(S)-3-Hydroxy-gamma-butyrolactone

Product Name: (S)-3-Hydroxy-gamma-butyrolactone
CAS No.: 7331-52-4
Chemical Name: (S)-3-Hydroxy-gamma-butyrolactone
Synonyms: (S)-4-Hydroxydihydrofuran-2(3H)-one;(s)-(-)-á-hydroxy-;-4-Hydroxydihydrofuran-2(3H);(S)-(-)-3-HYDROXYBUTYROLACTONE;(S)-(-)-3-HYDROXY-GAMMA-BUTYROLACTONE;2(3H)-FURANONE, DIHYDRO-4-HYDROXY-, (S);2(3H)-FURANONE, DIHYDRO-3-HYDROXY-, (S);(S)-3-Hydroxy-gamma-;Levetiracetam Impurity 65;(S)-3-HYDROXYBUTYROLACTONE
CBNumber: CB6360496
Molecular Formula: C4H6O3
Formula Weight: 102.09
MOL File: 7331-52-4.mol

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(S)-3-Hydroxy-gamma-butyrolactone Property

Boiling point:: 98-100 °C0.3 mm Hg(lit.)
Density: 1.241 g/mL at 25 °C(lit.)
refractive index: n20/D 1.464(lit.)
Flash point:: >230 °F
storage temp.: Inert atmosphere,2-8°C
pka: 12.87±0.20(Predicted)
optical activity: [α]21/D 81°, c = 2 in ethanol
Water Solubility: Miscible with water, alcohol and other organic solvent. Immiscible with light petroleum.
BRN: 1280864
InChI: InChI=1S/C4H6O3/c5-3-1-4(6)7-2-3/h3,5H,1-2H2/t3-/m0/s1
InChIKey: FUDDLSHBRSNCBV-VKHMYHEASA-N
SMILES: O1C[C@@H](O)CC1=O
CAS DataBase Reference: 7331-52-4(CAS DataBase Reference)

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Safety

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 26-36-37/39
WGK Germany: 3
F: 3-10
HS Code: 29322090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 422797
Product name: (S)-β-Hydroxy-γ-butyrolactone
Purity: 96%
Packaging: 1g
Price: $27.48
Updated: 2024/03/01

TCI Chemical

Product number: H0939
Product name: (S)-3-Hydroxy-gamma-butyrolactone
Purity: >95.0%(GC)
Packaging: 1g
Price: $53
Updated: 2021/12/16

TCI Chemical

Product number: H0939
Product name: (S)-3-Hydroxy-gamma-butyrolactone
Purity: >95.0%(GC)
Packaging: 5g
Price: $149
Updated: 2021/12/16

Alfa Aesar

Product number: L20256
Product name: (S)-(-)-beta-Hydroxy-gamma-butyrolactone, 90+%, ee 99%
Packaging: 5g
Price: $74.6
Updated: 2021/12/16

TRC

Product number: H956325
Product name: (S)-3-Hydroxy-γ-butyrolactone
Packaging: 2.5g
Price: $90
Updated: 2021/12/16

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(S)-3-Hydroxy-gamma-butyrolactone Chemical Properties,Usage,Production

Description

(S)-3-Hydroxy-gamma-butyrolactone is an important intermediate in organic synthesis and an important chiral pool. It is mainly used in the synthesis of some natural products and some bioactive chiral drugs or antibiotic chiral drugs. For example, it is a key intermediate in synthesis of nerve regulator (R)-GABOB and brain metabolic accelerant S-oxiracetam (S-ORC). It can be deoxidized to (S)-(+)-3-Hydroxytetrahydrofuran which is an important intermediate of anti-AIDS drugs. It is also used in the synthesis of S(-)-3-hydroxy-4-bromobutyric acid which is a potential stabilizer.

Chemical Properties

Colorless to light yellow liquid.

Uses

(S)-3-Hydroxy-γ-butyrolactone can be used as an anticancer drug resistance inhibitor.

Application

(S)-3-Hydroxy-gamma-butyrolactone is an important synthetic intermediate for a variety of chiral compounds. It is a key intermediate for preparing neuromediator (R)-GABOB, l-carnitine, and HMG-CoA reductase inhibitor, CI-981. (S)-3-Hydroxy-gamma-butyrolactonef has been reported as a satiety and potentiating agent to neuroleptic drugs. It is widely used in the pharmaceutical industry as a chiral building block for the statin class of cholesterol-reducing drugs such as Crestor and Lipitor, as well as the antibiotic Zyvox and the antihyperlipidemic medication Zetia. Other pharmaceuticals derived from 3HBL include HIV inhibitors and the nutritional supplement L-carnitine. 3HBL can readily be transformed into a variety of three-carbon building blocks and has been listed as one of the top value-added chemicals from biomass by the US Department of Energy[1-2].

Synthesis

Optically pure (S)-3-hydroxy-gamma-butyrolactone, a crucial chiral building block in the pharmaceutical industry, was synthesized from L: -malic acid by combining selective hydrogenation and lipase-catalyzed hydrolysis. Lipase from Candida rugosa was found to be the most efficient enzyme for the hydrolysis of (S)-beta-benzoyloxy-gamma-butyrolactone[1].

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.

References

[1] Pradeep Kumar. “A simple and practical approach to enantiomerically pure (S)-3-hydroxy-γ-butyrolactone: synthesis of (R)-4-cyano-3-hydroxybutyric acid ethyl ester.” Tetrahedron, asymmetry 16 16 (2005): Pages 2717-2721. [2] Sang-Hyun Lee, Hong-Sun Uh, Oh-Jin Park. “A chemoenzymatic approach to the synthesis of enantiomerically pure (S)-3-hydroxy-γ-butyrolactone.” Applied Microbiology and Biotechnology 79 3 (2008): 355–362.

(S)-3-Hydroxy-gamma-butyrolactone Preparation Products And Raw materials

Raw materials

Preparation Products

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(S)-3-Hydroxy-gamma-butyrolactone Suppliers

Americas 1 Belgium 2 Canada 3 China 252 Europe 1 France 1 Germany 7 India 12 Japan 6 Slovakia 2 South Korea 4 Spain 1 Switzerland 3 The Netherlands 2 Ukraine 1 United Kingdom 21 United States 49 Global 368

Shanghai YuLue Chemical Co., Ltd.

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View Lastest Price from (S)-3-Hydroxy-gamma-butyrolactone manufacturers

Dorne Chemical Technology co. LTD

Product: (S)-3-Hydroxy-γ-butyrolactone 7331-52-4
Price: US $1.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 10 tons
Release date: 2024-03-26

CONTIDE BIOTECH CO.,LTD

Product: (S)-3-Hydroxy-gamma-butyrolactone 7331-52-4
Price: US $0.00/G
Min. Order: 1G
Purity: 99%
Supply Ability: 20
Release date: 2024-03-22

Hebei Dangtong Import and export Co LTD

Product: (S)-3-Hydroxy-gamma-butyrolactone 7331-52-4
Price: US $14.00-13.00/Grams
Min. Order: 1Grams
Purity: 99%
Supply Ability: 100Tons
Release date: 2023-03-03

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(S)-3-Hydroxy-gamma-butyrolactone 7331-52-4

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Levetiracetam Impurity 65

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7331-52-4

73311-52-4

Asymmetric Synthesis

Chiral Building Blocks

Simple Alcohols (Chiral)

Lactones

Organic Building Blocks

Chiral Building Blocks

Simple Alcohols (Chiral)

Synthetic Organic Chemistry

Tetrahydrofuran Series

chiral

7331-52-4