617-31-2

Usage

Uses

Used in Insect Attractants:
2-Hydroxyvaleric acid is used as a key component in the preparation method of high-efficiency attractants for Aedes albopictus, a mosquito species known to transmit diseases such as dengue fever and chikungunya. The application reason is that it serves as a crucial ingredient in the formulation of attractants that effectively lure and trap these mosquitoes, helping to control their population and reduce the spread of diseases.

InChI:InChI=1/C5H10O3/c1-2-3-4(6)5(7)8/h4,6H,2-3H2,1H3,(H,7,8)

Upstream product

• 26735-71-7 hydroxy-propyl-malonic acid 
• 74-90-8 hydrogen cyanide 
• 123-72-8 butyraldehyde 
• 584-93-0 2-Bromovaleric acid 
• 96139-47-8 rac-(E)-2-hydroxy-3-pentenoic acid methyl ester 
• 193805-19-5 (E)-2-hydroxypent-3-enenitrile 
• 5343-92-0 1,2-pentanediol 
• 87503-46-6 2-hydroxylpentanal 
• 109-52-4 valeric acid 
• 39149-86-5 2-bromopent-4-enoic acid ethyl ester 
• 87089-12-1 (E)-2-(trimethylsilyloxy)pent-3-enenitrile 
• 78119-42-3 rac-(E)-2-hydroxy-3-pentenoic acid 
• 42990-12-5 (R)-2-bromopentanoic acid 
• 615-83-8 2-bromo-pentanoic acid ethyl ester 

Downstream Products

• 88945-70-4 ethyl 2-hydroxy-n-valerate 
• 41014-93-1 2-(S)-hydroxyvaleric acid 
• 1003855-66-0 2-hydroxy-valeric acid anilide 
• 120821-89-8 1-(2-benzothiazolyl)-1-butanol 
• 123-72-8 butyraldehyde 
• 1821-02-9 2-oxopentanoic acid 
• 95513-34-1 benzyl 2-hydroxypentanoate 
• 24809-83-4 (2R)-2-hydroxypentanoic acid 
• 802294-64-0 propionic acid 
• 107-92-6 butyric acid 
• 64-18-6 formic acid 
• 144-62-7 oxalic acid 
• 41881-84-9 1-(benzo[d]thiazol-2-yl)butan-1-one 
• 86353-86-8 (3,5-Dichloro-phenyl)-carbamic acid 1-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-butyl ester 

Relevant academic research and scientific papers

Synthesis of Dicarboxylic Acids from Aqueous Solutions of Diols with Hydrogen Evolution Catalyzed by an Iridium Complex

A catalytic system for the synthesis of dicarboxylic acids from aqueous solutions of diols accompanied by the evolution of hydrogen was developed. An iridium complex bearing a functional bipyridonate ligand with N,N-dimethylamino substituents exhibited a high catalytic performance for this type of dehydrogenative reaction. For example, adipic acid was synthesized from an aqueous solution of 1,6-hexanediol in 97 % yield accompanied by the evolution of four equivalents of hydrogen by the present catalytic system. It should be noted that the simultaneous production of industrially important dicarboxylic acids and hydrogen, which is useful as an energy carrier, was achieved. In addition, the selective dehydrogenative oxidation of vicinal diols to give α-hydroxycarboxylic acids was also accomplished.

Catalytic Fehling's Reaction: An Efficient Aerobic Oxidation of Aldehyde Catalyzed by Copper in Water

The first example of homogeneous copper-catalyzed aerobic oxidation of aldehydes is reported. This method utilizes atmospheric oxygen as the sole oxidant, proceeds under extremely mild aqueous conditions, and covers a wide range of various functionalized aldehydes. Chromatography is generally not necessary for product purification.

α-Hydroxylation of Carboxylic Acids Catalyzed by Taurine Dioxygenase

Enzymes still have a limited application scope in synthetic organic chemistry. To expand this, different strategies exist that range from the de novo design of enzymes to the exploitation of the catalytic capabilities of known enzymes by converting different substrates; denoted as substrate promiscuity. We harnessed the synthetic potential offered by the taurine dioxygenase (TauD) from Escherichia coli (E. coli) by studying its promiscuous catalytic properties in the hydroxylation of carboxylic acid substrates. TauD showed high selectivities in the hydroxylation reaction but reduced levels of activity (26 % conversion, >96 % ee). We enhanced the enzyme substrate scope and improved the conversions for the tested substrates by introducing a point mutation at position 206 (F206Y). The conversions of the improved catalyst increased by at least 140 % compared to that of the wild-type enzyme. The number of carboxylic acids that accepted by the enzyme variant doubled from four to eight carboxylic acids.

Exploring the biocatalytic scope of alditol oxidase from Streptomyces coelicolor

The substrate scope of the flavoprotein alditol oxidase (AldO) from Streptomyces coelicolor A3(2), recombinantly produced in Escherichia coli, was explored. While it has been established that AldO efficiently oxidizes alditols to D-aldoses, this study revealed that the enzyme is also active with a broad range of aliphatic and aromatic alcohols. Alcohols containing hydroxy groups at the C-1 and C-2 positions like 1,2,4-butanetriol (Km=170 mM, k cat -4.4s-1), 1,2-pentanediol (Km=52 mM, k cat=0.85 s-1) and 1,2-hexanediol (Km=97 mM, kcat=2.0s-1) were readily accepted by AldO. Furthermore, the enzyme was highly enantioselective for the oxidation of 1,2-diols [e.g., for l-phenyl-1,2-ethanediol the (R)-enantiomer was preferred with an Is-value of 74]. For several diols the oxidation products were determined by GC-MS and NMR. Interestingly, for all tested 1,2-diols the products were found to be the a-hydroxy acids instead of the expected α-hydroxy aldehydes. Incubation of (R)-1-phenyl-1,2-ethanediol with 18O-labelled water (H 218O) revealed that a second enzymatic oxidation step occurs via the hydrate product intermediate. The relaxed substrate specificity, excellent enantioselectivity, and independence of coenzymes make AldO an attractive enzyme for the preparation of optically pure 1,2-diols and α-hydroxy acids.

PROCESS FOR PREPARING 1,2-DIOLS FROM CARBONYL COMPOUNDS

1,2-diols can be obtained in good yields and in very high purity by a process of a) reacting a carbonyl compound of the general formula (I) with hydrocyanic acid to give the corresponding cyanohydrin, wherein R1 and R2 are each independently H, an optionally substituted straight-chain or branched C1-C18-alkyl radical, or an optionally substituted phenyl or C5-C6-cycloalkyl radical, b) subjecting the cyanohydrin obtained in process step a) to an acidic hydrolysis, and c) catalytically hydrogenating the 2-hydroxycarboxylic acid obtained from process step b) in the presence of a noble metal catalyst comprising ruthenium and rhenium.

The substrate spectrum of mandelate racemase: Minimum structural requirements for substrates and substrate model

Mandelate racemase (EC 5.1.2.2) is one of the few biochemically well-characterized racemases. The remarkable stability of this cofactor-independent enzyme and its broad substrate tolerance make it an ideal candidate for the racemization of non-natural α-hydroxycarboxylic acids under physiological reaction conditions to be applied in deracemization protocols in connection with a kinetic resolution step. This review summarizes all aspects of mandelate racemase relevant for the application of this enzyme in preparative-scale biotransformations with special emphasis on its substrate tolerance. Collection and evaluation of substrate structure-activity data led to a set of general guidelines, which were used as basis for the construction of a general substrate model, which allows a quick estimation of the expected activity for a given substrate.

Method and product for skin lightening

A method and cosmetic product for lightening skin is provided, the method including wiping the skin with a cosmetic towelette. Impregnated on the towelette is an alpha-hydroxy carboxylic acid or salt thereof and a sunscreen agent.

Towelette product

A disposable towelette product is provided which includes a flexible water-insoluble substrate such as a tissue impregnated with an alpha- or beta-hydroxycarboxylic acid in a cosmetically acceptable carrier vehicle. Impregnated cosmetic composition in water will have a pH no higher than 6.8. A silicone microemulsion is present to minimize any stickiness resulting from deposition of the hydroxycarboxylic acid by the towelette onto the skin. In the presence of fatty acid group containing surfactants, the silicone microemulsion controls foul odors that the surfactants may emit through hydrolysis at low pH.

Towelette product for minimizing facial fine lines and wrinkles

A disposable towelette is provided which includes a flexible substrate such as a cellulosic tissue impregnated with an alpha-hydroxycarboxylic add delivered in a cosmetically acceptable carrier vehicle. There is further provided a method for cleansing skin and simultaneously inhibiting fine lines and wrinkles by wiping the skin with the impregnated towelette.

Processes for producing alpha -cyanohydrin esters and alpha -hydroxy acids

In the presence of a metal catalyst such as a samarium compound, an enol ester compound shown by the formula (1) is reacted with a carbonyl compound shown by the formula (3) and a cyanogenation agent to produce an alpha -cyanohydrin ester shown by the formula (4): wherein R1, R7, and R8 are the same or different from each other, each representing a non-reactive atom or a non-reactive organic group; R2, R3, and R4 are the same or different from each other, each representing a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. By hydrolyzing the obtained compound, the corresponding alpha -hydroxy acid or a salt thereof can be obtained. According to the above processes, an alpha -cyanohydrin ester and an alpha -hydroxy acid can be obtained in high yields.