sinapyl alcohol
phenol, 4-(3-hydroxy-1-propen-1-yl)-2,6-dimethoxy-
Identification
| Name | sinapyl alcohol |
| IUPAC | 4-(3-hydroxyprop-1-enyl)-2,6-dimethoxyphenol |
| CAS Number | 537-33-7 |
| FDA UNII | 8O6NO04SMV |
| Molecular Formula | C11 H14 O4 |
| Molecular Weight | 210.22938000 |
| MDL Number | MFCD00192441 |
| Beilstein | 3084125 |
Regulatory
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 |
| Insoluble in | water |
No sensory data available
Safety Information
| Preferred SDS | View |
| 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 | 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. |
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Potential Uses
Natural Occurrence
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
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.