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sinapyl alcohol
phenol, 4-(3-hydroxy-1-propen-1-yl)-2,6-dimethoxy-

Supplier Sponsors

Name:4-(3-hydroxyprop-1-enyl)-2,6-dimethoxyphenol
CAS Number: 537-33-7Picture of molecule3D/inchi
FDA UNII: 8O6NO04SMV
Beilstein Number:3084125
MDL:MFCD00192441
XlogP3-AA:1.30 (est)
Molecular Weight:210.22938000
Formula:C11 H14 O4
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 384.00 to 385.00 °C. @ 760.00 mm Hg (est)
Flash Point: 368.00 °F. TCC ( 186.40 °C. ) (est)
logP (o/w): 1.361 (est)
Soluble in:
 alcohol
 water, 1.713e+004 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
4-[(1E)-3-hydroxyprop-1-en-1-yl]-2,6-dimethoxyphenol 95%
Carbosynth
For experimental / research use only.
Sinapyl Alcohol
Santa Cruz Biotechnology
For experimental / research use only.
Sinapyl Alcohol
Sigma-Aldrich: Aldrich
For experimental / research use only.
Sinapyl alcohol technical grade, 80%
sds
 
Safety Information:
Preferred SDS: View
 
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:
natural substances and extractives
Recommendation for sinapyl alcohol usage levels up to:
 not for fragrance use.
 
Recommendation for sinapyl alcohol flavor usage levels up to:
 not for flavor use.
 
Safety References:
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 :439703
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
4-(3-hydroxyprop-1-enyl)-2,6-dimethoxyphenol
Chemidplus:0000537337
 
References:
 4-(3-hydroxyprop-1-enyl)-2,6-dimethoxyphenol
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):439703
Pubchem (sid):135250914
 
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
Metabolomics Database:Search
KEGG (GenomeNet):C02325
HMDB (The Human Metabolome Database):HMDB13070
FooDB:FDB029281
Export Tariff Code:2909.50.4500
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
 found in nature
 
Synonyms:
4-(3-hydroxy-1-propenyl)-2,6-dimethoxyphenol
4-(3-hydroxyprop-1-en-1-yl)-2,6-dimethoxyphenol
4-(3-hydroxyprop-1-enyl)-2,6-dimethoxyphenol
 phenol, 4-(3-hydroxy-1-propen-1-yl)-2,6-dimethoxy-
 sinapic alcohol
 sinapoyl alcohol
 

Articles:

PubMed:Phenylcoumaran Benzylic Ether Reductase Prevents Accumulation of Compounds Formed under Oxidative Conditions in Poplar Xylem.
PubMed:Molecular cloning of two novel peroxidases and their response to salt stress and salicylic acid in the living fossil Ginkgo biloba.
PubMed:Catalytic profile of Arabidopsis peroxidases, AtPrx-2, 25 and 71, contributing to stem lignification.
PubMed:Molecular cloning and functional analysis of nine cinnamyl alcohol dehydrogenase family members in Populus tomentosa.
PubMed:Microphynolides A and B, new spiro-γ-lactone glycosides from Thymelaea microphylla.
PubMed:Molecular modeling and docking of novel laccase from multiple serotype of Yersinia enterocolitica suggests differential and multiple substrate binding.
PubMed:Enzymatic and metabolic engineering for efficient production of syringin, sinapyl alcohol 4-O-glucoside, in Arabidopsis thaliana.
PubMed:Soluble phenylpropanoids are involved in the defense response of Arabidopsis against Verticillium longisporum.
PubMed:Laccase is necessary and nonredundant with peroxidase for lignin polymerization during vascular development in Arabidopsis.
PubMed:Surface-initiated dehydrogenative polymerization of monolignols: a quartz crystal microbalance with dissipation monitoring and atomic force microscopy study.
PubMed:Visualization of plant cell wall lignification using fluorescence-tagged monolignols.
PubMed:Elucidation of the structure and reaction mechanism of sorghum hydroxycinnamoyltransferase and its structural relationship to other coenzyme a-dependent transferases and synthases.
PubMed:Sinapyl alcohol derivatives from the lipo-soluble part of Dichrocephala benthamii C. B. Clarke.
PubMed:Structural characterization of lignin isolated from coconut (Cocos nucifera) coir fibers.
PubMed:Selective sorption of dissolved organic carbon compounds by temperate soils.
PubMed:Suspension cell culture as a tool for the characterization of class III peroxidases in sugarcane.
PubMed:Phylogeny and structure of the cinnamyl alcohol dehydrogenase gene family in Brachypodium distachyon.
PubMed:Down-regulation of the caffeic acid O-methyltransferase gene in switchgrass reveals a novel monolignol analog.
PubMed:Chemical changes in Ulmus minor xylem tissue after salicylic acid or carvacrol treatments are associated with enhanced resistance to Ophiostoma novo-ulmi.
PubMed:In vitro analysis of the monolignol coupling mechanism using dehydrogenative polymerization in the presence of peroxidases and controlled feeding ratios of coniferyl and sinapyl alcohol.
PubMed:Biochemical characterization and identification of a cinnamyl alcohol dehydrogenase from Artemisia annua.
PubMed:Phenolic compound production in relation to differentiation in cell and tissue cultures of Larrea divaricata (Cav.).
PubMed:AtABCG29 is a monolignol transporter involved in lignin biosynthesis.
PubMed:Environmental stresses of field growth allow cinnamyl alcohol dehydrogenase-deficient Nicotiana attenuata plants to compensate for their structural deficiencies.
PubMed:Identifying new lignin bioengineering targets: impact of epicatechin, quercetin glycoside, and gallate derivatives on the lignification and fermentation of maize cell walls.
PubMed:Purification and kinetic characterization of two peroxidases of Selaginella martensii Spring. involved in lignification.
PubMed:Unusual NADPH conformation in the crystal structure of a cinnamyl alcohol dehydrogenase from Helicobacter pylori in complex with NADP(H) and substrate docking analysis.
PubMed:Changes in cinnamyl alcohol dehydrogenase activities from sugarcane cultivars inoculated with Sporisorium scitamineum sporidia.
PubMed:Membrane protein complexes catalyze both 4- and 3-hydroxylation of cinnamic acid derivatives in monolignol biosynthesis.
PubMed:Syringyl lignin is unaltered by severe sinapyl alcohol dehydrogenase suppression in tobacco.
PubMed:Identification of Tyr74 and Tyr177 as substrate oxidation sites in cationic cell wall-bound peroxidase from Populus alba L.
PubMed:Molecular and biochemical basis for stress-induced accumulation of free and bound p-coumaraldehyde in cucumber.
PubMed:Optimized refolding and characterization of S-peroxidase (CWPO_C of Populus alba) expressed in E. coli.
PubMed:Cloning, expression, functional validation and modeling of cinnamyl alcohol dehydrogenase isolated from xylem of Leucaena leucocephala.
PubMed:Antinociceptive, free radical-scavenging, and cytotoxic activities of Acanthus hirsutus Boiss.
PubMed:Characterization of lignin-rich residues remaining after continuous super-critical water hydrolysis of poplar wood (Populus albaglandulosa) for conversion to fermentable sugars.
PubMed:Vacuum-ultraviolet photoionization and mass spectrometric characterization of lignin monomers coniferyl and sinapyl alcohols.
PubMed:Single-conformation ultraviolet and infrared spectra of jet-cooled monolignols: p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol.
PubMed:Isolation and identification of compounds responsible for antioxidant capacity of Euryale ferox seeds.
PubMed:Cinnamyl alcohols and methyl esters of fatty acids from Wedelia prostrata callus cultures.
PubMed:Distribution of lignin monomers and the evolution of lignification among lower plants.
PubMed:A new phenylpropanoid glycoside from Cirsium setosum.
PubMed:Increase in 4-coumaryl alcohol units during lignification in alfalfa (Medicago sativa) alters the extractability and molecular weight of lignin.
PubMed:Mathematical modeling of monolignol biosynthesis in Populus xylem.
PubMed:Evolution of the Cinnamyl/Sinapyl Alcohol Dehydrogenase (CAD/SAD) gene family: the emergence of real lignin is associated with the origin of Bona Fide CAD.
PubMed:Arabidopsis peroxidase-catalyzed copolymerization of coniferyl and sinapyl alcohols: kinetics of an endwise process.
PubMed:Modeling lignin polymerization. I. Simulation model of dehydrogenation polymers.
PubMed:Sequencing around 5-hydroxyconiferyl alcohol-derived units in caffeic acid O-methyltransferase-deficient poplar lignins.
PubMed:Probing native lignin macromolecular configuration in Arabidopsis thaliana in specific cell wall types: further insights into limited substrate degeneracy and assembly of the lignins of ref8, fah 1-2 and C4H::F5H lines.
PubMed:Continuous UV-B irradiation induces endoreduplication and peroxidase activity in epidermal cells surrounding trichomes on cucumber cotyledons.
PubMed:Influence of syringyl to guaiacyl ratio on the structure of natural and synthetic lignins.
PubMed:The effects on lignin structure of overexpression of ferulate 5-hydroxylase in hybrid poplar.
PubMed:Grass lignin acylation: p-coumaroyl transferase activity and cell wall characteristics of C3 and C4 grasses.
PubMed:The presence of sinapyl lignin in Ginkgo biloba cell cultures changes our views of the evolution of lignin biosynthesis.
PubMed:Monolignol acylation and lignin structure in some nonwoody plants: a 2D NMR study.
PubMed:Novel tetrahydrofuran structures derived from beta-beta-coupling reactions involving sinapyl acetate in Kenaf lignins.
PubMed:Highly acylated (acetylated and/or p-coumaroylated) native lignins from diverse herbaceous plants.
PubMed:A potential role for sinapyl p-coumarate as a radical transfer mechanism in grass lignin formation.
PubMed:Redirection of flux through the phenylpropanoid pathway by increased glucosylation of soluble intermediates.
PubMed:Probabilistic path ranking based on adjacent pairwise coexpression for metabolic transcripts analysis.
PubMed:Looking for syringyl peroxidases.
PubMed:Role of Tyr residues on the protein surface of cationic cell-wall-peroxidase (CWPO-C) from poplar: potential oxidation sites for oxidative polymerization of lignin.
PubMed:Both caffeoyl Coenzyme A 3-O-methyltransferase 1 and caffeic acid O-methyltransferase 1 are involved in redundant functions for lignin, flavonoids and sinapoyl malate biosynthesis in Arabidopsis.
PubMed:Structural motifs of syringyl peroxidases are conserved during angiosperm evolution.
PubMed:Characterization of arabinoxylan-dehydrogenation polymer (synthetic lignin polymer) nanoparticles.
PubMed:The cationic cell-wall-peroxidase having oxidation ability for polymeric substrate participates in the late stage of lignification of Populus alba L.
PubMed:The glucosyltransferase UGT72E2 is responsible for monolignol 4-O-glucoside production in Arabidopsis thaliana.
PubMed:Characterization of two laccases of loblolly pine (Pinus taeda) expressed in tobacco BY-2 cells.
PubMed:Characterization of the last step of lignin biosynthesis in Zinnia elegans suspension cell cultures.
PubMed:Evidence for a role of AtCAD 1 in lignification of elongating stems of Arabidopsis thaliana.
PubMed:Crystal structures and catalytic mechanism of the Arabidopsis cinnamyl alcohol dehydrogenases AtCAD5 and AtCAD4.
PubMed:Monolignol oxidation by xylem peroxidase isoforms of Norway spruce (Picea abies) and silver birch (Betula pendula).
PubMed:Isolation and characterization of a novel peroxidase gene ZPO-C whose expression and function are closely associated with lignification during tracheary element differentiation.
PubMed:GOLD HULL AND INTERNODE2 encodes a primarily multifunctional cinnamyl-alcohol dehydrogenase in rice.
PubMed:Effects of coumarate 3-hydroxylase down-regulation on lignin structure.
PubMed:Design, synthesis, and SAR analysis of cytotoxic sinapyl alcohol derivatives.
PubMed:Differential accumulation of monolignol-derived compounds in elicited flax (Linum usitatissimum) cell suspension cultures.
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:Cloning and molecular characterization of the basic peroxidase isoenzyme from Zinnia elegans, an enzyme involved in lignin biosynthesis.
PubMed:Characterization in vitro and in vivo of the putative multigene 4-coumarate:CoA ligase network in Arabidopsis: syringyl lignin and sinapate/sinapyl alcohol derivative formation.
PubMed:CINNAMYL ALCOHOL DEHYDROGENASE-C and -D are the primary genes involved in lignin biosynthesis in the floral stem of Arabidopsis.
PubMed:Simplified preparation of coniferyl and sinapyl alcohols.
PubMed:Structural and kinetic basis for substrate selectivity in Populus tremuloides sinapyl alcohol dehydrogenase.
PubMed:[Advances in research on lignin biosynthesis and its genetic engineering].
PubMed:The regulation from guaiacyl to syringyl lignin in the differentiating xylem of Robinia pseudoacacia.
PubMed:Anti-inflammatory and antinociceptive effects of sinapyl alcohol and its glucoside syringin.
PubMed:Profiling of oligolignols reveals monolignol coupling conditions in lignifying poplar xylem.
PubMed:Preparation and relevance of a cross-coupling product between sinapyl alcohol and sinapyl p-hydroxybenzoate.
PubMed:Lignins and ferulate-coniferyl alcohol cross-coupling products in cereal grains.
PubMed:Lignification and structural biomass production in tobacco with suppressed caffeic/5-hydroxy ferulic acid-O-methyl transferase activity under ambient and elevated CO concentrations.
PubMed:Lignin dehydrogenative polymerization mechanism: a poplar cell wall peroxidase directly oxidizes polymer lignin and produces in vitro dehydrogenative polymer rich in beta-O-4 linkage.
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: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:Arabidopsis glucosyltransferases with activities toward both endogenous and xenobiotic substrates.
PubMed:Efficiency of lignin biosynthesis: a quantitative analysis.
PubMed:Singlet oxygen mediated degradation of lignin--isolation of oxidation products from steam-exploded lignin from pine.
PubMed:Acylated phenolic glycosides from Solenostemma argel.
PubMed:Multiform biosynthetic pathway of syringyl lignin in angiosperms.
PubMed:Structural and compositional modifications in lignin of transgenic alfalfa down-regulated in caffeic acid 3-O-methyltransferase and caffeoyl coenzyme A 3-O-methyltransferase.
PubMed:O-4-Linked coniferyl and sinapyl aldehydes in lignifying cell walls are the main targets of the Wiesner (phloroglucinol-HCl) reaction.
PubMed:Trends in lignin modification: a comprehensive analysis of the effects of genetic manipulations/mutations on lignification and vascular integrity.
PubMed:Syntheses of two cytotoxic sinapyl alcohol derivatives and isolation of four new related compounds from Ligularia nelumbifolia.
PubMed:Evidence for the biosynthetic pathway from sinapic acid to syringyl lignin using labeled sinapic acid with stable isotope at both methoxy groups in Robinia pseudoacacia and Nerium indicum.
PubMed:Two new steroids from Adenophora stenanthina subsp. xifengensis.
PubMed:Quantitative analysis of detailed lignin monomer composition by pyrolysis-gas chromatography combined with preliminary acetylation of the samples.
PubMed:Progress of lignification mediated by intercellular transportation of monolignols during tracheary element differentiation of isolated Zinnia mesophyll cells.
PubMed:The last step of syringyl monolignol biosynthesis in angiosperms is regulated by a novel gene encoding sinapyl alcohol dehydrogenase.
PubMed:Caffeoyl coenzyme A O-methyltransferase and lignin biosynthesis.
PubMed:Oxidation of cinnamyl alcohols and aldehydes by a basic peroxidase from lignifying Zinnia elegans hypocotyls.
PubMed:The biosynthesis of monolignols: a "metabolic grid", or independent pathways to guaiacyl and syringyl units?
PubMed:Arabidopsis ATP A2 peroxidase. Expression and high-resolution structure of a plant peroxidase with implications for lignification.
PubMed:Identification of glucosyltransferase genes involved in sinapate metabolism and lignin synthesis in Arabidopsis.
PubMed:NMR characterization of altered lignins extracted from tobacco plants down-regulated for lignification enzymes cinnamylalcohol dehydrogenase and cinnamoyl-CoA reductase.
PubMed:Antisense suppression of 4-coumarate:coenzyme A ligase activity in Arabidopsis leads to altered lignin subunit composition.
PubMed:Elicitor-Induced Cinnamyl Alcohol Dehydrogenase Activity in Lignifying Wheat (Triticum aestivum L.) Leaves.
PubMed:Purification and Characterization of Cinnamyl Alcohol Dehydrogenase Isoforms from the Periderm of Eucalyptus gunnii Hook.
PubMed:On the stereoselective synthesis of (+)-pinoresinol in Forsythia suspensa from its achiral precursor, coniferyl alcohol.
PubMed:Synergistic action of phenolic signal compounds and carbohydrates in the induction of virulence gene expression of Agrobacterium tumefaciens.
 
Notes:
Sinapyl alcohol is an organic compound derived from cinnamic acid. This phytochemical is one of the monolignols. It is biosynthetized via the phenylpropanoid biochemical pathway, its immediate precursor being sinapaldehyde. Sinapyl alcohol is a precursor to lignin or lignans. It is also a biosynthetic precursor to various stilbenes and coumarins.[From Wiki] [HMDB]
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