5469-16-9

Basic information

• Product Name: (+/-)-3-HYDROXY-GAMMA-BUTYROLACTONE
• Synonyms: 4-HYDROXYDIHYDROFURAN-2-ONE;(+/-)-3-HYDROXY-GAMMA-BUTYROLACTONE;(+/-)-BETA-HYDROXY-GAMMA-BUTYROLACTONE;(-3-Hydroxy-g-butyrolactone;(n)-3-hydroxy-;3,4-dihydroxybutanoic acid gamma-lactone;3-HYDROXY--BUTYROLACTONE;(^+)-^b-Hydroxy-^y-butyrolactone, 96%
• CAS NO: 5469-16-9
• Molecular Formula: C₄H₆O₃
• Molecular Weight: 102.09
• EINECS: 434-990-4
• Mol File: 5469-16-9.mol
• Article Data: 65

Chemical Properties

• Melting Point: 68℃
• Boiling Point: 98-100°C 0,3mm
• Flash Point: >110°C
• Appearance: /
• Density: 1,241 g/cm3
• Vapor Pressure: 5.42E-05mmHg at 25°C
• Refractive Index: 1.4640
• PKA: 12.87±0.20(Predicted)
• Water Solubility: Fully miscible in water.
• BRN: 107670
• CAS DataBase Reference: (+/-)-3-HYDROXY-GAMMA-BUTYROLACTONE(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-3-HYDROXY-GAMMA-BUTYROLACTONE(5469-16-9)
• EPA Substance Registry System: (+/-)-3-HYDROXY-GAMMA-BUTYROLACTONE(5469-16-9)

Safety Data

• Hazard Codes: Xi:Irritant
• Statements: 36/38
• Safety Statements: 26-36
• Hazardous Substances Data: 5469-16-9(Hazardous Substances Data)

Usage

General Description

(+/-)-3-Hydroxy-gamma-butyrolactone, also known as 3-Hydroxy-GHB, is a chemical compound that is structurally similar to gamma-hydroxybutyrate (GHB), a central nervous system depressant and a recreational drug. 3-Hydroxy-GHB is a chiral compound, meaning it has two different forms, both of which have the same chemical composition but differ in their spatial arrangement. It is a precursor to GHB and is often used as an intermediate in the synthesis of the drug. 3-Hydroxy-GHB is a colorless liquid with a slightly sweet taste, and it is considered to have similar effects to GHB when ingested, including sedation, relaxation, and euphoria. However, it is also associated with similar risks and potential for abuse as GHB.

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

Upstream product

• 109-75-1 but-3-enenitrile 
• 151-50-8 potassium cyanide 
• 96-24-2 3-monochloro-1,2-propanediol 
• 104323-16-2 3(S)-amino-γ-butyrolactone·hydrobromide 
• 10488-69-4 ethyl (S)-4-chloro-3-hydroxybutanoate 
• 10488-69-4 ethyl (L)-4-chloro-3-hydroxybutyrate 
• 1341195-54-7 ethyl 4-[(tert-butyldimethylsilyl)oxy]-3-oxobutanoate 
• 35594-15-1 ethyl 4-acetoxyacetoacetate 
• 85518-49-6 ethyl γ-hydroxyacetoacetate 
• 86728-85-0 ethyl 4-chloro-3-hydroxybutanoate 
• 36850-80-3 [(1-methoxyvinyl)oxy]trimethylsilane 
• 60656-87-3 benzyloxyacetoaldehyde 
• 19405-98-2 (S)-β-acetoxy-γ-butyrolactone 
• 112635-76-4 (S)-ethyl 3,4-dihydroxybutanoate 

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 
• 1518-61-2 3,4-dihydroxybutyric acid 
• 131690-27-2 (5S)-6-benzoyloxy-5-hydroxy-3-oxohexanoic acid tert-butyl ester 
• 95422-24-5 methyl (3S)-3,4-O-isopropylidene-3,4-dihydroxybutanoate 
• 697767-42-3 5-oxotetrahydrofuran-3-yl 4-nitrobenzoate 
• 671223-56-6 (S)-β-[4-nitrophenyl]carbonyloxy-γ-butyrolactone 
• 671223-58-8 (R)-β-[4-nitrophenyl]carbonyloxy-γ-butyrolactone 
• 191403-65-3 (3S)-β-acetoxy-γ-butyrolactone 
• 86728-85-0 ethyl 4-chloro-3-hydroxybutanoate 
• 263164-11-0 (S)-3-(1-ethoxy)ethoxy-γ-butyrolactone 
• 101999-38-6 (S)-4-benzyloxy-dihydrofuran-2(3H)-one 
• 221349-56-0 (3S,4S)-4-(4-Benzyloxy-phenyl)-3-((S)-1,2-dihydroxy-ethyl)-1-(4-fluoro-phenyl)-azetidin-2-one 

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.

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.