(S)-(+)-4-AMINO-3-HYDROXYBUTANOIC ACID Chemical Properties

Melting point:

207-212 °C

alpha 

20 º (C=1.7 IN H2O)

Boiling point:

374.5±32.0 °C(Predicted)

Density 

1.312±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

Solid

pka

4.04±0.10(Predicted)

optical activity

[α]20/D +20.0°, c = 1.7 in H2O

InChI

InChI=1S/C4H9NO3/c5-2-3(6)1-4(7)8/h3,6H,1-2,5H2,(H,7,8)/t3-/m0/s1

InChIKey

YQGDEPYYFWUPGO-VKHMYHEASA-N

SMILES

C(O)(=O)C[C@H](O)CN

CAS DataBase Reference

7013-05-0(CAS DataBase Reference)

Safety Information

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

(S)-(+)-4-AMINO-3-HYDROXYBUTANOIC ACID Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

S-(+)-GABOB anticonvulsant and is used in the treatment of epilepsy as it binds to the GABAB receptor.

General Description

(S)-(+)-4-Amino-3-hydroxybutyric acid [(S)-GABOB] can be prepared starting from ethyl (S)-4-chloro-3-hydroxybutyrate.

Synthesis

GENERAL METHODS: Compound 7 (400 mg, 0.92 mmol) was dissolved in EtOAc (20 mL) and 10% Pd/C (785 mg, 0.74 mmol, 80 mol%) was added. The reaction system was degassed and hydrogenated under 1 atm H2 atmosphere for 12 hours. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to afford (S)-(+)-4-amino-3-hydroxybutyric acid ((S)-GABOB, 2) (95 mg, 87% yield) as a white solid. The product was purified by recrystallization from EtOH-H2O mixed solvent. Melting point: 200-202°C (literature value 13e: 198-201°C); [α]27D +17.2 (c 1.23, H2O) (literature value 13e: [α]25D +16.7 (c 0.41, H2O)).1H NMR (600 MHz, D2O): δ 2.44 (d, J = 6.6 Hz, 2H), 3.97 (dd J = 13.2, 9.6 Hz, 1H), 3.18 (dd, J = 13.2, 3.0 Hz, 1H), 4.19-4.23 (m, 1H). 13C NMR (150 MHz, D2O): δ 42.3, 44.1, 65.5, 178.6. HRMS (ESI): m/z [M + Na]+ calculated value C4H9NNaO3: 142.0480; measured value: 142.0462. ref 22: Abdel-Magid, A. F.; Carson, K.

References

[1] Tetrahedron Letters, 2013, vol. 54, # 21, p. 2637 - 2640

(S)-(+)-4-AMINO-3-HYDROXYBUTANOIC ACID(7013-05-0)Related Product Information

• ACETYL-PEPSTATIN
• D(+)-Carnitine
• L-Carnitine hydrochloride
• EST
• Pepstatin
• 4-Amino-2-hydroxybutanoic acid
• (R)-3-AMINO-4-HYDROXYBUTANOIC ACID HYDROCHLORIDE
• DL-4-Amino-3-hydroxybutyric acid
• allo-DL-Threonine
• L(+)-allo-Threonine
• (S)-N-Carbobenzyloxy-4-amino-2-hydroxybutyric acid
• DL-2-AMINO-3-HYDROXYBUTANOIC ACID 3-PHOSPHATE
• L-carnitine
• L-Threonine
• DL-2-AMINO-3-HYDROXYBUTANOIC ACID
• D(-)-allo-Threonine
• (3S,4S)-4-AMINO-3-HYDROXY-5-PHENYLPENTANOIC ACID
• FMOC-(3S,4S)-4-AMINO-3-HYDROXY-5-PHENYL PENTANOIC ACID