JPH1135417A - Active ingredient and preparation for lightcoloring and sunburn-prevention of skin - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a preparation for preventing and treating a pigmentation in skin by including a substituted phenylalanine and extracts from plant and animal containing the same. SOLUTION: This objective preparation is obtained by including at least one compound selected from the group consisting of a substituted phenylalanine [pref. βphenylalanine of formula I (R is a group of sulfate, sulfuric acid group, group of phosphate, phosphoric acid group or sulfonate; R' and R" are each H or an 1-21C alkyl; and X is H, a metal cation, or 1-22C alkyl) or formula II the 3-site or 4-site of whose phenyl ring is substituted, e.g. L-3-[4- hydroxyphenyl]-2-aminopropionic sulfuric ester], the derivatives thereof, and any extracts from plant and animal containing any of these compounds in the ratio of 0.01 to 10 wt.%, pref. 0.1 to 5 wt.% based on the total weight of the objective preparation.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The invention relates in particular to cosmetic and topical dermatological lightening of the skin, or to the prevention of sunburn on the skin, in particular UV-induced skin tanning. As such they relate to the use of known substances.

[0002] In a preferred embodiment, the invention relates to cosmetic or dermatological treatments on the skin, such as, for example, undesirable pigmentation, for example local hyperpigmentation and abnormal pigmentation (eg senile plaques, liver spots, freckles). Cosmetic and topical dermatological preparations for the prevention and treatment of changes or for purely cosmetic lightening of a larger area of skin, pigmented very well on the individual's skin type About things.

[0003]

BACKGROUND OF THE INVENTION Pigmentation of the skin, for example, exists either individually or as clusters of various sizes depending on the type of skin, alongside the basal cells as pigment-forming cells, the lowermost epidermal layer, It is provided by melanocytes found in stratum (Stratum besale). Melanocytes contain melanosomes that form melanin in large quantities when stimulated by UV light as a characteristic cellular function.
This melanin is transported into the keratinocytes (keratinocytes), resulting in a more or less brownish or brown skin color on the skin.

[0004] Melanin is characterized in that tyrosine, under the action of the enzyme tyrosine-degrading enzyme, 3,4-dihydroxyphenyl-2-aminopropionic acid (dopa), dopaquinone, leucodopachrome, dopachrome, 5,6-dihydroxy Formed as the last step in the oxidation process, which is ultimately converted to melanin via indole and indole-5,6-quinone.

[0005] Problems involving hyperpigmentation of the skin have a number of different causes and include a number of biological processes such as UV light (eg freckles, Ephelides), genetic predisposition, wound healing or scarring. Abnormal pigmentation of the skin during the aging period, or skin aging [eg senile moles (Lentigines senile
s)].

[0006] Active ingredients and preparations which counteract skin pigmentation are known. In fact, on the one hand, they show their effect only after several weeks of administration, and on the other hand,
Their prolonged administration is not without risk for toxicological reasons, but essentially hydroquinone-based preparations have been used. Although it has cosmetic and dermatological disadvantages, suppression of tyrosine-degrading enzymes by substances such as kojic acid, ascorbic acid and azelaic acid and their derivatives is also common.
The purpose of the present invention was to overcome these problems.

[0007]

This object has been achieved according to the present invention.

The present invention relates to the group consisting of substituted phenylalanines and their derivatives and also plant and animal extracts containing these compounds as active ingredients for the prophylactic treatment and treatment of unwanted pigmentation of the skin. Provides the use of one or more compounds from

[0009] Pigmentation is understood to mean any coloring of the skin and pigmented means colored.

Prevention or further prevention and treatment of undesired pigmentation of the skin includes, for example, lightening of dark skin, but also enhances hyperpigmentation, in particular local hyperpigmentation,
And the lightening or elimination of pigmentation disorders, also known under the name "skin whitening (effect)", and also the prophylactic use for these purposes.

The control or prevention and treatment of unwanted pigmentation of the skin also includes the prevention and treatment of skin tanning, especially skin tanning caused by UV light.

The present invention also relates to substituted phenylalanines and their derivatives as active ingredients for the prophylactic treatment and for the treatment of unwanted pigmentation of the skin and also extracts of plants and animals containing these compounds. Containing one or more compounds selected from the group consisting of
The use of a cosmetic or topical dermatological preparation is provided.

If the preparation contains more than one active ingredient according to the invention, two, three or four active ingredients are preferred.

Β-Phenylalanine substituted at the 3-position or, particularly, 4-position of the phenyl ring, and derivatives thereof are preferred.

The following formula:

[0016]

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[Wherein R represents a sulfate group or a sulfate group —O—SO ₃ H, a phosphate group or a phosphate group —O—
PO ₃ H ₂ or sulfonic acid group —SO ₃ H, provided that
These groups can also be present in the form of their salts, and R 'and R "are, independently of one another, hydrogen, C
₁ -C ₂₁ - alkyl, in particular C ₁ -C ₃ - alkyl and X is hydrogen, a metal cation or C ₁ -C ₂₂ -
Alkyl, preferably C ₁ -C ₁₂ -alkyl, but in particular C ₁ -C ₄ -alkyl], substituted phenylalanine is particularly preferred.

The compounds can be used as racemates or in optically active forms, the L-isomer being preferred.

The preferred L-isomer has the following structure

[0020]

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Wherein the groups R, R ′, R ″ and X are as defined above.

Examples of suitable derivatives are the compounds according to the invention in which the amino group is mono- or di-alkylated.

Each alkyl group may be straight-chain or branched.

Particularly suitable derivatives of the compounds according to the invention are salts and acid addition salts. Also preferred are esters of the carboxylic acid groups of the compounds according to the invention with alcohols.

Preferred salts of the carboxylic acid group and of the group R are water-soluble salts, for example sodium, potassium and ammonium salts. This also applies to acid addition salts. Suitable acid addition salts are obtained, for example, by using inorganic and organic acids. Hydrochloride, phosphate, sulfate, acetate, caprylate, citrate, lactate, malate or tartrate are preferred.

Examples of suitable esters are those formed by short-chain or medium-length alcohols, preferably monoalcohols. They may be straight-chain or branched. Methanol, ethanol, n-propanol and isopropanol are preferred.

Esters with long-chain alcohols are also particularly preferred derivatives. They also have, for example, good permeability characteristics.

Compounds having a sulfate group or a sulfate group are preferred. They also have an O at the 3- or 4-position of tyrosine.
Depending on whether an H group or a sulfate group is present, it can also be considered as a tyrosine O-sulfate ester, where meta-tyrosine or preferably para-tyrosine may be present.

3- [4-hydroxyphenyl] -2-aminopropionic acid sulfate, 3- [3-hydroxyphenyl] -2-aminopropionic acid sulfate (tyrosine O-sulfate), and derivatives thereof It is a particularly good active ingredient for unwanted pigmentation, especially for local hyperpigmentation, and also for tanning of the skin caused by UV light, both as a prophylactic and also therapeutic agent It has been found.

L-3- [4-hydroxyphenyl] -2
-Aminopropionic acid sulfate or L-3- [3
-Hydroxyphenyl] -2-aminopropionic acid sulfate (tyrosine O-sulfate) and, in some cases, their derivatives according to the invention are also particularly preferred.

Preferred substances according to the invention have the structure:

[0032]

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Has the following.

The active ingredients according to the invention are known, commercially available or can be obtained in a known manner. It is also possible to use natural substances or concentrates or extracts of natural substances containing these active ingredients.

The content of the active ingredient used according to the invention in the preparation is, for example, 0.0% of the total weight of the preparation
It can be 1 to 10% by weight, preferably 0.1 to 5% by weight, especially 0.2 to 2.0% by weight.

Surprisingly, it has been found that the active ingredients used according to the invention achieve the objects on which the invention is based. By using the active ingredient used according to the invention or a cosmetic or topical dermatological preparation containing an active amount of the active ingredient used according to the invention, an effective prevention against unwanted pigmentation is achieved. For example, unwanted pigmentation caused by UV light can be prevented. However, the active ingredients used according to the invention, or cosmetic or topical dermatological preparations containing an active amount of the active ingredients used according to the invention, can be used to remove unwanted skin pigmentation,
Use according to the invention, for example, as cosmetics for senile moles (Lentigines seniles) or for dermatological treatments is also very advantageous.

By the active ingredient used according to the invention or by a cosmetic or topical dermatological preparation containing an active amount of the active ingredient used according to the invention.
The prophylactic or cosmetic or dermatological treatment is carried out in the usual way and, on a diseased area of the skin, the active ingredient used according to the invention or the cosmetic or cosmetic composition comprising an active amount of the active ingredient used according to the invention Involves administering a topical dermatological preparation.

The active ingredients used according to the invention can be conveniently incorporated into conventional cosmetic and dermatological preparations, which can be in various forms.
They may be, for example, solutions, water-in-oil (W / O) or oil-in-water (O / W) emulsions, or, for example, water-in-oil-in-water (W / O / W) or oil-in-oil-in-water (O / W).
/ W / O) type emulsions, hydrodispersions or lipodispersions, gels, solid sticks or aerosols.

For the purposes of the present invention, emulsions according to the invention, for example in the form of creams, lotions or cosmetic emulsions, are advantageous and include, for example, fats,
Oils, waxes and / or other fatty substances, as well as water and one such as is usually used for preparations of this kind.
Contains more than one emulsifier.

For the purposes of the present invention, it is also possible and convenient to add the active ingredients used according to the invention to aqueous systems or surfactant preparations for the cleansing of the skin, scalp and hair. It is.

It is known to those skilled in the art, of course, that the most sought after cosmetic compositions cannot in most cases be imagined without the usual auxiliaries and additives. These are, for example, consistency regulators, fillers, fragrances, dyes, emulsifiers,
Contains additional active ingredients such as vitamins or proteins, light-blocking agents, stabilizers, repellents, alcohol, water, salts, antimicrobial agents, proteolytic agents or keratolytics, and the like.

The corresponding requirements for the preparation of pharmaceutical preparations apply mutatis mutandis.

Pharmaceutical topical compositions for the purposes of the present invention generally contain one or more effective concentrations of the active ingredient. For simplicity, the legal provisions of the Federal Republic of Germany (eg cosmetic regulations, food and pharmaceutical regulations) to clearly distinguish between cosmetic and pharmaceutical uses and the corresponding products
Is referred to. It is also advantageous to add the active ingredients used according to the invention as additives to preparations already containing other active ingredients for other purposes. Thus, for the purposes of the present invention, cosmetic or topical dermatological compositions, depending on their composition,
For example, they can be used as skin protection creams, cleansing emulsions, sunscreen lotions, nourishing creams, day or night creams, and the like. If desired, the compositions according to the invention can be advantageously used as a base for pharmaceutical preparations.

The pH of the preparation according to the invention can be, for example, from 4 to 9, but in particular from 4.5 to 7.

If appropriate, cosmetic and dermatological preparations which are in the form of sunscreens are also preferred. In addition to the active ingredients used according to the invention, they also preferably contain at least one UVA filter substance and / or at least one UVB filter substance and / or at least one inorganic pigment. However, it is also advantageous for the purposes of the present invention to provide cosmetic and dermatological preparations whose primary purpose is not to shield against sunlight, but still contain anti-UV substances. Thus, for example, UV-A and UV-B
Filter substances are usually incorporated into day creams.

The preparations according to the invention are advantageously prepared with UVB
Can contain substances that absorb UV light in the area,
The total amount of said filter substance is, for example, from 0.1% to 30% by weight, preferably from 0.5 to 1% by weight of the total weight of the preparation.
0% by weight, in particular 1 to 6% by weight.

The UVB filter may be oil-soluble or water-soluble. Examples of oil-soluble substances are: -3-benzylidenecamphor and derivatives thereof, such as 3- (4-methylbenzylidene) camphor, -4-aminobenzoic acid derivatives, preferably 2-ethylhexyl 4- (dimethylamino) benzoate, -Amyl (dimethylamino) benzoate;-Esters of cinnamic acid, preferably 2-ethylhexyl 4-methoxycinnamate, isopentyl 4-methoxycinnamate;-Esters of salicylic acid, preferably 2- salicylic acid.
Ethylhexyl, 4-isopropylbenzyl salicylate, homomenthyl salicylate; derivatives of benzophenone, preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4
-Methoxy-4'-methylbenzophenone, 2,2'-
Dihydroxy-4-methoxybenzophenone;-an ester of benzalmalonic acid, preferably di (2-ethylhexyl) 4-methoxybenzalmalonate;-2,4,6-trianilino- (p-carbo-2'-
Ethyl-1′-hexyloxy) -1,3,5-triazine:

The water-soluble substance is advantageously: 2-phenylbenzimidazole-5-sulfonic acid and its salts, such as sodium, potassium or triethanolammonium salts; sulfonic acid derivatives of benzophenone, preferably
-Hydroxy-4-methoxybenzophenone-5-sulfonic acid and salts thereof; -sulfonic acid derivative of 3-benzylidenecamphor,
For example, 4- (2-oxo-3-bornylidenemethyl) benzenesulfonic acid, 2-methyl-5- (2-oxo-3)
-Bornylidenemethyl) sulfonic acid and its salts:

Certain UVBs that can be used in accordance with the present invention
The filter table is, of course, not intended to be limiting.

The present invention also provides a UVB filter or a UB filter.
There is provided a combination of a UVA filter according to the invention with a cosmetic or dermatological preparation according to the invention which also contains a VB filter.

In the preparations according to the invention, it may also be advantageous to use UVA filters which are normally contained in cosmetic and / or dermatological preparations. Such a filter substance is preferably a derivative of dibenzoylmethane, in particular 1- (4'-tert-butylphenyl) -3- (4'-methoxyphenyl) -propane-
1,3-dione and 1-phenyl-3- (4'-isopropylphenyl) -propane-1,3-dione. Preparations containing these combinations are also objects of the present invention. The same amount of UVA filter material as given for the UVB filter material can be used.

For the purposes of the present invention, cosmetic and / or dermatological preparations can also contain inorganic pigments usually used in cosmetics for protecting the skin against UV radiation. . These are oxides of titanium, zinc, iron, zircon, silicon, manganese, aluminum, cerium and mixtures thereof, and derivatives in which the oxide is the active substance. Pigments based on titanium dioxide are particularly preferred. The amounts given for the above combinations can be used.

The cosmetic and dermatological preparations according to the invention contain cosmetically active ingredients, adjuvants and / or additives, such as antioxidants, preservatives, bactericidal agents, as usually used in such preparations. Agents, fragrances, bubble suppressants, dyes, pigments having a coloring effect, thickeners, surfactants, emulsifiers, softeners, humectants and / or humectants, fats, oils, waxes, alcohols, polyols, polymers, It can contain other usual ingredients of cosmetic or dermatological preparations, such as foam stabilizers, electrolytes, organic solvents or silicone derivatives.

It is likewise advantageous to add customary antioxidants to the preparations for the purposes of the invention. Preferred antioxidants according to the invention are any antioxidants suitable or customary for cosmetic and / or dermatological applications.

The antioxidants are advantageously amino acids (eg, glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (eg, urocanic acid) in very small tolerated doses (eg, pmol to μmol / kg). And derivatives thereof, D, L-carnosine,
Peptides such as D-carnosine, L-carnosine and their derivatives and their derivatives (eg anserine), carotenoids, carotenes (eg α-carotene,
β-carotene, lycopene) and their derivatives, lipoic acid and its derivatives (eg, dihydrolipoic acid), aurothioglucose, propylthiouracil and other thiols (eg, thioredoxin, glutathione, cysteine, cystine, cystamine, and their glycosyls) , N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, γ
-Linoleyl, cholesteryl and glyceryl esters)
And their salts, dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and its derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) and sulfoximine compounds (eg buthionine sulfoximine) , Homocysteine sulfoximine, buthionine sulfone, penta-, hexa-, heptathionine sulfoximine),
Further, (metal) chelating agents (for example, α-hydroxy fatty acid, palmitic acid, phytic acid, lactoferrin),
α-hydroxy acids (eg, citric acid, lactic acid, malic acid), humic acids, bile acids, bile extracts, bilirubin, biliverdin, EDTA, EGTA and derivatives thereof,
Unsaturated fatty acids and their derivatives (eg, γ-linolenic acid, linoleic acid, oleic acid), folic acid and its derivatives,
Alanine diacetate, flavonoids, polyphenols, catechol, ubiquinone and ubiquinol and derivatives thereof, vitamin C and derivatives (eg, ascorbyl palmitate, Mg ascorbyl phosphate, ascorbyl acetate), tocopherols and derivatives (eg, vitamin E acetate), and benzoin Coniferyl benzoate, rutinic acid and its derivatives, ferulic acid and its derivatives, butylated hydroxytoluene, butylated hydroxyanisole, nordihydroguaiac resin acid, nordihydroguaiaretic acid, trihydroxybutyrophenone, uric acid and its derivatives , mannose and derivatives thereof, zinc and derivatives thereof (e.g. ZnO, ZnSO _4), selenium and derivatives thereof (e.g. selenium methionine), stilbenes and derivatives thereof ( Example, if stilbene oxide, oxide trans - stilbene) and, as appropriate in accordance with the invention, these derivatives of the active ingredients (salt of the ester, ether, sugar, nucleotide, nucleoside, selected from the group consisting of peptides and lipids).

The amount of antioxidant (one or more compounds) in the preparation is preferably from 0.001 to 30% by weight of the total weight of the preparation, particularly preferably from 0.05 to 20% by weight, in particular Is from 1 to 10% by weight.

If vitamin E and / or its derivatives are used as antioxidant (s), their respective concentrations can range from 0.001 to 10% by weight of the total weight of the preparation. It is convenient to choose.

If, for the purposes of the present invention, the cosmetic or dermatological preparation is a solution or an emulsion or a dispersion, the solvent used is: water or aqueous solution; such as capric or caprylic triglycerides. Oils, but preferably castor oils; fats, waxes and other natural and synthetic fatty substances, preferably low-carbon alcohols, such as isopropanol, propylene glycol or glycerol, and esters of fatty acids, or low-carbon Esters of fatty alcohols with alkanoic acids or fatty acids-low carbon alcohols, diols or polyols,
And their ethers, preferably ethanol, isopropanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or monobutyl ether, diethylene glycol monomethyl or monoethyl ether and similar products: Can be.

In particular, mixtures of the abovementioned solvents are used. In the case of alcoholic solvents, water can be a further component.

The oil phases of the emulsions, oleogels or hydrodispersions or lipid dispersions for the purposes of the present invention are advantageously saturated and / or unsaturated, branched, having a chain length of from 3 to 30 carbon atoms. Or from the group of esters of unbranched and / or unbranched alkanecarboxylic acids with saturated and / or unsaturated, branched and / or unbranched alcohols having a chain length of from 3 to 30 carbon atoms, or Aromatic carboxylic acids and 3
Selected from the group of esters with saturated and / or unsaturated, branched and / or unbranched alcohols having a chain length of from 30 to 30 carbon atoms. The oils of such esters are then conveniently prepared from isopropyl myristate, isopropyl palmitate, isopropyl stearate, isopropyl oleate, n-butyl stearate, n-hexyl laurate, n-decyl oleate, stearic acid. Isooctyl, isononyl stearate, isononyl isononanoate, 2-ethylhexyl palmitate, 2-laurate
Ethylhexyl, 2-hexyldecyl stearate, 2-octyldodecyl palmitate, oleyl oleate, oleyl erucate, ersyl oleate and ersyl erucate and mixtures of such synthetic, semi-synthetic and natural esters, such as Jojoba Oil, can be selected from the group consisting of:

Furthermore, the oily phase is advantageously composed of branched and unbranched hydrocarbons and waxes, silicone oils, dialkyl ethers, saturated or unsaturated, branched or unbranched alcohols, and fatty acid triglycerides. Selected from the group consisting of triglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids having a chain length of from 8 to 24, in particular from 12 to 18 carbon atoms. it can. The fatty acid triglycerides conveniently comprise, for example, synthetic, semi-synthetic and natural oils such as olive oil, sunflower oil, soybean oil, peanut oil, rapeseed oil, almond oil, coconut oil, coconut oil, coconut oil and the like. You can choose from groups.

[0062] Any desired mixtures of such oil and wax components can also be used advantageously for the purposes of the present invention. If desired, it may also be expedient to use waxes, for example cetyl palmitate, as the sole lipid component of the oily phase.

The oily phase is conveniently 2-isostearic acid 2-
Ethylhexyl, octyl dodecanol, isotridecyl isononanoate, isoeicosane, cocoa, 2-ethylhexyl benzoate C _{12 to 15} - alkyl, caprylic /
It is selected from the group consisting of capric triglyceride and dicaprylyl ether.

Mixtures of C _12-15 -alkyl benzoate and 2-ethylhexyl isostearate, benzoic acid C
_12-15 - mixtures of alkyl and isotridecyl isononanoate, as well as benzoic acid C _12-15 - alkyl, isotridecyl, 2-ethylhexyl isostearate and isononanoate are particularly advantageous.

Advantageous hydrocarbons for the purposes of the present invention are paraffin oil, squalane and squalene.

[0066] In addition to the silicone oil or silicone oils, it is preferred to use additional amounts of other oil phase components, but the oil phase conveniently contains further cyclic or linear silicone oils or It can consist exclusively of such oils.

Cyclomethicone (octamethylcyclotetrasiloxane) is advantageously used as a silicone oil which can be used according to the invention. But,
Other silicone oils such as hexamethylcyclotrisiloxane, polydimethylsiloxane, poly (methylphenylsiloxane) are also advantageous for the purposes of the present invention.

Furthermore, mixtures of cyclomethicone and isotridecyl isononanoate and mixtures of cyclomethicone and 2-ethylhexyl isostearate are particularly advantageous.

The gel used according to the invention is usually
Includes low carbon alcohols such as ethanol, isopropanol, 1,2-propanediol, glycerol and water or the oils described above in the presence of a thickener, provided that the thickener is added to the oily alcoholic gel. Preferably, silicon dioxide or aluminum silicate, and for hydroalcoholic or alcoholic gels, polyalcoholates.

[0070] Solid sticks include, for example, natural or synthetic waxes, fatty alcohols or fatty acid esters. Lipstick sticks and stick preparations for body deodorants are preferred.

For the purposes of the present invention, suitable base materials suitable for use as cosmetic sticks are fluid oils (eg, paraffin oil, castor oil, isopropyl myristate), semi-solid components (eg, petrolatum, lanolin) ), Solid components (eg beeswax, ceresin and microcrystalline waxes and ozokerite) and high melting point waxes (eg carnauba wax, candelilla wax).

For the purposes of the present invention, suitable propellants for cosmetic and / or dermatological preparations which can be sprayed from aerosol containers are the commonly known, readily volatile, liquefied propellants, for example those Hydrocarbons (propane, butane, isopban) which can be used as such or as a mixture with one another. Compressed air is also advantageous.

Those skilled in the art will obviously appreciate that, in the form of aerosol preparations, it will in principle be suitable for practicing the invention, but because of their detrimental effects on the environment or other attendant situations, It is known that there are propellant gases which are themselves non-toxic and have to be avoided, especially fluorinated hydrocarbons and chlorofluorocarbons (CFCs).

For the purposes of the present invention, cosmetic preparations may also contain, in addition to an effective amount of the active ingredients according to the invention and the solvents usually used therefor, preferably water, organic thickeners such as Arabic. Rubber, xanthan gum, sodium alginate, cellulose derivatives, preferably methylcellulose, hydroxymethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, or an inorganic thickener,
For example, it can be in the form of a gel containing aluminum silicate such as bentonite, or a mixture of polyethylene glycol and stearic acid or polyethylene glycol distearate. The thickener is included in the gel in an amount between 0.1 and 30% by weight, preferably between 0.5 and 15% by weight.

Unless stated otherwise, all amounts, proportions and percentages are based on the weight and the total amount of the preparation or on the total weight.

[0076]

The following examples serve to illustrate the invention.

Example 1 W / O cream wt% paraffin oil (DAB9) 10.00 petrolatum 4.00 wool wax alcohol 1.00 PEG-7 hydrogenated castor oil 3.00 aluminum stearate 0.40 L- 3- [4-hydroxyphenyl] -2-aminopropionic acid sulfate (tyrosine O-sulfate) 0.50 glycerol 2.00 Preservative, dye, perfume Appropriate water, all 100.00 (Example 2) W / O lotion% by weight Paraffin oil (DAB9) 20.00 Petrolatum 4.00 Glucose sesquiisostearate 2.00 Aluminum stearate 0.40 L-3- [4-hydroxyphenyl] -2-aminopropionic acid sulfate (tyrosine O -Sulfuric ester) 0.50 α-tocopheryl acetate 1 0.000 Glycerol 5.00 Preservative, Dye, Fragrance As needed Water Total 100.00 (Example 3) O / W lotion% by weight Paraffin oil (DAB9) 8.00 Isopropyl palmitate 3.00 Petrolatum 4.00 Cetylstearyl alcohol 2.00 PEG-40 castor oil 0.50 Cetyl stearyl sodium sulfate 0.50 Carbomer sodium 0.40 L-3- [4-hydroxyphenyl] -2-aminopropionic acid sulfate (tyrosine O-sulfate) 0 .50 glycerol 3.00 α-tocopherol 0.20 octyl methoxycinnamate 5.00 butyl methoxydibenzoylmethane 1.00 Preservative, dye, fragrance Suitable water Total 100.00 (Example 4) O / W cream weight % Paraffin oil (DAB9) 7.00 abo Cad oil 4.00 Glyceryl monostearate 2.00 L-3- [4-hydroxyphenyl] -2-aminopropionic acid sulfate (tyrosine O-sulfate) 0.50 Titanium dioxide 1.00 Sodium lactate 3.00 Glycerol 3.00 Preservative, Dye, Fragrance As needed Water Total 100.00 (Example 5) Liposomal gel-containing agent wt% Lecithin 6.00 Shea butter 3.00 L-3- [4-hydroxyphenyl] -2-amino Propionic acid sulfate (tyrosine O-sulfate) 0.50 α-Tocopherol 0.20 Biotin 0.08 Sodium citrate 0.50 Glycine 0.20 Urea 0.20 PCA sodium 0.50 Hydrolyzed collagen 2.00 Xanthan Rubber 1.40 Sorbitol 3.00 Preservative, Dye, Fragrance Suitable Water Total 100.00 (Example 6) Sunscreen emulsion weight% cyclomethicone 2.00 cetyl dimethicone copolyol 0.20 PEG-22 dodecyl copolymer 3.00 paraffin oil (DAB9) 2.00 caprylic / capric acid Triglyceride 5.80 Octyl methoxycinnamate 5.80 Butylmethoxydibenzoylmethane 4.00 L-3- [4-hydroxyphenyl] -2-aminopropionic acid sulfate (tyrosine O-sulfate) 0.50 Acetic acid α - tocopheryl 0.50 ZnSO ₄ 0.70 Na ₄ EDTA 0.30 preservative, dye, perfume qs water total 100.00 (example 7) sunscreen emulsion wt% cyclomethicone 2.00 cetyl stearyl alcohol + PEG-40 Hydrogenated castor oil + sulphate sulfate Rustearyl sodium 2.50 Glyceryl lanolinate 1.00 Caprylic acid / capric triglyceride 0.10 Laurylmethicone copolyol 2.00 Octyl stearate 3.00 Castor oil 4.00 Glycerol 3.00 Acrylamide / Sodium acrylate Copolymer 0.30 Hydroxypropylmethylcellulose 0.30 Octyl methoxycinnamate 5.00 Butylmethoxydibenzoylmethane 0.50 L-3- [4-Hydroxyphenyl] -2-aminopropionic acid sulfate (tyrosine O-sulfate ) 0.50 acetic acid α- tocopheryl 1.00 Na ₄ HEDTA 1.50 preservatives, dyes, perfumes qs water total 100.00 (example 8) sunscreen emulsion wt% cyclomethicone 2.00 Sechirusute Ryl alcohol + PEG-40 hydrogenated castor oil + sodium cetyl stearyl sulfate 2.50 glyceryl lanolinate 1.00 caprylic acid / capric triglyceride 0.10 lauryl methicone copolyol 2.00 octyl stearate 3.00 castor oil 4 0.000 glycerol 3.00 acrylamide / sodium acrylate copolymer 0.30 hydroxypropylmethylcellulose 0.30 octyl methoxycinnamate 5.00 butylmethoxydibenzoylmethane 0.75 L-3- [4-hydroxyphenyl] -2 - aminopropionic acid sulfate (tyrosine O- sulfate) 0.50 Na ₄ HEDTA 1.50 preservatives, dyes, perfumes qs water total 100.00 (example 9) spray preparation wt% alpha-tocopherol 0.10 L-3- [4-hydroxyphenyl] -2-aminopropionic acid sulfate (tyrosine O-sulfate) 0.50 Ethanol 28.20 Preservative, dye, fragrance Propane / butane 25/75 Total 100 0.000 (Example 10) W / O cream wt% paraffin oil (DAB9) 10.00 petrolatum 4.00 wool wax alcohol 1.00 PEG7 hydrogenated castor oil 3.00 aluminum stearate 0.40 L-3- [ 4-sulfophenyl] -2-aminopropionic acid (phenylalanine-p-sulfonic acid) 0.50 glycerol 2.00 Preservative, dye, perfume Water 100.00 (Example 11) W / O lotion weight% paraffin Oil (DAB9) 20.00 Petrolatum 4.00 Sesqui-isostear Glucose 2.00 aluminum stearate 0.40 L-3- [4-hydroxyphenyl] -2-aminopropionic acid sulfate (tyrosine O-sulfate) 0.50 α-tocopheryl acetate 1.00 glycerol 5. 00 Preservative, Dye, Fragrance Suitable amount Water Total 100.00 The features and aspects of the present invention are shown below.

1. Substituted phenylalanines and their derivatives and also plant and animal extracts containing these compounds, as active ingredients for prophylactic and therapeutic treatment of undesired pigmentation of the skin,
Use of one or more compounds from the group consisting of:

2. Substituted phenylalanines and their derivatives and also plant and animal extracts containing these compounds, as active ingredients for prophylactic and therapeutic treatment of undesired pigmentation of the skin,
Use of a cosmetic or topical dermatological preparation containing one or more compounds selected from the group consisting of:

3. The following formula:

[0081]

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[Wherein R represents a sulfate group or a sulfate group —O—SO ₃ H, a phosphate group or a phosphate group —O—
PO ₃ H ₂ or a sulfonic acid group —SO ₃ H, provided that these groups can also exist in the form of their salts, R ′ and R ″ independently of one another be hydrogen, C ₁
-C ₂₁ -alkyl, especially C ₁ -C ₃ -alkyl,
And X is hydrogen, a metal cation or a C ₁ -C ₂₂ -alkyl, preferably a C ₁ -C ₁₂ -alkyl, but especially a C ₁ -C ₄ -alkyl] substituted phenylalanine. Use according to claim 1 or 2, characterized in that:

4. Use according to claim 1 or 2, characterized in that the L-isomer of the active ingredient is used.

5. L-3- [4-hydroxyphenyl] -2-aminopropionic acid sulfate or L-3
3. Use according to claim 1 or 2, characterized in that-[3-hydroxyphenyl] -2-aminopropionic acid sulfate and optionally further derivatives thereof are used.

6. The active ingredient content in the preparation is from 0.
Second to 0.1 to 10% by weight, preferably 0.1 to 5% by weight, particularly 0.2 to 2.0% by weight.
Use as described in section.

Claims (2)

[Claims] Claims 1. A skin comprising one or more compounds from the group consisting of substituted phenylalanines and their derivatives and plant and animal extracts containing these compounds as active ingredients. Preparations for prophylactic and therapeutic treatment of unwanted pigmentation. 2. A substituted phenylalanine having the formula: Wherein R is a sulfate group or a sulfate group —O—SO ₃ H, a phosphate group or a phosphate group —O—PO ₃ H ₂ , or a sulfonic acid group —SO ₃ H; However, these groups can also be present in the form of their salts. R ′ and R ″ are independently of one another hydrogen, C ₁ -C ₂₁ -alkyl, in particular C ₁ -C ₃ -alkyl. And X
It is hydrogen, a metal cation or C ₁ -C ₂₂ - alkyl, preferably C ₁ -C ₁₂ - alkyl, but especially, C ₁ -C
₄ -alkyl).