Structure-function analyses of a caffeic acid O-methyltransferase from perennial ryegrass reveal the molecular basis for substrate preference.
PubMed:
[Chemical constituents from rhizomes of Illicium henryi].
PubMed:
Lignin-derived oak phenolics: a theoretical examination of additional potential health benefits of red wine.
PubMed:
The simultaneous repression of CCR and CAD, two enzymes of the lignin biosynthetic pathway, results in sterility and dwarfism in Arabidopsis thaliana.
PubMed:
Induction of heme oxygenase-1 by whisky congeners in human endothelial cells.
PubMed:
Enzymatic grafting of simple phenols on flax and sisal pulp fibres using laccases.
PubMed:
Application of laccase-natural mediator systems to sisal pulp: an effective approach to biobleaching or functionalizing pulp fibres?
PubMed:
Effect of phenolic aldehydes and flavonoids on growth and inactivation of Oenococcus oeni and Lactobacillus hilgardii.
PubMed:
Interaction of tertiary phosphines with lignin-type, alpha,beta-unsaturated aldehydes in water.
PubMed:
Improved forage digestibility of tall fescue (Festuca arundinacea) by transgenic down-regulation of cinnamyl alcohol dehydrogenase.
PubMed:
High performance liquid chromatography method for the determination of cinnamyl alcohol dehydrogenase activity in soybean roots.
PubMed:
GOLD HULL AND INTERNODE2 encodes a primarily multifunctional cinnamyl-alcohol dehydrogenase in rice.
PubMed:
Preliminary study of oaklins, a new class of brick-red catechinpyrylium pigments resulting from the reaction between catechin and wood aldehydes.
PubMed:
Tetramethylammonium hydroxide (TMAH) thermochemolysis of lignin: behavior of 4-O-etherified cinnamyl alcohols and aldehydes.
PubMed:
Metabolite profiling reveals a role for atypical cinnamyl alcohol dehydrogenase CAD1 in the synthesis of coniferyl alcohol in tobacco xylem.
PubMed:
Identification and characterisation of Arabidopsis glycosyltransferases capable of glucosylating coniferyl aldehyde and sinapyl aldehyde.
PubMed:
Simplified preparation of coniferyl and sinapyl alcohols.
PubMed:
Structural and kinetic basis for substrate selectivity in Populus tremuloides sinapyl alcohol dehydrogenase.
PubMed:
Phenolic profiling of caffeic acid O-methyltransferase-deficient poplar reveals novel benzodioxane oligolignols.
PubMed:
Comparison between cachaça and rum using pattern recognition methods.
PubMed:
Purification and characterization of cinnamyl alcohol-NADPH-dehydrogenase from the leaf tissues of a basin mangrove Lumnitzera racemosa Willd.
PubMed:
Signatures of cinnamyl alcohol dehydrogenase deficiency in poplar lignins.
PubMed:
Functional reclassification of the putative cinnamyl alcohol dehydrogenase multigene family in Arabidopsis.
PubMed:
The Arabidopsis thaliana REDUCED EPIDERMAL FLUORESCENCE1 gene encodes an aldehyde dehydrogenase involved in ferulic acid and sinapic acid biosynthesis.
PubMed:
NMR analysis of lignins in CAD-deficient plants. Part 1. Incorporation of hydroxycinnamaldehydes and hydroxybenzaldehydes into lignins.
PubMed:
Purification and characterization of a novel lignin peroxidase from white-rot fungus Phanerochaete sordida YK-624.
PubMed:
Expression pattern of two paralogs encoding cinnamyl alcohol dehydrogenases in Arabidopsis. Isolation and characterization of the corresponding mutants.
PubMed:
Singlet oxygen mediated degradation of lignin--isolation of oxidation products from steam-exploded lignin from pine.
PubMed:
Initial steps of the peroxidase-catalyzed polymerization of coniferyl alcohol and/or sinapyl aldehyde: capillary zone electrophoresis study of pH effect.
PubMed:
Monolignol biosynthesis in microsomal preparations from lignifying stems of alfalfa (Medicago sativa L.).
PubMed:
O-4-Linked coniferyl and sinapyl aldehydes in lignifying cell walls are the main targets of the Wiesner (phloroglucinol-HCl) reaction.
PubMed:
Syntheses of two cytotoxic sinapyl alcohol derivatives and isolation of four new related compounds from Ligularia nelumbifolia.
PubMed:
Quantitative analysis of detailed lignin monomer composition by pyrolysis-gas chromatography combined with preliminary acetylation of the samples.
PubMed:
Analysis of aromatic aldehydes in brandy and wine by high-performance capillary electrophoresis.
PubMed:
The last step of syringyl monolignol biosynthesis in angiosperms is regulated by a novel gene encoding sinapyl alcohol dehydrogenase.
PubMed:
Oxidation of cinnamyl alcohols and aldehydes by a basic peroxidase from lignifying Zinnia elegans hypocotyls.
PubMed:
Elucidation of new structures in lignins of CAD- and COMT-deficient plants by NMR.
PubMed:
Cross-coupling of hydroxycinnamyl aldehydes into lignins.
PubMed:
Coniferyl aldehyde 5-hydroxylation and methylation direct syringyl lignin biosynthesis in angiosperms.
PubMed:
NMR characterization of altered lignins extracted from tobacco plants down-regulated for lignification enzymes cinnamylalcohol dehydrogenase and cinnamoyl-CoA reductase.
PubMed:
A novel aromatic alcohol dehydrogenase in higher plants: molecular cloning and expression.
PubMed:
A novel type of pathogen defense-related cinnamyl alcohol dehydrogenase.
PubMed:
Purification and characterization of isoforms of cinnamyl alcohol dehydrogenase from Eucalyptus xylem.
PubMed:
Purification, Characterization, and Cloning of Cinnamyl Alcohol Dehydrogenase in Loblolly Pine (Pinus taeda L.).
PubMed:
Pharmacologically active phenylpropanoids from Senra incana.
PubMed:
[Simultaneous analysis of aromatic aldehydes and coumarins with high pressure liquid chromatography. Application to wines and brandies stored in oak barrels].
PubMed:
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.