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methacrolein

Methacrolein is a naturally occurring unsaturated aldehyde with a floral aroma, commonly present in strawberry fruit and used in natural substances and extractives.
Chemical Structure

General Material Description

Methacrolein is an unsaturated aliphatic aldehyde with the molecular formula C4H6O. It appears as a volatile liquid with characteristic floral odor notes reminiscent of wild hyacinth foliage when diluted. Recognized synonyms include methyl acrolein, 2-methylpropenal, and methacrylic aldehyde among others. Its sensory character, combined with physico-chemical traits, positions it as a natural volatile compound of interest. Methacrolein occurs naturally in various fruits such as strawberry, contributing to their aroma profile. Sourced commonly from natural extracts, it is cataloged in chemical databases like PubChem. The compound is often stabilized with hydroquinone to inhibit polymerization during storage and handling.

Occurrence, Applicability & Potential Uses

Methacrolein is found naturally in the volatile fractions of strawberry fruit, where it contributes to distinctive floral and fruity scents. It is utilized primarily within the realm of natural substances and extractives, serving as a valuable aromatic component in various applications. Regulatory guidance such as FEMA (US) indicates restrictions on the compound's direct use in flavor and fragrance formulations, recommending against such usage. This suggests that while methacrolein imparts notable olfactory characteristics, its application is typically limited to specialized natural extract contexts rather than broad consumer products.

Physico-Chemical Properties Summary

Methacrolein exhibits a low molecular weight of approximately 70.09 g/mol and possesses a moderate volatility profile, boiling between 67 and 68°C at standard atmospheric pressure. It has a vapor density greater than air, at 2.4, and a vapor pressure of 155 mmHg at 25°C, indicating significant volatility that influences its evaporation and dispersion in formulations. The compound's specific gravity ranges from 0.84 to 0.858 at 20°C, and its refractive index lies between 1.412 and 1.419 at the same temperature, indicative of its liquid optical properties. Methacrolein is soluble in water at about 50,000 mg/L at 20°C, which affects its behavior in aqueous systems. Its relatively low estimated log P of 0.681 corresponds to modest lipophilicity, impacting its partitioning in multiphase formulations. Additionally, the compound is shipped with hydroquinone inhibitor to prevent polymerization, a factor critical for handling and storage conditions.

FAQ

What is methacrolein and what synonyms does it have?
Methacrolein is an unsaturated aliphatic aldehyde with the molecular formula C4H6O. It is known by several synonyms including methyl acrolein, 2-methylpropenal, methacryl aldehyde, and isobutenal. This compound is recognized for its floral odor characteristics and natural occurrence in fruits such as strawberries. Methacrolein is used in natural extractives and is cataloged in authoritative databases like PubChem.
Where does methacrolein occur naturally and in what applications is it used?
Methacrolein naturally occurs in certain fruits, notably in the aroma profile of strawberry fruit where it contributes floral and fruity scent notes. It is mainly applied in the realm of natural substances and extractives, being a valued volatile component in natural flavor and fragrance-related materials. However, standards such as FEMA (US) recommend against its direct use in flavor or fragrance formulations due to safety considerations, thus its applications are typically restricted to specialized uses within natural extract contexts.
What are the key safety and regulatory considerations for methacrolein?
Methacrolein is not recommended for direct use in flavor or fragrance products according to specific regulatory guidance, including FEMA (US). Safety data indicate no GHS classification under OSHA (US) hazard communication standards, though toxicity studies report oral LD50 of 140 mg/kg in rats and inhalation LCLo at 125 ppm over four hours. The compound is typically supplied with hydroquinone as a polymerization inhibitor to enhance safe handling. Numerous authoritative sources such as EFSA (EU) and EPA databases provide detailed evaluations on its safety profile, emphasizing cautious use restricted to natural extractives rather than direct additive applications.

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

2-methylprop-2-enal
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:78-85-3
Pubchem (cid):6562
Pubchem (sid):134971081
Pherobase:View
Publications by Info
Volatile Flavor Components in Bogyojosaeng and Suhong Cultivars of Strawberry (Fragaria ananassa Duch.)
Publications by PubMed
Photocatalysis of sub-ppm limonene over multiwalled carbon nanotubes/titania composite nanofiber under visible-light irradiation.
Application of chemical vapor generation systems to deliver constant gas concentrations for in vitro exposure to volatile organic compounds.
Inhalable constituents of thirdhand tobacco smoke: chemical characterization and health impact considerations.
OH-Initiated Photooxidations of 1-Pentene and 2-Methyl-2-propen-1-ol: Mechanism and Yields of the Primary Carbonyl Products.
Hydrogen peroxide enhances the oxidation of oxygenated volatile organic compounds on mineral dust particles: a case study of methacrolein.
Ethanol, isobutanol, and biohydrocarbons as gasoline components in relation to gaseous emissions and particulate matter.
Atmospheric reaction of Cl + methacrolein: a theoretical study on the mechanism, and pressure- and temperature-dependent rate constants.
Enantioselective ruthenium-catalyzed 1,3-dipolar cycloadditions between C-carboalkoxy ketonitrones and methacrolein: solvent effect on reaction selectivity and its rational.
Atmospheric aqueous phase radical chemistry of the isoprene oxidation products methacrolein, methyl vinyl ketone, methacrylic acid and acrylic acid--kinetics and product studies.
Emissions of putative isoprene oxidation products from mango branches under abiotic stress.
Half-sandwich rhodium and iridium complexes containing homochiral imidazolyl-imine ligands: synthesis, characterization and catalytic applications.
Epoxide as a precursor to secondary organic aerosol formation from isoprene photooxidation in the presence of nitrogen oxides.
Formation of dimethylketene and methacrolein by reaction of the CH radical with acetone.
Quantum chemical study of Diels-Alder reactions catalyzed by Lewis acid activated oxazaborolidines.
Sulfate radical-initiated formation of isoprene-derived organosulfates in atmospheric aerosols.
Investigating the impact of aqueous-phase chemistry and wet deposition on organic aerosol formation using a molecular surrogate modeling approach.
Racing carbon atoms. Atomic motion reaction coordinates and structural effects on Newtonian kinetic isotope effects.
Scanning tunneling microscopy study of nano-structured polyatom-substituted H4PW11M1O40 Keggin and H7P2W17M1O62 (M = Nb, Ta) Wells-Dawson heteropolyacid catalysts.
Reaction of methacrolein with the hydroxyl radical in air: incorporation of secondary O2 addition into the MACR + OH master equation.
Branching ratios for the reaction of selected carbonyl-containing peroxy radicals with hydroperoxy radicals.
Atmospheric fate of methacrolein. 2. Formation of lactone and implications for organic aerosol production.
Atmospheric fate of methacrolein. 1. Peroxy radical isomerization following addition of OH and O2.
Measurements of secondary organic aerosol formed from OH-initiated photo-oxidation of isoprene using online photoionization aerosol mass spectrometry.
New types of reactivity of α,β-unsaturated N,N-dimethylhydrazones: chemodivergent diastereoselective synthesis of functionalized tetrahydroquinolines and hexahydropyrrolo[3,2-b]indoles.
Mukaiyama-Michael reactions with acrolein and methacrolein: a catalytic enantioselective synthesis of the C17-C28 fragment of pectenotoxins.
The overall reaction process of ozone with methacrolein and isoprene in the condensed phase.
A VUV photoionization mass spectrometric study on the OH-initiated photooxidation of isoprene with synchrotron radiation.
Direct detection of isoprene photooxidation products by using synchrotron radiation photoionization mass spectrometry.
Uptake of methacrolein into aqueous solutions of sulfuric acid and hydrogen peroxide.
Nanostructured H(3+x)PW(12-x)NbxO40 (x = 0-3) Keggin heteropolyacid catalysts.
Denuder sampling techniques for the determination of gas-phase carbonyl compounds: a comparison and characterisation of in situ and ex situ derivatisation methods.
[Level and characteristics of indoor air pollutants in a furniture mall in Beijing].
Radical dependence of the yields of methacrolein and methyl vinyl ketone from the OH-initiated oxidation of isoprene under NO(x)-free conditions.
Quantitative determination of biogenic volatile organic compounds in the atmosphere using proton-transfer reaction linear ion trap mass spectrometry.
Uptake of methacrolein and methyl vinyl ketone by tree saplings and implications for forest atmosphere.
Quantum chemical study of the acrolein (CH2CHCHO) + OH + O2 reactions.
Kinetics and mechanism of the reaction of methacrolein with chlorine atoms in 1-950 Torr of N2 or N2/O2 diluent at 297 K.
Aluminium complexes derived from tridentate thioetherbis(phenolate) ligands and their activity in Diels-Alder catalysis.
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.
Heterogeneous reactions of methacrolein and methyl vinyl ketone on α-Al2O3 particles.
Chemical composition and size distribution of secondary organic aerosol formed from the photooxidation of isoprene.
Reactive intermediates revealed in secondary organic aerosol formation from isoprene.
Quantum chemistry and TST study of the mechanisms and branching ratios for the reactions of OH with unsaturated aldehydes.
Enantioselective synthesis of allylic alcohols via an oxazaborolidinium ion catalyzed Diels-Alder/Retro-Diels-Alder sequence.
Kinetics of the gas-phase reactions of OH and NO(3) radicals and O(3) with allyl alcohol and allyl isocyanate.
[Contribution of isoprene emitted from vegetable to atmospheric formaldehyde in the ambient air of Beijing city].
Release of volatile organic compounds (VOCs) from the lung cancer cell line CALU-1 in vitro.
[Heterogeneous reactions on the surface of atmospheric particles: a transmission FTIR spectroscopy study].
Development of a proton-transfer reaction-linear ion trap mass spectrometer for quantitative determination of volatile organic compounds.
Volatile aldehydes in the mainstream smoke of the narghile waterpipe.
6,6'-Substituent effect of BINOL in bis-titanium chiral Lewis acid catalyzed 1,3-dipolar cycloaddition of nitrones.
Chiral pyridylamino-ruthenium(II) complexes: synthesis, structure and catalytic properties in Diels-Alder reactions.
A direct route to fluostatin C by a fascinating Diels-Alder reaction.
Asymmetric 1,3-dipolar cycloadditions of N-benzyl and N-diphenylmethyl nitrones and alpha,beta-unsaturated aldehydes catalyzed by bis-titanium chiral Lewis acids.
Substituent effects on dynamics at conical intersections: alpha,beta-enones.
Asymmetric 1,3-dipolar cycloadditions of nitrones and methacrolein catalyzed by chiral bis-titanium lewis acid: a dramatic effect of N-substituent on nitrone.
Pentamethylcyclopentadienyl-iridium(III) complexes with pyridylamino ligands: synthesis and applications as asymmetric catalysts for Diels-Alder reactions.
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.
Overall rate constant measurements of the reaction of hydroxy- and chloroalkylperoxy radicals derived from methacrolein and methyl vinyl ketone with nitric oxide.
Conformational preferences of methacrolein in Diels-Alder and 1,3-dipolar cycloaddition reactions.
Catalytic enantioselective Diels-Alder reaction in ionic liquid via a recyclable chiral In(III) complex.
Methyl vinyl ketone+OH and methacrolein+OH oxidation reactions: a master equation analysis of the pressure- and temperature-dependent rate constants.
Chemical composition of secondary organic aerosol formed from the photooxidation of isoprene.
Ruthenium complexes of thiocinnamaldehydes: synthesis, structure, and [4+2]-cycloaddition reactions.
Stereoselective alkylation of alpha,beta-unsaturated imines via C-H bond activation.
A sensitive method for the quantification of acrolein and other volatile carbonyls in ambient air.
The uptake of methyl vinyl ketone, methacrolein, and 2-methyl-3-butene-2-ol onto sulfuric acid solutions.
Priming of plant defense responses in nature by airborne signaling between Artemisia tridentata and Nicotiana attenuata.
Differentiation of isobaric compounds using chemical ionization reaction mass spectrometry.
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.
[Ozonolysis of methacrolein and methyl vinyl ketone in aqueous solutions].
Pressure dependence in the methyl vinyl ketone + OH and methacrolein + OH oxidation reactions: an electronic structure study.
Oxidative coupling of benzenes with alpha,beta-unsaturated aldehydes by the Pd(OAc)2/molybdovanadophosphoric acid/O2 system.
Catalytic enantioselective Diels-Alder reaction via a chiral indium(III) complex.
Quantitative determination of volatile organic compounds in indoor dust using gas chromatography-UV spectrometry.
Kinetics and products of the OH radical-initiated reaction of 3-methyl-2-butenal.
Total synthesis of (+)-tubelactomicin A. 1. Stereoselective synthesis of the lower-half segment by an intramolecular Diels-Alder approach.
Optimization of MoVSb oxide catalyst for partial oxidation of isobutane by combinatorial approaches.
Measurements of biogenic hydrocarbons and carbonyl compounds emitted by trees from temperate warm Atlantic rainforest, Brazil.
Simple diastereoselectivity of the BF3.OEt2-catalyzed vinylogous Mukaiyama aldol reaction of 2-(trimethylsiloxy)furans with aldehydes.
Monitoring OH-initiated oxidation kinetics of isoprene and its products using online mass spectrometry.
The effect on human eye blink frequency of exposure to limonene oxidation products and methacrolein.
Effects of 1,3-butadiene, isoprene, and their photochemical degradation products on human lung cells.
Cp*Rh complexes with pyridyloxazolines: synthesis, fluxionality and applications as asymmetric catalysts for Diels-Alder reactions.
[CpRu((R)-Binop-F)(H2O)][SbF6], a new fluxional chiral Lewis acid catalyst: synthesis, dynamic nmr, asymmetric catalysis, and theoretical studies.
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.
Airborne observations of vegetation and implications for biogenic emission characterization.
Proton transfer reaction ion trap mass spectrometer.
A new cationic, chiral catalyst for highly enantioselective Diels-Alder reactions.
Description and characterization of an on-line system for long-term measurements of isoprene, methyl vinyl ketone, and methacrolein in ambient air.
Cycloaldol approach to the isobenzofuran core of eunicellin diterpenes.
Highly stereoselective hydroxy-directed Diels-Alder reaction.
New bulky chiral Lewis acid catalyst: 3,3'-di(2-mesitylethynyl)binaphthol-titanium(IV) complex.
Emissions of aldehydes and ketones from a two-stroke engine using ethanol and ethanol-blended gasoline as fuel.
Formation of strong airway irritants in terpene/ozone mixtures.
Airborne carbonyls from motor vehicle emissions in two highway tunnels.
Broadly effective enantioselective Diels-Alder reactions of 1-amino-substituted-1,3-butadienes.
Enantioselective synthesis of the antiinflammatory agent (-)-acanthoic acid.
1-Amino-3-siloxy-1,3-butadienes: Highly Reactive Dienes for the Diels-Alder Reaction.
Formation of strong airway irritants in mixtures of isoprene/ozone and isoprene/ozone/nitrogen dioxide.
An application of electronic asymmetry to highly enantioselective catalytic Diels-Alder reactions.
Characterization of chemical interferences in the determination of unsaturated aldehydes using aromatic hydrazine reagents and liquid chromatography.
GC/ITMS measurement of carbonyls and multifunctional carbonyls in PM2.5 particles emitted from motor vehicles.
On-road emissions of carbonyls from light-duty and heavy-duty vehicles.
Ozone removal in the sampling of parts per billion levels of terpenoid compounds: an evaluation of different scrubber materials.
Diastereoselectivity an chiral ruthenium complexes of chiraphos monoxide ligands: epimerization, quasiracemates, and Lewis acid catalysis.
Effects of methacrolein on the respiratory tract in mice.
Asymmetric Diels-Alder Reaction of Methacrolein with Cyclopentadiene Using Polymer-Supported Catalysts: Design of Highly Enantioselective Polymeric Catalysts.
Formation yields of methyl vinyl ketone and methacrolein from the gas-phase reaction of o3 with isoprene.
The lipid peroxidation product 4-hydroxynonenal is a potent inducer of the SOS response.
Influence of sagebrush terpenoids on mule deer preference.
Cytochemistry and electron microscopy. The preservation of cellular ultrastructure and enzymatic activity by aldehyde fixation.

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
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2912.19.5000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
Formulations/Preparations:
shipped with 0.1% hydroquinone, as polymerization inhibitor

General Material Information

Preferred name methacrolein
Trivial Name Methacrolein
Short Description acrylaldehyde, methyl-
Formula C4 H6 O
CAS Number 78-85-3
ECHA Number 201-150-1
FDA UNII 9HRB24892H
Nikkaji Number J1.484B
Beilstein Number 1209258
MDL MFCD00006974
xLogP3-AA 0.70 (est)
NMR Predictor External link
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-
  • 2-Propenal, 2-methyl-
  • 2-Methyl-2-propenal
  • Isobutenal
  • α-Methylacrolein
  • 2-Methylacrolein
  • Methylacrolein
  • 2-Methylpropenal
  • 2-Methyl-2-propen-1-al
  • 2-Methylenepropanal
  • α-Methacrolein
  • α-Methylacrylaldehyde
  • 2-Formyl-1-propene
  • 2-Methacrolein
  • NSC 8260

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 70.091018676758
Specific gravity @ 20 °C
Pounds per Gallon 6.998 to 7.148
Refractive Index 1.412 to 1.419 @ 20 °C
Boiling Point 67 to 68°C @ 760 mm Hg
Vapor Pressure 155 mmHg @ 25 °C
Vapor Density 2.4
Flash Point TCC Value 1.67 °C TCC
logP (o/w) 0.681 est
Solubility
water, 5.00E+04mg/L @ 20 °C (exp) Yes

Organoleptic Properties

Odor Type: Floral
hyacinth, foliage, green
General comment At 0.01 % in dipropylene glycol. wild hyacinth foliage

Occurrences

Safety Information

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:
oral-rat LD50 140 mg/kg
Union Carbide Data Sheet. Vol. 7/21/1965

Dermal Toxicity:
skin-rabbit LD50 430 ul/kg
Journal of Industrial Hygiene and Toxicology. Vol. 31, Pg. 60, 1949.

Inhalation Toxicity:
inhalation-rat LCLo 125 ppm/4H
Journal of Industrial Hygiene and Toxicology. Vol. 31, Pg. 343, 1949.

Safety in use information

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.

Safety references

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

List of apha, beta-Unsaturated Aldehydes and Ketones representative of FGE.19 substances for Genotoxicity Testing [1] - Statement of the Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids (CEF)
View page or View pdf

Flavouring Group Evaluation 201: 2-Alkylated aliphatic acyclic alpha,beta-unsaturated aldehydes and precursors with or without additional double bonds from chemical subgroup 1.1.2 of FGE.19[1]
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 201 Revision 1 (FGE.201Rev1): 2-Alkylated, aliphatic, acyclic alpha,beta-unsaturated aldehydes and precursors, with or without additional double-bonds, from chemical subgroup 1.1.2 of FGE.19.
View page or View pdf

EPI System: View
NIOSH International Chemical Safety Cards:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):78-85-3
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :6562
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
2-methylprop-2-enal
Chemidplus:0000078853
EPA/NOAA CAMEO:hazardous materials
RTECS:78-85-3