Aspartyl dipeptide ester derivatives and sweeteners

Details Aspartyl dipeptide ester derivatives and sweeteners Aspartyl dipeptide ester derivatives and sweeteners

2000-10-10

2003-04-15

Wong, Leslie (Department: 1761)

Food or edible material: processes, compositions, and products

Products per se, or processes of preparing or treating...

Noncarbohydrate sweetener or composition containing same

C560S041000, C562S433000

Reexamination Certificate

active

06548096

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to novel aspartyl dipeptide ester derivatives, a sweetener and products such as foods which contain the sweetener.
2. Discussion of the Background
Fatness caused by excessive intake of sugar and diseases accompanied by fatness have been at issue in recent years, as eating habits have improved. Accordingly, a low-calory sweetener that replaces sugar has been in demand. Aspartame is a widely used sweetener which has excellent safety and taste properties. However, aspartame is not very stable.
WO 94/1139 discloses that derivatives having an alkyl substituted amino group in aspartic acid exhibit improved sweetening potency and slightly improved stability. The best compound described in this document is N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl ]-L-phenylalanine 1-methyl ester having a 3,3-dimethylbutyl group as an alkyl group. The sweetening potency of this compound is 10,000 times that of sugar.
Other aspartame derivatives having 20 other types of substituents are described in above reference. However, their sweetening potency is reported to be less than 2,500 times that of sugar. Derivatives having a 3-(substituted phenyl)propyl group as an alkyl group are also disclosed. However, the sweetening potency of N-[N-(3-phenylpropyl)-L-&agr;-aspartyl ]-L-phenylalanine 1-methyl ester is 1,500 times and that of N-[N-[3-(3-methoxy-4-hydroxyphenyl)propyl]-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester is 2,500 times that of sugar. Thus, their sweetening potency is far less than that of N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester (10,000 times). (U.S. Pat. No. 5,480,668 is the equivalent to WO 94/1139).
SUMMARY OF THE INVENTION
It is an object of the invention to provide novel aspartyl dipeptide ester derivatives which are safe and have a sweetening potency equal to or higher than that of the N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester.
It is another object of the present invention to provide a low-calory sweetener containing the novel derivatives as an active ingredient.
These and other objects are achieved according to the invention, the first embodiment of which includes a compound of Formula (1):
wherein
R
1
, R
2
, R
3
, R
4
and R
5
, independently represent a substituent selected from the group consisting of a hydrogen atom, a hydroxyl group, an alkoxy group having from 1 to 3 carbon atoms, an alkyl group having from 1 to 3 carbon atoms and a hydroxyalkyloxy group having 2 or 3 carbon atoms; or
R
1
and R
2
, or R
2
and R
3
together form a methylenedioxy group, wherein R
4
, R
5
, and R
1
or R
3
which do not form said methylenedioxy group independently represent a substituent selected from the group consisting of a hydrogen atom, a hydroxyl group, an alkoxy group having from 1 to 3 carbon atoms, an alkyl group having from 1 to 3 carbon atoms and a hydroxyalkyloxy group having 2 or 3 carbon atoms;
R
6
represents a hydrogen atom or a hydroxyl group; and
R
7
represents a substituent selected from the group consisting of a methyl group, an ethyl group, an isopropyl group, an n-propyl group and a t-butyl group;
wherein R
1
to R
5
do not all represent hydrogen atoms; and
wherein R
2
or R
4
do not represent a methoxy group if R
3
represents a hydroxyl group; and
the salt thereof.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
In order to achieve above objects, the present inventors have synthesized several aspartame derivatives in which various 3-(substituted phenyl) propyl groups are introduced into an amino group of aspartic acid using cinnamaldehyde having various substituents and 3-phenylpropianaldehyde having various substituents.
The inventors have examined the sweetening potency of above aspartame derivatives. They have found that their sweetening potency is far higher than that of N-[N-(3-phenylpropyl)-L-&agr;-aspartyl]-L-phenylalanine-1-methyl ester and N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester. For example, N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester has a sweetening potency of 10,000 times that of sugar and N-[N-(3-phenylpropyl)-L-&agr;-aspartyl]-L-phenylalanine-1-methyl ester has a sweetening potency of 1,500 times that of sugar (WO94/11391). The compounds represented by Formula (1), below, are excellent as a sweetener. These findings have led to the completion of the invention.
The novel aspartyl dipeptide ester derivatives of the invention include the compounds represented by Formula (1) and salts thereof.
wherein
R
1
, R
2
, R
3
, R
4
and R
5
, independently from each other, represent a substituent selected from a hydrogen atom (H), a hydroxyl group (OH), an alkoxy group (OR; methoxy group, ethoxy group, propoxy groups, or the like) having from 1 to 3 carbon atoms, an alkyl group (R; methyl group, ethyl group, propyl groups, or the like) having from 1 to 3 carbon atoms and a hydroxyalkyloxy group (for example, O(CH
2
)
2
OH or OCH
2
CH(OH)CH
3
) having 2 or 3 carbon atoms, or
R
1
and R
2
, or R
2
and R
3
together form a methylenedioxy group (OCH
2
O);
wherein R
4
, R
5
and, R
1
or R
3
which does not form the methyl enedioxy group as a part thereof, independently from each other, represent any substituents as mentioned above designated for the R
1
, R
3
, R
4
and R
5
, respectively, provided the case where R
1
to R
5
are all hydrogen atoms and the case where R
2
is a methoxy group and R
3
is a hydroxyl group and the case where R
4
is a methoxy group and R
3
is a hydroxyl group are excluded,
R
6
represents a hydrogen atom or a hydroxyl group, and
R
7
represents a substituent selected from a methyl group (CH
3
), an ethyl group (CH
2
CH
3
), an isopropyl group (CH(CH
3
)
2
, an n-propyl group (CH
2
CH
2
CH
3
) and a t-butyl group (C(CH
3
)
3
).
Amino acids constituting the derivatives are preferably L-isomers since L-isomers are present in nature.
With respect to the compounds of the invention, the following inventions are preferably included.
[1] Compounds of Formula (1)
wherein R
3
is a substituent selected from a hydroxyl group, an alkoxy group having from 1 to 3 carbon atoms, an alkyl group having from 1 to 3 carbon atoms and a hydroxyalkyloxy group having 2 or 3 carbon atoms,
R
1
, R
2
, R
4
and R
5
are, independently from each other, each a substituent selected from a hydrogen atom, a hydroxyl group, an alkoxy group having from 1 to 3 carbon atoms, an alkyl group having from 1 to 3 carbon atoms and a hydroxyalkyloxy group having 2 or 3 carbon atoms, or
R
1
and R
2
, or R
2
and R
3
together form a methylenedioxy group (OCH
2
O)
wherein R
4
, R
5
and, R
1
or R
3
which does not form the methylenedioxy group as a part thereof, independently from each other, represent any substituents as mentioned above for the R
1
, R
3
, R
4
and R
5
;
R
6
is a hydrogen atom or a hydroxyl group, and
R
7
is a substituent selected from a methyl group, an ethyl group, an isopropyl group, an n-propyl group and a t-butyl group.
[2] Compounds of Formula (1)
wherein R
3
is a hydrogen atom,
R
1
, R
2
, R
4
and R
5
are, independently from each other, each a substituent selected from a hydroxyl group, an alkoxy group having from 1 to 3 carbon atoms, an alkyl group having from 1 to 3 carbon atoms and a hydroxyalkyloxy group having 2 or 3 carbon atoms, or
R
1
and R
2
, or R
2
and R
3
together form a methylenedioxy group (OCH
2
O)
wherein R
4
, R
5
and, R
1
or R
3
which does not form the methylenedioxy group as a part thereof, independently from each other, represent any substituents as mentioned above designated for the R
1
, R
3
, R
4
and R
5
, respectively,
R
6
is a hydrogen atom or a hydroxyl group, and
R
7
is a substituent selected from a methyl group, an ethyl group, an isopropyl group, an n-propyl group and a t-butyl group.
[3] Compounds of Formula (1)
wherein R
3
is a hydroxyl group,
R
1
, R
2
, R
4
and R
5

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