116-53-0

Usage

Uses

Used in Food Industry:
2-Methyl butyric acid is used as a food additive for butter, cream, and cheese flavor deployment due to its pleasant fruity taste at low dilutions and its ability to provide acyl moiety for the preparation of respective flavor esters.
Used in Organic Synthesis:
2-Methyl butyric acid is an important raw material and intermediate used in organic synthesis for the synthesis of various compounds.
Used in Pharmaceutical Industry:
2-Methyl butyric acid is used as a raw material and intermediate in the pharmaceutical industry for the synthesis of various drugs.
Used in Agrochemicals Industry:
2-Methyl butyric acid is used as a raw material and intermediate in the agrochemicals industry for the synthesis of various agrochemical products.
Used in Dyestuff Industry:
2-Methyl butyric acid is used as a raw material and intermediate in the dyestuff industry for the synthesis of various dyes.
Used in Synthesis of 2-Methylbutyric Anhydride:
2-Methyl butyric acid is used in the synthesis of 2-methylbutyric anhydride, which is an acylating agent.
Occurrence:
2-Methyl butyric acid occurs as the d-, l-, and dl-isomers and has been found in various natural sources such as angelica root oil, coffee, lavender oil, apple, apricot, berries, grapes, papaya, peach, guava, pineapple, potato, bell pepper, tomato, peppermint and spearmint oil, vinegar, wheat breads, cheeses, chicken, mutton, pork, hop oil, beer, cognac, rum, whiskies, cider, cocoa, coffee, tea, peanuts, passion fruit, trassi, mango, plum, tamarind, rice, corn oil, loquat, scallops, Chinese quince, maté, mammee apple, and Roman chamomile oil, cranberry, grape brandy, oriental tobacco, and strawberry.

References

[1] George A. Burdock, Encyclopedia of Food and Color Additives, Band 1, 1996 [2] T. Tachihara, H. Hashimoto, S. Ishizaki, T. Komai, A. Fujita, M. Ishikawa and T. Kitahara, Microbial resolution of 2-methylbutyric acid and its application to several chiral flavour compounds, Developments in Food Science, 2006, vol. 43, 97-100

Preparation

By decarboxylation of methyl ethyl malonic acid (with heat); also by oxidation of fermentation amyl alcohol (fusel oil).

Flammability and Explosibility

Notclassified

Biochem/physiol Actions

Taste at 10 ppm

InChI:InChI=1/C5H10O2/c1-3-4(2)5(6)7/h4H,3H2,1-2H3,(H,6,7)/p-1/t4-/m0/s1

Upstream product

• 64-18-6 formic acid 
• 78-92-2 iso-butanol 
• 80-59-1 Tiglic acid 
• 96-17-3 2-Methylbutyraldehyde 
• 6874-30-2 2,6-dimethyl-oct-4-ene 
• 595-84-6 2-ethyl-2-methylmalonic acid 
• 565-63-9 Angelic acid 
• 938-87-4 2-methyl-1-phenyl-butan-1-one 
• 671795-46-3 sec-butylmagnesium bromide 
• 15719-64-9 methylammonium carbonate 
• 78-76-2 s-butyl bromide 
• 74-85-1 ethene 
• 802294-64-0 propionic acid 
• 94-36-0 dibenzoyl peroxide 

Downstream Products

• 5856-79-1 iso-butyl chloroformate 
• 19549-84-9 3-butyl ketone 
• 95338-79-7 2-bromo-2-methyl-butyric acid 
• 100129-06-4 2-methyl-butyric acid-(4-bromo-anilide) 
• 7511-29-7 p-Phenyl-phenacy-(α-methyl-butyrat) 
• 7452-79-1 ethyl 2-methylbutyrate 
• 53004-93-6 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-methylbutanoate 
• 3739-30-8 2-hydroxy-2-methylbutyric acid 
• 62492-20-0 5-sec-butyl-[1,3,4]thiadiazol-2-ylamine 
• 1519-23-9 2-methylbutanoic anhydride 
• 54394-78-4 2-methylbutanoic acid anilide 
• 58265-40-0 2-methyl-N-(phenylmethyl)-butanamide 
• 495-82-9 (+/-)-3endo-(2-methyl-butyryloxy)-tropane 
• 1185-29-1 2-methyl-2-ethylhexanoic acid 

Relevant academic research and scientific papers

Effect of particle restructuring during reduction processes over polydopamine-supported Pd nanoparticles

The effect of catalyst restructuring on the polydopamine-supported Pd catalyzed transfer hydrogenation of ethyl 4-nitrobenzoate and the catalytic hydrogenation of (E)-2-methyl-2-butenoic acid is reported. Transmission electron microscopy investigation of different catalyst pre-treatment and reaction conditions revealed high catalytic activity in both reactions unless drastic aggregation of the active metal occurred. In the transfer hydrogenation reaction aggregation was primarily dependent on the H-source used, while in the catalytic hydrogenation additives in combination with the reductive environment led to extensive Pd aggregation and thus decreased catalytic activity. The enantioselective hydrogenation of (E)-2-methyl-2-butenoic acid showed increased enantioselectivity and decreased conversion with increased particle size.

Kinetics and mechanism of oxidation of isoleucine by n-bromophthalimide in aqueous perchloric acid medium

The kinetics of oxidation of isoleucine with N-bromophthalimide has been studied in perchloric acid medium potentiometrically. The reaction is of first order each in [NBP] and [amino acid] and negative fractional order in [H +]. The rate is decreased by the addition of phthalimide. A decrease in the dielectric constant of the medium increases the rate. Addition of halide ions or acrylonitrile has no effect on the kinetics. Similarly, variation of ionic strength of the medium does not affect the reaction rate. The reaction rate has been determined at different temperatures and activation parameters have been calculated. A suitable mechanism involving hypobromous acid as reactive species has been proposed. Copyright E-Journal of Chemistry 2004-2011.

Synthesis and reactions of allenic amides. Allenes-XXXI

Allenic amides are prepared from allenic nitriles using alkaline hydrogen peroxide and by a Ritter reaction with t-butyl alcohol, when N-t-butylamides are obtained. Strong nucleophiles attack the central carbon of the allene system to give α,β-unsaturated addition products.

Synthesis and characterization of chiral phosphirane derivatives of [(μ-H)4Ru4(CO)12] and their application in the hydrogenation of an α,β-unsaturated carboxylic acid

Ruthenium clusters containing the chiral binaphthyl-derived mono-phosphiranes [(S)-([1,1′-binaphthalen]-2-yl)phosphirane] (S)-1a, [(R)-(2′-methoxy-1,1′-binaphthyl-2-yl)phosphirane] (R)-1b, and the diphosphirane [2,2′-di(phosphiran-1-yl)-1,1′-binaphthalene] (S)-1c have been synthesized and characterized. The clusters are [(μ-H)4Ru4(CO)11((S)-1a)] (S)-2, [(μ-H)4Ru4(CO)11((R)-1b)] (R)-3, 1,1-[(μ-H)4Ru4(CO)10((S)-1c)] (S)-4, [(μ-H)4Ru4(CO)11((S)-binaphthyl-P(s)(H)Et)] (S,Sp)-5, [(μ-H)4Ru4(CO)11((S)-binaphthyl-P(R)(H)Et)] (S,Rp)-6, [(μ-H)4Ru4(CO)11((R)-binaphthyl-P(s)(H)Et)] (R,Sp)-7, [(μ-H)4Ru4(CO)11((R)-binaphthyl-P(R)(H)Et)] (R,Rp)-8 and the phosphinidene-capped triruthenium cluster [(μ-H)2Ru3(CO)9(PEt)] 9. Clusters 5–8 are formed via hydrogenation and opening of the phosphirane ring in clusters (S)-2 and (R)-3. The phosphirane-substituted clusters were found to be able to catalyze the hydrogenation of trans-2-methyl-2-butenoic acid (tiglic acid), but no enantioselectivity could be detected. The molecular structures of (S)-4, (R,Sp)-7 and 9 have been determined and are presented.

Expedient method for oxidation of alcohol by hydrogen peroxide in the presence of amberlite IRA 400 resin (basic) as phase-transfer catalyst

Amberlite IRA 400 (strongly basic), a classical polymer imparts phase-transfer catalysis in the oxidation of primary and secondary alcohols by hydrogen peroxide to give excellent yields of the corresponding carbonyl compounds or carboxylic acids in acetonitrile solvent at reflux temperature in 4-6 h. The catalytic system is inert to other susceptible oxidation sites such as carbon-carbon double bonds. Copyright Taylor & Francis Group, LLC.

Diterpenoid alkaloids from the lateral root of Aconitum carmichaelii

Twenty-six new diterpenoid alkaloids, 1-26 (1-4: hetisan-type C 20-diterpenoid alkaloids; 5-26: aconitane C19-diterpenoid alkaloids), and two known analogues, hypaconitine 27 and benzoylmesaconine 28, have been isolated from a water extract of the lateral root of Aconitum carmichaelii. Compounds 7 and 8 are rare examples of conformational isomers obtained from the same material. The conformation and conformational transformation of ring A in the C19- diterpenoid alkaloids are discussed on the basis of NMR data analysis in combination with single-crystal X-ray crystallography of 6 and 27 by anomalous scattering of Cu K7α radiation. In preliminary analgesic and toxicity assays, the isomer with ring A in the chair conformation (8 or 27) was found to be more active than that with ring A in the boat conformation (7 or 27a). In addition, 15, 16, and 19 showed neuroprotective activity.

Reaction of Carbocations Derived from Alkanes with Carbon Monoxide in HF-SbF5 Superacid

Alkanes readily react with CO and H2O in HF-SbF5 at 30 deg C under atmospheric pressure and give considerably different product distributions from those in the usual Koch-Haaf reaction.When using C5- or C6-alkanes with tertiary C-H bonds, a considerable amount of secondary carboxylic acids are produced by the reaction of CO with secondary alkyl cations.Such cations may appear as transient intermediates in the course of the carbon skeletal isomerization of initially formed tertiary cations.For the straightchain alkanes, the protonolysis at C-C bonds initiated the reaction to give fragment alkyl cations.This resulted in the formation of carboxylic acids with a lower number of carbon atoms than the starting alkanes.Intermolecular hydride shift between the fragment cations and the starting alkanes occured at the same time to form a large amount of carboxylic acids with the alkyl group of the same number of carbon atoms as the starting alkane.On the other hand, for alkanes with more than seven carbon atoms, β-scission occurs exclusively to produce C4-, C5-, and C6-carboxylic acids.

Synthesis and pyrolysis of two novel pyrrole ester flavor precursors

In order to develop the high-temperature-released pyrrole aroma, two novel flavors precursors of methyl 2-methyl-5-(((2-methylbutanoyl)oxy)methyl)-1-propyl-1H-pyrrole-3-carboxylate and methyl 2-methyl-5-(((2-methylbutanoyl)oxy)methyl)-1-propyl-1H-pyrrole-3-carboxylate were synthesized using glucosamine hydrochloride and methyl acetoacetate as raw materials through cyclization, oxidation, alkylation, reduction, and esterification. The target compounds were characterized by nuclear magnetic resonance (1H NMR, 13C NMR), infrared spectroscopy (IR) and high-resolution mass spectrometry (HRMS). Thermogravimetry (TG), differential scanning calorimeter (DSC) and the pyrolysis-gas chromatography/mass spectrometry (Py-GC/MS) methods were used to analyze the heating-stability of the target compounds, and the pyrolysis mechanism was inferred. Py-GC/MS results indicated that some fragrance compounds were formed during?thermal degradation such as 2-methylbutyric acid, 2-methylbutyrate, alkylpyrroles, and benzoic acid, which were important aroma components or flavor additives. This provided a theoretical reference for the application of pyrrole ester in cigarette and heat-processed food flavoring.

Nucleophilic reactivity of a mononuclear cobalt(iii)-bis(: Tert -butylperoxo) complex

A mononuclear cobalt(III)-bis(tert-butylperoxo) adduct (CoIII-(OOtBu)2) bearing a tetraazamacrocyclic ligand was synthesized and characterized using various physicochemical methods, such as X-ray, UV-vis, ESI-MS, EPR, and NMR analyses. The crystal structure of the CoIII-(OOtBu)2 complex clearly showed that two OOtBu ligands bound to the equatorial position of the cobalt(iii) center. Kinetic studies and product analyses indicate that the CoIII-(OOtBu)2 intermediate exhibits nucleophilic oxidative reactivity toward external organic substrates.

Oxidation of aromatic and aliphatic aldehydes to carboxylic acids by Geotrichum candidum aldehyde dehydrogenase

Oxidation reaction is one of the most important and indispensable organic reactions, so that green and sustainable catalysts for oxidation are necessary to be developed. Herein, biocatalytic oxidation of aldehydes was investigated, resulted in the synthesis of both aromatic and aliphatic carboxylic acids using a Geotrichum candidum aldehyde dehydrogenase (GcALDH). Moreover, selective oxidation of dialdehydes to aldehydic acids by GcALDH was also successful.