10603-03-9

Usage

Uses

Used in Food and Beverage Industry:
2-Methyl-5-hydroxypentanoic acid lactone is used as a flavor enhancer for its ability to impart a sweet, caramel-like aroma and taste to various food and beverage products, enhancing their overall sensory appeal.
Used in Tobacco Products:
In the tobacco industry, 2-Methyl-5-hydroxypentanoic acid lactone is used as a flavoring agent to improve the taste and aroma of tobacco products, making them more enjoyable for consumers.
Used in Pharmaceutical Industry:
2-Methyl-5-hydroxypentanoic acid lactone is utilized as a fragrance and flavoring component in the pharmaceutical industry, adding pleasant scents and tastes to medications, which can improve patient compliance and experience.
Used in Cosmetic Industry:
In cosmetics, 2-Methyl-5-hydroxypentanoic acid lactone is employed for its fragrance properties, contributing to the pleasant smell of various cosmetic products and enhancing consumer satisfaction.
Used in Production of Synthetic Flavoring Agents:
2-Methyl-5-hydroxypentanoic acid lactone is used as a precursor in the synthesis of synthetic flavoring agents, providing a base for creating a wide range of flavors used across different industries.
Used in Synthesis of Pharmaceuticals and Agrochemicals:
As a versatile chemical intermediate, 2-Methyl-5-hydroxypentanoic acid lactone is used in the synthesis of various pharmaceuticals and agrochemicals, playing a crucial role in the development of new and improved products in these fields.

InChI:InChI=1/C6H10O2/c1-5-3-2-4-8-6(5)7/h5H,2-4H2,1H3

Upstream product

• 542-28-9 3,4,5,6-tetrahydro-2H-pyran-2-one 
• 74-88-4 methyl iodide 
• 1120-72-5 2-Methylcyclopentanone 
• 821-09-0 n-Pent-4-enyl alcohol 
• 201230-82-2 carbon monoxide 
• 64180-78-5 4-bromopent-4-en-1-ol 
• 97-61-0 2-Methylpentanoic acid 
• 42856-62-2 2-methyl-1,5-pentanediol 
• 26093-63-0 3-methyltetrahydropyran 
• 119124-49-1 O-pent-4-en-1-yl Se-phenyl selenocarbonate 
• 107270-41-7 4-(1,3-dithian-2-ylidene)pentan-1-ol 
• 31468-33-4 2-methylglutaric anhydride 
• 108-18-9 diisopropylamine 
• 68258-41-3 3-methylpyran-2-ol 

Downstream Products

• 107174-18-5 3-Methyl-2-phenyl-tetrahydro-pyran-2-ol 
• 42856-62-2 2-methyl-1,5-pentanediol 
• 820244-25-5 5-hydroxy-2,N-dimethyl-N-phenylpentanamide 
• 820244-29-9 methyl 4-methyl-5-[methyl(phenyl)amino]-5-oxopentanoate 
• 820244-27-7 4-methyl-5-[methyl(phenyl)amino]-5-oxopentanoic acid 
• 820244-21-1 methyl 3-(3-amino-2,N-dimethyl-N-phenyl-2H-azirin-2-yl)propanoate 
• 820244-31-3 methyl 4-methyl-5-[methyl(phenyl)amino]-5-thioxopentanoate 
• 820244-45-9 methyl 3-[(RS)-2-((S)-1-{[(benzyloxy)carbonyl]amino}-2-methylpropyl)-4-methyl-5-oxo-1,3-oxazol-4-yl]propanoate 
• 820244-35-7 methyl (RS)-4-[((S)-2-{[(benzyloxy)carbonyl]amino}-3-methyl-1-oxobutyl)amino]-4-methyl-5-[methyl(phenyl)amino]-5-oxopentanoate 
• 406486-22-4 5-benzyloxy-2,N-dimethyl-N-methoxypentanamide 
• 406486-24-6 phosphorous acid benzyl ester 2-cyano-ethyl ester 4,8,12,16,20-pentamethyl-pentacosyl ester 

Relevant academic research and scientific papers

Palladium-catalysed Conversion of Alkenols into Five- and Six-membered Ring Lactones at Room Temperature and Atmospheric Pressure

Unsaturated alcohols react with carbon monoxide, oxygen, palladium chloride, copper(II) chloride, and hydrochloric acid in tetrahydrofuran to give lactones in 42-80percent yield.

Nanoflow microreactor for dramatic increase not only in reactivity but also in selectivity: Baeyer-Villiger oxidation by aqueous hydrogen peroxide using lowest concentration of a fluorous lanthanide catalyst

Not only the reaction rate but also the regioselectivity in the scandium bis(perfluorooctanesulfonyl)amide-catalyzed Baeyer-Villiger reaction is remarkably increased by the development of the fluorous nanoflow microreactor system continuously controlled by the nanofeeder DiNaS (Direct Nanoflow System) even in the lowest concentration of the catalyst (?0.1 mol%). The Baeyer-Villiger reaction completes within few seconds as a contact time in the nanoflow microreactor to give the lactone products with high regioselectivity without hydrolysis.

Nanoflow system for perfect regiocontrol in the Baeyer-Villiger oxidation by aqueous hydrogen peroxide using lowest concentration of a fluorous lanthanide catalyst

The scandium bis(perfluorooctanesulfonyl)amide-catalyzed Baeyer-Villiger reaction significantly increased the regioselectivity as well as the reaction rate by nanoflow system continuously controlled by a nanofeeder even in the lowest concentration of the catalyst (0.1mol%). The Baeyer-Villiger reaction completed within few seconds as a contact time in the microcell to afford the lactone products high regioselectively without hydrolysis.

A New Synthesis of Alkylated 2H-Pyran-2-ones and Its Application to the Determination of the Relative and Absolute Configuration of Supellapyrone, Sex Pheromone of the Brownbanded Cockroach, Supella longipalpa

The sex pheromone of the brownbanded cockroach, Supella longipalpa, can be synthesized by direct coupling of a brominated pyrone with an alkylzinc reagent.The stereochemistry of the natural pheromone has been assigned as (2'R,4'R)-5-(2',4'-dimethylheptanyl)-3-methyl-2H-pyran-2-one by a combination of synthesis, chiral gas chromatrography, and electrophysiological measurement.

Reductive Opening of α-Methylspiroketals

Syntheses of 5-methyl-1,7-dioxaspiroundecane 4 and its three congeners 5, 6, and 7 (α-methylspiroketals), and their reductive ring opening using aluminum hydride or silane - Lewis acid system have been investigated.Each spiroketal was synthesized through stereocontrolled acetalization with 42 - 96percent diastereomeric excess (de).The diisobutylaluminum hydride reduction of α-methylspiroketals proceeded via the tight oxocarbenium ion pair complex wherein the C-O bond which located at the opposite site against the C(α) - methyl bond was cleaved, affording a configuration-retentive product with 50 - 100percent de.The regioselectivity in the silane - Lewis acid reduction of the simplest monomethylspiroketal 4 was controlled by the equilibration of the two possible oxocarbenium ionic intermediates.On the other hand, dimethylspiroketal 5 and siloxyspiroketal 6 showed moderate to high regio- and stereoselectivity (10-100percent de), that originated from regioselective formation of the oxocarbenium ionic species and the subsequent stereoselective hydride attack.In these cases, the coordination site of the Lewis acid was controlled by the steric interaction of the methyl group on C(α) with the Lewis acid.To the resultant oxocarbenium ion, stereoelectronically-favored axial hydride attack occured with high stereoselection.The reduction of benzyloxyspiroketal 7 also exhibited good selectivity (62 - 100percent de) while the outcome was opposite to those of 5 and 6.Such a dramatic change could be attributed to the bidentate chelation of the Lewis acid to both the benzyl ether and the neighboring acetal oxygens.The whole procedure, the thermodynamic spiroketalization and the subsequent reductive ring opening, could be regarded as a remote stereochemical control using the spiroketal templates.

Isomerisation of ω-hydroxyalkenes under hydroxycarbonylation conditions in palladium catalysed aqueous phase systems

The ω-hydroxyolefins 3-buten-1-ol, 3-buten-1-methyl-1-ol and 4-penten-1-ol were subjected to hydroxycarbonylation conditions in water in the presence of PdCl2(PhCN)2 and 4-8 equiv. of water soluble tris(3-sodiumsulfonatophenyl)phosphine (TPPTS), or N-bis(N′,N′-diethyl-2-aminoethyl)-4-aminomethylphenyl-diphenylphosphine (N3P). Under conditions of high conversion, the olefins primarily undergo isomerisation through a chain walking mechanism with selectivities for aldehyde ranging from 65% to 98%, with the lower values for longer chain alcohols. The lactones formed as the minor product are almost exclusively branched, indicating that in the first step 2,1-insertion is strongly favoured over 1,2-insertion. In the N3P system also linear lactone is produced at lower conversion. Running the reaction in D2O produces multiple deuterium incorporation in all positions of the carbon chain. A mechanism is discussed.

Aldol Additions of Titanium and Boron Enolates of Achiral and Chiral δ-Lactones to Achiral Model Aldehydes: Simple and Induced Diastereoselectivities

We studied the steric course of aldol additions of CpTiCl2 (novel) or Bu2B enolates of the unsubstituted δ-lactone and of the four monomethylated δ-lactones to isobutyraldehyde, crotonaldehyde, and para-bromobenzaldehyde. The titanium enolates reacted syn-selectively with >95:5 ds in most cases. The boron enolates reacted anti-selectively without exception (ds = 98:2 to 92:8). These selectivities paired with a preferred trans-orientation of the α-hydroxyalkyl substituents relative to the lactone's β- or γ-methyl group and with a preferred cis-orientation relative to the lactone's δ-methyl group. Our preparation of γ-methyl-δ-lactone (20) features a tandem glycol cleavage/lactol → lactone conversion with cat. TEMPO/stoichiom. PhI(OAc)2, which we believe is novel. Aldol additions of CpTiCl2 and Bu2B enolates of δ-lactone and its monomethyl derivatives to model aldehydes were studied. The CpTiCl2 enolates reacted syn-selectively (ds >95:5), the Bu2B enolates anti-selectively (ds up to 98:2). The α-hydroxyalkyl groups were oriented trans relative to the lactone's β- or γ-methyl group but cis relative to the lactone's δ-methyl group.

Baeyer-Villiger oxidation of ketones to esters with sodium percarbonate/trifluoroacetic acid

Sodium percarbonate in trifluoroacetic acid has been found to be an effective reagent for the Baeyer-Villiger oxidation of ketones to esters. The scope and limitations of the reaction were explored.

Autocatalytic oxidation of ethers with sodium bromate

Sodium and potassium bromate are stable and easily stored oxidants. They can oxidize both open and cyclic ethers in aqueous solution at room temperature yielding esters and lactones. Kinetic studies of the oxidation of tetrahydrofuran to γ-butyrolactone indicate that the major active oxidation species is bromine and not bromate. The bromate is only a supporting agent, responsible for the initiation step and supplying bromine molecules by oxidizing bromide ions during the propagation step. In the oxidation of tetrahydrofuran, high yields of γ-butyrolactone were obtained. (C) 2000 Elsevier Science Ltd.

Catalytic oxidation of cyclic ethers to lactones over various titanosilicates

Various crystalline microporous metallosilicates have been used in the liquid phase catalytic oxidation of different cyclic ethers into their corresponding lactones in the presence of dilute aqueous H2O 2 as oxidant. Among the various metallosilicates studied for the oxidation of tetrahydrofuran to γ-butyrolactone, titanosilicates exhibited the best activity than the other metallosilicates such as chromium silicalite-1 (CrS-1), chromium silicalite-2 (CrS-2) and vanadium silicalite-1 (VS-1). The intrinsic activity of TS-1 was found to be marginally higher than the other titanosilicates. Cyclic ethers undergo αC-H oxidation to give the corresponding lactones; whereas open-chain ether produce carboxylic acids by initial αC-H bond oxidation to give ester as an intermediate product, which further undergoes cleavage of -O- linkage to give the final carboxylic acids. The conversion of substituted tetrahydrofuran is decreased with number of -CH3 groups at α- and/or β-position. The lactone formation is hindered when both the α-positions are substituted with methyl substituents. Mechanistically, titanium hydroperoxo complex formed in the titanosilicate/H2O2/H2O system is believed to oxidize the αC-H bond of ethers producing the respective α-hydroxylated product, which undergoes further oxidation to give the lactones (for cyclic ethers) or carboxylic acids (for open-chain ethers).