methyl crotonate

2-butenoic acid methyl ester

CAS: 18707-60-3 C5 H8 O2 MW: 100.11716000

Identification

Namemethyl crotonate
IUPACmethyl but-2-enoate
CAS Number18707-60-3
EINECS242-517-6
FDA UNII3T02JIH93S
Molecular FormulaC5 H8 O2
Molecular Weight100.11716000
Nikkaji NumberJ183.087B
Beilstein1720292

Regulatory

Physical Properties

Appearance colorless to pale yellow clear liquid (est)
Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 121.00 °C. @ 760.00 mm Hg
Vapor Pressure 0.005000 mmHg @ 25.00 °C. (est)
Flash Point 197.00 °F. TCC ( 91.50 °C. ) (est)
logP (o/w) 3.381 (est)
Soluble in alcohol
Insoluble in water

No sensory data available

Safety Information

Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
IFRA Critical EffectDermal sensitization
Recommendation for methyl crotonate usage levels up toPROHIBITED: Should not be used as a fragrance ingredient.
Recommendation for methyl crotonate flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

jasminum sambac lily amazon water lily papaya fruit

Synonyms

2- butenoic acid methyl ester crotonic acid methyl ester 1-( methoxycarbonyl) propene methyl 2-butenoate methyl but-2-enoate PubMed: Cross-Metathesis of Biosourced Fatty Acid Derivatives: A Step Further Toward Improved Reactivity. PubMed: Synthesis of carbon-11-labeled 4-(phenylamino)-pyrrolo[2,1-f][1,2,4]triazine derivatives as new potential PET tracers for imaging of p38α mitogen-activated protein kinase. PubMed: N-Alkylated dinitrones from isosorbide as cross-linkers for unsaturated bio-based polyesters. PubMed: Arylboration of alkenes by cooperative palladium/copper catalysis. PubMed: Accurate bond energies of biodiesel methyl esters from multireference averaged coupled-pair functional calculations. PubMed: Chemical constituents from Inula wissmanniana and their anti-inflammatory activities. PubMed: Thiol-ene click chemistry: computational and kinetic analysis of the influence of alkene functionality. PubMed: The vinylogous aldol reaction of unsaturated esters and enolizable aldehydes using the novel Lewis acid aluminum tris(2,6-di-2-naphthylphenoxide). PubMed: Gas-phase oxidation of methyl crotonate and ethyl crotonate. kinetic study of their reactions toward OH radicals and Cl atoms. PubMed: Phospha-Michael additions to activated internal alkenes: steric and electronic effects. PubMed: Chemopreventive activity of sesquiterpene lactones (SLs) from yacon against TPA-induced Raji cells deformation. PubMed: Rhodium-catalyzed 1,4-addition of lithium 2-furyltriolborates to unsaturated ketones and esters for enantioselective synthesis of γ-oxo-carboxylic acids by oxidation of the furyl ring with ozone. PubMed: Triterpenoids from the leaves of Toona ciliata. PubMed: A versatile strategy for divergent and diastereoselective synthesis of natural product-like polyhydroxylated indolizidines. PubMed: Conjugate addition of 2- and 4-pyridylcuprates: an expeditious asymmetric synthesis of natural (-)-evoninic acid. PubMed: Density functional theory study of electroreductive hydrocoupling of alpha,beta-unsaturated carbonyl compounds. PubMed: Identification of potent odorants in different cultivars of snake fruit [Salacca zalacca (Gaert.) Voss] using gas chromatography-olfactometry. PubMed: An experimental study of the gas-phase reaction of the NO3 radical with alpha,beta-unsaturated carbonyl compounds. PubMed: Gas-phase reactivity of the O=P(OCH3)2 + phosphonium ion towards alpha,beta-unsaturated esters in a quadrupole ion trap. PubMed: 1H chemical shifts in NMR. Part 21--prediction of the 1H chemical shifts of molecules containing the ester group: a modelling and ab initio investigation. PubMed: Theoretical study of the photochemical [2 + 2]-cycloadditions of cyclic and acyclic alpha,beta-unsaturated carbonyl compounds to ethylene. PubMed: First total syntheses of the phytotoxins solanapyrones D and E via the domino Michael protocol. PubMed: Synergistic catalysis of anthrone Diels-Alder reactions. PubMed: Unusual Regioselectivity of the Dipolar Cycloaddition Reactions of Nitrile Oxides and Tertiary Cinnamides and Crotonamides(1). PubMed: Characterization of partially transesterified poly(beta-hydroxyalkanoate)s by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. PubMed: The first total synthesis of (-)-solanapyrone E based on domino Michael strategy. PubMed: Metabolism of ethyl tiglate in apple fruits leads to the formation of small amounts of (R)-ethyl 2-methylbutanoate. PubMed: Characterization of partially transesterified poly(beta-hydroxyalkanoate)s using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. PubMed: Synthesis and analgesic activity of N-aryl/arylalkyl 3-(1-pyrrolidinyl/piperidinyl)butyramides. PubMed: Acylated flavonoids from pseudognaphalium species PubMed: A synthetic approach to benanomicin A. 2. Synthesis of the substituted 5,6-dihydrobenzo[a]naphthacenequinone. PubMed: Carbodications. 4.(1) Hydrogen Isotope Exchange of Crotonyl Cations in Superacid. PubMed: Synthesis of 4-methoxy-2,3,5-trimethylpyridine: a specific building block for compounds with gastric-acid inhibiting activity. PubMed: On the kinetics and mechanism of enoate reductase. PubMed: Identification or urinary mercapturic acids formed from acrylate, methacrylate and crotonate in the rat. PubMed: Purification and some properties of a hitherto-unknown enzyme reducing the carbon-carbon double bond of alpha, beta-unsaturated carboxylate anions. PubMed: Properties of two Clostridia strains acting as catalysts for the preparative stereospecific hydrogenation of 2-enoic acids and 2-alken-1-ols with hydrogen gas. PubMed: [On the specifity and stereospecificity of the conversion of different 2,3-unsaturated acids by Clostridium kluyveri (author's transl)].