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

(S)-3-Hydroxy-gamma-butyrolactone

Bezeichnung:(S)-3-Hydroxy-gamma-butyrolactone

CAS-Nr7331-52-4

Englisch Name:(S)-3-Hydroxy-gamma-butyrolactone

CBNumberCB6360496

SummenformelC4H6O3

Molgewicht102.09

MOL-Datei7331-52-4.mol

(S)-3-Hydroxy-gamma-butyrolactone physikalisch-chemischer Eigenschaften

Siedepunkt	98-100 °C0.3 mm Hg(lit.)
Dichte	1.241 g/mL at 25 °C(lit.)
Brechungsindex	n20/D 1.464(lit.)
Flammpunkt	>230 °F
storage temp.	Inert atmosphere,2-8°C
pka	12.87±0.20(Predicted)
Optische Aktivität	[α]21/D 81°, c = 2 in ethanol
Wasserlöslichkeit	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 Datenbank	7331-52-4(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36-37/39
WGK Germany	3
F	3-10
HS Code	29322090

Gefahreninformationscode (GHS)

(S)-3-Hydroxy-gamma-butyrolactone Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Beschreibung
(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.
Chemische Eigenschaften
Colorless to light yellow liquid.
Verwenden
(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].
Synthese
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].
Vorsichtsmaßnahmen
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.
Einzelnachweise
[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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