Title: Mimosine
CAS Registry Number: 500-44-7
CAS Name: a-Amino-3-hydroxy-4-oxo-1(4H)-pyridinepropanoic acid
Additional Names: 3-hydroxy-4-oxo-1(4H)-pyridinealanine; b-[N-(3-hydroxy-4-pyridone)]-a-aminopropionic acid; leucenol; leucenine; leucaenine; leucaenol
Molecular Formula: C8H10N2O4
Molecular Weight: 198.18
Percent Composition: C 48.48%, H 5.09%, N 14.14%, O 32.29%
Literature References: A naturally occurring amino acid found in large quantities in the seeds and foliage of the legume genera Mimosa and Leucena. Isoln from Leucena glauca (Willd.) Benth., Leguminosae: Renz, Z. Physiol. Chem. 244, 153 (1936); Mascré, Compt. Rend. 204, 890 (1937); improved large-scale isoln: N. K. Hart et al., Heterocycles 7, 265 (1977). Structure: Adams, Jones, J. Am. Chem. Soc. 69, 1803 (1947). Synthesis: Adams, Johnson, ibid. 71, 705 (1949). Identity of mimosine and leucenol: Kleipool, Wibaut, Rec. Trav. Chim. 69, 37 (1950); Wibaut, Schuhmacher, ibid. 71, 1017 (1952). Crystal structure: A. Mostad et al., Acta Chem. Scand. 27, 164 (1973). Shown to cause inhibition of hair growth and loss of hair in mice: Crounse et al., Nature 194, 694 (1962). Explanation of the toxicity in animals: J. F. Thompson et al., Annu. Rev. Biochem. 38, 137 (1969).
Derivative Type: dl-Form
Properties: Crystals from water, mp 235-236°. Slightly sol in water, much less sol in methanol and ethanol. Practically insol in the higher alcohols, in dioxane, ethyl acetate, ether, benzene, chloroform, glacial acetic acid, pyridine, Cellosolve. Sol in dil acids or bases and may be recovered from these solns by adjusting the pH so that it is just acid to bromcresol green. uv max: 282 nm (log e 4.23).
Melting point: mp 235-236°
Absorption maximum: uv max: 282 nm (log e 4.23)
Derivative Type: dl-Hemihydrate
Properties: Crystals, darkens at 215-226°, mp 227-228°.
Melting point: mp 227-228°
Derivative Type: l-Form
Properties: Crystals from water, mp 225°. [a]D22 -20°.
Melting point: mp 225°
Optical Rotation: [a]D22 -20°
Derivative Type: Hydrochloride
Molecular Formula: C8H11ClN2O4
Molecular Weight: 234.64
Percent Composition: C 40.95%, H 4.73%, Cl 15.11%, N 11.94%, O 27.27%
Properties: Dec 175°, sol in water.
Derivative Type: Hydrobromide
Molecular Formula: C8H11BrN2O4
Molecular Weight: 279.09
Percent Composition: C 34.43%, H 3.97%, Br 28.63%, N 10.04%, O 22.93%
Properties: Dec 179.5°, sol in water.
Use: Depilatory agent, Hegarty et al., Aust. J. Agric. Res. 15, 153 (1964), C.A. 60, 16405e (1964). |