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
• Article Data: 65

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

Description

(S)-3-Hydroxy-gamma-butyrolactone, also known as (S)-3-HB, is a vital organic compound that serves as a crucial intermediate in the synthesis of various natural products, bioactive chiral drugs, and antibiotic chiral drugs. It is predominantly utilized in the production of pharmaceuticals, particularly those with neurological and metabolic applications. Its unique chiral structure allows for the creation of specific drug formulations that target particular biological pathways.

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.]

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.

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.