4-Amino-3-hydroxybutyric Acid
Title: 4-Amino-3-hydroxybutyric Acid
CAS Registry Number: 352-21-6
CAS Name: 4-Amino-3-hydroxybutanoic acid
Additional Names: g-amino-b-hydroxybutyric acid; buksamin; GABOB
Trademarks: Gabomade (Knoll); Gamibetal (SIT)
Molecular Formula: C4H9NO3
Molecular Weight: 119.12
Percent Composition: C 40.33%, H 7.62%, N 11.76%, O 40.29%
Line Formula: H2NCH2CH(OH)CH2COOH
Literature References: Prepn of DL-form: Tomita, Z. Physiol. Chem. 124, 255 (1923); Balenovic et al., J. Org. Chem. 19, 1589 (1964); Hayashi et al., JP 58 772 C.A. 53, 1172d (1959); Sakai et al., JP 62 12264 (to Kaken), C.A. 59, 9805e (1963); ES 278780 (1963 to Antonio Gallardo, S.A.), C.A. 60, 2779a (1964); Hayashi, FR 1348105 (1964 to Kaken), C.A. 60, 11956b (1964); D'Alo, Masserini, Farmaco Ed. Sci. 19, 30 (1964); M. Pinza, G. Pifferi, J. Pharm. Sci. 67, 120 (1978). Prepn of L-form: Tomita, Sendju, Z. Physiol. Chem. 169, 270 (1927); Kaneko, Yoshida, Bull. Chem. Soc. Jpn. 35, 1153 (1962); M. E. Jung, T. J. Shaw, J. Am. Chem. Soc. 102, 6304 (1980); of D-form: Tomita, Sendju, loc. cit. Improved synthesis of L-form: S. Takano et al., Tetrahedron Lett. 28, 1783 (1987). Purification: Yamagiwa, Tanaka, JP 63 24365 (to Kaken), C.A. 60, 10515a (1964).
 
Derivative Type: DL-Form
Properties: Crystals from dil alc, dec 218°. Fairly readily sol in water; very sparingly sol in methanol, alc, ether, chloroform, ethyl acetate.
 
Derivative Type: D(+)-Form
Properties: Crystals from water, dec 214°. [a]D20 +18.3° (c = 2 in H2O).
Optical Rotation: [a]D20 +18.3° (c = 2 in H2O)
 
Derivative Type: L(-)-Form
Properties: Crystals from water or water + ethanol, dec 212°, also reported as dec 216-217°. [a]D20 -21.06° (c = 2 in H2O); -20.7° (c = 1.83 in H2O).
Optical Rotation: [a]D20 -21.06° (c = 2 in H2O); -20.7° (c = 1.83 in H2O)
 
Therap-Cat: Anticonvulsant.
Keywords: Anticonvulsant.

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