DE19720339A1 - Treatment or prevention of undesired skin pigmentation - Google Patents

Abstract

Use of one or more substituted phenylalanines, derivatives of these or animal or plant extracts which contain these compounds, as active agents for treatment and prophylactic treatment of undesired pigmentation of skin, is new.

Description

The present invention relates in particular to the use be be known substances for cosmetic and dermatological topical Hautauf brightening or to prevent the tanning of the skin, in particular by UV radiation-induced skin tanning.

In a preferred embodiment, the present invention relates to kos metic and dermatological topical preparations for prophylaxis and Treatment of cosmetic or dermatological lesions such as z. As the unwanted pigmentation, such as local hyper- and False pigmentation (for example, age spots, liver spots, summer sprouts), but also for the cosmetic whitening larger, the individuel The skin type is in fact suitably pigmented skin areas.

Responsible for the pigmentation of the skin are, for. The melanocytes, which in the lowest layer of the epidermis, the stratum basale, beside the basal cells as - depending on the skin type either isolated or more or less frequently occurring pigment-forming cells are to be found. Melanocytes contain as characteristic cell organelles melanosomes, which upon excitation by UV radiation increasingly form melanin. This will transported into the horny cells (keratinocytes) and calls a more or less pronounced brownish or brown skin color.  

Melanin is formed as the final stage of an oxidative process in which Tyrosine with the participation of the enzyme tyrosinase via 3,4-dihydroxy phenyl-2-amino-propionic acid (Dopa), Dopa-quinone, Leucodopachrom, Do pachrom, 5,6-dihydroxyindole and indole-5,6-quinone finally in melanin is converted.

Problems with hyperpigmentation of the skin have many causes or are concomitants of many biological processes, eg. B. UV radiation (eg freckles, ephelides), genetic predisposition, miscarriage pigmentation of the skin during wound healing or scarring or Skin aging (eg Lentigines seniles).

There are known active ingredients and preparations, which skin pigmentation counteract. In practical use are essentially Präpa rate based on hydroquinone, which, however, partly after several weeks of application show their effect, the very long application On the other hand, it is not always safe for toxicological reasons is. Also, the inhibition of tyrosinase with substances such as kojic acid, Ascorbic acid and azelaic acid and their derivatives is well known, but has cosmetic and dermatological disadvantages.

To remedy these evils was the object of the present invention.

This object has been achieved according to the invention.

The invention relates to the use of a compound or several compounds from the group of substituted phenylalanines and their derivatives as well as plant and animal extracts containing them Contain compounds as active ingredients for prophylactic treatment and for the treatment of unwanted pigmentation of the skin.

Under pigmentation (or pigmented) are all discolorations of (or discolored) skin understood.  

For the prevention or prophylaxis and treatment of unwanted Pigmentation of the skin, include, for example, the lightening of dark skin, but also the lightening or removal of hyperpigmentation, ins special local hyperpigmentation, and false pigmentation, the For example, under the term "skin-whitening (effect)" are known and also the preventative application for these purposes.

Furthermore, prevention or prophylaxis and treatment are of no importance Desired skin pigmentation preventing and treating the skin Skin tanning, in particular that caused by UV radiation Skin tanning.

The invention also relates to the use of cosmetic or dermatological topical preparations containing Ver or more compounds from the group of substituted Phenylalanines and their derivatives as well as herbal and animal extracts th, which contain these compounds, as active ingredients for prophylactic Treatment and treatment of unwanted pigmentation of the Skin.

If the preparations contain several of the active substances according to the invention, two, three or four active ingredients are preferred.

Are preferred in the 3-position or in particular in the 4-position of Phenyl rings substituted β-phenylalanines and their derivatives.

Particularly preferred are the substituted phenylalanines of the following formulas:

or

wherein
R is a sulfate radical or sulfuric acid radical -O-SO ₃ H, a phosphate radical or phosphoric acid radical -O-PO ₃ H ₂ or a sulfonic acid radical -SO ₃ H, where these radicals can also be present in the form of their salts, and R is 'and R'', independently of one another, hydrogen, C ₁ -C ₂₁ -alkyl, especially C ₁ - C ₃ alkyl, and wherein X is hydrogen, a metal cation or C ₁ -C ₂₂ - alkyl, preferably C ₁ -C ₁₂ alkyl, but especially C ₁ -C ₄ alkyl.

The compounds can be used as a racemate or in optically active form be set, the L-isomers are preferred.

The preferred L-isomers are represented by the following structures

or

in which the radicals R, R ', R "and X are those indicated above have meanings.

Suitable derivatives are, for example, those at the amino groups monoal alkylated or dialkylated compounds of the invention.

In each case, the alkyl radicals can be straight-chain or branched.

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

Preferred salts of the carboxylic acid group and the radicals R are water-soluble Liche salts, eg. For example, sodium, potassium and ammonium salts. This also applies to the acid addition salts. Suitable acid addition salts are z. B. with obtained inorganic and organic acids. Preferably, the Hy drochloride, phosphates, sulfates, acetates, caprylates, citrates, lactates, malates or tartrate.

Suitable esters are, for. For example, those with short-chain or medium-chain Al be formed, preferably with mono-alcohols. You can ge Radkettig or branched. Preference is given to methanol, ethanol, n- Propanol and iso-propanol.

The esters with long-chain alcohols are also particularly preferred Deri vate. They are z. B. also by a good penetration.

Preference is given to compounds having a sulfuric acid radical or sulfate rest. They can also be regarded as tyrosine O-sulfate esters, wherein meta-tyrosine or preferably para-tyrosine may be present according to the 3- or 4-position of the OH group or sulfuric acid residue of Tyro sins.  

3- [4-hydroxyphenyl sulfate ester] -2-aminopropionic acid and 3- [3- Hydroxyphenylsulfate ester] -2-aminopropionic acid (tyrosine O-sulfate ester), and their derivatives have been ge particularly excellent agents undesirable pigmentation, especially local hyperpigmentation and against the skin tanning caused by UV radiation, and Although both preventive and in terms of treatment, proven.

Particularly preferred are L-3- [4-hydroxyphenyl sulfate ester] -2- Aminopropionic acid or L-3- [3-hydroxyphenylsulfate ester] -2- Aminopropionic acid (tyrosine O-sulfate ester), optionally also he inventive derivatives.

The structures which result for the substances preferred according to the invention are:

or

The active compounds according to the invention are known, commercially available, or can be obtained by known methods. It can also be nature substances or concentrates or extracts of natural substances containing these active substances to be used.

The content of active ingredient used in the preparation according to the invention gen can z. B. 0.01-10 wt .-%, preferably 0.1-5 wt .-%, in particular  0.2-2.0 wt .-%, based on the total weight of Zuberei obligations.

It has surprisingly been found that the invention used active ingredient fulfills the task underlying the invention. When using the active ingredient according to the invention or kosme topical dermatological preparations with an effective Content of active ingredient used in the invention is an effective Pro phylaxis against unwanted pigmentation, so for example Ver prevention of unwanted pigmentation by exposure to UV rays Radiation possible. However, it is also extremely advantageous according to the invention, the active ingredient used according to the invention or cosmetic or derma topical preparations with an effective content of erfin used according to the active ingredient for cosmetic or dermatologi rule treatment of unwanted skin pigmentation, so for example Lentigines seniles to use.

The prophylaxis or the cosmetic or dermatological treatment with the active ingredient used according to the invention or with the cosmetic or topical dermatological preparations with an effective Ge halt to active ingredient used in the invention takes place in the usual Wei se, in such a way that the active ingredient used in the invention or the cosmetic or topical dermatological preparations with an effective content of active ingredient used in the invention the affected skin is applied.

Advantageously, the active ingredient used in the invention can be incorporated are in usual cosmetic and dermatological preparations, which can exist in different forms. So they can z. B. a Lö solution, a water-in-oil (W / O) or oil-in-oil type emulsion. Water (O / W), or a multiple emulsions, for example of the type Water in oil in water (W / O / W) or oil in water in oil (O / W / O), one Hydrodispersion or lipodispersion, a gel, a solid stick or too represent an aerosol.  

According to the invention emulsions, z. In Form of a cream, a lotion, a cosmetic milk are beneficial and contain z. As fats, oils, waxes and / or other fatty substances, and Water and one or more emulsifiers, as is customary for egg Such type of formulation can be used.

It is also possible and advantageous in the context of the present invention, the Active ingredient used in aqueous systems or Ten to prepare sid preparations for cleansing the skin, scalp and hair gene.

Of course, it is known to those skilled in the art that sophisticated cosmetic Compositions usually not without the usual auxiliaries and additives fe are conceivable. These include, for example, bodying agents, fillers, Perfume, dyes, emulsifiers, additional active ingredients such as vitamins or Proteins, light stabilizers, stabilizers, insect repellents, alcohol, Water, salts, antimicrobial, proteolytic or keratolytic active Substances etc.

Mutatis mutandis apply appropriate formulation requirements medical preparations.

Medical topical compositions within the meaning of the present invention usually contain one or more active ingredients in effective Concentration. For the sake of simplicity, it becomes a clear distinction between cosmetic and medical use and corresponding Products to the statutory provisions of the Federal Republic of Germany referenced (eg Kosmetikverordnung, Lebensmittel- und Arzneimittelge Act).

It is also advantageous, the Wirk used in the invention as an additive to preparations already containing other active substances fe for other purposes.  

Accordingly, cosmetic or topical dermatological co Compositions according to the present invention, depending on their structure, For example, be used as skin protection cream, cleansing milk, Sunscreen lotion, Nährcréme, daytime or Nachtcréme etc. It is gege if appropriate and advantageous, the composition according to the invention to use as a basis for pharmaceutical formulations.

The pH of the preparations according to the invention can be, for example, 4 to 9, but especially 4.5 to 7 amount.

If appropriate, such cosmetic and dermatologi are also favorable preparations which are in the form of a sunscreen. Preferably, these contain in addition to the invention used Active ingredient additionally at least one UVA filter substance and / or minde at least one UVB filter substance and / or at least one inorganic pig ment.

But it is also advantageous in the sense of the present inventions, such to prepare cosmetic and dermatological preparations whose The main purpose is not the protection from sunlight, but the still contain a content of UV protective substances. So be with For example, in Tagescrémes usually UV-A or UV-B filter substances incorporated.

Advantageously, preparations according to the invention may contain substances, absorb the UV radiation in the UVB range, the total amount of Filter substances z. 0.1 wt.% To 30 wt.%, Preferably 0.5 to 10 Wt .-%, in particular 1 to 6 wt .-%, based on the Ge total weight of the preparations.

The UVB filters may be oil-soluble or water-soluble. As oil-soluble sub punching z. To name, for example:

• - 3-Benzylidencampher and its derivatives, for. B. 3- (4-Methylbenzyli the) camphor,
• 4-aminobenzoic acid derivatives, preferably 4- (dimethylamino) -benz 2-ethylhexyl (2-ethylhexyl) ester, 4- (dimethylamino) benzoic acid amyl ester;
• Esters of cinnamic acid, preferably 4-methoxycinnamic acid (2- ethylhexyl) ester, 4-methoxycinnamic acid isopentyl ester;
• Esters of salicylic acid, preferably 2-ethylhexyl salicylate, Salicylic acid (4-isopropylbenzyl) ester, salicylic acid homomenthyl ester;
• - Derivatives of benzophenone, preferably 2-hydroxy-4-methoxyben zophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'- Dihydroxy-4-methoxybenzophenone; Esters of benzalmalonic acid, preferably 4- Methoxybenzalmalonate (2-ethylhexyl) ester;
• 2,4,6-trianilino (p-carbo-2'-ethyl-1'-hexyloxy) -1,3,5-triazine.

As water-soluble substances are advantageous:

• - 2-phenylbenzimidazole-5-sulfonic acid and its salts, eg. For example, sodium, Potassium or triethanolammonium salts,
• Sulfonic acid derivatives of benzophenones, preferably 2-hydroxy-4- methoxybenzophenone-5-sulfonic acid and its salts;
• - Sulfonic acid derivatives of 3-Benzylidencamphers, such as. B. 4- (2-oxo-3- bornylidenemethyl) benzenesulfonic acid, 2-methyl-5- (2-oxo-3-bomylidene methyl) sulfonic acid and its salts.

The list of said UVB filters, the invention according to use fin of course, should not be limiting.

The invention also relates to the combination of an invention according to UVA filter with a UVB filter or an inventive cosmetic or dermatological preparation which also contains a UVB Contains filter.

It may also be advantageous to use UVA emulsions in preparations according to the invention. Use filters commonly used in cosmetic and / or dermatologi  preparations are contained. In such filter substances it is preferably derivatives 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. Also preparations that the Se contained combinations are the subject of the invention. It can be the equal amounts of UVA filter substances are used, which for UVB filter substances were called.

Cosmetic and / or dermatological preparations as defined in the underlying invention may also contain inorganic pigments, the üb Licherweise in cosmetics to protect the skin from UV rays verwen be. These are oxides of titanium, zinc, iron, zirconium of silicon, manganese, aluminum, cerium and mixtures thereof, and modifications in which the oxides are the active agents. Be most preferably they are pigments based on titanium oxide. It may be the quantities mentioned for the above combinations be used.

The cosmetic and dermatological preparations according to the invention may contain cosmetic active substances, auxiliaries and / or additives, such as commonly used in such preparations, e.g. B. antioxidant onsmittel, preservatives, bactericides, perfumes, substances for Prevent foaming, dyes, pigments, the coloring effect have, thickeners, surface-active substances, emulsifiers, softening, moisturizing and / or moisturizing substances, fats, Oils, waxes or other common ingredients of a cosmetic or the matological formulation such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives.

It is also advantageous to the preparations according to the present Er to add conventional antioxidants. According to the invention can as cheap antioxidants all for cosmetic and / or dermatological uses suitable or customary antioxidants who used the.  

Advantageously, the antioxidants are selected from the group consisting of amino acids (eg glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (eg urocaninic acid) and their derivatives, peptides such as D, L-carnosine, D Carnosine, L-carnosine and their derivatives (eg anserine), carotenoids, carotenes (eg α-carntine, β-carntine, lycopene) and their derivatives, lipoic acid and derivatives thereof (eg. Dihydrolipoic acid), aurothioglucose, propylthiouracil and other thiols (eg thioredoxin, glutathione, gysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl , Palmitoyl, oleyl, γ-linoleyl, cholesteryl and glyceryl esters) and their salts, dilaurylthiodipropionate, distearylthio dipropionate, thiodipropionic acid and its derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) and sulfoximine compounds (eg. B. Buthioninsulfoximine, Homocysteinsulfoximin, Buthioninsulfone, penta-, hexa-, heptathioni nsulfoximin) in very low tolerated dosages (eg. Pmol to pmol / kg), furthermore (metal) chelators (for example α-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), α-hydroxy acids (for example citric acid, lactic acid, malic acid), humic acid, Bile acids, bile extracts, bilirubin, biliverdin, EDTA, EGTA and their derivatives, unsaturated fatty acids and their derivatives (eg γ-linolenic acid, linoleic acid, oleic acid), folic acid and its derivatives, -2-aminopropionic acid, flavonoids, polyphenols, Catechins, ubiquinone and ubiquinol and their derivatives, vitamin C and derivatives (eg ascorbyl palmitate, Mg ascorbyl phosphate, Ascor bylacetat), tocopherols and derivatives (eg., Vitamin E acetate), and Koni ferylbenzoat of Benzoëharzes, rutinic acid and their derivatives, Ferulasäu re and their derivatives, butylhydroxytoluene, Butylhydroxyanisol, Nordihydro guajakharzsäure, Nordihydroguajaretsäure, Trihydroxybutyrophenon, uric acid and its derivatives, mannose and its derivatives, zinc and its derivatives (eg ZnO, ZnSO ₄ ) Selenium and its derivatives (z. B. Selenmethio nin), stilbenes and their derivatives (eg stilbene oxide, trans-stilbene oxide) and the present invention suitable derivatives (salts, esters, ethers, sugars, Nu kleotide, nucleosides, peptides and lipids) of these drugs.

The amount of antioxidants (one or more compounds) in the Zu Preparations is preferably 0.001 to 30 wt .-%, especially before zugt 0.05-20 wt .-%, in particular 1-10 wt .-%, based on the Ge total weight of the preparation.

If vitamin E and / or its derivatives, the antioxidant (s) is advantageous, their respective concentrations from the field from 0.001 to 10% by weight, based on the total weight of the formulation, to choose.

If the cosmetic or dermatological preparation in the sense of the present invention is a solution or emulsion or dispersion, it is possible to use as solvent:

• - water or aqueous solutions
• - Oils, such as triglycerides of capric or caprylic, preferably but castor oil;
• - fats, waxes and other natural and synthetic fats, preferably esters of fatty acids with alcohols of low C number, z. B. with isopropanol, propylene glycol or glycerol, or esters of Fatty alcohols with alkanoic acids of low C number or with fatty acids;
• - Alcohols, diols or polyols low C number, and their ethers, before preferably ethanol, isopropanol, propylene glycol, glycerol, ethyl glycol, ethylene glycol monoethyl or monobutyl ether, Propy glycol monomethyl, monoethyl or monobutyl ether, diethylene glycol monomethyl or monoethyl ether and analogous products.

In particular, mixtures of the abovementioned solvents used. For alcoholic solvents, water can be another Be be part of the concept.

The oil phase of the emulsions, oleogels or hydrodispersions or Lipodi Sparsions in the sense of the present invention is advantageously selected the group of esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids of a chain length of 3 to 30  C atoms and saturated and / or unsaturated, branched and / or unbranched alcohols of a chain length of 3 to 30 carbon atoms, from the Group of esters of aromatic carboxylic acids and saturated and / or unsaturated, branched and / or unbranched alcohols of a ketone length of 3 to 30 carbon atoms. Such ester oils can then be advantageous are selected from the group isopropyl myristate, isopropyl palmitate, isopro pylstearate, isopropyl oleate, n-butyl stearate, n-hexyl laurate, n-decyl oleate, isooc tylstearate, isononyl stearate, isononyl isononanoate, 2-ethylhexyl palmitate, 2- Ethyl hexyl laurate, 2-hexyl decyl stearate, 2-octyl dodecyl palmitate, oleyl oleate, Oleyl erucate, erucyl oleate, erucyl erucate and synthetic, semisynthetic and natural mixtures of such esters, e.g. B. jojoba oil.

Furthermore, the oil phase can be advantageously selected from the group of branched and unbranched hydrocarbons and waxes, Sil the dialkyl ether, the saturated or unsaturated group, branched or unbranched alcohols, as well as the fatty acid triglycerides, namely the triglycerol esters saturated and / or unsaturated, branched ter and / or unbranched alkanecarboxylic acids of a chain length of 8 to 24, in particular 12-18 G atoms. The fatty acid triglycerides may be included For example, be selected from the group of synthetic, semisynthetic and natural oils, e.g. B. olive oil, sunflower oil, so jaöl, peanut oil, rapeseed oil, almond oil, palm oil, coconut oil, palm kernel oil and derglei more.

Also, any mixtures of such oil and wax components are advantageous to use in the context of the present invention. It can also optionally be advantageous, waxes, such as cetyl palmitate, as use only lipid component of the oil phase.

The oil phase is advantageously selected from the group 2-ethylhexyl isostearate, octyldodecanol, isotridecyl isononanoate, isoeicosane, 2-ethylhexyl cocoate, C _{12 15} alkyl benzoate, caprylic-capric acid triglyceride, dicaprylyl ether.

Particularly advantageous are mixtures of C _12-15 -alkyl benzoate and 2-ethyl hexylisostearat, mixtures of C _12-15 -alkyl benzoate and Isotridecyliso nonanoate and mixtures of C _12-15 -alkyl benzoate, 2-Ethylhexylisostearat and Isotridecylisononanoat.

Of the hydrocarbons are paraffin oil. Squalane and squalene benefit to be used in the sense of the present invention.

Advantageously, the oil phase may further contain cyclic or linear content Silicone oils or consist entirely of such oils, wherein however, it is preferred to use one except the silicone oil or silicone oils to use additional content of other oil phase components.

Advantageously, cyclomethicone (Octamethylcyclotetrasiloxan) as fiction used according to silicone oil to be used. But also other silicone oils are advantageous for the purposes of the present invention to use, in For example, hexamethylcyclotrisiloxane, polydimethylsiloxane, Po poly (methylphenylsiloxane).

Also particularly advantageous are mixtures of cyclomethicone and Isotri decylisononanoate, from cyclomethicone and 2-ethylhexyl isostearate.

Gels used in the present invention usually contain lower alcohols ger C number, z. As ethanol, isopropanol, 1,2-propanediol, glycerol and water or an above-mentioned oil in the presence of a thickener, in oily-alcoholic gels, preferably silica or an aluminum miniumsilikat, preference in aqueous-alcoholic or alcoholic gels example, a polyacrylate.

Fixed pins contain z. As natural or synthetic waxes, fat alcohols or fatty acid esters. Preference is given to lip balms as well Pen formulations for body deodorization.

Usual raw materials which are suitable for use as cosmetic sticks in the Meaning of the present invention, liquid oils (e.g.  Paraffin oils, castor oil, isopropyl myristate), semi-solid components (eg vase line, lanolin), solid ingredients (eg, beeswax, ceresin and microkri stalline waxes or ozokerite) and high-melting waxes (eg Carnauba wax, candelilla wax).

As a propellant for sprayable from aerosol containers cosmetic and / or dermatological preparations within the meaning of the present invention the usual known volatile, liquefied propellants, for example wise hydrocarbons (propane, butane, isobutane) suitable alone or in mixture with each other. Also compressed air is advantageous to use.

Of course, the person skilled in the art knows that there are nontoxic propellants per se, in principle for the realization of the present invention in the form aerosol preparations would be suitable, but nevertheless due to be effect on the environment or other concomitant circumstances should be tet, in particular fluorocarbons and Fluorchlorkoh Hydrocarbons (CFCs).

Cosmetic preparations according to the present invention can are also present as gels, which in addition to an effective content of the invention appropriate active ingredient and solvents commonly used for this, preferably water, organic thickeners, z. B. Gummiara bikum, xanthan gum, sodium alginate, cellulose derivatives, preferably Methylcellulose, hydroxymethylcellulose, hydroxyethylcellulose, hydroxy propylcellulose, hydroxypropylmethylcellulose or inorganic ver thickener, z. As aluminum silicates such as bentonites, or a mixture of polyethylene glycol and polyethylene glycol stearate or distearate. The thickener is in the gel z. B. in a menu between 0.1 and 30% by weight, preferably between 0.5 and 15% by weight, contain.

All quantities, percentages and percentages are, unless otherwise stated indicated, on the weight and the total quantity or on the Ge based on the total weight of the preparations.

The following examples are intended to illustrate the present invention.  

example 1 W / O cream

Wt .-% Paraffin oil (DAB 9) 10.00 petrolatum 4.00 Wool alcohol 1.00 PEG-7 hydrogenated castor oil 3.00 aluminum stearate 0.40 L-3- [4-hydroxyphenylsulfate ester] -2-aminopropionic acid (tyrosine O-sulfate ester) 0.50 glycerin 2.00 Preservatives, dyes, perfume q. s. water ad 100.00

Example 2 W / O lotion

Wt .-% Paraffin oil (DAB 9) 20.00 petrolatum 4.00 Glucosesesquiisostearat 2.00 aluminum stearate 0.40 L-3- [4-hydroxyphenylsulfate ester] -2-aminopropionic acid (tyrosine O-sulfate ester) 0.50 α-tocopheryl acetate 1.00 glycerin 5.00 Preservatives, dyes, perfume q. s. water ad 100.00

Example 3 O / W lotion

Wt .-% Paraffin oil (DAB 9) 8.00 isopropyl palmitate 3.00 petrolatum 4.00 Cetylstearylalkohol 2.00 PEG 40 castor oil 0.50 sodium cetylstearyl 0.50 Sodium carbomer 0.40 L-3- [4-hydroxyphenylsulfate ester] -2-aminopropionic acid (tyrosine O-sulfate ester) 0.50 glycerin 3.00 α-tocopherol 0.20 octyl 5.00 butylmethoxydibenzoylmethane 1.00 Preservatives, dyes, perfume q. s. water ad 100.00

Example 4 O / W cream

Wt .-% Paraffin oil (DAB 9) 7.00 avocado oil 4.00 glyceryl 2.00 L-3- [4-hydroxyphenylsulfate ester] -2-aminopropionic acid (tyrosine O-sulfate ester) 0.50 Titanium dioxide 1.00 sodium lactate 3.00 glycerin 3.00 Preservatives, dyes, perfume q. s. water ad 100.00

Example 5 Liposome-containing gel

Wt .-% lecithin 6.00 shea butter 3.00 L-3- [4-hydroxyphenylsulfate ester] -2-aminopropionic acid (tyrosine O-sulfate ester) 0.50 α-tocopherol 0.20 biotin 0.08 sodium citrate 0.50 glycine 0.20 urea 0.20 Sodium PCA 0.50 Hydrolyzed collagen 2.00 Xanthan gum 1.40 sorbitol 3.00 Preservatives, dyes, perfume q. s. water ad 100.00

Example 6 Sunscreen Emulsion

Wt .-% cyclomethicone 2.00 Cetyl dimethicone copolyol 0.20 PEG 22-dodecyl copolymer 3.00 Paraffin oil (DAB 9) 2.00 Caprylic / capric acid triglyceride 5.80 octyl 5.80 Butyl methoxydibenzoylmethane 4.00 L-3- [4-hydroxyphenylsulfate ester] -2-aminopropionic acid (tyrosine O-sulfate ester) 0.50 α-tocopheryl acetate 0.50 ZnSO ₄ 0.70 Na ₄ EDTA 0.30 Preservatives, dyes, perfume q. s. water ad 100.00

Example 7 Sunscreen Emulsion

Wt .-% cyclomethicone 2.00 Cetylstearyl alcohol + PEG 40-hydrogenated castor oil + sodium cetylstearylsulfate 2.50 glyceryl 1.00 Caprylic / capric acid triglyceride 0.10 Laurylmethicone copolyol 2.00 octyl 3.00 castor oil 4.00 glycerin 3.00 Acrylamide / sodium acrylate copolymer 0.30 Hydroxyproplymethylcellulose 0.30 octyl 5.00 Butyl methoxydibenzoylmethane 0.50 L-3- [4-hydroxyphenylsulfate ester] -2-aminopropionic acid (tyrosine O-sulfate ester) 0.50 α-tocopheryl acetate 1.00 Well ₃ HEDTA 1.50 Preservatives, dyes, perfume q. s. water ad 100.00

Example 8 Sunscreen Emulsion

Wt .-% cyclomethicone 2.00 Cetylstearyl alcohol + PEG 40-hydrogenated castor oil + sodium cetylstearylsulfate 2.50 glyceryl 1.00 Caprylic / capric acid triglyceride 0.10 Laurylmethicone copolyol 2.00 octyl 3.00 castor oil 4.00 glycerin 3.00 Acrylamide / sodium acrylate copolymer 0.30 hydroxypropyl methylcellulose 0.30 octyl 5.00 Butyl methoxydibenzoylmethane 0.75 L-3- [4-hydroxyphenylsulfate ester] -2-aminopropionic acid (tyrosine O-sulfate ester) 0.50 Well ₃ HEDTA 1.50 Preservatives, dyes, perfume q. s. water ad 100.00

Example 9 spray formulation

Wt .-% α-tocopherol 0.10 L-3- [4-hydroxyphenylsulfate ester] -2-aminopropionic acid (tyrosine O-sulfate ester) 0.50 ethanol 28,20 Preservatives, dyes, perfume q. s. Propane / butane 25/75 ad 100.00

Example 10 W / O cream

Wt .-% Paraffin oil (DAB 9) 10.00 petrolatum 4.00 Wool alcohol 1.00 PEG-7 hydrogenated castor oil 3.00 aluminum stearate 0.40 L-3- [4-sulfonic acid phenyl] -2-aminopropionic acid (phenylalanine p-sulfonic acid) 0.50 glycerin 2.00 Preservatives, dyes, perfume q. s. water ad 100.00

Example 11 W / O lotion

Wt .-% Paraffin oil (DAB 9) 20.00 petrolatum 4.00 Glucosesesquiisostearat 2.00 aluminum stearate 0.40 L-3- [4-hydroxyphenyl phosphate ester] -2-aminopropionic acid (tyrosine O-phosphate ester) 0.50 α-tocopheryl acetate 1.00 glycerin 5.00 Preservatives, dyes, perfume q. s. water ad 100.00

Claims (6)

1. Use of one or more compounds from the Group of substituted phenylalanines and derivatives thereof and plantl and animal extracts containing these compounds as active substances for prophylactic treatment and treatment of uner desired pigmentation of the skin. 2. Use of cosmetic or dermatological topical preparations tions containing one or more compounds from the group of substituted phenylalanines and derivatives thereof as well vegetable and animal extracts containing these compounds, as Active ingredients for prophylactic treatment and treatment of uner desired pigmentation of the skin. 3. Use according to claim 1 or 2, characterized in that substituted phenylalanines of the following formulas:
or
wherein
R is a sulfate radical or sulfuric acid radical -O-SO ₃ H, a phosphate radical or phosphoric acid radical -O-PO ₃ H ₂ or a sulfonic acid radical -SO ₃ H, where these radicals can also be present in the form of their salts, and R is 'and R'', independently of one another, hydrogen, C ₁ -C ₂₁ -alkyl, especially C ₁ - C ₃ alkyl, and wherein X is hydrogen, a metal cation or C ₁ -C- alkyl, preferably C ₁ -C ₁₂ Alkyl, but in particular C ₁ -C ₄ alkyl, ver used. 4. Use according to claim 1 or 2, characterized in that the L-isomers of the active ingredients are used. 5. Use according to claim 1 or 2, characterized in that L 3- [4-hydroxyphenyl sulfate ester] -2-aminopropionic acid or L-3- [3- Hydroxyphenylsulfatester] -2-aminopropionic acid is used, given if necessary also their derivatives. 6. Use according to claim 2, characterized in that the Ge content of active ingredient in the preparations 0.01-10 wt .-%, preferably 0.1-5 Wt .-%, in particular 0.2-2.0 wt .-% is.