444. 4-Amino-3-hydroxybutyric Acid

Nomenclature

CAS number: 352-21-6
4-Amino-3-hydroxybutanoic acid; γ-amino-β-hydroxybutyric acid; buksamin; GABOB; Gabomade (Knoll); Gamibetal (SIT).
C4H9NO3; mol wt 119.12.
C 40.33%, H 7.62%, N 11.76%, O 40.29%.

Description and 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).

Chemical structure

Derivative

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

d(+)-Form.

Properties

Crystals from water, dec 214°. [α]D20 +18.3° (c = 2 in H2O).

Derivative

l()-Form.

Properties

Crystals from water or water + ethanol, dec 212°, also reported as dec 216-217°. [α]D20 21.06° (c = 2 in H2O); 20.7° (c = 1.83 in H2O).

Therapeutic Category

Anticonvulsant.

Keywords

Anticonvulsant