EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

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

Supplier Sponsors

Name:(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enal
CAS Number: 4206-58-0Picture of molecule3D/inchi
FDA UNII: Search
Nikkaji Web:J329.696B
Beilstein Number:2215799
MDL:MFCD00075980
CoE Number:10341
XlogP3-AA:1.40 (est)
Molecular Weight:208.21344000
Formula:C11 H12 O4
NMR Predictor:Predict (works with chrome, Edge or firefox)
EFSA/JECFA Comments:
E-isomer (EFFA, 2010a). Register name to be changed accordingly.
Category:flavoring agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
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)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Sinapaldehyde
Carbosynth
For experimental / research use only.
Sinapaldehyde
ExtraSynthese
For experimental / research use only.
trans-3,5-Dimethoxy-4-hydroxycinnamaldehyde (GC) ≥95%
Penta International
TRANS-3,5-DIMETHOXY-4-HYDROXYCINNAMALDEHYDE
Sigma-Aldrich: Aldrich
For experimental / research use only.
trans-3,5-Dimethoxy-4-hydroxycinnamaldehyde 98%
sds
 
Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 37/39 - Wear suitable gloves and eye/face protection.
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
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
 
Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i).
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm.
 average usage mg/kgmaximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0): 3.0000015.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): 2.0000010.00000
Edible ices, including sherbet and sorbet (03.0): 3.0000015.00000
Processed fruit (04.1): 7.0000035.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 4.0000020.00000
Chewing gum (05.3): --
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 2.0000010.00000
Bakery wares (07.0): 5.0000025.00000
Meat and meat products, including poultry and game (08.0): 1.000005.00000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): 1.000005.00000
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 2.0000010.00000
Foodstuffs intended for particular nutritional uses (13.0): 3.0000015.00000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): 2.0000010.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 4.0000020.00000
Ready-to-eat savouries (15.0): 5.0000025.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): 2.0000010.00000
 
Safety References:
European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Flavouring Group Evaluation 214: alpha,beta-Unsaturated aldehydes and precursors from chemical subgroup 3.1 of FGE.19: Cinnamyl derivatives[1]
View page or View pdf

Flavouring Group Evaluation 15, Revision 2 (FGE.15Rev2): Aryl-substituted saturated and unsaturated primary alcohol/aldehyde/acid/ester derivatives from chemical group 22
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5280802
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enal
Chemidplus:0004206580
 
References:
 (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enal
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5280802
Pubchem (sid):135074162
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
Golm Metabolome Database:Search
Metabolomics Database:Search
KEGG (GenomeNet):C05610
HMDB (The Human Metabolome Database):Search
FooDB:FDB001515
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 bamboo moso bamboo
Search Trop Picture
 different brandy and whiskey types - up to 2.7 mg/kg
 oak wood
Search PMC Picture
 quercus spp.
Search Trop Picture
 senra incana
Search Trop Picture
 walnut black walnut
Search Trop Picture
 walnut black walnut wood
Search Trop Picture
 
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
 

Articles:

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.
 
Notes:
from aqueous extract of senra incana.
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