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methyl propionate

Chemical Structure

General Material Information

Preferred name methyl propionate
Trivial Name Methyl propionate
Short Description propanoic acid, methyl ester
Formula C4 H8 O2
CAS Number 554-12-1
FEMA Number 2742
Flavis Number 9.134
ECHA Number 209-060-4
FDA UNII NB21C0D33W
Nikkaji Number J2.654I
Beilstein Number 1737628
MDL MFCD00009306
COE Number 415
NMR Predictor External link
JECFA Food Flavoring 141 methyl propionate
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 554-12-1 ; METHYL PROPIONATE
Synonyms
  • methyl propanoate
  • nat. methyl propionate
  • methyl propionate, natural
  • methyl propylate
  • methylpropanoate
  • methylpropionate
  • propanoic acid methyl ester
  • propanoic acid, methyl ester
  • propionic acid methyl ester
  • propionic acid, methyl ester
  • NSC 9375

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

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Literature & References

methyl propanoate
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:554-12-1
Pubchem (cid):11124
Pubchem (sid):134976147
Pherobase:View
Publications by Info
Volatile Flavor Components in Bogyojosaeng and Suhong Cultivars of Strawberry (Fragaria ananassa Duch.)
Publications by PubMed
Iridium(I) PNP complexes in the sp³ C-H bond activation of methyl propanoate and related esters.
Carbonylation of ethene catalysed by Pd(II)-phosphine complexes.
Synthesis of methyl propanoate by Baeyer-Villiger monooxygenases.
Mikania glomerata: Phytochemical, Pharmacological, and Neurochemical Study.
Crystal structures of (μ2-η(2),η(2)-4-hydroxybut-2-yn-1-yl 2-bromo-2-methylpropanoate-κ(4) C (2),C (3):C (2),C (3))bis[tricarbonylcobalt(II)](Co-Co) and [μ2-η(2),η(2)-but-2-yne-1,4-diyl bis(2-bromo-2-methyl-propanoate)-κ(4) C (2),C (3):C (2),C (3)]bis[tricarbonylcobalt(II)](Co-Co).
Theoretical study of the rate constants for the hydrogen atom abstraction reactions of esters with (•)OH radicals.
Reactions of Cl atoms with alkyl esters: kinetic, mechanism and atmospheric implications.
Endophytic fungi producing of esterases: evaluation in vitro of the enzymatic activity using pH indicator.
Elucidation of the upper pathway of alicyclic musk Romandolide degradation in OECD screening tests with activated sludge.
Applicability of non-halogenated methyl propionate to microencapsulation.
Theoretical and kinetic study of the hydrogen atom abstraction reactions of esters with H(O.)2 radicals.
Gas signatures from Escherichia coli and Escherichia coli-inoculated human whole blood.
Redirecting catalysis from proteolysis to perhydrolysis in subtilisin Carlsberg.
Determination of odor release in hydrocolloid model systems containing original or carboxylated cellulose at different pH values using static headspace gas chromatographic (SHS-GC) analysis.
High-temperature measurements of the reactions of OH with small methyl esters: methyl formate, methyl acetate, methyl propanoate, and methyl butanoate.
Solvent- or temperature-controlled diastereoselective aldol reaction of methyl phenylacetate.
Transferable force field for carboxylate esters: application to fatty acid methylic ester phase equilibria prediction.
Benzyl 2-{4-[2-(4-chloro-benzoyl-amino)-eth-yl]phen-oxy}-2-methyl-propionate.
Volatile compounds responsible for aroma of Jutrzenka liquer wine.
Atmospheric chemistry of two biodiesel model compounds: methyl propionate and ethyl acetate.
Characterization of odor-active compounds of various cherry wines by gas chromatography-mass spectrometry, gas chromatography-olfactometry and their correlation with sensory attributes.
The first example of main-chain cyclic azobenzene polymers.
An engineered methanogenic pathway derived from the domains Bacteria and Archaea.
Effect of nitroethane, dimethyl-2-nitroglutarate and 2-nitro-methyl-propionate on ruminal methane production and hydrogen balance in vitro.
Absolute configuration of methyl isoeichlerialactone.
tert-Butyl 2-(4-chloro-benzo-yl)-2-methyl-propanoate.
tert-Butyl 2-benzoyl-2-methyl-propanoate.
On the low volatility of cyclic esters: an infrared spectroscopy comparison between dimers of gamma-butyrolactone and methyl propionate.
Effect of methylene spacers on the spectral, electrochemical, and structural properties of bis(4,4'-disubstituted-2,2'-bipyridyl) ruthenium(II) dye analogues.
Controllable nanostructured surface modification on quantum dot for biomedical application in aqueous medium.
Diphenylphosphine containing macromolecules in the methoxycarbonylation of ethene: the effect of macromolecular architecture on the selectivity of the reaction.
Theoretical studies on structures and spectroscopic properties of self-assembled bis(2,4,8,10-tetramethyl-9-methoxycarbonylethyldipyrrin-3-yl)methane with Co(II).
Polymer producing palladium complexes of unidentate phosphines in the methoxycarbonylation of ethene.
Poly[(μ(2)-2-hydr-oxy-2-methyl-propionato-κO,O:O)(μ(2)-2-hydr-oxy-2-methyl-propionato-κO:κO)dioxido-uranium(VI)].
Facile functionalization of multilayer fullerenes (carbon nano-onions) by nitrene chemistry and "grafting from" strategy.
In-situ polymerization at the interfaces of micelles: a "grafting from" method to prepare micelles with mixed coronal chains.
New polyethylene macroinitiators and their subsequent grafting by atom transfer radical polymerization.
Kinetic studies of fusarium solani pisi cutinase used in a gas/solid system: transesterification and hydrolysis reactions.
One- and two-dimensional direct chiral liquid chromatographic determination of mixtures of diclofop-Acid and diclofop-methyl herbicides.
2-Methyl-2-(4-nitro-phen-oxy)propanoic acid.
Methyl 3-(4-{6-methyl-4-[3-(trifluoro-meth-yl)phen-yl]pyridazin-3-yl-oxy}phen-yl)propanoate.
Opposite signs of capacitive microsensor signals upon exposure to the enantiomers of methyl propionate compounds.
Effects of short-chain nitrocompounds against Campylobacter jejuni and Campylobacter coli in vitro.
Correlating volatile compounds, sensory attributes, and quality parameters in stored fresh-cut cantaloupe.
Solvent as a competitive inhibitor for Candida antarctica lipase B.
Ester versus polyketone formation in the palladium-diphosphine catalyzed carbonylation of ethene.
Isolation and characterization of dihydromonacolin-MV from Monascus purpureus for antioxidant properties.
Recognition of small polar molecules with an ionic crystal of alpha-Keggin-type polyoxometalate with a macrocation.
NMR spectroscopy and MALDI-TOF MS characterisation of end-functionalised PVP oligomers prepared with different esters as chain transfer agents.
Behaviour of [PdH(dppe)2]X (X=CF3SO3-, SbF6-, BF4-) as proton or hydride donor: relevance to catalysis.
Effect of oil substitution in chiral microemulsion electrokinetic chromatography.
Solid/gas biocatalysis: an appropriate tool to study the influence of organic components on kinetics of lipase-catalyzed alcoholysis.
Alcoholysis catalyzed by Candida antarctica lipase B in a gas/solid system: effects of water on kinetic parameters.
Alcoholysis of acylpalladium(II) complexes relevant to the alternating copolymerization of ethene and carbon monoxide and the alkoxycarbonylation of alkenes: the importance of Cis-coordinating phosphines.
Total synthesis of Elisabethin A: intramolecular Diels-Alder reaction under biomimetic conditions.
Determination of PNU-248686A, a novel matrix metalloproteinase inhibitor, in human plasma by liquid chromatography-tandem mass spectrometry, following protein precipitation in the 96-well plate format.
Water plays a different role on activation thermodynamic parameters of alcoholysis reaction catalyzed by lipase in gaseous and organic media.
Gas-phase reactivity of the O=P(OCH3)2+ phosphonium ion with aliphatic esters in a quadrupole ion trap. Spontaneous elimination of ketenes.
Alcoholysis catalyzed by Candida antarctica lipase B in a gas/solid system obeys a Ping Pong Bi Bi mechanism with competitive inhibition by the alcohol substrate and water.
Identification and effects of interaction phytotoxic compounds from exudate of Cistus ladanifer leaves.
Stereoselective synthesis of iso-dolaproine via dynamic kinetic resolution.
Systematic studies on synthesis, structural elucidation, and biological evaluation of A-ring diastereomers of 2-methyl-1alpha,25-dihydroxyvitamin D(3) and 20-epi-2-methyl-1alpha,25-dihydroxyvitamin D(3).
Syntheses of carbon-11 labeled piperidine esters as potential in vivo substrates for acetylcholinesterase.
[Interpretation of the resonance Raman spectrum of cytochrome P-450].
Determination of remifentanil, an ultra-short-acting opioid anesthetic, in rat blood by high performance liquid chromatography with ultraviolet detection.
Methyl propionate radical cation.
Seed Dormancy in Red Rice (Oryza sativa) (IX. Embryo Fructose-2,6-Bisphosphate during Dormancy Breaking and Subsequent Germination).
Purification and characterization of a carboxylesterase from Pseudomonas sp. KWI-56.
Determination of remifentanil in human and dog blood by HPLC with UV detection.
Seed Dormancy in Red Rice : VIII. Embryo Acidification during Dormancy-Breaking and Subsequent Germination.
Gas phase transesterification reactions catalyzed by lipolytic enzymes.
Enhancement of the CDC ovitrap with hay infusions for daily monitoring of Aedes aegypti populations.
The effect of short term feeding of the antioxidant triethyleneglycol-bis-3(3-tert-butyl-4-hydroxy-5-methyl)propionate on serum thyrotropin and thyroid hormones in the male rat.
Effect of peroxisome proliferators on intrachromosomal and interchromosomal recombination in yeast.
Species differences in the chirality of the carbonyl reduction of [14C] fenofibrate in laboratory animals and humans.
[Synthesis of carbon-14 labeled 1-acetoxyethyl 2-(2-fluoro-4-biphenyl)propionate (14C-FP 83)].
Observations concerning the nature of sites of anaesthetic action in Gammarus.
Factors affecting oviposition site preference by Toxorhynchites splendens in the laboratory.
Purification and characterization of 3-hydroxyisobutyrate dehydrogenase from rabbit liver.
Local anesthetic action of carboxylic esters: evidence for the significance of molecular volume and for the number of sites involved.
Properties of the Mg-Protoporphyrin IX Monomethyl Ester (Oxidative) Cyclase System.
Ethyl acrylate-induced gastric toxicity. II. Structure-toxicity relationships and mechanism.
Proposed structure for the noncovalently associated heme prosthetic group of dissimilatory nitrite reductases. Configuration of substituents of acrylochlorin.
Evaluation of selected hypolipidemic agents for the induction of peroxisomal enzymes and peroxisome proliferation in the rat liver.
Induction of hamster hepatic peroxisomal beta-oxidation and peroxisome proliferation-associated 80000 mol. wt. polypeptide by hypolipidemic drugs.
Uricosuric effect of fenofibrate in healthy volunteers.
[Chemistry of phenoxyacetic acid esters of oxyalkyltheophyllines and 1-(theophyllin-7-yl)-ethyl-2-[2-(p-chlorophenoxy)-2-methyl-propionate] (etofylline clofibrate), a novel antilipaemic agent (author's transl)].
Volatiles produced by microorganisms isolated from refrigerated chicken at spoilage.
Antilipidemic drugs. Part 4: The metabolic fate of the hypolipidemic agent isopropyl-[4'-(p-chlorobenzoyl)-2-phenoxy-2-methyl]-protionate (LF 178) in rats, dog and man.
Antilipidemic drugs. Part 3: On the synthesis of 14C-radiolabelled isopropyl-[4'-chlorobenzoyl)-2-phenoxy-2-methyl]-propionate (LF-178).
Antilipidemic drugs. Part 2: Experimental study of a new potent hypolipidemic drug, isopropyl-[4'-(p-chlorobenzoyl)-2-phenoxy-2-methyl]-propionate (LF178).
Antilipidemic drugs. Part 6: LF 178 in man. A preliminary note on a multicenter investigation bearing on 393 subjects with pure or mixed forms of hyperlipidemia.
Atilipidemic drugs. Part 5: Evaluation of the hypolipidemic effect of LF 178 in 191 patients affected by the atherogenic form of endogenous hyperlipoproteinemia (types IIa, IIb and IV).
The oxidation products of crude mesobilirubinogen.
Influence of ethyl-2 [chlorophenoxy]--2--methyl propionate [atromid--s] on liposoluble vitamins.

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
FDA Substances Added to Food (formerly EAFUS):View
CHEMBL:View
Golm Metabolome Database:Search
HMDB (The Human Metabolome Database):HMDB30062
FooDB:FDB001370
Export Tariff Code:2915.50.3000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
Formulations/Preparations:
grade: technical

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 88.106163024902
Specific gravity @ 25 °C
Pounds per Gallon 7.597 to 7.639
Refractive Index 1.375 to 1.379 @ 20 °C
Melting Point -88 to -87°C @ 760 mm Hg
Boiling Point 79 to 80°C @ 760 mm Hg
Boiling Point 28 to 29°C @ 100 mm Hg
Vapor Pressure 142.778 mmHg @ 25 °C
Vapor Density 3
Flash Point TCC Value 6.11 °C TCC
logP (o/w) 0.84
Solubility
alcohol Yes
dipropylene glycol Yes
water, 6.24E+04 mg/L @ 25 °C (exp) Yes
water No

Organoleptic Properties

Odor Type: Fruity
fresh, rummy, fruity, strawberry, apple
Odor strength medium
Substantivity 4 hour(s) at 100.00 %
Luebke, William tgsc, (1988) At 100.00 %. fresh harsh rum fruity strawberry apple
Flavor Type: Fruity
fruity, ethereal, juicy fruit, rummy, banana
Luebke, William tgsc, (1988) Fruity ethereal juicy fruit rummy banana

Occurrences

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 11 - Highly flammable.
R 20 - Harmful by inhalation.
S 02 - Keep out of the reach of children.
S 16 - Keep away from sources of ignition - No Smoking.
S 23 - Do not breath vapour.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 37/39 - Wear suitable gloves and eye/face protection.
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.
Human Experience:
2 % solution: no irritation or sensitization.
Oral/Parenteral Toxicity:
oral-rat LD50 5000 mg/kg
(Moreno, 1977b)

oral-mouse LD50 3460 mg/kg
(Lewis,1996)

oral-rabbit LD50 2025 mg/kg
(Munch,1972)

Dermal Toxicity:
skin-rabbit LD50 > 5000 mg/kg
Food and Chemical Toxicology. Vol. 20, Pg. 765, 1982.

Inhalation Toxicity:
inhalation-mouse LC50 27000 mg/m3
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 18(3), Pg. 48, 1974.

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for methyl propionate usage levels up to:
2.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 9.30 (μg/capita/day)
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 3
Click here to view publication 3
average usual ppmaverage maximum ppm
baked goods: -130.00000
beverages(nonalcoholic): -20.00000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -29.00000
fruit ices: -29.00000
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: -96.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: --

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

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

Flavouring Group Evaluation 2, Revision 1 (FGE.02) : Branched- and straight-chain aliphatic saturated primary alcohols and related esters of primary alcohols and straight-chain carboxylic acids and one straight-chain aldehyde from chemical groups 1 and 2 (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)
View page or View pdf

Scientific Opinion on the safety and efficacy of straight-chain primary aliphatic alcohols/aldehydes/acids, acetals and esters with esters containing saturated alcohols and acetals containing saturated aldehydes (chemical group 1) when used as flavourings for all animal species
View page or View pdf

EPI System: View
NIOSH International Chemical Safety Cards:search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):554-12-1
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :11124
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 1248
WGK Germany:1
methyl propanoate
Chemidplus:0000554121
RTECS:554-12-1