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methyl crotonate
2-butenoic acid methyl ester

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Flavor Demo Formulas
Name:methyl but-2-enoate
CAS Number: 18707-60-3Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:242-517-6
FDA UNII: 3T02JIH93S
Nikkaji Web:J183.087B
Beilstein Number:1720292
XlogP3-AA:0.90 (est)
Molecular Weight:100.11716000
Formula:C5 H8 O2
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
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Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
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
 water, 1.241e+004 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Godavari Biorefineries
Methyl Crotonate
SRS Aromatics
METHYL CROTONATE
Synerzine
Methyl Crotonate
 
Safety Information:
 
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:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
IFRA Critical Effect:
Dermal sensitization
 View the IFRA Standard
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.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):18707-60-3
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :638132
National Institute of Allergy and Infectious Diseases:Data
methyl but-2-enoate
Chemidplus:0018707603
 
References:
 methyl but-2-enoate
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:18707-60-3
Pubchem (cid):638132
Pubchem (sid):134977110
Pherobase:View
 
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
CHEMBL:View
HMDB (The Human Metabolome Database):Search
FooDB:FDB004707
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 jasminum sambac
Search Trop Picture
 lily amazon water lily
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 papaya fruit
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Synonyms:
2-butenoic acid methyl ester
 crotonic acid methyl ester
1-(methoxycarbonyl) propene
 methyl 2-butenoate
 methyl but-2-enoate
 

Articles:

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)].
 
Notes:
None found
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