Cosmetic and pharmaceutical preparations comprising ascorbic...

Details Cosmetic and pharmaceutical preparations comprising ascorbic... Cosmetic and pharmaceutical preparations comprising ascorbic...

1998-11-05

2002-02-12

Clardy, S. Mark (Department: 1616)

Drug, bio-affecting and body treating compositions

Preparations characterized by special physical form

Cosmetic, antiperspirant, dentifrice

C514S474000

Reexamination Certificate

active

06346254

ABSTRACT:

Ascorbic acid (vitamin C) is an antioxidant which is widely employed in cosmetics. Together with vitamin E it counteracts the oxidation of unsaturated fatty acids and thus also prevents lipoperoxide formation O. Isler, G. Brubacher, S. Ghisla, B. Kräutler eds.; Vitamine II (vitamins II), G. Thieme Verlag, Stuttgart, N.Y., 431, 1988). As a vitamin, ascorbic acid is also involved in the metabolism, for instance in the hydroxylation of proline in collagen synthesis (J. J. Burns, J. M. Rivers, L. J. Machin eds.; Third Conference on vitamin C, Ann. N. Y. Acad. Sci., 498 (1987) 1-533).
On account of the excessively low stability of ascorbic acid in cosmetic formulations, it is often necessary to employ stabilized derivatives of ascorbic acid. Examples of these are sodium L-ascorbate monophosphate (JP 07082127, JP 05331020), L-ascorbic acid 2-O-D-glucoside (T. Sakamoto et al.; 19th IFSCC Congress, Sydney, 1996, Vol. 2, Paper No. 14) and 5,6-isopropylidene-L-ascorbic acid 2-phosphate (JP 08269074).
The abovementioned stabilized ascorbic acid derivatives, however, frequently have the disadvantage that they are too poorly soluble in cosmetic or pharmaceutical oils.
It is therefore an object of the invention to make available stable ascorbic acid derivatives, which do not have the abovementioned disadvantages, for cosmetic and pharmaceutical preparations.
We have found that this object is achieved according to the invention by use of ascorbic acid derivatives of the formula I,
where the variables independently of one another have the following meanings:
R
1
is hydrogen, C
1
-C
20
-acyl, C
1
-C
12
-alkoxycarbonyl, C
1
-C
12
-alkyl;
R
2
is hydrogen, C
1
-C
20
-acyl, C
1
-C
12
-alkoxycarbonyl, C
1
-C
12
-alkyl,
where R
1
and R
2
, together with the oxygen atoms to which they are bonded and the carbon atoms bonded to the oxygen atoms, can form an unsubstituted or substituted heterocycle;
R
3
is hydrogen or a cation selected from the group consisting of NH
4
+
, alkali metal and alkaline earth metal cations;
R
4
is C
1
-C
12
-alkoxycarbonyl,
for cosmetic and pharmaceutical preparations.
Preferred compounds of formula I are those where the variables have the following meanings:
R
1
is hydrogen, C
1
-C
20
-acyl, C
1
-C
12
-alkoxycarbonyl, C
1
-C
12
-alkyl;
R
2
is hydrogen, C
1
-C
20
-acyl, C
1
-C
12
-alkoxycarbonyl, C
1
-C
12
-alkyl,
where R
1
and R
2
, together with the oxygen atoms to which they are bonded and the carbon atoms bonded to the oxygen atoms, can form an unsubstituted or substituted heterocycle, and
R
1
must not be a C
1
-C
12
-alkoxycarbonyl radical if R
2
is hydrogen;
R
3
is hydrogen or a cation selected from the group consisting of NH
4
+
, alkali metal and alkaline earth metal cations;
R
4
is C
1
-C
12
-alkoxycarbonyl.
Very particularly preferred compounds of the formula I are those where the variables have the following meanings:
R
1
is hydrogen, C
1
-C
20
-acyl, C
1
-C
6
-alkoxycarbonyl;
R
2
is hydrogen, C
1
-C
20
-acyl, C
1
-C
6
-alkoxycarbonyl,
where R
1
must not be a C
1
-C
6
-alkoxycarbonyl radical if R
2
is hydrogen;
R
3
is hydrogen or a cation selected from the group consisting of NH
4
+
, alkali metal and alkaline earth metal cations;
R
4
is C
1
-C
6
-alkoxycarbonyl.
In the ascorbic acid derivatives of the formula I according to the invention, acyl radicals for R
1
and R
2
are to be understood as meaning branched or unbranched, saturated or unsaturated, if appropriate polyunsaturated, C
1
-C
20
-acyl chains.
Examples of these are acyl radicals of formic, acetic, propionic, n-butyric, isobutyric, sorbic, n-valeric, isovaleric, caproic, caprylic, capric, undecanoic, lauric, tridecanoic, myristic, pentadecanoic, palmitic, palmitoleic, stearic, oleic, linoleic, linolenic, nonadecanoic and arachidonic acid.
Preferred acyl radicals are those of long-chain fatty acids having C
10
to C
20
carbon chains, in particular acyl radicals of lauric, palmitic, palmitoleic, stearic, oleic and linoleic acid.
Alkyl radicals R
1
and R
2
which may be mentioned are branched or unbranched C
1
-C
12
-alkyl chains, preferably methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl.
Particularly preferred alkyl radicals are C
l
-C
6
-alkyl chains, in particular methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl.
The radicals R
1
and R
2
, together with the oxygen atoms to which they are bonded and the carbon atoms bonded to the oxygen atoms, can form unsubstituted or substituted heterocycles. These are intended to include, for example, cyclic acetals and ketals which, inter alia, are employed as a protective group for the two terminal hydroxyl functions (in the 5- and 6-position) of the acorbic acid. A preferred heterocyclic system is, inter alia, the 5,6-isopropylidene radical, which is formed by reaction of the two free hydroxyl groups in the 5- and 6-position with acetone.
Suitable alkoxycarbonyl radicals for R
1
, R
2
and R
4
are those whose alkoxy group contains 1 to 12 C atoms, preferably 1 to 6 C atoms, particularly preferably 1 to 4 C atoms.
Examples of the preferred radicals which may be mentioned are:
methoxycarbonyl
isopropoxycarbonyl
1-methylpropoxycarbonyl
n-pentoxycarbonyl
3-methylbutoxycarbonyl
2,2-dimethylpropoxycarbonyl
1-methyl-1-ethylpropoxycarbonyl
ethoxycarbonyl
n-propoxycarbonyl
n-butoxycarbonyl
2-methylpropoxycarbonyl
1,1-dimethylpropoxycarbonyl
hexoxycarbonyl
Particularly preferred alkoxycarbonyl radicals are:
methoxycarbonyl
isopropoxycarbonyl
1-methylpropoxycarbonyl
ethoxycarbonyl
n-propoxycarbonyl
n-butoxycarbonyl
Possible cations for R
3
are NH
4
+
and representatives from the group consisting of the alkali and alkaline earth metals, preferably Na, K, Li, Ca and Mg, particularly preferably Na, K and Mg.
The term ascorbic acid derivatives is understood as meaning both derivatives of L- and D-ascorbic acid (isoascorbic acid), preferably L-ascorbic acid.
Some di- and tricarbonates of ascorbic acid are already known. Thus U.S. Pat. No. 2,980,702 describes compounds of the 2,5,6-tri-O-(C
1
-C
3
-alkoxycarbonyl)-L-ascorbic acid type and their use as a heat-resistant additive in foodstuffs, especially in baked goods.
JP 42020050 describes the synthesis of 2,6-di-O-(C
1
-C
3
-alkoxy-carbonyl)-L-ascorbic acid as a heat-stable derivative of ascorbic acid.
The use of the abovementioned ascorbic acid derivatives in cosmetic and pharmaceutical applications, however, is novel.
The stable ascorbic acid derivatives of the formula I according to the invention are outstandingly suitable as active compounds for cosmetic and pharmaceutical preparations.
Thus the compounds are distinguished, inter alia, in that, by variation of the radicals R
1
, R
2
and R
4
, the lipophilicity of the ascorbic acid derivatives can be adjusted in a controlled manner. Depending on the demand in the formulation of cosmetic and pharmaceutical preparations, a wide range of stable vitamin C derivatives is thus available to the expert in the field. The tricabonates and the fatty acid esters of vitamin C 2-mono-carbonate particularly can be incorporated very readily into preparations such as, for example, ointments, lotions, gels or emulsions on account of their good oil solubility.
Accordingly, the present invention also relates to cosmetic and pharmaceutical preparations comprising an effective amount of at least one of the compounds of the formula I, and customary cosmetic and pharma

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