(S)-3-Hydroxy-gamma-butyrolactone Chemical Properties

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)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

F 

3-10

HS Code 

29322090

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

(S)-3-Hydroxy-gamma-butyrolactone Usage And Synthesis

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.

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