sinapaldehyde

2-propenal, 3-(4-hydroxy-3,5-dimethoxyphenyl)-, (2E)-

CAS: 4206-58-0 C11 H12 O4 MW: 208.21344000

Identification

Namesinapaldehyde
IUPAC(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enal
CAS Number4206-58-0
FDA UNIISearch
Molecular FormulaC11 H12 O4
Molecular Weight208.21344000
MDL NumberMFCD00075980
Nikkaji NumberJ329.696B
Beilstein2215799
CoE Number10341

Regulatory

DG SANTE Food Flavourings05.154 (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 SDSView
European informationMost important hazard(s):
Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categoryflavoring agents
Recommendation for sinapaldehyde usage levels up tonot 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 Concern1800 (μg/person/day)
Structure ClassI
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

None Found

Natural Occurrence

bamboo moso bamboo different brandy and whiskey types - up to 2.7 mg/kg oak wood PMC quercus spp. senra incana walnut black walnut walnut black walnut wood

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⁺ 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.