ChemicalBook > CAS DataBase List > (S)-3-Hydroxy-gamma-butyrolactone

(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

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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

7331-52-4, (S)-3-Hydroxy-gamma-butyrolactoneRelated Search:

(+)-DIBENZOYL-L-TARTARIC ANHYDRIDE 2-Deoxy-2,2-difluoro-D-erythro-pentafuranous-1-ulose-3,5-dibenzoate 5-BROMO-5-DEOXY-2,3-O-ISOPROPYLIDENE-D-RIBONOLACTONE D-ERYTHRONOLACTONE (-)-O-ACETYL-L-MALIC ANHYDRIDE 2,3-O-ISOPROPYLIDENE-D-ERYTHRONOLACTONE 2,3-O-Isopropylidene-D-ribonic gamma-lactone D-GLUCOHEPTONO-1,4-LACTONE L-Mannono-1,4-lactone D-(-)-Gulonic acid gamma-lactone L-GALACTONO-1,4-LACTONE 2-HYDROXY-GAMMA-BUTYROLACTONE 99%,ALPHA-HYDROXY-GAMMA-BUTYROLACTONE, TECH.,2-HYDROXY-GAMMA-BUTYROLACTONE,ALPHA-HYDROXY-GAMMA-BUTYROLACTONE DL-3,3-DIMETHYL-2-HYDROXY-GAMMA-BUTYROLACTONE,3,3-DIMETHYL-2-HYDROXY-GAMMA-BUTYROLACTONE,BETA,BETA-DIMETHYL-ALPHA-HYDROXY-GAMMA-BUTYROLACTONE (R)-(+)-ALPHA-HYDROXY-GAMMA-BUTYROLACTONE,(R)-2-HYDROXY-GAMMA-BUTYROLACTONE,(R)-(+)-ALPHA-HYDROXY-GAMMA-BUTYROLACTONE 98+% (+/-)-BETA-HYDROXY-GAMMA-BUTYROLACTONE,(+/-)-3-HYDROXY-GAMMA-BUTYROLACTONE (S)-2-Hydroxy-gamma-butyrolactone,(S)-(-)-ALPHA-HYDROXY-GAMMA-BUTYROLACTONE,(S)-(-)-~-Hydroxy-gamma-butyrolactone, 94% S(+)-3,3-DIMETHYL-2-HYDROXY-GAMMA-BUTYROLACTONE (R)-(+)-3-Hydroxybutyrolactone

  • 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
  • (S)-3-HYDROXY-GAMMA-BUTYROLACTONE
  • (S)-(-)-BETA-HYDROXY-GAMMA-BUTYROLACTONE
  • (S)-BETA-HYDROXY-GAMMA-BUTYROLACTONE
  • (s)-(-)-á-hydroxy-
  • (S)-(-)-BETA-HYDROXY-GAMMA-BUTYROLACTONE , EE 99%
  • (S)-(-)-SS-HYDROXY-GAMMA-BUTYROLACTONE: 94%
  • (S)-(-)--HYDROXY-G-BUTYROLACTONE
  • 4(S)-Hydroxytetrahydrofuran-2-ONE
  • (S)-(-)-b-Hydroxy-g-butyrolactone
  • (S)-DIHYDRO-4-HYDROXY-2(3H)-FURANONE
  • (S)-(-)-~-Hydroxy-gamma-butyrolactone, 97%, ee 99%
  • (S)-(-)-^b-Hydroxy-^y-butyrolactone, 97%, ee 99%
  • (S)-(-)-β-Hydroxy-γ-butyrolactone, 97%, ee 99%
  • (S)-(-)-^b-Hydroxy-^y-butyrolactone, 94%
  • S-(-)-3-Hydroxy-gammalactone
  • (S)-3-Hydroxy-γ-butyrolactone ,98%
  • (S)-3-Hydroxy-gamma-
  • (S)-4-Hydroxydihydrofuran-2(3H)-one
  • 2(3H)-Furanone,dihydro-4-hydroxy-, (4S)-
  • (S)-beta-Hydroxy-gamma-butyrolactone 96%
  • (S)-(-)-3-Hydroxy-g-butyrolactone
  • -4-Hydroxydihydrofuran-2(3H)
  • (S)-3-Hydroxy-gamma-butyrolactone,97%
  • (S)-(-)-beta-Hydroxy-gamma-butyrolactone, 97%, ee 99%
  • (S)-3-Hydroxy-γ-butyrolactone&gt
  • (4S)-4-Hydroxytetrahydrofuran-2-one
  • (S)-β-Hydroxy-γ-butyrolactone
  • S)-3-Hydroxy-gamma-butyrolactttone
  • Tetramethylene Glycol powder
  • (S)-3-Hydroxyl group-gamma-Butyl lactone
  • (S)-3-Hydroxy-gamma-butyrolactone 7331-52-4
  • (S)-3-Hydroxy-gamma-butyroctone
  • Levetiracetam Impurity 65
  • Phenyl Acetate Impurity 61
  • 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