RU2087105C1 - Taste addition - sodium chloride substituent - Google Patents

Abstract

FIELD: food industry. SUBSTANCE: invention proposes N-acetyl-dehydrophenylalanyl-L-methionine of the general formula L-C₆H₅CH=C(NHCOCH₃)CONHCH(COOH)CH₂CH₂SCH₃ as a taste addition in place of sodium chloride. EFFECT: enhanced effectiveness and quality of addition.

Description

 The invention relates to the field of chemistry of biologically active substances. It can be most effectively used in diets for special nutrition for patients with diabetes, hypertension and obesity.

 It is known that many dipeptides and their derivatives have a wide variety of taste properties from sweet and sour to bitter and salty. Flavors such as sodium glutamate (a specific taste called umami) and aspartame, a “sweet” dipeptide, a sugar substitute, are widely used. The most common peptides with a bitter taste, the least salty. The need for substitutes for the carrier of the salty taste of sodium chloride is very high, because in the diet of patients with hypertension, diabetes and obesity, sodium chloride should be absent, and this is due to psychological discomfort.

 It is known that some dipeptides containing lysine and ornithine residues have a salty taste or, at least, enhance it [M. Taba, I. Shinoda, H. Okai, J. Agris. Food Chem. 32, 992, (1984)] and we have taken as a prototype. However, the described method for producing these substances involves many stages, based on the use of toxic derivatives of the named amino acids and hard-to-reach reagents, which do not allow the synthesis of these compounds on a large scale.

 The objective of the invention is to obtain a derivative of the methionine dipeptide, which would be a substitute for sodium chloride.

 The problem is achieved by the synthesis of N-acetyldehydrophenylalanyl-L-methionine.

 The following are examples of the synthesis of the target product.

1. 2-Methyl-4-benzylidenoxazolone-5 (azlactone N-acetyl-alpha-aminocinnamic acid). To a mixture of 11.7 g (0.1 mol) of acetylglycine and 7.2 g (0.05 mol) of anhydrous potash, 33 ml of acetic anhydride and 22 g (0.2 mol) of freshly distilled benzaldehyde are added. The mass is gradually heated to 60 ^o C. At this temperature, there is a strong foaming. When foaming stops, the temperature is raised to 120 ^{° C.} and kept for 1 hour. Upon cooling, the dark mass hardens, it is triturated with water and filtered. To completely remove benzaldehyde, the precipitate is washed with petroleum ether and dried. T. pl. 146-148 ^o C, yield 85% ("Reactions and methods for the study of organic compounds", book 9, p. 202. Moscow, 1959).

N-Acetyl-dehydrophenylalanyl-L-methionine. To a suspension of 1.49 g (10 moles) of L-methionine in 10 ml of acetone was added with stirring 10 ml of 1 N. NaOH and after complete dissolution of the amino acid gradually 1.88 g (10 moles) of azlactone N-acetyl-aminocinnamic acid. After 2 hours, 7 ml of 2 N was added to the clear solution. HCl; after cooling the mixture to 0 ^{° C., a} crystalline precipitate of N-acetyl-dehydrophenylalanyl-L-methionine precipitated, yield 2.68 g (80%), mp 171-172 ^o С (from water) (Lisichkina I.N. Vinogradova A.I. Saporovskaya M. B. Latov V.K. Belikov V.M. Izv. AN SSSR Ser.chem. 1989, 2828).

The white crystalline substance obtained in this way [α] $\genfrac{}{}{0ex}{}{\text{twenty}}{\text{D}}$ + 3.8 ^o , s 1, methanol) is odorless, has a bitter-salty taste in solid form, and has a bitter-sour taste in an aqueous solution.

 The use of the proposed dehydrodipeptide will reduce the amount of sodium chloride in the diet of patients with diabetes, hypertension and obesity.

Claims (1)

The use of N-acetyldehydrophenylalanyl-L-methionine of the General formula
LC ₆ H ₅ CH C (NHCOCH ₃ ) CONHCH (COOH) CH ₂ CH ₂ SCH ₃
as a flavoring additive for sodium chloride substitute.