5234. Isovaline

Nomenclature

CAS number: 595-39-1
dl-2-Amino-2-methylbutyric acid; α-amino-α-methylbutyric acid.
C5H11NO2; mol wt 117.15.
C 51.26%, H 9.46%, N 11.96%, O 27.31%.

Description and references

Prepn: Kurono, Biochem. Z. 134, 427 (1922); Levene, Steiger, J. Biol. Chem. 76, 299 (1928); Bucherer, Steiner, J. Prakt. Chem. 141, 5 (1934); Upham, Dermer, J. Org. Chem. 22, 799 (1957). Optical enantiomorphs: Ehrlich, Wendel, Biochem. Z. 8, 438 (1908); Fischer, von Gravenitz, Ann. 406, 5 (1914); Baker et al., J. Am. Chem. Soc. 74, 4701 (1952); Greenstein et al., J. Biol. Chem. 204, 307 (1953).

Chemical structure

Properties

Monoclinic prisms, mp 307-308° (closed tube). Sublimes at around 300°. Soly in cold water about 39 g/100 ml; in alc about 6.6 g/100 g alc at 75°. Slightly sol in ether.

Derivative

l-Form.

Nomenclature

CAS number: 595-40-4

Properties

Crystals. [α]D25 +11.13° (c = 5 in H2O). [M]D +9.7° (5N HCl); [M]D +26.3° (glacial acetic acid).

Derivative

d-Form.

Nomenclature

CAS number: 3059-97-0

Properties

Long needles from water + acetone. [α]D25 11.28° (c = 5 in H2O).