methacrolein
acrylaldehyde, methyl-
Identification
| Name | methacrolein |
| CAS Number | 78-85-3 |
| EINECS | 201-150-1 |
| FDA UNII | 9HRB24892H |
| Molecular Formula | C4 H6 O |
| Molecular Weight | 70.09102000 |
| MDL Number | MFCD00006974 |
| Nikkaji Number | J1.484B |
| Beilstein | 1209258 |
Regulatory
Physical Properties
| Appearance | colorless clear liquid (est) |
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 0.84000 to 0.85800 @ 20.00 °C. |
| Pounds per Gallon - (est). | 6.998 to 7.148 |
| Refractive Index | 1.41200 to 1.41900 @ 20.00 °C. |
| Melting Point | -81.00 °C. @ 760.00 mm Hg |
| Boiling Point | 68.40 °C. @ 760.00 mm Hg, 67.00 to 68.00 °C. @ 760.00 mm Hg (est) |
| Vapor Pressure | 155.000000 mmHg @ 25.00 °C. |
| Vapor Density | 2.4 ( Air = 1 ) |
| Flash Point | 35.00 °F. TCC ( 1.67 °C. ) |
| logP (o/w) | 0.681 (est) |
| Soluble in | water, 5.00E+04mg/L @ 20 °C (exp) |
Organoleptic Properties
| Odor Description | at 0.01 % in dipropylene glycol. |
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | oral-rat LD50 140 mg/kg |
| Dermal Toxicity | skin-rabbit LD50 430 ul/kg |
| Inhalation Toxicity | inhalation-rat LCLo 125 ppm/4H |
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 methacrolein usage levels up to | not for fragrance use. |
| Recommendation for methacrolein flavor usage levels up to | not for flavor use. |
Potential Uses
Natural Occurrence
Synonyms
acrolein, 2-methyl-
acrylaldehyde, methyl-
iso
butenal
methacryl aldehyde
methacrylaldehyde
methacrylaldehyde, inhibited [UN2396] [Flammable liquid]
methacrylic aldehyde
methyl acrolein
2-
methyl acrolein
alpha-
methyl acrolein
methyl acryl aldehyde
2-
methyl propenal
2-
methyl-2-propenal
2-
methyl-propenal
2-
methylacrolein
methylacrylaldehyde
2-
methylacrylaldehyde
2-
methylene propanal
2-
methylenepropanal
2-
methylprop-2-enal
2-
methylpropenal
2-
propenal, 2-methyl-
Info:
Volatile Flavor Components in Bogyojosaeng and Suhong Cultivars of Strawberry (Fragaria ananassa Duch.)
PubMed:
Photocatalysis of sub-ppm limonene over multiwalled carbon nanotubes/titania composite nanofiber under visible-light irradiation.
PubMed:
Application of chemical vapor generation systems to deliver constant gas concentrations for in vitro exposure to volatile organic compounds.
PubMed:
Inhalable constituents of thirdhand tobacco smoke: chemical characterization and health impact considerations.
PubMed:
OH-Initiated Photooxidations of 1-Pentene and 2-Methyl-2-propen-1-ol: Mechanism and Yields of the Primary Carbonyl Products.
PubMed:
Hydrogen peroxide enhances the oxidation of oxygenated volatile organic compounds on mineral dust particles: a case study of methacrolein.
PubMed:
Ethanol, isobutanol, and biohydrocarbons as gasoline components in relation to gaseous emissions and particulate matter.
PubMed:
Atmospheric reaction of Cl + methacrolein: a theoretical study on the mechanism, and pressure- and temperature-dependent rate constants.
PubMed:
Enantioselective ruthenium-catalyzed 1,3-dipolar cycloadditions between C-carboalkoxy ketonitrones and methacrolein: solvent effect on reaction selectivity and its rational.
PubMed:
Atmospheric aqueous phase radical chemistry of the isoprene oxidation products methacrolein, methyl vinyl ketone, methacrylic acid and acrylic acid--kinetics and product studies.
PubMed:
Emissions of putative isoprene oxidation products from mango branches under abiotic stress.
PubMed:
Half-sandwich rhodium and iridium complexes containing homochiral imidazolyl-imine ligands: synthesis, characterization and catalytic applications.
PubMed:
Epoxide as a precursor to secondary organic aerosol formation from isoprene photooxidation in the presence of nitrogen oxides.
PubMed:
Formation of dimethylketene and methacrolein by reaction of the CH radical with acetone.
PubMed:
Quantum chemical study of Diels-Alder reactions catalyzed by Lewis acid activated oxazaborolidines.
PubMed:
Sulfate radical-initiated formation of isoprene-derived organosulfates in atmospheric aerosols.
PubMed:
Investigating the impact of aqueous-phase chemistry and wet deposition on organic aerosol formation using a molecular surrogate modeling approach.
PubMed:
Racing carbon atoms. Atomic motion reaction coordinates and structural effects on Newtonian kinetic isotope effects.
PubMed:
Scanning tunneling microscopy study of nano-structured polyatom-substituted H4PW11M1O40 Keggin and H7P2W17M1O62 (M = Nb, Ta) Wells-Dawson heteropolyacid catalysts.
PubMed:
Reaction of methacrolein with the hydroxyl radical in air: incorporation of secondary O2 addition into the MACR + OH master equation.
PubMed:
Branching ratios for the reaction of selected carbonyl-containing peroxy radicals with hydroperoxy radicals.
PubMed:
Atmospheric fate of methacrolein. 2. Formation of lactone and implications for organic aerosol production.
PubMed:
Atmospheric fate of methacrolein. 1. Peroxy radical isomerization following addition of OH and O2.
PubMed:
Measurements of secondary organic aerosol formed from OH-initiated photo-oxidation of isoprene using online photoionization aerosol mass spectrometry.
PubMed:
New types of reactivity of α,β-unsaturated N,N-dimethylhydrazones: chemodivergent diastereoselective synthesis of functionalized tetrahydroquinolines and hexahydropyrrolo[3,2-b]indoles.
PubMed:
Mukaiyama-Michael reactions with acrolein and methacrolein: a catalytic enantioselective synthesis of the C17-C28 fragment of pectenotoxins.
PubMed:
The overall reaction process of ozone with methacrolein and isoprene in the condensed phase.
PubMed:
A VUV photoionization mass spectrometric study on the OH-initiated photooxidation of isoprene with synchrotron radiation.
PubMed:
Direct detection of isoprene photooxidation products by using synchrotron radiation photoionization mass spectrometry.
PubMed:
Uptake of methacrolein into aqueous solutions of sulfuric acid and hydrogen peroxide.
PubMed:
Nanostructured H(3+x)PW(12-x)NbxO40 (x = 0-3) Keggin heteropolyacid catalysts.
PubMed:
Denuder sampling techniques for the determination of gas-phase carbonyl compounds: a comparison and characterisation of in situ and ex situ derivatisation methods.
PubMed:
[Level and characteristics of indoor air pollutants in a furniture mall in Beijing].
PubMed:
Radical dependence of the yields of methacrolein and methyl vinyl ketone from the OH-initiated oxidation of isoprene under NO(x)-free conditions.
PubMed:
Quantitative determination of biogenic volatile organic compounds in the atmosphere using proton-transfer reaction linear ion trap mass spectrometry.
PubMed:
Uptake of methacrolein and methyl vinyl ketone by tree saplings and implications for forest atmosphere.
PubMed:
Quantum chemical study of the acrolein (CH2CHCHO) + OH + O2 reactions.
PubMed:
Kinetics and mechanism of the reaction of methacrolein with chlorine atoms in 1-950 Torr of N2 or N2/O2 diluent at 297 K.
PubMed:
Aluminium complexes derived from tridentate thioetherbis(phenolate) ligands and their activity in Diels-Alder catalysis.
PubMed:
Comparison of carcinogen, carbon monoxide, and ultrafine particle emissions from narghile waterpipe and cigarette smoking: Sidestream smoke measurements and assessment of second-hand smoke emission factors.
PubMed:
Heterogeneous reactions of methacrolein and methyl vinyl ketone on α-Al2O3 particles.
PubMed:
Chemical composition and size distribution of secondary organic aerosol formed from the photooxidation of isoprene.
PubMed:
Reactive intermediates revealed in secondary organic aerosol formation from isoprene.
PubMed:
Quantum chemistry and TST study of the mechanisms and branching ratios for the reactions of OH with unsaturated aldehydes.
PubMed:
Enantioselective synthesis of allylic alcohols via an oxazaborolidinium ion catalyzed Diels-Alder/Retro-Diels-Alder sequence.
PubMed:
Kinetics of the gas-phase reactions of OH and NO(3) radicals and O(3) with allyl alcohol and allyl isocyanate.
PubMed:
[Contribution of isoprene emitted from vegetable to atmospheric formaldehyde in the ambient air of Beijing city].
PubMed:
Release of volatile organic compounds (VOCs) from the lung cancer cell line CALU-1 in vitro.
PubMed:
[Heterogeneous reactions on the surface of atmospheric particles: a transmission FTIR spectroscopy study].
PubMed:
Development of a proton-transfer reaction-linear ion trap mass spectrometer for quantitative determination of volatile organic compounds.
PubMed:
Volatile aldehydes in the mainstream smoke of the narghile waterpipe.
PubMed:
6,6'-Substituent effect of BINOL in bis-titanium chiral Lewis acid catalyzed 1,3-dipolar cycloaddition of nitrones.
PubMed:
Chiral pyridylamino-ruthenium(II) complexes: synthesis, structure and catalytic properties in Diels-Alder reactions.
PubMed:
A direct route to fluostatin C by a fascinating Diels-Alder reaction.
PubMed:
Asymmetric 1,3-dipolar cycloadditions of N-benzyl and N-diphenylmethyl nitrones and alpha,beta-unsaturated aldehydes catalyzed by bis-titanium chiral Lewis acids.
PubMed:
Substituent effects on dynamics at conical intersections: alpha,beta-enones.
PubMed:
Asymmetric 1,3-dipolar cycloadditions of nitrones and methacrolein catalyzed by chiral bis-titanium lewis acid: a dramatic effect of N-substituent on nitrone.
PubMed:
Pentamethylcyclopentadienyl-iridium(III) complexes with pyridylamino ligands: synthesis and applications as asymmetric catalysts for Diels-Alder reactions.
PubMed:
The first aza Diels-Alder reaction involving an alpha,beta-unsaturated hydrazone as the dienophile: stereoselective synthesis of C-4 functionalized 1,2,3,4-tetrahydroquinolines containing a quaternary stereocenter.
PubMed:
Overall rate constant measurements of the reaction of hydroxy- and chloroalkylperoxy radicals derived from methacrolein and methyl vinyl ketone with nitric oxide.
PubMed:
Conformational preferences of methacrolein in Diels-Alder and 1,3-dipolar cycloaddition reactions.
PubMed:
Catalytic enantioselective Diels-Alder reaction in ionic liquid via a recyclable chiral In(III) complex.
PubMed:
Methyl vinyl ketone+OH and methacrolein+OH oxidation reactions: a master equation analysis of the pressure- and temperature-dependent rate constants.
PubMed:
Chemical composition of secondary organic aerosol formed from the photooxidation of isoprene.
PubMed:
Ruthenium complexes of thiocinnamaldehydes: synthesis, structure, and [4+2]-cycloaddition reactions.
PubMed:
Stereoselective alkylation of alpha,beta-unsaturated imines via C-H bond activation.
PubMed:
A sensitive method for the quantification of acrolein and other volatile carbonyls in ambient air.
PubMed:
The uptake of methyl vinyl ketone, methacrolein, and 2-methyl-3-butene-2-ol onto sulfuric acid solutions.
PubMed:
Priming of plant defense responses in nature by airborne signaling between Artemisia tridentata and Nicotiana attenuata.
PubMed:
Differentiation of isobaric compounds using chemical ionization reaction mass spectrometry.
PubMed:
Enantioselective 1,3-dipolar cycloaddition of nitrones to methacrolein catalyzed by (eta5-C5Me5)M{(R)-prophos} containing complexes (M = Rh, Ir; (R)-prophos = 1,2-bis(diphenylphosphino)propane): on the origin of the enantioselectivity.
PubMed:
[Ozonolysis of methacrolein and methyl vinyl ketone in aqueous solutions].
PubMed:
Pressure dependence in the methyl vinyl ketone + OH and methacrolein + OH oxidation reactions: an electronic structure study.
PubMed:
Oxidative coupling of benzenes with alpha,beta-unsaturated aldehydes by the Pd(OAc)2/molybdovanadophosphoric acid/O2 system.
PubMed:
Catalytic enantioselective Diels-Alder reaction via a chiral indium(III) complex.
PubMed:
Quantitative determination of volatile organic compounds in indoor dust using gas chromatography-UV spectrometry.
PubMed:
Kinetics and products of the OH radical-initiated reaction of 3-methyl-2-butenal.
PubMed:
Total synthesis of (+)-tubelactomicin A. 1. Stereoselective synthesis of the lower-half segment by an intramolecular Diels-Alder approach.
PubMed:
Optimization of MoVSb oxide catalyst for partial oxidation of isobutane by combinatorial approaches.
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Measurements of biogenic hydrocarbons and carbonyl compounds emitted by trees from temperate warm Atlantic rainforest, Brazil.
PubMed:
Simple diastereoselectivity of the BF3.OEt2-catalyzed vinylogous Mukaiyama aldol reaction of 2-(trimethylsiloxy)furans with aldehydes.
PubMed:
Monitoring OH-initiated oxidation kinetics of isoprene and its products using online mass spectrometry.
PubMed:
The effect on human eye blink frequency of exposure to limonene oxidation products and methacrolein.
PubMed:
Effects of 1,3-butadiene, isoprene, and their photochemical degradation products on human lung cells.
PubMed:
Cp*Rh complexes with pyridyloxazolines: synthesis, fluxionality and applications as asymmetric catalysts for Diels-Alder reactions.
PubMed:
[CpRu((R)-Binop-F)(H2O)][SbF6], a new fluxional chiral Lewis acid catalyst: synthesis, dynamic nmr, asymmetric catalysis, and theoretical studies.
PubMed:
The complete characterization of a rhodium Lewis acid-dipolarophile complex as an intermediate for the enantioselective catalytic 1,3-dipolar cycloaddition of C,N-diphenylnitrone to methacrolein.
PubMed:
Airborne observations of vegetation and implications for biogenic emission characterization.
PubMed:
Proton transfer reaction ion trap mass spectrometer.
PubMed:
A new cationic, chiral catalyst for highly enantioselective Diels-Alder reactions.
PubMed:
Description and characterization of an on-line system for long-term measurements of isoprene, methyl vinyl ketone, and methacrolein in ambient air.
PubMed:
Cycloaldol approach to the isobenzofuran core of eunicellin diterpenes.
PubMed:
Highly stereoselective hydroxy-directed Diels-Alder reaction.
PubMed:
New bulky chiral Lewis acid catalyst: 3,3'-di(2-mesitylethynyl)binaphthol-titanium(IV) complex.
PubMed:
Emissions of aldehydes and ketones from a two-stroke engine using ethanol and ethanol-blended gasoline as fuel.
PubMed:
Formation of strong airway irritants in terpene/ozone mixtures.
PubMed:
Airborne carbonyls from motor vehicle emissions in two highway tunnels.
PubMed:
Broadly effective enantioselective Diels-Alder reactions of 1-amino-substituted-1,3-butadienes.
PubMed:
Enantioselective synthesis of the antiinflammatory agent (-)-acanthoic acid.
PubMed:
1-Amino-3-siloxy-1,3-butadienes: Highly Reactive Dienes for the Diels-Alder Reaction.
PubMed:
Formation of strong airway irritants in mixtures of isoprene/ozone and isoprene/ozone/nitrogen dioxide.
PubMed:
An application of electronic asymmetry to highly enantioselective catalytic Diels-Alder reactions.
PubMed:
Characterization of chemical interferences in the determination of unsaturated aldehydes using aromatic hydrazine reagents and liquid chromatography.
PubMed:
GC/ITMS measurement of carbonyls and multifunctional carbonyls in PM2.5 particles emitted from motor vehicles.
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On-road emissions of carbonyls from light-duty and heavy-duty vehicles.
PubMed:
Ozone removal in the sampling of parts per billion levels of terpenoid compounds: an evaluation of different scrubber materials.
PubMed:
Diastereoselectivity an chiral ruthenium complexes of chiraphos monoxide ligands: epimerization, quasiracemates, and Lewis acid catalysis.
PubMed:
Effects of methacrolein on the respiratory tract in mice.
PubMed:
Asymmetric Diels-Alder Reaction of Methacrolein with Cyclopentadiene Using Polymer-Supported Catalysts: Design of Highly Enantioselective Polymeric Catalysts.
PubMed:
Formation yields of methyl vinyl ketone and methacrolein from the gas-phase reaction of o3 with isoprene.
PubMed:
The lipid peroxidation product 4-hydroxynonenal is a potent inducer of the SOS response.
PubMed:
Influence of sagebrush terpenoids on mule deer preference.
PubMed:
Cytochemistry and electron microscopy. The preservation of cellular ultrastructure and enzymatic activity by aldehyde fixation.