96. N-Acetylmethionine

Nomenclature

CAS number: 65-82-7
N-Acetyl-l-methionine.
C7H13NO3S; mol wt 191.25.
C 43.96%, H 6.85%, N 7.32%, O 25.10%, S 16.77%.

Description and references

Naturally occurring derivative of methionine, q.v. Prepn of l-form and racemate: V. du Vigneaud, C. E. Meyer, J. Biol. Chem. 98, 295 (1932); of d-form and racemate: G. P. Wheeler, A. W. Ingersoll, J. Am. Chem. Soc. 73, 4604 (1951). Resolution of isomers: B. F. Tullar, US 3056799 (1962 to Sterling Drug). Evaluation of stability and organoleptic suitability for food supplementation: R. Damico, J. Agric. Food Chem. 23, 30 (1975). Methionine replacement activity of isomers: D. H. Baker, J. Nutr. 109, 970 (1979). Detection and stability in model food systems: K. L. Schleske, J. J. Warthesen, J. Agric. Food Chem. 30, 1172 (1982).

Chemical structure

Properties

Crystals, mp 104° (Tullar). [α]D25 20.3°(c = 4 in water). Also reported as crystals from acetone + ether, mp 102-103° (Damico).

Derivative

dl-Form.

Nomenclature

CAS number: 1115-47-5

Properties

Large prisms from water, mp 114-115°. Soly at 25° (g/100 ml): water, 9.12; acetone, 10.0; ethyl acetate, 2.29; chloroform, 1.33.

Derivative

d-Form.

Nomenclature

CAS number: 1509-92-8

Properties

Plates from water or ethyl acetate, mp 104-105°. [α]D25 +20.3° (c = 4 in water). Soly at 25° (g/100 ml): water, 30.7; acetone, 29.6; ethyl acetate, 7.04; chloroform, 6.43.

Use

Food additive for methionine supplementation.