116-53-0

Basic information

• Product Name: 2-Methyl butyric acid
• Synonyms: METHYLBUTYRIC ACID, DL-2-;METHYLETHYL ACETIC ACID;BUTANE-2-CARBOXYLIC ACID;FEMA 2695;CARBOXYLIC ACID C5;DL-METHYLETHYLACETIC ACID;(+/-)-2-METHYLBUTYRIC ACID;2-METHYLBUTYRIC ACID
• CAS NO: 116-53-0
• Molecular Formula: C₅H₁₀O₂
• Molecular Weight: 102.13
• EINECS: 204-145-2
• Product Categories: Certified Natural ProductsFlavors and Fragrances;Alphabetical Listings;Flavors and Fragrances;M-N;C1 to C5;Carbonyl Compounds;Carboxylic Acids
• Mol File: 116-53-0.mol
• Article Data: 84

Chemical Properties

• Melting Point: -70 °C
• Boiling Point: 176-177 °C(lit.)
• Flash Point: 165 °F
• Appearance: Clear colorless to pale yellow/Liquid
• Density: 0.936 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.5 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.405(lit.)
• Storage Temp.: 0-6°C
• Solubility: 20g/l
• PKA: 4.8(at 25℃)
• Explosive Limit: 1.6-7.3%(V)
• Water Solubility: 45 g/L (20 ºC)
• BRN: 1720486
• CAS DataBase Reference: 2-Methyl butyric acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl butyric acid(116-53-0)
• EPA Substance Registry System: 2-Methyl butyric acid(116-53-0)

Safety Data

• Hazard Codes: C
• Statements: 21/22-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 3
• WGK Germany: 1
• RTECS: EK7897000
• F: 13
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 116-53-0(Hazardous Substances Data)

Usage

Description

2-Methyl butyric acid is a clear colorless to pale yellowish liquid with a pungent, acrid odor and taste, similar to Roquefort cheese. It has a pleasant fruity taste at low dilutions and is produced from amino acid leucine during nutrient starvation in bacteria. It can be prepared by decarboxylation of methyl ethyl malonic acid or by the oxidation of fermentation amyl alcohol (fusel oil).

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 
• 861540-65-0 4-hydroxy-5-methyl-heptanoic 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 

Downstream Products

• 53004-93-6 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-methylbutanoate 
• 3739-30-8 2-hydroxy-2-methylbutyric acid 
• 106-98-9 1-butylene 
• 107-01-7 butene-2 
• 19549-84-9 3-butyl ketone 
• 100955-64-4 2-methylbutyric acid 1-naphthylamide 
• 6668-42-4 2-methyl-1-phenylbutan-1-one oxime 
• 32231-50-8 (R)-2-methylbutyric acid 
• 1730-91-2 (S)-2-Methylbutyric acid 

Relevant articles and documents

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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.

Asymmetric hydrogenation and catalyst recycling using ionic liquid and supercritical carbon dioxide [13]

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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.

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.

Organocatalyzed Aerobic Oxidation of Aldehydes to Acids

The first example organocatalyzed aerobic oxidation of aldehydes to carboxylic acids in both organic solvent and water under mild conditions is developed. As low as 5 mol % N-hydroxyphthalimide was used as the organocatalyst, and molecular O2 was used as the sole oxidant. No transition metals or hazardous oxidants or cocatalysts were involved. A wide range of carboxylic acids bearing diverse functional groups were obtained from aldehydes, even from alcohols, in high yields.