methyl crotonate
2-butenoic acid methyl ester
Identification
| Name | methyl crotonate |
| IUPAC | methyl but-2-enoate |
| CAS Number | 18707-60-3 |
| EINECS | 242-517-6 |
| FDA UNII | 3T02JIH93S |
| Molecular Formula | C5 H8 O2 |
| Molecular Weight | 100.11716000 |
| Nikkaji Number | J183.087B |
| Beilstein | 1720292 |
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 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 |
| IFRA Critical Effect | Dermal sensitization |
| Recommendation for methyl crotonate usage levels up to | PROHIBITED: Should not be used as a fragrance ingredient. |
| Recommendation for methyl crotonate flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
2-
butenoic acid methyl ester
crotonic acid methyl ester
1-(
methoxycarbonyl) propene
methyl 2-butenoate
methyl but-2-enoate
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Cross-Metathesis of Biosourced Fatty Acid Derivatives: A Step Further Toward Improved Reactivity.
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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.
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The vinylogous aldol reaction of unsaturated esters and enolizable aldehydes using the novel Lewis acid aluminum tris(2,6-di-2-naphthylphenoxide).
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Gas-phase oxidation of methyl crotonate and ethyl crotonate. kinetic study of their reactions toward OH radicals and Cl atoms.
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Phospha-Michael additions to activated internal alkenes: steric and electronic effects.
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Chemopreventive activity of sesquiterpene lactones (SLs) from yacon against TPA-induced Raji cells deformation.
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An experimental study of the gas-phase reaction of the NO3 radical with alpha,beta-unsaturated carbonyl compounds.
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Gas-phase reactivity of the O=P(OCH3)2 + phosphonium ion towards alpha,beta-unsaturated esters in a quadrupole ion trap.
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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.
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Theoretical study of the photochemical [2 + 2]-cycloadditions of cyclic and acyclic alpha,beta-unsaturated carbonyl compounds to ethylene.
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First total syntheses of the phytotoxins solanapyrones D and E via the domino Michael protocol.
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Synergistic catalysis of anthrone Diels-Alder reactions.
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Unusual Regioselectivity of the Dipolar Cycloaddition Reactions of Nitrile Oxides and Tertiary Cinnamides and Crotonamides(1).
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Characterization of partially transesterified poly(beta-hydroxyalkanoate)s by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.
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The first total synthesis of (-)-solanapyrone E based on domino Michael strategy.
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Metabolism of ethyl tiglate in apple fruits leads to the formation of small amounts of (R)-ethyl 2-methylbutanoate.
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Characterization of partially transesterified poly(beta-hydroxyalkanoate)s using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.
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Acylated flavonoids from pseudognaphalium species
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A synthetic approach to benanomicin A. 2. Synthesis of the substituted 5,6-dihydrobenzo[a]naphthacenequinone.
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Carbodications. 4.(1) Hydrogen Isotope Exchange of Crotonyl Cations in Superacid.
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Synthesis of 4-methoxy-2,3,5-trimethylpyridine: a specific building block for compounds with gastric-acid inhibiting activity.
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On the kinetics and mechanism of enoate reductase.
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Identification or urinary mercapturic acids formed from acrylate, methacrylate and crotonate in the rat.
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Purification and some properties of a hitherto-unknown enzyme reducing the carbon-carbon double bond of alpha, beta-unsaturated carboxylate anions.
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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.
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[On the specifity and stereospecificity of the conversion of different 2,3-unsaturated acids by Clostridium kluyveri (author's transl)].