13532-37-1

Usage

Uses

Used in Pharmaceutical Industry:
4-Hydroxyvaleric acid is used as a potential therapeutic agent for neurological disorders, particularly Parkinson's disease, due to its implication in the metabolism of neurotransmitters and its potential neuroprotective properties.
Used in Biochemical Research:
4-Hydroxyvaleric acid serves as a subject of interest in biochemical research for its antioxidant and anti-inflammatory properties, contributing to the understanding of various biological processes and the development of new therapeutic strategies.
Used in Diagnostics:
4-Hydroxyvaleric acid can be used as a biomarker in the diagnosis and monitoring of neurological conditions, given its association with neurotransmitter metabolism and its presence in the human body.
Used in Drug Development:
4-Hydroxyvaleric acid is utilized in the development of new drugs targeting neurological disorders, leveraging its potential therapeutic effects and understanding of its role in neurotransmitter metabolism.

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

Upstream product

• 626-95-9 1,4-Pentanediol 
• 626-94-8 (S)-5-hexen-2-ol 
• 67-66-3 chloroform 
• 123-76-2 levulinic acid 
• 76293-75-9 (4R)-hydroxypent-2-ynoic acid 
• 7732-18-5 water 
• 108-29-2 5-methyl-dihydro-furan-2-one 
• 64-17-5 ethanol 
• 18545-25-0 5-methyl-tetrahydro-furan-2-ol 
• 3128-06-1 5-ketohexanoic acid 
• 624-45-3 levulinic acid methyl ester 
• 57-48-7 D-Fructose 
• 539-88-8 4-oxopentanoic acid ethyl ester 
• 1490-24-0 4-oxo-pentanoyl chloride 

Downstream Products

• 108-29-2 5-methyl-dihydro-furan-2-one 
• 58917-25-2 (R)-5-methyl-2-oxotetrahydrofuran 
• 19041-15-7 (S)-γ-valerolactone 
• 123-76-2 levulinic acid 
• 56279-37-9 (S)-4-HVA sodium salt 

Relevant academic research and scientific papers

Tuning the selectivity of electrochemical levulinic acid reduction to 4-hydroxyvaleric acid: A monomer for biocompatible and biodegradable plastics

Levulinic acid (LA) is a biomass-derived feedstock that can be converted to a wide array of value-added products; several of these can be accessed efficiently by electrochemical conversion. Herein, we present a study of factors governing LA conversion in electrochemical environments. Most notably, we identify an unprecedentedly efficient pathway forming 4-hydroxyvaleric acid (HVA), a valuable monomer that can be used for production of bio-polyesters - specifically, poly(hydroxy acids) - as well as γ-valerolactone (GVL) (a green fuel/solvent) and other fine chemicals. This method shows >99.9% selectivity and >80% faradaic efficiency for conversion above 80%. Production rates higher than 40 g L-1 h-1 (or 200 kg L-1 mgeom.-2 h-1) were achieved; these are substantially higher than reports for compatible biochemical methods. We further identify mechanistic insights regarding the steering of selectivity toward this new pathway in comparison to known electrochemical routes toward valeric acid (VA) or to GVL. Finally, we provide a fast, sequential one-pot synthesis route to transform electrochemically-produced HVA to GVL with higher overall selectivity and faradaic efficiency than can be achieved by direct aqueous electrochemical conversion of LA to GVL (96% conversion and >99.9% selectivity, giving a total yield of 93% from LA). This journal is

Ir(triscarbene)-catalyzed sustainable transfer hydrogenation of levulinic acid to γ-valerolactone

Sustainable iridium-catalyzed transfer hydrogenation using glycerol as the hydride source was employed to convert levulinic acid to γ-valerolactone (GVL) with exceptionally high turnover numbers (TONs) (500,000) and turnover frequencies (TOFs) (170,000 h?1). The highly efficient triscarbene-modified iridium catalysts demonstrated good catalytic activities with low catalyst loadings (0.7 ppm) and good recyclability with an accumulated TON of over two million in the fourth reaction. In addition to glycerol, propylene glycol (PG), ethylene glycol (EG), isopropanol (IPA), and ethanol (EtOH) successfully transferred hydrides to levulinic acid, producing GVL with TONs of 339,000 (PG), 242,000 (EG), 334,000 (IPA), and 208,000 (EtOH), respectively. Deuterium-labeling experiments were conducted to gain insight into the reaction mechanism.

Highly efficient selective hydrogenation of levulinic acid to γ-valerolactone over Cu-Re/TiO2bimetallic catalysts

Highly active and thermally stable Cu-Re bimetallic catalysts supported on TiO2 with 2.0 wt% loading of Cu were prepared via an incipient wetness impregnation method and were applied for liquid phase selective hydrogenation of levulinic acid (LA) to γ-valerolactone (GVL) in H2. The effect of the molar ratios of Cu?:?Re on the physico-chemical properties and the catalytic performance of the Cu-Re/TiO2 catalysts was investigated. Moreover, the influence of various reaction parameters on the hydrogenation of LA to GVL was studied. The results showed that the Cu-Re/TiO2 catalyst with a 1?:?1 molar ratio of Cu to Re (Cu-Re(1?:?1)/TiO2) exhibited the highest performance for the reaction. Complete conversion of LA with a 100% yield of GVL was achieved in 1,4-dioxane solvent under the reaction conditions of 180 °C, 4.0 MPa H2 for 4 h, and the catalyst could be reused at least 6 times with only a slight loss of activity. Combined with the characterization results, the high performance of the catalyst was mainly attributed to the well-dispersed Cu-Re nanoparticles with a very fine average size (ca. 0.69 nm) and the co-presence of Cu-Re bimetal and ReOx on the catalyst surface.

Efficient Conversion of Biomass-Derived Levulinic Acid to γ-Valerolactone over Polyoxometalate@Zr-Based Metal-Organic Frameworks: The Synergistic Effect of Bro?nsted and Lewis Acidic Sites

Catalytic transformation of levulinic acid (LA) to γ-valerolactone (γ-GVL) is an important route for biomass upgradation. Because both Bro?nsted and Lewis acidic sites are required in the cascade reaction, herein we fabricate a series of H3PW12O40@Zr-based metal-organic framework (HPW@MOF-808) by a facile impregnation method. The synthesized HPW@MOF-808 is active for the conversion of LA to γ-GVL using isopropanol as a hydrogen donor. Interestingly, with the increase in the HPW loading amount, the yield of γ-GVL increases first and then decreases, and 14%-HPW@MOF-808 gave the highest γ-GVL yield (86%). The excellent catalytic performance was ascribed to the synergistic effect between the accessible Lewis acidic Zr4+ sites in MOF-808 and Bro?nsted acidic HPW sites. Based on the experimental results, a plausible reaction mechanism was proposed: the Zr4+ sites catalyze the transfer hydrogenation of carbonyl groups and the HPW clusters promote the esterification of LA with isopropanol and lactonization to afford γ-GVL. Moreover, HPW@MOF-808 is resistant to leaching and can be reused for five cycles without significant loss of its catalytic activity.

Ammonia borane enabled upgrading of biomass derivatives at room temperature

Simplifying biomass conversion to valuable products with high efficiency is pivotal for the sustainable development of society. Herein, an efficient catalyst-free system using ammonia borane (AB) as the hydrogen donor is described, which enables controllable reaction selectivity towards four value-added products in excellent yield (82-100%) under very mild conditions. In particular, the system is uniquely efficient to produce γ-valerolactone (GVL) at room temperature. Combined in situ NMR and computational studies elucidate the hydrogen transfer mechanism of AB in methanol, the novel pathway of GVL formation from levulinate in water, and a competitive mechanism between reduction and reductive amination in the same system. Moreover, carbohydrates are converted directly into GVL in good yield, using a one-pot, two-step strategy. Products of a rather broad scope are prepared within a short reaction time of 30 min by using this catalyst-free strategy in methanol at room temperature. This journal is

Carboxyl Group-Directed Iridium-Catalyzed Enantioselective Hydrogenation of Aliphatic ?-Ketoacids

Although the transition metal-catalyzed asymmetric hydrogenation of aromatic ketones has been extensively explored, the enantioselective hydrogenation of aliphatic ketones remains a challenge because chiral catalysts cannot readily discriminate between the re and si faces of these ketones. Herein, we report a carboxyl-directing strategy for the asymmetric hydrogenation of aliphatic ?-ketoacids. With catalysis by iridium complexes bearing chiral spiro phosphino-oxazoline ligands, hydrogenation of aliphatic ?-ketoacids afforded chiral ?-hydroxylacids with high enantioselectivity (up to 99% ee). Mechanistic studies revealed that the carboxyl group of the substrate directs hydrogen transfer and ensures high enantioselectivity. Density functional theory calculations suggested the occurrence of chiral induction involving a hydrogen-hydrogen interaction between a hydride on the iridium atom and the substituent on the oxazoline ring of the ligand, and on the basis of the calculations, we proposed a catalytic cycle involving only Ir(III), which differs from the Ir(III)/Ir(V) catalytic cycle that operates in the hydrogenation of α,β-unsaturated carboxylic acids.

Catalytic transfer hydrogenation of biomass-derived levulinic acid to γ-valerolactone over Sn/Al-SBA-15 catalysts

Gamma valerolactone (GVL) is an important chemical feedstock from which several value-added fine chemicals, fuels and fuel additives are manufactured. GVL is the product obtained in the hydrogenation of levulinic acid (LA), which in turn is generally manufactured from several renewable resources such as pentoses and hexoses. The present work deals with the synthesis of SBA-15 and Sn loaded catalysts [x% Sn/Al-SBA-15 (x = Si/Sn = 10, 25, 50, 75 and 100 with Si/Al = 25)] using a hydrothermal in situ method. A variety of both bulk and surface characterization techniques such as XRD, FT-IR, BET, FE-SEM, HR-TEM, XPS, TGA/DTA and UV-DRS were used to characterize the bare and Sn/Al-SBA-15 catalysts. The characterization studies revealed the presence of Sn species well dispersed in the uniform pore channels of Al-SBA-15. All the synthesized catalysts were tested in the liquid-phase catalytic transfer hydrogenation of levulinic acid at atmospheric N2 pressure under mild reaction conditions. Among them, the Sn/Al-SBA-15 (Si/Sn = 25) catalyst showed remarkable conversion of levulinic acid (99%) and very high selectivity towards GVL (100%). The various reaction parameters such as metal loading, reaction temperature, reaction time and catalyst weight were optimized to get the maximum conversion of levulinic acid with high selectivity towards the desired product. The stability and reusability of the best catalysts were also tested up to five cycles and there was not much variation in the catalytic activity in terms of conversion.

Hydrogenation of levulinic acid to γ-valerolactone over bifunctional Ru/(AlO)(ZrO)n catalyst: Effective control of Lewis acidity and surface synergy

A bifunctional Ru/(AlO)(ZrO)n catalyst was reported for efficient hydrogenation of levulinic acid to γ-valerolactone, an important and environmental-benign upgrading process of bio-platform compound. The optimal Ru/(AlO)(ZrO)0.1 catalyst showed 100% yield to γ-valerolactone in water at 120 °C under 1 MPa H2, one of the best performances among Ru catalysts under mild conditions. And this catalyst also presented good stability and reusability. PXRD, TEM, XPS, CO chemisorption, CO adsorption DRIFT-IR, NH3-TPD and pyridine adsorption IR gave insights into the acidic property and surface synergy of the catalysts. Highly active electron-rich Ru0 sites stabilized by strong metal-support interaction (SMSI) can effectively adsorb and activate molecular H2 and C[dbnd]O bond in levulinic acid. Varying Zr/Al ratio and calcination temperature can rationally control the acid strength and acid sites distribution of support, and (AlO)(ZrO)0.1 calcined at 400 °C exhibited the maximal proportion of Lewis acid sites. Ru0 species and Lewis acid sites synergistically enhanced the conversion of levulinic acid and facilitated the intramolecular dehydration of 4-hydroxypentanoic acid as intermediate to γ-valerolactone (i.e., the rate-limiting step).

Transfer hydrogenation of levulinic acid from glycerol and ethanol using water-soluble iridium N-heterocyclic carbene complexes

The upgrading of biomass derivatives to biofuels and chemicals through transfer hydrogenation (TH) is attractive relative to direct hydrogenation, especially when the hydrogen donors can be sourced renewably. Here we report the first process that uses glycerol, a renewable waste material from biodiesel processing, as a hydrogen donor in the catalytic TH of a biomass-derived platform chemical, levulinic acid, to selectively afford γ-hydroxyvaleric acid (GHV) and lactic acid (LA). GHV can be further converted to γ-valerolactone (GVL), a widely used platform chemical. Levulinic acid can be used directly, without esterification, which is typically needed for transfer hydrogenation. The process is efficiently facilitated by robust iridium N-heterocyclic carbene (NHC) complexes with sulfonate functional groups at low catalyst loading (1–10 ppm), affording quantitative conversion of levulinic acid in the presence of KOH to GHV, with >100,000 TON in 2 h at 150 °C, using 1 ppm catalyst. The most prolific catalyst, [(NHC-SO3-)2(CO)2Ir]Na, can also facilitate transfer hydrogenation from other hydrogen donors, such as 2-propanol, potassium formate, and most notably, ethanol, which can also be derived from renewables. Ethanol is a highly efficient hydrogen donor for levulinic acid using this catalyst, affording >7,000 turnovers in 2 h using 10 ppm catalyst.

Highly active bidentate N-heterocyclic carbene/ruthenium complexes performing dehydrogenative coupling of alcohols and hydroxides in open air

Eight bidentate NHC/Ru complexes, namely [Ru]-1-[Ru]-8, were designed and prepared. In particular, [Ru]-2 displayed extraordinary performance even in open air for the dehydrogenative coupling of alcohols and hydroxides. Notably, an unprecedentedly low catalyst loading of 250 ppm and the highest TON of 32 800 and TOF of 3200 until now were obtained.