| Identification | More | [Name]
(S)-(+)-4-AMINO-3-HYDROXYBUTANOIC ACID | [CAS]
7013-05-0 | [Synonyms]
BUTANOIC ACID, 4-AMINO-3-HYDROXY-, (S)
(S)-(+)-4-AMINO-3-HYDROXYBUTANOIC ACID
(S)-4-AMINO-3-HYDROXYBUTANOIC ACID
(S)-4-AMINO-3-HYDROXYBUTYRIC ACID
(S)-(+)-AMINO-3-HYDROXYBUTANOIC ACID
(3S)-(+)-4-Amino-3-hydroxybutanoic acid
(3S)-4-Amino-3-hydroxybutanoic acid
(S)-(+)-3-Hydroxy-GABA
(S)-(+)-β-hydroxy-GABA
Butanoic acid, 4-amino-3-hydroxy-, (3S)-
S-(+)-γ-Amino-β-hydroxybutyric acid
[S,(+)]-3-Hydroxy-4-aminobutyric acid
D-4-Amino-3-hydroxybutyric acid
S-(+)-GABOB | [Molecular Formula]
C4H9NO3 | [MDL Number]
MFCD00672884 | [Molecular Weight]
119.12 | [MOL File]
7013-05-0.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powde | [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 Rotation]
[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) |
| Hazard Information | Back Directory | [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 |
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