7331-52-4

Basic information

• Product Name: (S)-3-Hydroxy-gamma-butyrolactone
• Synonyms: 2(3H)-FURANONE, DIHYDRO-3-HYDROXY-, (S);2(3H)-FURANONE, DIHYDRO-4-HYDROXY-, (S);(S)-4-HYDROXYTETRAHYDROFURAN-2-ONE;(S)-4,5-DIHYDRO-4-HYDROXY-2(3H)-FURANONE;(S)-(-)-3-HYDROXYBUTYROLACTONE;(S)-3-HYDROXYBUTYROLACTONE;(S)-(-)-3-HYDROXY-GAMA-BUTYROLACTONE;(S)-(-)-3-HYDROXY-GAMMA-BUTYROLACTONE
• CAS NO: 7331-52-4
• Molecular Formula: C₄H₆O₃
• Molecular Weight: 102.09
• EINECS: 434-990-4
• Product Categories: chiral;Tetrahydrofuran Series;Chiral Building Blocks;Simple Alcohols (Chiral);Synthetic Organic Chemistry
• Mol File: 7331-52-4.mol

Chemical Properties

• Melting Point: 1.24
• Boiling Point: 98-100 °C0.3 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Colorless to light yellow liquid
• Density: 1.241 g/mL at 25 °C(lit.)
• Vapor Pressure: 5.42E-05mmHg at 25°C
• Refractive Index: n20/D 1.464(lit.)
• Storage Temp.: 2-8°C
• PKA: 12.87±0.20(Predicted)
• Water Solubility: Miscible with water, alcohol and other organic solvent. Immiscible with light petroleum.
• BRN: 1280864
• CAS DataBase Reference: (S)-3-Hydroxy-gamma-butyrolactone(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-Hydroxy-gamma-butyrolactone(7331-52-4)
• EPA Substance Registry System: (S)-3-Hydroxy-gamma-butyrolactone(7331-52-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 7331-52-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
(S)-3-Hydroxy-gamma-butyrolactone is used as a key intermediate in the synthesis of neurological regulators and metabolic enhancers. It plays a significant role in the production of (R)-GABOB, a nerve regulator, and S-oxiracetam (S-ORC), a brain metabolic accelerant. Its importance in these applications stems from its ability to provide the necessary chiral framework for the development of these drugs.
Used in Anticancer Drug Resistance:
(S)-3-Hydroxy-gamma-butyrolactone is used as an anticancer drug resistance inhibitor, helping to overcome resistance mechanisms in cancer cells and improving the effectiveness of chemotherapy treatments. This application is particularly relevant in the ongoing battle against drug-resistant cancers, where novel approaches to treatment are essential.
Used in the Synthesis of Anti-AIDS Drugs:
(S)-3-Hydroxy-gamma-butyrolactone is used as a precursor in the synthesis of (S)-(+)-3-Hydroxytetrahydrofuran, an important intermediate for the development of anti-AIDS drugs. Its role in this process highlights its versatility and the wide range of therapeutic applications it can support.
Used in the Synthesis of Potential Stabilizers:
(S)-3-Hydroxy-gamma-butyrolactone is also used in the synthesis of S(-)-3-hydroxy-4-bromobutyric acid, a compound with potential applications as a stabilizer in various industrial processes. This further demonstrates the compound's utility across different sectors, from pharmaceuticals to industrial chemistry.

Precautions

For best results, Store in cool, dry place in tightly closed containers, under inert gas and protected from moisture as this substance is moisture sensitive. (S)-3-Hydroxy-gamma-butyrolactone is incompatible with oxidizing agents. This chemical causes skin irritation and serious eye irritation.

InChI:InChI=1/C4H6O3/c5-3-1-4(6)7-2-3/h3,5H,1-2H2/t3-/m0/s1

Upstream product

• 625-38-7 but-3-enoic acid 
• 1518-61-2 3,4-dihydroxybutyric acid 
• 16507-32-7 (±)-3,4-dibromobutanoic acid 
• 109-75-1 but-3-enenitrile 
• 151-50-8 potassium cyanide 
• 96-24-2 3-monochloro-1,2-propanediol 
• 33282-42-7 4-bromomethyl-β-lactone 
• 104323-16-2 3(S)-amino-γ-butyrolactone·hydrobromide 
• 556-52-5 oxiranyl-methanol 
• 74-90-8 hydrogen cyanide 
• 7664-93-9 sulfuric acid 
• 32223-97-5 (+/-)-ethyl-3,4-epoxybutanoate 
• 88246-12-2 methyl 3,4-dihydroxybutanoate 
• 201230-82-2 carbon monoxide 

Downstream Products

• 497-23-4 2-buten-4-olide 
• 112100-39-7 (S)-4-iodo-3-hydroxy-butyric acid ethyl ester 
• 161772-32-3 (S)-4-(4-Methoxy-benzyloxy)-dihydro-furan-2-one 
• 308357-84-8 (-)-(3S)-3-[(4-methoxybenzyl)oxy]dihydrofuran-2(3H)-one 
• 32224-01-4 (S)-4-bromo-3-hydroxy-butyric acid ethyl ester 
• 126495-84-9 (S)-3,4-dihydroxybutyramide 
• 221349-56-0 (3S,4S)-4-(4-Benzyloxy-phenyl)-3-((S)-1,2-dihydroxy-ethyl)-1-(4-fluoro-phenyl)-azetidin-2-one 
• 101999-38-6 (S)-4-benzyloxy-dihydrofuran-2(3H)-one 
• 263164-11-0 (S)-3-(1-ethoxy)ethoxy-γ-butyrolactone 
• 86728-85-0 ethyl 4-chloro-3-hydroxybutanoate 
• 1518-61-2 3,4-dihydroxybutyric acid 
• 617-48-1 malic acid 

Relevant articles and documents

Ru/SiO2 Catalyst for Highly Selective Hydrogenation of Dimethyl Malate to 1,2,4-Butanetriol at Low Temperatures in Aqueous Solvent

Catalytic selective hydrogenation of esterified malic acid to produce 1,2,4-butanetriol (1,2,4-BT) using H2 as the reducing reagent suffers from the low 1,2,4-BT selectivity. Here, Ru/SiO2 catalyst was employed for selective hydrogenation of dimethyl malate (DM) to produce 1,2,4-BT, which gave abnormal high DM conversion (100%) and 1,2,4-BT selectivity (92.4%) in aqueous solvent at 363?K, especially, the 1,2,4-BT yield even is higher than the optimal catalyst reported (Ru-Re, 79.8%). The reaction pathways for the DM hydrogenation on Ru/SiO2 were also proposed, suggesting that extremely high 1,2,4-BT selectivity require for the much high hydrogenation rates at low temperatures, where side-reaction transesterification rates are relatively low. The extremely high hydrogenation activity and 1,2,4-BT selectivity on Ru/SiO2 in aqueous solvent at low temperatures arise from that H2O may coordinate to Ru2+ and prevent the reduction of Ru2+ to Ru under high H2 pressure. Ru/SiO2 surface presents abundant Ru2+ in aqueous solvent, can activate H2 through heterolytic cleavage mode to form hydride, which can significantly increase hydrogenation rates of C = O groups at low temperatures. In addition, the activity and 1,2,4-BT selectivity on Ru/SiO2 catalyst only reduced by 2.3% and 2.6%, respectively over a period of 550?h. Graphical Abstract: [Figure not available: see fulltext.]

A Concise Stereoselective Total Synthesis of Methoxyl Citreochlorols and Their Structural Revisions

A concise, stereoselective and protecting group free approaches for the total synthesis of (?)-(2S,4R)- and (+)-(2R,4S)-3′-methoxyl citreochlorols and their stereoisomers are demonstrated. All four stereoisomers were synthesized to establish the absolute stereochemistry of the reported structures and the structures were revised accordingly. The approach involves chelation controlled regioselective reduction of a diester, silyl iodide promoted ring-opening iodo esterification of lactones, highly chemo- and regioselective ring-opening of an epoxy ester, dichloromethylation of a carboxyl group, and syn- and anti-selective reduction of the resulted β-hydroxy ketone as key steps.

Synthesis of nature product kinsenoside analogues with anti-inflammatory activity

Kinsenoside is the major bioactive component from herbal medicine with a broad range of pharmacological functions. Goodyeroside A, an epimer of kinsenoside, remains less explored. In this report we chemically synthesized kinsenoside, goodyeroside A and their analogues with glycan variation, chirality inversion at chiral center(s), and bioisosteric replacement of lactone with lactam. Among these compounds, goodyeroside A and its mannosyl counterpart demonstrated superior anti-inflammatory efficacy. Furthermore, goodyeroside A was found to suppresses inflammatory through inhibiting NF-κB signal pathway, effectively. Structure-activity relationship is also explored for further development of more promising kinsenoside analogues as drug candidates.

Synthesis method of R-3-propyl-gamma-butyrolactone

The invention discloses a synthetic method of R-3-propyl-gamma-butyrolactone, and belongs to the technical field of organic synthesis. The method comprises the following steps: by taking D-malic acidas a raw material, performing monomethyl esterification, reduction, halogenation or sulfonic acid esterification, and finally coupling with a Grignard reagent under the catalysis of zinc chloride to obtain a brivaracetam intermediate that is the R-3-propyl-gamma-butyrolactone. The method has the advantages of cheap and easily available starting raw materials, good stereoselectivity, no need of chiral resolution, mild condition, short route and the like, and provides a feasible scheme for brivaracetam process research.

Intercepted dehomologation of aldoses by N-heterocyclic carbene catalysis-a novel transformation in carbohydrate chemistry

The development of an N-heterocyclic carbene (NHC) catalysed intercepted dehomologation of aldoses is reported. The unique selectivity of NHCs for aldehydes is exploited in the complex context of reducing sugars. Examples of strong substrate governance for either intercepted dehomologation or a subsequent redox-lactonisation were identified and mechanistically understood. More importantly, it was shown that catalyst design allowed the tuning of the selectivity of the reaction with structurally unbiased starting materials towards either of the two scenarios.

Practical Cleavage of Acetals by Using an Odorless Thiol Immobilized on Silica

A practical, efficient and general method was developed for the deprotection of a variety of aromatic and aliphatic acetals to their corresponding catechol or diol derivatives using thiol immobilized on silica gel. This is an application for the well-known commercial solid-supported thiol (SiliaMetS Thiol). The procedure is mild and amenable to scale-up. It does not require inert atmosphere and clean conversions were observed. This method is applicable to substituted 1,3-benzodioxole and aliphatic acetals with different functionalities. It offers the advantage of a general route with high yield, which can be undertaken at ambient temperature.

Total synthesis and stereochemical assignment of nostosin B

Nostosins A and B were isolated from a hydrophilic extract of Nostoc sp. strain from Iran, which exhibits excellent trypsin inhibitory activity. Nostosin A was the most potent natural tripeptide aldehyde as trypsin inhibitor up to now. Both R- and S-2-hydroxy-4-(4-hydroxy-phenyl)butanoic acid (Hhpba) were prepared and incorporated into the total synthesis of nostosin B, respectively. Careful comparison of the NMR spectra and optical rotation data of synthetic nostosin B (1a and 1b) with the natural product led to the unambiguous identification of the R-configuration of the Hhpba fragment, which was further confirmed by co-injection with the authentic sample on HPLC using both reversed phase column and the chiral AD-RH column.

A high selective (S)-β-hydroxy-γ-butyrolactone simple method for preparing

The invention relates to a simple and convenient preparation method of highly selective (S)-beta-hydroxy-gamma-butyrolactone. The simple and convenient preparation method comprises the following steps: with allyl alcohol as a starting material, preparing (R)-2, 3-epoxy propanol by virtue of asymmetric epoxidation, and carrying out cyanidation, cyan-hydrolysis and esterification on (R)-2, 3-epoxy propanol to prepare the (S)-beta-hydroxy-gamma-butyrolactone. The simple and convenient preparation method is short in reaction route, easily available in raw material, easy in reaction condition operation, high in reaction selectivity and suitable for industrial production.

Study of Class i and Class III Polyhydroxyalkanoate (PHA) Synthases with Substrates Containing a Modified Side Chain

Polyhydroxyalkanoates (PHAs) are carbon and energy storage polymers produced by a variety of microbial organisms under nutrient-limited conditions. They have been considered as an environmentally friendly alternative to oil-based plastics due to their renewability, versatility, and biodegradability. PHA synthase (PhaC) plays a central role in PHA biosynthesis, in which its activity and substrate specificity are major factors in determining the productivity and properties of the produced polymers. However, the effects of modifying the substrate side chain are not well understood because of the difficulty to accessing the desired analogues. In this report, a series of 3-(R)-hydroxyacyl coenzyme A (HACoA) analogues were synthesized and tested with class I synthases from Chromobacterium sp. USM2 (PhaCCs and A479S-PhaCCs) and Caulobacter crescentus (PhaCCc) as well as class III synthase from Allochromatium vinosum (PhaECAv). It was found that, while different PHA synthases displayed distinct preference with regard to the length of the alkyl side chains, they could withstand moderate side chain modifications such as terminal unsaturated bonds and the azide group. Specifically, the specific activity of PhaCCs toward propynyl analogue (HHxyCoA) was only 5-fold less than that toward the classical substrate HBCoA. The catalytic efficiency (kcat/Km) of PhaECAv toward azide analogue (HABCoA) was determined to be 2.86 × 105 M-1 s-1, which was 6.2% of the value of HBCoA (4.62 × 106 M-1 s-1) measured in the presence of bovine serum albumin (BSA). These side chain modifications may be employed to introduce new material functions to PHAs as well as to study PHA biogenesis via click-chemistry, in which the latter remains unknown and is important for metabolic engineering to produce PHAs economically.

Development of Noviomimetics as C-Terminal Hsp90 Inhibitors

KU-32 and KU-596 are novobiocin-derived, C-terminal heat shock protein 90 (Hsp90) modulators that induce Hsp70 levels and manifest neuroprotective activity. However, the synthetically complex noviose sugar requires 10 steps to prepare, which makes translational development difficult. In this study, we developed a series of "noviomimetic" analogues of KU-596, which contain noviose surrogates that can be easily prepared, while maintaining the ability to induce Hsp70 levels. Both sugar and sugar analogues were designed, synthesized, and evaluated in a luciferase reporter assay, which identified compound 37, a benzyl containing noviomimetic, as the most potent inducer of Hsp70.