646-07-1

Usage

Uses

1. Used in Chemical Synthesis:
4-Methylvaleric acid is used as an intermediate for the synthesis of various compounds, including plasticizers, pharmaceuticals, and perfumes. It serves as a versatile building block in the creation of different products due to its unique chemical structure.
2. Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Methylvaleric acid is used as a key component in the asymmetric synthesis of (4S)-4-isopropyl-3-[(2′S)-2′,4′-dimethyl-valeryl)]-2-oxazolidinone. 4-Methylvaleric acid is a vital building block for the synthesis of various pharmaceutical and biologically active compounds, such as inhibitors and antagonists. It is also involved in the synthesis of a novel series of high affinity, functionally potent antagonists of the CCR1 receptor.
3. Used in Flavor and Fragrance Industry:
4-Methylvaleric acid is found in various natural sources, including apple, roasted barley, beef, prefermented bread, Camembert cheese, Emmenthal cheese, roasted cocoa beans, dry cured ham, hops, roasted pecans, rum, soybeans, black tea, wine, guava, papaya, strawberry fruit and jam, baked potato, bell pepper, tomato, many cheeses, fish, beef, mutton, hop oil, mushrooms, mango, rice, sake, malt, wort, dried bonito, and mussels. Due to its presence in these sources, it can be used in the flavor and fragrance industry to create natural and authentic scents and flavors.
4. Used in Analytical Chemistry:
The conductimetric detection of 4-methylvaleric acid on unfunctionized polymethacrylate resin (TSKgel G3000PWXL) columns has been reported. This indicates that 4-Methylvaleric acid can be used in analytical chemistry for the detection and analysis of various compounds in different samples.

Synthesis Reference(s)

The Journal of Organic Chemistry, 40, p. 1844, 1975 DOI: 10.1021/jo00900a040

InChI:InChI=1/C6H12O2/c1-5(2)3-4-6(7)8/h5H,3-4H2,1-2H3,(H,7,8)/p-1

Upstream product

• 10359-02-1 4-(1-methylethyl)oxetan-2-one 
• 3123-97-5 dihydro-5,5-dimethyl-2(3H)-furanone 
• 60-29-7 diethyl ether 
• 74-85-1 ethene 
• 1888-75-1 isopropyllithium 
• 56523-31-0 3,7-dimethyl-oct-3-ene 
• 542-54-1 isocapronitrile 
• 540-88-5 acetic acid tert-butyl ester 
• 111-02-4 squalene 
• 626-89-1 4-Methyl-1-pentanol 
• 105-44-2 4-methyl-pentan-2-one oxime 
• 10321-71-8 4-methyl-pent-2-enoic acid 
• 4361-06-2 isobutylmalonic Acid 
• 604-35-3 Cholesteryl acetate 

Downstream Products

• 2412-80-8 methyl 4-methylpentanoate 
• 27993-43-7 5-methyl-1-phenylhexan-2-one 
• 25415-67-2 ethyl isocaproate 
• 2724-57-4 isomyristic acid 
• 2050-99-9 2,8-dimethylnonan-5-one 
• 28659-87-2 2-Bromo-4-methylpentanoic Acid 
• 626-89-1 4-Methyl-1-pentanol 
• 38136-29-7 4-methylvaleroyl chloride 
• 1119-16-0 isocaproic aldehyde 
• 802294-64-0 propionic acid 
• 79-31-2 isobutyric Acid 
• 110-12-3 5-Methyl-2-hexanone 
• 98338-02-4 5-isopentyl-[1,3,4]thiadiazol-2-ylamine 
• 83594-04-1 4-methylpentanoic anhydride 

Relevant academic research and scientific papers

NEW ASSAYS FOR THE ENZYMATIC CONVERSION OF CHOLESTEROL TO PREGNENOLONE

Cholesterol side chain cleavage is determined by means of separation of (26-14C)-cholesterol and its radioactively labeled side chain (1-14C)-isocaproic acid.Alumina minicolumn assay (AMCA): adsorption of cholesterol from an aqueous phase by aluminium oxide, while isocaproic acid can percolate through the column.In modification of a previously described technique, cholesterol is quantitatively eluted by ethanol.Filter assay (FA): retention of cholesterol by a membrane filter (pore size =/ 0.1 μm) while isocaproic acid can pass the filter.Two-phase scintillation assay (TPSA): pH-dependent partition of isocaproic acid between an organic scintillation mixture and an aqueous phase.The TPSA can be applied for all enzymatic reactions in which the polarity of the radioactive residue which is split off depends on pH values or when the total charge of apolar molecule is changed to an apolar state by cleaving one non-radioactive group (e.g. steroid sulfates) and vice versa.The criteria of reliability of the test systems are described.Bovine adrenal mitochondria were incubated and the side chain cleavage of (26-14C)-cholesterol was studied by the new test systems and compared to the conversion rates of (4-14C)-cholesterol to its metabolites as determined by thin layer chromatography.A good agreement of all tests was found.

Strategic Approach to the Metamorphosis of γ-Lactones to NH γ-Lactams via Reductive Cleavage and C-H Amidation

A new approach has elaborated on the conversion of γ-lactones to the corresponding NH γ-lactams that can serve as γ-lactone bioisosteres. This approach consists of reductive C-O cleavage and an Ir-catalyzed C-H amidation, offering a powerful synthetic tool for accessing a wide range of valuable NH γ-lactam building blocks starting from γ-lactones. The synthetic utility was further demonstrated by the late-stage transformation of complex bioactive molecules and the asymmetric transformation.

Preparation method of carboxylic acid compound

The invention provides a preparation method of a carboxylic acid compound. The preparation method comprises the following step of taking a lactone component to react with hydrogen in the presence of a compound catalyst to obtain the carboxylic acid compound. The compound catalyst comprises a hydrogenation catalyst and Lewis acid. In the presence of the compound catalyst comprising the hydrogenation catalyst and the Lewis acid, the lactone component is subjected to hydrogenation ring-opening reaction to obtain the carboxylic acid compound. The preparation method has the advantages of moderate reaction conditions and high yield; compared with a traditional method, less byproducts are generated, green and chemical requirements are met and the industrial value is better.

A Comprehensive Study on Metal Triflate-Promoted Hydrogenolysis of Lactones to Carboxylic Acids: From Synthetic and Mechanistic Perspectives

Direct hydrogenolysis of lactone to carboxylic acid (i.e., hydrogenolysis of the Calkoxy-O bond with the carbonyl group untouched) is generally difficult, as the current strategies employing Br?nsted acids as the catalyst usually require harsh conditions such as a high temperature and a high H2 pressure. Herein, we report a developed solvent-free catalytic transformation, in which W(OTf)6 is believed to promote the hydrogenolysis process. This strategy could efficiently hydrogenate lactones to carboxylic acids under extra mild conditions (e.g., a reaction temperature of 2) and showed a broad substrate scope. In addition, the catalytic protocol can be further applied to the hydrogenolysis of polyhydroxyalkanoate, as a renewable polymer, to the corresponding straight-chain carboxylic acids. An extensive mechanistic study was subsequently performed, and the density functional theory calculations revealed a reaction pattern, including the complete cleavage of the C=O bond with the assistance of the W(OTf)6 catalyst. Moreover, the key intermediate created in the mechanism, as an oxonium with an OTf moiety, was successfully detected by electrospray ionization mass spectra. Through a comparison with the Br?nsted acid-catalyzed system, the study confirmed that the existence of the OTf moiety can significantly lower the barriers associated with the rearrangement and elimination processes. Meanwhile, emphasis was placed on the critical role that the anion plays, as well as the fact that the anion effect is directly related to the chemoselectivity.

PROCESS FOR PRODUCING ALKANES USING MICROORGANISMS COMBINED WITH KOLBE SYNTHESIS

The present invention relatesto a method of producing at least one alkane, the method comprising, -producing at least one carboxylic acid from a carbon source using a genetically modified microorganism, and -performing Kolbe electrolysis on the carboxylic acid to produce the alkane, wherein the alkane comprises at least 6 carbon atoms and the carboxylic acid comprises at least 4 carbon atomsand wherein the carbon source is selected from the group consisting of ethanol, acetate, propionate, butyrate, isobutyrate, valerate, hexanoate and combinations thereof and the microorganism is capable of producing the carboxylic acid using ethanol-carboxylate fermentation.

1H-pyrrole-2,4-dicarbonyl-derivatives and their use as flavoring agents

The present invention primarily relates to 1H-pyrrole-2,4-dicarbonyl-derivatives of Formula (I) wherein R1, R2, R3, Z. Z' and J are as defined in the description, to mixtures thereof and to the use thereof as flavoring agents. The compounds in accordance with the present invention are suitable for producing, imparting, or intensifying an umami flavor. The invention further relates to flavoring mixtures, compositions for oral consumption as well as ready-to-eat, ready-to-use and semifinished products, comprising an effective amount of the compound of Formula (I) or of a mixture of compounds of Formula (I) and to specific methods for producing, imparting, modifying and/or intensifying specific flavor impressions.

Imidazo[1,2-a]pyridine-ylmethyl-derivatives and their use as flavoring agents

The present invention primarily relates to imidazo[1,2-a]pyridine-ylmethyl-derivatives of Formula (I) wherein R1, R2, X, W e J are as defined in the description, to mixtures thereof and to the use thereof as flavoring agents. The compounds in accordance with the present invention are suitable for producing, imparting, or intensifying an umami flavor. The invention further relates to flavoring mixtures, compositions for oral consumption as well as ready-to-eat, ready-to-use and semifinished products, comprising an effective amount of the compound of Formula (I) and to specific methods for producing, imparting, modifying and/or intensifying specific flavor impressions.

One-pot synthesis of micro/nano structured β-Bi2O3 with tunable morphology for highly efficient photocatalytic degradation of methylparaben under visible-light irradiation

β-Bi2O3 micro/nanostructures with tunable morphologies were synthesized via a one-pot solvothermal-calcining route, and their photocatalytic activity toward degrading methylparaben (MeP, a widely used preservative with estrogenic activity) was evaluated under visible-light (λ ≥ 420 nm) irradiation. The formation process of β-Bi2O3 catalysts can be described as reduction of Bi3+ through a solvothermal reaction, followed by oxidization of metal Bi via calcination in air. During this process, the organic reductants (single or a mixture of ethylene glycol, d-fructose, and ascorbic acid) play important roles in determining the final morphologies and structures of the materials. Photocatalytic tests reveal that MeP can be effectively degraded and mineralized by using synthetic β-Bi2O3 catalysts, and the reaction rate constant of an optimum sample is more than 25 and 160 times faster than a commercial Bi2O3 and synthetic N-TiO2, respectively. The superior photocatalytic activity of the optimum product is ascribed to its pure beta phase with a narrower band gap, good absorption of visible light, more efficient separation of electrons and holes, relatively higher BET specific surface area, and three-dimensional architectures, which favor more surface active sites and easier mass and photoinduced charge transportations. In addition, the main reactive oxygen species and possible degradation intermediates were detected, and the results suggest that photogenerated holes and superoxide radicals are the predominant species in the photochemical oxidation process.

Novel aerobic oxidation of primary sulfones to carboxylic acids

Primary alkyl aryl sulfones are converted to the corresponding carboxylic acids in fair to excellent yield through double deprotonation and exposure to atmospheric oxygen. The methodology allows for the convenient synthesis of 13C labeled carboxylic acids.

Structure and reactivity in the hydrolyses of aliphatic carboxylic acid esters and chlorides

For hexanoic acid and its seven isomers, relative rates have been determined for acid catalysed esterification with methanol, and compared with those for saponification of the methyl esters. A good correlation between logarithms of relative rates for the two reactions is obtained, and it is suggested that the eight isomers provide a test set of compounds in which steric effects alone act on reactivity at the acyl carbon. A full set of steric parameters (Es′ values) are presented. Rates of solvolyses of the acid chlorides- of the isomers have been determined conductometrically in 3:1 wt:wt acetonitrile water. Logarithms of relative rates show a poor correlation with Es′, and, taking into account the solvent dependence of the rates, the pattern excludes both rate-limiting formation of a tetrahedral intermediate and rate-limiting dissociation of chloride to form acylium ions. The remaining possibilities, a concerted process (ANDN?) and rapid reversible formation of a hydrate followed by rate-limiting dissociation of chloride (AN + DN?,) are considered. Copyright