(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-3-HYDROXY-, (S);2(3H)-FURANONE, DIHYDRO-4-HYDROXY-, (S);(S)-3-Hydroxy-gamma-;Levetiracetam Impurity 65;(S)-3-HYDROXYBUTYROLACTONE
- CBNumber:
- CB6360496
- Molecular Formula:
- C4H6O3
- Molecular Weight:
- 102.09
- MOL File:
- 7331-52-4.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/8/2 20:38:39
| Boiling point | 98-100 °C0.3 mm Hg(lit.) |
|---|---|
| Density | 1.241 g/mL at 25 °C(lit.) |
| refractive index |
n |
| 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
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H315-H319-H335 | |||||||||
| Precautionary statements | P261-P264-P271-P280-P302+P352-P305+P351+P338 | |||||||||
| Hazard Codes | Xi | |||||||||
| Risk Statements | 36/37/38 | |||||||||
| Safety Statements | 26-36-37/39 | |||||||||
| WGK Germany | 3 | |||||||||
| F | 3-10 | |||||||||
| HS Code | 29322090 | |||||||||
| NFPA 704 |
|
(S)-3-Hydroxy-gamma-butyrolactone Chemical Properties,Uses,Production
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].
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
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| DAVY CHEM LABS | +91-9603460845 +91-9493444489 | Hyderabad, India | 109 | 58 | Inquiry |
| Chaturya Biotech (Tanuj Life Sciences) | 91-7702707258 | Hyderabad, India | 399 | 58 | Inquiry |
| Clearsynth Labs | 91-22-45045900 | Maharashtra, India | 3889 | 58 | Inquiry |
| TCI Chemicals (India) Pvt. Ltd. | 1800 425 7889 | New Delhi, India | 6778 | 58 | Inquiry |
| Bharavi Laboratories (P) Ltd. | 91 80 2666 7742 | New Delhi, India | 359 | 54 | Inquiry |
| Manus Aktteva Biopharma LLP | 08048250218Ext 800 | Ahmedabad, India | 655 | 58 | Inquiry |
| A.J Chemicals | 91-9810153283 | New Delhi, India | 6124 | 58 | Inquiry |
| Bharavi Laboratories (P) Limited | +91 80 2666 7742 | Bangalore, India | 68 | 58 | Inquiry |
| Bhuvar Technologies | 09849396291 | Mallapur, India | 47 | 58 | Inquiry |
| Atlanta Associates | 08048372939Ext 940 | Mumbai, India | 184 | 58 | Inquiry |
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