FR3027515B1 - USE OF ESTERS OF PHENYLALANINE AND POLYOLS AS A LIGHTENING AGENT FOR THE SKIN OF THE HUMAN BODY - Google Patents

Abstract

Use of a compound of formula (I) R'-O-CH 2 -CH (OH) - [CH 2 -O-CH 2] s- [CH (OH)] p -CH 2 -OR "(1) in which s is equal to 0 or 1 and p is 0, 1, 2 or 3 and R 'and R "represent either a hydrogen atom or a monovalent radical of formula (II): formula (II) in which the group R1 (C = O) represents an acyl radical or a composition (C1) comprising for 100% of its mass from 99% by weight to 20% by weight of at least one compound of formula (Ia): R'-O- CH 2 -CH (OH) - [CH 2 -O-CH 2] s- [CH (OH)] p -CH 2 -OH (la) in which s is 0 or 1 and p is 0, 1, 2 or 3 and in which R 'represents a monovalent radical of formula (II) and from 1% by mass to 80% by weight of at least one compound of formula (Ib): RO-CH 2 -CH (OH) - [CH 2 -O] -CH2] s- [CH (OH)] p-CH2-OR, formula (Ib) wherein s is 0 or 1 and p is 0, 1, 2 or 3, wherein R represents a radical monovalent of formula (II), for the purpose of lightening human skin. Lightening process and therapeutic composition

Description

The subject of the present invention is the use of esters of N-acyl derivatives of amino acids and polyols as lightening agents for the skin of the human body, as well as non-therapeutic methods for lightening human skin comprising at least one step of applying to said human skin a topical cosmetic formulation comprising said esters of N-acyl derivatives of amino acids and deglycerol.

Human skin is the first image offered in the eyes of others, and as a result, the improvement of its appearance is a subject of constant concern for human beings. The skin is a reflection of a state of well-being, often associated with youth, and a contrario a state of fatigue and / or aging. While consumers in many countries seek to brown the skin, either naturally under the action of UV radiation from the sun or artificially under the action of chemical compounds, some consumers seek to clear their skin, to provide an external image of purity, or in some cases countries in Asia or Africa to provide a good image. For Caucasian skin, the need for clarification may also be part of a desire to mask the appearance of age-related pigment spots (so-called "senescence tasks").

The color and radiance of the complexion of the skin result from the combination of two biological components: the vascularization and the pigmentation of the skin; said pigmentation of the skin being the resultant of the amounts of melanins and carotenes present in human skin.

Melanins are produced by specific epidermal cells: the melanocytes. These are found at the level of the basal layer of the epidermis or in the hair follicles. Melanins are large cells with many long extensions called dendrites. These dendrites enter encontact with the surrounding keratinocytes, which can be up to two upper cell layers, to transmit melanin grouped in melanosomes.

Epidermal Unit of Melanization (EMU) is defined as the group consisting of melanocytes and keratinocytes, interacting together to give color to the skin.

An EMU comprises in particular a melanocyte and forty keratinocytes. The melanogenesis process itself comprises the synthesis of melanins by the melanocytes, their transfer and their distribution to neighboring keratinocytes.

The synthesis of melanins occurs in melanocytes, and more particularly in specialized organelles, melanosomes. This synthesis is made from tyrosine and involves several enzymes, including tyrosinase which is the first enzyme to intervene in the reaction chain.

The pigmentation of the skin can either be constitutive or induced. The pigmentationconstitutive is based on the genetic heritage of the individual, hormonal factors and age. Induced pigmentation results mainly from ultraviolet radiation exposures. It appears between 48 hours and 72 hours after exposure of the skin to ultraviolet radiation and disappears quickly after the exposure has stopped. This induction of pigmentation results in particular from an activation of tyrosinase, an increase in the size and number of melanocytes and an increase in the transfer of melanosomes to keratinocytes. An indirect action on keratinocytes is also involved to promote the process of melanogenesis by the secretion of soluble agents. On the other hand, inhibition of tyrosinase activity will induce a decrease in the quantity of melanins produced by melanocytes and lead to its visible manifestation, namely the natural lightening of human skin.

Many cosmetic formulations include kojic acid, arbutin and / or magnesium ascorbyl phosphate as skin lightening agents. Hydroquinone, a substance historically used to lighten the skin, is now prohibited in some countries because of its altering action on the skin and the dangers it brings to the health of the consumer.

The European patent application published under the number EP 1 471 881 discloses that N-acylated derivatives of alpha-amino acids and in particular N-undecylenoylphenylalanine have an affinity for the specific melanocyte-hormone receptor (α-MSH) and thus induce the lightening of the skin according to the following biochemical mechanism: the competition between the α-MSH hormone and the molecule having an affinity towards the α-MSH receptor, results in a lower rate of attachment of said hormone to the cellular receptors; this competition results in an inhibition of the activity of the adenylate cyclase which causes a less transformation of ΓΑΤΡ into intracellular cyclic AMP; the decrease in cyclic AMP results in inhibition of Protein Kinase A (PKA) enzyme; inhibition of Protein Kinase A induces less activation of tyrosinase due to less transformation of tyrosinase into phosphorylated tyrosinase; this less activation of tyrosinase leads to a decrease in melanin synthesis, which results in less pigmentation of the skin.

Japanese Patent Application No. 2000-229121 describes the use of polyolsesters of N-acylamino acids as effective surfactants

The international application published under the number WO 2010/034917 describes the monoesters and di-esters of polyols of N- (undecylenoyl) phenylalanine, and more particularly the mono-esters and diesters resulting from the reaction of glycerol and duN- (co-undecylenoyl) phenylalanine, and their uses as lightening agents in the human skin.

In the context of their search for new skin-brightening active agents, improved over those of the state of the art cited above, the inventors are attached to developing a new use as a lightening agent for N-acylated amino acid derivatives. . Therefore, according to a first aspect, the subject of the invention is the use of a compound of formula (I): R'-O-CH 2 -CH (OH) - [CH 2 -O-CH 2] S- [ CH (OH)] p-CH2-OR ", wherein s is 0 or 1 and p is 0, 1, 2 or 3 and R 'and R", which are the same or different, represent either a hydrogen atom or a monovalent radical of formula (II):

formula (II) in which the group R1 (C = O) represents an acyl radical chosen from octanoyl, decanoyl, dodecanoyl, tetradecanoyl and optionally hexadecanoyl, octadecanoyl, 9-octadecenoyl and octadeca-9,12-dienoyl, it being understood that in said formula (I), at least one of the radicals R 'or R "does not represent a hydrogen atom and that when none of the radicals R' and R" nerepresents a hydrogen atom, R 'and R "are identical, or a mixture of compounds of formula (I), said use being for the purpose of lightening human skin and said use being in a cosmetic composition.

According to a first particular aspect, the subject of the invention is the use as defined above of a composition (C1) comprising for 100% of its mass: from 99% by mass to 20% by weight, more particularly by 99% mass at 50% by weight, and even more particularly at 95% by mass at 75% of at least one compound of formula (Ia):

in which s is 0 or 1 and p is 0, 1, 2 or 3 and wherein R 'is a monovalent radical of formula (II):

formula (II) in which the group R 1 (C = O) represents an acyl radical chosen from the radicals octanoyl, decanoyl, dodecanoyl, tetradecanoyl, hexadecanoyl, octadecanoyl, 9-octadecenoyl and octadeca-9,12-dienoyl; and from 1% by weight to 80% by weight, more particularly from 1% by weight to 50% by weight, and even more particularly from 5% by weight to 25% by weight of at least one compound of formula (Ib):

formula (Ib) wherein s is 0 or 1 and p is 0, 1,2 or 3, wherein R represents a monovalent radical of formula (II):

formula (II) wherein the group R1 (C = O) is an acyl radical selected from octanoyl, decanoyl, dodecanoyl, tetradecanoyl, and optionally hexadecanoyl, octadecanoyl, 9-octadecenoyl and octadeca-9,12-dienoyl radicals.

According to a more particular aspect, the subject of the invention is the use as defined above, for which, in formulas (I), (la) or (Ib), s is equal to 0. According to this particular aspect, the compound of formula (I) as defined above is a glycerol ester when p is 0, an ester of erythritol when p is 1, a duxylitol ester when p is 2 and a sorbitol ester when p is The invention particularly relates to the use as defined above, for which, in formulas (I), (Ia) or (Ib), s and p are equal to 0.

According to a very particular aspect, the subject of the invention is the use as defined above, for which the compound of formula (I) is N-octanoyl phenylalaninated (2,3-dihydroxy) propyl, or N-cocoyl phenylalaninate. (2,3-dihydroxy) propyl or for which the composition (C1) comprises for 100% of its mass from 99% by weight to 20% by weight, more particularly from 99% by weight to 50% by weight, and even more particularly from 95% by weight to 75% by weight. % by mass of (2,3-dihydroxy) propyl N-octanoyl phenylalaninate and 1% by mass at 80% by weight, more particularly from 1% by weight to 50% by mass, and even more particularly from 5% by mass to 25% by mass of bis (N-octanoylphenylalaninate) of 2-hydroxy-1,3-propanediyl, or for which the composition (C1) comprises for 100% of its mass of 99% by mass at 20% by mass, more particularly of 99% by weight at 50% by mass and even more particularly from 95% by weight to 75% by mass of N-cocoyl ph (2,3-dihydroxy) propyl enylalaninate and 1% by weight to 80% by weight, more particularly from 1% by mass to 50% by mass, and even more particularly from 5% by weight to 25% by mass of bis (N-cocoyl phenylalaninate) ) 2-hydroxy 1,3-propanediyl.

By N-cocoyl phenylalaninate of (2,3-dihydroxy) propyl, is meant in the definitions of the compounds of formula (I) and (la) a mixture comprising for 100 mol%: - 5 mol% to 15 mol% of N- (2,3-dihydroxy) propyl octanoyl phenylalaninate; - from 5 mol% to 10 mol% of (2,3-dihydroxy) propyl N-decanoyl phenylalaninate; - from 45 mol% to 55 mol% of N-dodecanoyl phenylalaninate of (2,3-dihydroxy) propyl; - from 10 mol% to 20 mol% of (2,3-dihydroxy) propyl N-tetradecanoyl phenylalaninate; - from 5 mol% to 15 mol% of N-hexadecanoyl phenylalaninate ( 2,3-dihydroxy) propyl, and - From 5 mol% to 10 mol% of a mixture of N- (9-octadecenoyl) phenylalaninate N-octadecanoyl phenylalaninated (2,3-dihydroxy) propyl dihydroxy) propyl and (2,3-dihydroxy) propyl N- (octadeca-9,12-dienoyl) phenylalaninate.

By bis (N-cocoylphenylalaninate) of 2-hydroxy-1,3-propanediyl is meant in the definitions of the compounds of formula (I) and (Ib) a mixture comprising for 100 mol%: - 5 mol% to 15 mol% of 2-hydroxy-1,3-propanediyl bis (N-octanoyl phenylalaninate), - 5 mol% to 10 mol% of bis (N-decanoyl phenylalaninate) of 2-hydroxy-1,3-propanediyl, - 45 mol% to 55 mol% of bis (N-dodecanoyl phenylalaninate) of 2-hydroxy-1,3-propanediyl, - from 10 mol% to 20 mol% of bis (N-tetradecanoyl phenylalaninate) of 2-hydroxy-1,3-propanediyl, mol% to 15 mol% of bis (N-hexadecanoyl phenylalaninate) of 2-hydroxy 1,3-propanediyl, and - from 5 mol% to 10 mol% of a mixture of bis (N-octadecanoylphenylalaninate) of 2-hydroxy-1 3-propanediyl, 2-hydroxy-1,3-propanediyl bis [N- (9-octadecenoyl) phenylalaninate], and 2-hydroxy-1-bis [N- (octadeca-9,12-dienoyl) phenylalaninate], 3-propanediyl.

The compound of formula (I) as defined above can be prepared according to a preparation process comprising: a step a) of esterification of a compound of formula (IVa):

in which R1-C (= O) - is as defined in formula (IIa), with a compound of formula (V): HOAOH (V), in which A represents a divalent radical of formula (III) as defined previously to obtain either the compound of formula (Ia) or the compound of formula (Ib) or a mixture (M) of the compound of formula (Ia) and the compound of formula (Ib); and, if necessary, - a step b) of separating the compounds of formula (Ia) and formula (Ib) from the said mixture (M) obtained in step (a).

The compounds of formulas (IVa) are known or can be synthesized by N-acylation of the corresponding α-amino acids according to methods known to those skilled in the art.

In the process as defined above, the compound molar ratio of formula (IVa) on compound of formula (V) is generally between 3/1 and 1/5, more particularly between 1/1 and 1/5, and even more particularly between 1/1 and 1/3.

In the process as defined above, the step b) of separating the compounds of formula (Ia) and of formula (Ib) is carried out by the conventional methods of separation known to those skilled in the art.

The compound of formula (I) as defined above can also be prepared by a preparation process comprising: a step a1) of esterification of a compound of formula (IVa)

wherein R1-C (= O) - is as defined in formula (IIa), with an alcohol of formula (VI): R5-OH (VI), wherein R5 represents a linear aliphatic radical having from 1 to 4 decarbon atoms, to form a compound of formula (VIIa):

in which R1-C (= O) - and R5 are as defined above, - a step a2) of trans-esterification of the compound of formula (VIla) obtained in step a1), by reaction with the compound of formula ( V) to obtain either the compound of formula (Ia) or the compound of formula (Ib) or a mixture (M) of the compound of formula (Ia) and the compound of formula (Ib); and if necessary or desired, - The implementation of step b).

In the process as described above, step a1) is generally carried out at a temperature of about 60 ° C to 120 ° C, under an inert gas, and in the presence of an acidic catalyst system. By acidic catalytic system are meant strong acids such as sulfuric acid, hydrochloric acid, phosphoric acid, nitric acid, hypophosphorous acid, methanesulfonic acid, para-toluene sulfonic acid, acid trifluoromethanesulfonic acid, or acidic ion exchange resins.

In step a1) of the variant of the process as described above, the molar ratio compound of formula (IVa) on alcohol of formula (VI) is generally between 1/1 and 1/10, more particularly between 1/1 and 1/8, and even more particularly between 1/2 and 1/8.

In the variant of the process for the preparation of the compounds of formula (I) as described above, step a2) of transesterification of the ester of formula (VIIa) obtained in step a1) is generally carried out at a temperature approximately between 80 ° C and 180 ° C, more particularly between 100 ° C and 150 ° C, even more particularly between 120 ° C and 150 ° C under an inert gas, and in the presence of an acid catalyst system such as previously described, and with vacuum distillation of the alcohol of formula (VI) formed in-situ.

In step a2) of this variant of the process for the preparation of the compounds of the formula (I) as described above, the compound molar ratio of formula (Vlla) on the compound of formula (V) is between 3/1 and 1 / 5, more particularly between 1/1 and 1/5, and even more particularly between 1/1 and 1/3.

The composition (Cf) whose use as defined above is the subject of the invention may be prepared by various routes.

A first route of preparation of the composition (Cfl comprises mixing in the desired mass proportions the compound of formula (Ia) as defined above or the mixture of compounds of formula (Ia) with the compound of formula (Ib) as defined above, or the mixture of compounds of formula (Ib).

A second route of preparation of the composition (Cfl consists of carrying out the process for the preparation of the compound of formula (I) as described above, by reacting in the desired proportions, the compound of formula (V) with the compound of formula ( IVa) or a mixture of compounds of formula (IVa).

A third route for the preparation of the composition (Cfl) consists in implementing the variant of the process for preparing the compound of formula (I) as described above, by reacting in the desired proportions, the compound of formula (V) with the compound of formula (VIla) or a mixture of compounds of formula (VIla).

The compound of formula (I) and the composition (C1) as defined above and whose use as defined above is the subject of the present invention, may be administered orally, topically or parenterally, and more particularly by voietopique. The invention also relates to a method for lightening human skin, comprising at least one step of application to human skin, of a topical cosmetic formulation comprising at least one cosmetically acceptable excipient and an effective amount. of the compound of formula (I) or of the composition (C1) as defined above.

In the cosmetic process as described above, the topical cosmetic formulation is spread on the surface of the skin to be treated, then the skin is massaged a few moments. The expression "for topical use" used in the definition of the cosmetic formulation used in the cosmetic process that is the subject of the present invention means that said formulation is implemented by application to the skin, whether it is a direct application in the case of a cosmetic formulation or aindirect application when the cosmetic formulation according to the invention is impregnated on a supportdestiné to be put in contact with the skin (paper, wipe, textile, transdermal device, etc ...) . The term "cosmetically acceptable" used in the definition of the cosmetic formulation for topical use, used in the cosmetic process object of the present invention, means according to the Council Directive of the European Economic Community No. 76/768 / EEC of July 27 1976 amended by Directive 93/35 / EEC of 14 June 1993, that the said formulation for topical use includes any substance or preparation intended to be put in contact with the various parts of the human body (epidermis, hair and capillary system, nails, lips and genitals) or with the teeth and oral mucosa in view, exclusively and principally, to clean, perfume, modify the appearance and / or correct body odor and / or protect or keep in good condition.

An effective amount of the compound of formula (I) or of a composition (C1) as defined previously present in the cosmetic formulation for topical use implemented in the cosmetic process that is the subject of the present invention, is understood to mean100% of the mass of said cosmetic formulation for topical use, between 0.1% and 5% by weight, more particularly between 0.1% and 3% by weight, and even more particularly between 0.5% and 2% by weight of compound of formula (I) or composition (C1).

The cosmetic formulations for topical use implemented in the method of the present invention, are generally in the form of aqueous or hydro-alcoholic or hydro-glycolic solutions, in the form of suspension, an emulsion, a microemulsion or a nano-emulsion, whether water-in-oil, oil-in-water, water-in-oil-in-water or oil-in-water-in-oil, or in the form of a powder. These formulations may be packaged in a bottle, in a device of "pump" bottle type, in pressurized form in an aerosol device, in a device provided with a perforated wall such as a grid or in a device equipped with a ball applicator (called " roll-on ").

In general, the compound of formula (I) or the composition (C1) present, is associated with chemical additives usually used in the field offormulations for topical use, such as foaming surfactants and / or detergents, thickening surfactants and / or gelling agents, thickening and / or gelling agents, stabilizing agents, film-forming compounds, solvents and co-solvents, hydrotropic agents, thermal or mineral waters, plasticizing agents, emulsifying and co-emulsifying agents, opacifying agents, pearlescent agents, superfatting agents, sequestering agents, chelating agents, oils, waxes, antioxidants, perfumes, essential oils, preserving agents, conditioning agents, deodorants, whitening agents for hair dyeing and the skin, the active ingredients intended to provide a protective and / or protective action skin or hair screws, sunscreens, mineral fillers or pigments, particles providing a visual effect or intended for encapsulation of active ingredients, exfoliating particles, texture agents, optical brighteners, repellents for insects .

As examples of foaming and / or detergent surfactants which can be associated with the compound of formula (I) or with the composition (C1), mention may be made of anionic, cationic, amphoteric or nonionic surfactants and / or detergents.

Among the foaming and / or detergent anionic surfactants which may be combined with the compound of formula (I) or with the composition (C1), mention may be made of the alkali metal, alkaline earth metal, ammonium, amines, or aminoalcohols of alkyl ether sulfates, alkyl sulphates, alkylamido ether sulphates, alkylaryl polyether sulphates, monoglyceride sulphates, alpha-olefin sulphonates, paraffin sulphonates, alkyl phosphates, alkyl ether phosphates, alkyl sulphonates, alkyl amide sulphonates, alkylarylsulfonates, alkylcarboxylates, alkylsulfosuccinates, alkylethersulfosuccinates, alkylamidesulfosuccinates, alkylsulfoacetates, alkylsarcosinates, acylisethionates, N-acyltaurates, acyllactylates, N-acyl derivatives of amino acids , N-acyl derivatives of peptides, N-acylated protein derivatives, N-acyl derivatives of fatty acids.

Among the foaming and / or detergent amphoteric surfactants which may be associated with the compound of formula (I) or with the composition (C1), mention may be made of alkylbetaines, alkylamidobetaines, sultaines, alkylamidoalkylsulfobetaines, derivatives of imidazolines, phosphobetaines , amphopolyacetates and amphopropionates.

Among the foaming and / or detergent cationic surfactants which may be associated with the compound of formula (I) or with the composition (C1), particular mention may be made of quaternary ammonium derivatives.

Among the foaming and / or detergent nonionic surfactants which may be associated with the compound of formula (I) or with the composition (C1), mention may be made more particularly of alkylpolyglycosides comprising a linear, saturated, saturated or unsaturated aliphatic radical, and comprising from 8 to 16 carbon atoms, such as octyl polyglucoside, decyl polyglucoside, undecylenyl polyglucoside, dodecyl polyglucoside, tetradecyl polyglucoside, hexadecyl polyglucoside, 1-12-dodecanediyl polyglucoside; ethoxylated hydrogenated castor oil derivatives such as the product marketed under the INCI name "Peg-40 hydrogenated castor oil"; polysorbates such as Polysorbate 20, Polysorbate 40, Polysorbate 60, Polysorbate 70, Polysorbate 80, Polysorbate 85; coconut amides; N-alkylamines.

Examples of thickening and / or gelling surfactants that can be associated with the compound of formula (I) or with composition (C1) include fatty esters of optionally alkoxylated alkylpolyglycosides, such as methylpolyglucosideethoxylated esters such as PEG 120. methyl glucose trioleate and PEG 120 methyl glucosedioleate respectively marketed under the names GLUCAMATE ™ LT and GLUMATE ™ DOE120; alkoxylated fatty esters such as PEG 150 pentaerythritol tetrastearate marketed under the name CROTHIX ™ DS53, PEG 55 propylene glycol oleate sold under the name ANTIL ™ 141; fatty chain polyalkylene glycol carbamates, such as PPG-14 laureth isophoryl dicarbamat, marketed under the name ELFACOS ™ T211, PPG-14 palmeth-60-hexyldicarbamate sold under the name ELFACOS ™ GT2125.

Examples of thickening and / or gelling agents that can be combined with the compound of formula (I) or with the composition (C1) include polyelectrolytes, linear or branched or crosslinked polymers, such as homopolymer partially or totally salified acrylic acid, partially or totally salified methacrylic acid homopolymer, 2-methyl-[(1-oxo-2-propenyl) amino] -1-propanesulfonic acid (AMPS) homopolymer partially or fully salified, copolymers of acrylic acid and AMPS, copolymers of acrylamide and AMPS, copolymers of vinylpyrrolidone and AMPS, copolymers of AMPS and acrylate of (2-hydroxyethyl), copolymers of AMPS and (2-hydroxyethyl) methacrylate, copolymers of AMPS and hydroxyethylacrylamide, copolymers of AMPS and Ν, Ν-dimethyl acrylamide, copolymers of the AMPS and dutris (h ydroxy-methyl) acrylamido methane (THAM), copolymers of acrylic or methacrylic acid and (2-hydroxyethyl) acrylate, copolymers of acrylic or methacrylic acid and (2-hydroxyethyl) methacrylate, copolymers of acrylic or methacrylic acid and hydroxyethylacrylamide, copolymers of acrylic or methacrylic acid and THAM, copolymers of acrylic or methacrylic acid and Ν, Ν-dimethyl acrylamide, terpolymers of acrylic acid or methacrylic acid, AMPS and (2-hydroxyethyl) acrylate, terpolymers of acrylic or methacrylic acid, AMPS and (2-hydroxyethyl) methacrylate, terpolymers of acrylic or methacrylic acid, AMPS and THAM, terpolymers of acrylic or methacrylic acid, AMPS and N, N-dimethylacrylamide, terpolymers of acrylic or methacrylic acid, AMPS and acrylamid e, copolymers of acrylic acid or of methacrylic acid and of alkyl acrylates whose carbon chain comprises between four and thirty carbon atoms and more particularly between ten and thirty carbon atoms, the copolymers of AMPS and alkyl acrylates whose carbon chain comprises between four and three carbon trenteatomes and more particularly between ten and thirty carbon atoms, the linear, branched or crosslinked interpolymer of at least one monomer having a strong acid function, free, partially salified or totally salified, with at least one monomer, and at least one monomer of formula (VIII): CH2 = C (R6) -C (= O) - [CH2-CH2-O] n -R7in which R6 represents a hydrogen atom or a methyl radical, R7 representsa linear or branched alkyl radical having from eight to thirty carbon atoms and nrepresente a number greater than or equal to one and less than or equal to fifty.

The polyelectrolytes polymers, linear or branched or crosslinked that can be associated with the compound of formula (I) or with the composition (C1), can be presentersous in the form of a solution, an aqueous suspension, a water-in-oil emulsion, an oil-in-water emulsion, a powder. The linear or branched or crosslinked polyelectrolytic polymers which can be combined with the compound of formula (I) or with the composition (C1) can be selected from the products sold under the names SIMULGEL ™ EG, SIMULGEL ™ EPG, SEPIGEL ™ 305, SIMULGEL ™ 600, SIMULGEL ™ NS, SIMULGEL ™ INS 100, SIMULGEL ™ FL, SIMULGEL ™ A, SIMULGEL ™ SMS 88, SEPINOV ™ EMT 10, SEPIPLUS ™ 400, SEPIPLUS ™ 265, SEPIPLUS ™ S, SEPIMAX ™ Zen, ARISTOFLEX ™ AVS, ARISTOFLEX ™ AVS, NOVEMER ™ EC-1, NOVEMER ™ EC 2, ARISTOFLEX ™ HMB, COSMEDIA ™ SP, FLOCARE ™ AND 25, FLOCARE ™ AND 75, FLOCARE ™ AND 26, FLOCARE ™ AND 30, FLOCARE ™ AND 58 , FLOCARE ™ PSD 30, VISCOLAM ™ AT 64, VISCOLAM ™ AT 100.

Examples of thickening and / or gelling agents which can be combined with the compound of formula (I) or with composition (C1) include polysaccharides composed solely of monosaccharides, such as glucans or homopolymers of glucose, glucomannoglucans, xyloglycans, galactomannans whose degree of substitution (DS) of D-galactose units on the main D-mannose chain is between 0 and 1, and more particularly between 1 and 0.25, such as galactomannans originating from gum of cassia (DS = 1/5), locust bean gum (DS = 1/4), tara gum (DS = 1/3), guar gum (DS = 1/2), fenugreek gum (DS = 1).

Examples of thickening and / or gelling agents which can be combined with the compound of formula (I) or with composition (C1) include polysaccharides composed of monosaccharides, such as sulphated galactans and more particularly agar, uronans and more particularly algin, alginates and pectins, heteropolymers of monosaccharides and uronic acids, and more particularly xanthan gum, gellan gum, exudates of arabic gum and karaya gum, glucosaminoglycans .

Examples of thickening and / or gelling agents that can be combined with the compound of formula (I) or with the composition (C1) include cellulose, cellulose derivatives such as methylcellulose and ethylcellulose. , hydroxypropyl cellulose, silicates, starch, hydrophilic derivatives of starch, polyurethanes.

Examples of stabilizing agents that can be combined with the compound of Formula (I) or with the composition (C1) include microcrystalline waxes, and more particularly ozokerite, mineral salts such as sodium chloride or magnesium chloride, silicone polymers such as polysiloxane polyalkylpolyether copolymers.

Examples of solvents that can be combined with the compound of formula (I) or with the composition (C1) include water, organic solvents such as glycerol, glycerol, oligomers of glycerol, ethylene glycol, propylene glycol, butylene glycol, 1,3-propanediol, 1,2-propanediol, hexylene glycol, diethylene glycol, lexylitol, erythritol, sorbitol, water-soluble alcohols such as ethanol, isopropanol or butanol, water mixtures and said organic solvents.

Examples of thermal or mineral waters that can be combined with the compound of formula (I) or with the composition (C1) include thermal or mineral waters having a mineralization of at least 300 mg / l, particularly Avene water, the Vittel water, the waters of the Vichy basin, the water of Uriage, the water of the Roche Posay, the water of the Bourboule, the water of Enghien-les-bains, the water of Saint-Gervais-les Bains, the water of Neris-les-Bains, the water of Allevard-les-Bains, the water of Digne, the water of the Maizieres, the water of Neyrac- the baths, the water of Lons le Saunier, the water of Rochefort, the water of Saint Christau, the water of Fumades and the water of Tercis-les-bains.

Examples of hydrotropic agents that can be combined with the compound of Formula (I) or Composition (C1) include xylenesulfonates, cumenesulphonates, hexylpolyglucoside, 2-ethylhexylpolyglucoside, n-heptylpolyglucoside.

Examples of emulsifying surfactants that can be combined with the compound of formula (I) or with the composition (C1) include nonionic surfactants, anionic surfactants and cationic surfactants.

Examples of emulsifying nonionic surfactants that may be associated with the compound of formula (I) or with the composition (C1) include esters of fatty acids and of sorbitol, such as the products sold under the names MONTANE ™ 40, MONTANE ™ 60, MONTANE ™ 70, MONTANE ™ 80 and MONTANE ™ 85, the compositions comprising glycerol stearate and ethoxylated stearic acid between 5 mol and 150 moles of ethylene oxide, as the composition comprises ethoxylated acid estereal 135 moles of ethylene oxide and glycerol stearate marketed under the name SIMULSOL ™ 165; mannitan esters; ethoxylated mannitan esters; sucrose esters; methylglucoside esters; the alkylpolyglycosides having a linear or branched, saturated or unsaturated aliphatic radical containing from 14 to 36 carbon atoms, for instance tetradecylpolyglucoside, hexadecyl polyglucoside, octadecyl polyglucoside, hexadecylpolyxyloside, octadecylpolyxoside, eicosyl polyglucoside, dodecosyl polyglucoside, 2-octyldodecyl polyxyloside, 12-hydroxystearyl polyglucoside; compositions of saturated or unsaturated, linear or branched fatty alcohols containing from 14 to 36 carbon atoms, and of alkylpolyglycosides as described above, for example the compositions marketed under the tradename MONTANOV ™ 68, MONTANOV ™ 82, MONTANOV ™ 14, MONTANOV ™ 202, MONTANOV ™ S, MONTANOV ™ WO 18, FLUIDANOV ™ 20X and EASYNOV ™.

Examples of anionic surfactants that can be combined with the compound of formula (I) or with the composition (C1) include glyceryl stearate citrate, cetearyl sulphate, soaps such as sodium stearate or stearic acid detethanolammonium, N derivatives. acylated salified amino acids such as, for example, tetaroyl glutamate.

As examples of emulsifying cationic surfactants that can be associated with the compound of formula (I) or with the composition (C1), mention may be made of the aminoxides, the quaternium-82 and the surfactants described in the international application published under the number WO 96 / 00719 and mainly those whose fatty chain comprises at least 16 carbon atoms.

Examples of opacifying and / or pearling agents which may be combined with the compound of formula (I) or with the composition (C1) include sodium palmitate, sodium latarate, sodium hydroxystearate and palmitate. magnesium stearate, magnesium hydroxystearate, ethylene glycol monostearate, ethylene glycol stearate, polyethylene glycol monostearate, polyethylene glycol distearate, and fatty alcohols having from 12 to 22 carbon atoms.

Examples of texturizing agents that can be combined with the compound of formula (I) or with the composition (C1) include N-acyl derivatives of amino acids, such as lauroyl lysine marketed under the name AMINOHOPE. ™ LL, octenylstarch succinate marketed under the name DRYFLO ™, myristyl polyglucoside marketed under the name MONTANOV ™ 14, cellulose fibers, decoton fibers, chitosan fibers, talc, sericite, mica.

Examples of deodorant agents that can be combined with the compound of formula (I) or with the composition (C1) include alkali silicates, zinc salts such as zinc sulfate, zinc gluconate, sodium chloride, and the like. zinc, zinc lactate; quaternary ammonium salts such as cetyltrimethylammonium salts, cetylpyridinium salts; glycerol derivatives such as glycerol caprate, caprylate deglycerol, polyglycerol caprate; 1,2 decanediol; 1,3 propanediol; acidalicylic acid; sodium bicarbonate; cyclodextrins; metallic zeolites; TRICLOSAN ™; aluminum bromohydrate, aluminum chlorohydrates, aluminum chlorides, aluminum sulphate, aluminum and zirconium chlorohydrates, aluminum and zirconium hydrochloride, aluminum and zirconium tetrachlorohydrate, pentachlorhydrate aluminum and zirconium, aluminum and zirconium octochlorhydrate, aluminum sulphate, sodium and aluminum lactate, aluminum and glycol hydrochloride complexes, such as aluminum chlorohydrate complex and propylene glycol complex, aluminum dihydrochloride complex and propylene glycol complex, the complex of aluminum sesquichlorohydrate and propylene glycol, the complex of aluminum hydrochloride and polyethylene glycol, the complex of aluminum dihydrochloride and polyethylene glycol, the complex desesquichlorhydrate aluminum and polyethylene glycol.

Examples of oils which can be combined with the compound of formula (I) or with the composition (C1) include mineral oils such as paraffin oil, liquid petroleum jelly, isoparaffins or oils. mineral white; oils of animal origin, such as squalene or squalane, vegetable oils, such as phytosqualane, sweet almond oil, coconut oil, castor oil, jojoba oil, olive oil, rapeseed oil, peanut oil, sunflower oil, wheat germ oil, corn oil, soybean oil, oil cotton, alfalfa oil, poppy oil, pumpkin oil, evening primrose oil, millet oil, barley oil, rye oil, decartham oil , banana oil, passionflower oil, hazelnut oil, palm oil, shea butter, apricot kernel oil, calophyllum oil, sysymbrium oil, avocado oil, calendula oil, oils derived from flowers or vegetables, ethoxylated vegetable oils; synthetic oils such as fatty acid esters such as butyl emyristate, propyl myristate, isopropyl myristate, decetyl myristate, isopropyl palmitate, octyl palmitate, butyl stearate, steareate hexadecyl, isopropyl stearate, octyl stearate, isocetyl stearate, oléatedodecyl, hexyl laurate, propylene glycol dicaprylate, esters derived from anelanolic acid, such as isopropyl lanolate , isocetyl lanolate, monoglycerides, diglycerides and triglycerides of fatty acids such as glycerol triheptanoate, alkylbenzoates, hydrogenated oils, poly (alpha-olefin), polyolefins such as poly (isobutane), synthetic isoalkanes, isohexadecane, isododecane, perfluorinated oils; silicone oils such as dimethylpolysiloxanes, methylphenylpolysiloxanes, silicones modified with amines, silicones modified with fatty acids, silicones modified with alcohols, silicones modified with alcohols and fatty acids, silicones modified with polyether groups modified epoxy silicones, silicones modified with fluorinated groups, cyclic desilicones and silicones modified with alkyl groups. By "oils" is meant in the present application the compounds and / or mixtures of compounds insoluble in water, being in a liquid appearance at a temperature of 25 ° C.

Examples of waxes that can be combined with the compound of formula (I) or with the composition (C1) include beeswax, carnauba wax, candelilla wax, ouricoury wax, Japanese wax, cork fiber wax, sugar cane wax, paraffin waxes, lignite waxes, microcrystalline waxes, lanolin wax, zokokerite; polyethylene wax; silicone waxes; vegetable waxes; alcohols and solid fatty acids at room temperature; solid glycerides at room temperature. By "waxes" is meant in the present application the compounds and / or mixtures of water-insoluble compounds, having a solid appearance at a temperature greater than or equal to 45 ° C.

Examples of active principles that can be combined with the compound of formula (I) or with the composition (C1) include vitamins and their derivatives, especially their esters, such as retinol (vitamin A) and its esters ( retinyl palmitate, for example), ascorbic acid (vitamin C) and its esters, sugar derivatives of ascorbyl glucoside (as ascorbyl glucoside), tocopherol (vitamin E) and its esters (as tocopherol acetate) vitamins B3 or B10 (niacinamide and its derivatives); compounds showing a lightening or depigmenting action on the skin, such as ω-undecelynoyl phenylalanine sold under the name SEPIWHITE ™ MSH, SEPICALM ™ VG, mono-undecelynoylphenylalanine glycerol monoester and / or diester, ω-undecelynoyl dipeptides, arbutin, kojic acid, hydroquinone, the compounds showing a soothing action including SEPICALM ™ S, allantoin and bisabolol; anti-inflammatory agents; compounds showing an actionhydrating agent such as urea, hydroxyureas, glycerol, polyglycerols, glycerolglucoside, diglycerol glucoside, polyglyceryl glucosides, xylityl glucoside; plant extracts rich in polyphenols such as grape extracts, pine extracts, wine extracts, olive extracts; compounds showing a slimming or lipolytic action such as caffeine or its derivatives, ADIPOSLIM ™, ADIPOLESS ™, fucoxanthin; N-acylated proteins; N-acylated peptides such as MATRIXIL ™; N-acylated amino acids; partial hydrolysates of N-acylated proteins; the amino acids; peptides; total hydrolysts of protein; soy extracts, for example Raffermine ™; wheat extracts, for example TENSINE ™ or GILADINE ™; plant extracts, such as tannin-rich plant extracts, plant extracts rich in isoflavones or plant extracts rich in terpenes; extracts of freshwater or marine algae; marine plant extracts; marine extracts in general such as corals; essential waxes; bacterial extracts; ceramides; phospholipids; compounds exhibiting antimicrobial action or purifying action, such as LIPACIDE ™ C8G, LIPACIDE ™ UG, SEPICONTROL ™ A5; OCTOPIROX ™ or SENSIVA ™ SC50; compounds showing an energizing or stimulating property such as PHYSIOGENYL ™, panthenol and its derivatives such as SEPICAP ™ MP; anti-aging actives like SEPILIFT ™ DPHP, LIPACIDE ™ PVB, SEPIVINOL ™, SEPIVITAL ™, MANOLIVA ™, PHYTO-AGE ™, TIMECODE ™; SURVICODE ™; anti-aging photo active ingredients; the active ingredients protecting the integrity of the dermal-epidermal junction; actives enhancing the synthesis of extracellular matrix components such as collagen, elastins, glycosaminoglycans; assets acting favorably on chemical cell communication such as cytokines or physical ones such as integrins; actives creating a sensation of "heating" on the skin, such as cutaneous micro-circulation activators (such as nicotinic acid derivatives) or products that create a sensation of "freshness" on the skin (such as menthol and derivatives); the active ingredients improving the microcirculation of the skin, for example the venotonic ones; draining assets; decongestant assets such as extracts of ginko biloba, ivy, indian corn, bamboo, ruscus, small holly, centalla asiatica, fucus, deromarin, willow.

Examples of antioxidants that can be combined with the compound of Formula (I) or Composition (C1) include EDTA and its salts, citric acid, tartaric acid, oxalic acid , BHA (butylhydroxyanisol), BHT (butylhydroxytoluene), tocopherol derivatives such as tocopherol acetate, mixtures of antioxidant compounds such as DISSOLVINE ™ GL 47S sold by Akzo Nobel under the name INCI: Tetrasodium Glutamate Diacetate .

As examples of sunscreens that can be combined with the compound of formula (I) or with the composition (C1), mention may be made of all those appearing in the cosmetic directive76 / 768 / EEC modified as appendix VII. Among the solar organic filters which may be associated with the compound of formula (I) or with the composition (C1), mention may be made of the family of derivatives of benzoic acid such as para-aminobenzoic acids (PABA), in particular the esters of monoglycerol of PABA, the ethyl esters of N, N-propoxyPABA, the ethyl esters of Ν, Ν-diethoxy PABA, the ethyl esters of Ν, Ν-dimethylPABA, the methyl esters of Ν, Ν-dimethyl PABA, the butyl esters of Ν, Ν-dimethyl PABA; the family of anthranilic acid derivatives such as homomenthyl-N-acetyl anthranilate; the family of salicylic acid derivatives such as amyl salicylate, homomenthyl salicylate, ethylhexyl salicylate, phenyl salicylate, benzyl salicylate, p-isopropanolphenyl salicylate; the family of cinnamic acid derivatives such as ethylhexyl cinnamate, ethyl-4-isopropyl cinnamate, methyl-2,5-diisopropyl cinnamate, p-methoxypropyl cinnamate, p-methoxyisopropyl cinnamate, p-methoxyisoamyl cinnamate, p-methoxyoctyl cinnamate (p-methoxy 2-ethylhexyl cinnamate), p-methoxy 2-ethoxyethyl cinnamate, p-methoxycyclohexyl cinnamate, ethyl-a-cyano cinnamate -β-phenyl, 2-ethylhexyl-1-cyano-p-phenyl cinnamate, glycidyl mono-2-ethylhexanoyl diiparamethoxy cinnamate; the family of benzophenone derivatives such as 2,4-dihydroxybenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2 ', 4,4'-tetrahydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2 4-hydroxy-4-methoxy-4'-methylbenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonate, 4-phenylbenzophenone, 2-ethylhexyl-4'-phenylbenzophenone-2-carboxylate, 2-hydroxy-4 n-octyloxybenzophenone, 4-hydroxy-3-carboxybenzophenone; 3- (4'-methylbenzylidene) -d, 1-camphor, 3- (benzylidene) -d, 1-camphor, benzalkonium methosulfate camphor; urocanic acid, ethyl urocanate; the family of sulfonic acid derivatives such as sulfonic acid-2-phenylbenzimidazole-5 and its salts; the family of triazine derivatives such as hydroxyphenyl triazine, ethylhexyloxyhydroxyphenyl-4-methoxyphenyltriazine, 2,4,6-trianillino- (p-carbo-2'-ethylhexyl-1'-oxy) -1,3,5 triazine, 4,4 - ((6 - (((1,1-dimethylethyl) amino) carbonyl) phenyl) amino) -1,3,5-triazine-2,4-diyl diimino) bis- (2- ethylhexyl) benzoic acid ester, 2-phenyl-5-methylbenzoxazole, 2,2'-hydroxy-5-methylphenylbenzotriazole, 2- (2'-hydroxy-5'-t-octylphenyl) benzotriazole, 2- (2'-hydroxy-5'-methylphenyl) benzotriazole; dibenzazine; dianisoylmethane, 4-methoxy-4'-tert-butylbenzoylmethane, 5- (3,3-dimethyl-2-norbornylidene) -3-pentan-2-one, the family of diphenylacrylate derivatives such as 2-ethylhexyl-2 -cyano-3,3-diphenyl-2-propenoate, ethyl-2-cyano-3,3-diphenyl-2-propenoate, the family of polysiloxanes such as benzylidene malonate siloxane.

Among the inorganic solar filters, also called "inorganic screens", which can be associated with the compound of formula (I) or with the composition (C1), mention may be made of titanium oxides, zinc oxides, cerium oxide , zirconium oxide, iron oxides yellow, red or black, chromium oxides. These inorganic screens can be micronized or not, have undergone or not surface treatments and may bepresented in the form of aqueous or oily pre-dispersions. The subject of the invention is also a compound of formula (I) or a composition (C1) as defined above, for its use as a skin-brightening drug of human skin.

The following examples illustrate the invention without limiting it.

EXAMPLE 1 Preparation of a Composition (C1A) According to the Invention Comprising Compounds of Formulas (Ia) and (Ib)

500 grams of phenylalanine is introduced, one molar equivalent in a hydro-alcoholic mixture consisting of 1800 grams of water and 200 grams of isopropanol at a temperature of 20 ° C. The pH of the medium is adjusted to 10 by adding 30% sodium hydroxide solution. 393.8 grams of octanoyl chloride or 0.8 mol equivalents are then gradually added to the medium maintained between 20 ° C and 40; and at pH 10 and 10.5.

The reaction medium is then stirred for two hours and then heated to 70 ° C., then 413.5 grams of a 75% strength phosphoric acid solution are added to gradually reach a pH value of about 2%. 0. The aqueous phase of the medium is decanted and withdrawn and the organic phase remaining in the reactor is then washed several times with brine at 5% at room temperature with stirring. At the end and then drying by distillation under water, the organic phase comprising 641.5 g of N-octanoyl-phenylalanine desired.

An amount of 42.9 grams of glycerol is a molar equivalent of glycerol is introduced into the reactor comprising 135 grams of the dried reaction medium, obtained in the previous step in which there is 0.8 molar equivalent of N-octanoylphenyl alanine. The temperature is raised to 120 ° C., 0.38 grams of 98% sulfuric acid and 0.39 grams of 50% hypophosphorous acid are then added to the mixture and the resulting mixture is heated to a temperature of 125 ° C. a partial vacuum with nitrogen bubbling. The reaction mixture is then maintained for 11 hours under stirring and at this temperature, then neutralized by addition of a 30% sodium hydroxide solution so as to obtain a pH of the Composition (C1A), diluted to 5% in water, between 3.0 and 6.0.

The analytical characteristics of the composition (C1A) obtained are the following:

Acid value (according to NFT 60-204) = 12.2 μH 5% of the composition (C1A) in water (according to the method NFT 73-206) = 4.7 Hydroxyl value (according to US Pharmacopeia XXI NF XVI 01 / 011985) = 322.0 Ester number (calculated as the difference between the saponification number measured according to the method NFT 60-110 and the acid number measured according to the method NFT 60-204) = 147.7 saponification index ( according to NFT 60-206) = 159.9 mg KOH / g

Example 2 Preparation of a Composition (C1B) According to the Invention Comprising Compounds of Formulas (Ia) and (Ib)

The procedure is as in Example 1, replacing the 0.8 molar equivalent of octanoyl chloride with 0.8 equivalents (542.3 grams) of cocoyl chloride, which comprises 100% of its weight of 8% by weight of octanoyl chloride. 8% by weight of decanoyl chloride, 50% by weight of lauroyl chloride, 17% by weight of myristoyl chloride, 8% by weight of palmitoyl chloride, 3% by weight of stearoyl chloride, 4% by weight of oleoyl chloride (9-octadecenoyl) and 2% by weight of linoleoyl chloride (octadeca-9,12-dienoyl).

The analytical characteristics of the composition (C1B) are as follows: acid number (according to NFT 60-204) = 10.1 phr 5% of the composition (C1B) in water (according to the method NFT 73-206) = 5, 7Hydroxyl Index (US Pharmacopeia XXI NFXVI 01/011985) = 269.0 Ester Index (calculated as the difference between the saponification number measured according to NFT method 60-110 and the acid number measured according to the method NFT 60-204) = 125.3Saponification index (according to NFT 60-206) = 135.4 mg KOH / g

Example 3: Preparation of a comparative composition (D) comprising the products of the esterification reaction of N-hexadecanoyl phenylalanine and glycerol.

The procedure is as in Example 1, replacing the 0.8 molar equivalent of octanoyl chloride with 0.8 equivalent of hexadecanoyl chloride to obtain the Composition D, the analytical characteristics of which are as follows:

Acid value (according to NFT 60-204) = 12.4 pH 5% of composition D in water (according to the NFT 73-206 method) = 6.0

Hydroxyl number (according to U.S. Pharmacopeia XXI NF XVI 01/011985) = 230.1

Ester number (calculated as the difference between the saponification number measured by the NFT method 60-110 and the acid number measured by the NFT 60-204 method) = 112.9

Saponification number (according to NFT 60-206) = 125.3 mg KOH / g

Example 4: Preparation of a Comparative Composition (E) Comprising the Products of the Esterification Reaction of N-Undecylenoyl Phenylalanine and Glycerol

780 g of N-undecylenoyl phenylalanine, ie a molar equivalent, are introduced into a jacketed glass reactor, in which a heat transfer fluid is circulated, provided with efficient stirring, and a device for bubbling nitrogen through the reactor medium. at 125 ° C to allow the total melting of N-undecylenoyl phenylalanine. Subsequently, 218 g of glycerol, ie one molar equivalent, is introduced into N-undecylenoylphenylalanine at a temperature of about 120 ° C. The mixture thus prepared is maintained at 120 ° C. for 30 minutes, then supplemented with 2.2 g of 50% hypophosphorous acid and 2.2 g of 98% sulfuric acid and placed under a partial vacuum at 120 ° C. and left for 20 hours. with evacuation of the formed water. The reaction medium is then drained and obtains the composition (E) expected, whose analytical characteristics are as follows: Appearance at 20 ° C: cloudy liquid

Acid value (according to NFT 60-204) = 15.3 mg KOH / g

Hydroxyl number (according to U.S. Pharmacopeia XXI NF XVI 01/011985) = 278.3 mg KOH / gSaponification index (according to NFT 60-206) = 147.2 mg KOH / g

Iodine value (according to NFT 60-203) = 64g l2 / 100 g

Study of the lightening activity of the composition (C1) in B16 / F1 demanocyte cultures

Demonstration of the lightening activity was achieved by the implementation of a study model of the production of melanin on a line of melanocytesmurins B16 / F1. This test is commonly used in the field of cosmetics and pharmaceuticals.

The murine melanocytes of the B16 / F1 line grown in monolayers are seeded in 96-well culture plates at the density of 5000 cells / well. The cells are cultured in a culture medium (MCM medium) at 37 ° C., in a humid atmosphere containing 5% CO2. The MCM medium has the following composition: Medium DMEM (Dulbecco's Modified Eagle's Medium) containing 4.5 g / l of glucosadditioned L-Glutamine (2 mM), penicillin (50 IU / ml), streptomycin (50 μg / ml) ) and fetal calf serum (10% v / v). The products under study are tested at 10 μg / ml (0.001%) and at 50 μg / ml (0.005%) in MCM medium. The melanocyte cultures are incubated in the presence of the test product or reference products for 72 hours at 37 ° C in a humid atmosphere containing 5% CO 2. Control cultures are incubated, in the absence of product, in the MCM medium. These control cultures are carried out on each culture plate. Each test is performed three times (triplicate, n = 3).

Effects evaluation:

After 72 hours of incubation, cell incubation media (n = 3) are harvested and stored at -80 ° C until the effects are evaluated. The tapiscellulars are lysed in a solution of PBS (Phosphate Buffered Saline) using a sonic seal and intracellular melanin is evaluated in parallel with the amount of proteins. Melanin (extracellular and intracellular) is quantified by spectrophotometry at 450 nm. A melanin calibration range is made in parallel. The proteins are quantified using a BCA kit (Bicinchoninic Acid Assay) and expressed in mg / mL. The melanin results are expressed in μg / ml for melanintracellular and in μg / mg protein for intracellular melanin. A statistical analysis using the Student's test was performed to compare each condition with the control condition.

The results obtained are shown in Table 1 below:

Table 1: evaluation of the inhibition of the production of extracellular melanin compounds according to the invention and compounds of the state of the art.

The results indicated in Table 1 show a stronger inhibition of the production of extracellular melanin for the composition (C1A), comprising the products of the esterification reaction between glycerol and N-octanoylphenyl alanine, and of the composition. (C1B), comprising the products of the esterification reaction between glycerol and N-cocoyl phenyl alanine, compared with

compositions (D) and (E), comprising respectively glycerol and N-hexadecanoyl phenylalanine esters and esters of glycerol and N-undecylenoyl phenylalanine. It should be noted that the composition (E), which is different from the compositions (C1A) and (C1B) according to the invention that the length of the chain of the N-acyl group (16atoms of carbon), shows a performance d inhibition of the production of melanintracellular lower than the composition (E) of the state of the art, based on glycerol ester and N-undecylenoyl phenylalanine, described in the international publication WO2010 / 034917.

Examples of cosmetic formulations

In the following examples the proportions are expressed in percentagesponderal.

EXAMPLE 5 Emulsion-Lightening Care for Mature Skin MONTANOV ™ 202 02.00% MONTANOV ™ 68 02.00%

Caprylic Capric Triglycerides 10.00%

Squalane 10.00%

Water QSP 100%

Composition (A) 01.00% SEPIGEL ™ 305 00.70%

Magnesium Ascorbyl Phosphate 02.00% SEPICIDE ™ HB 00.30% SEPICIDE ™ Cl 00.20%

Perfume 0,50%

EXAMPLE 6 Emulsion-Lightening Firming Treatment MONTANOV ™ 202 03, 00%

Soda at 24% qs pH

Ethyl hexyl methoxycinnamate 06.00% LANOL ™ 1688 08.00%

Benzophenone-3 04.00%

Water QSP 100%

Composition (A) 02.00% SIMULGEL ™ NS 00.50% SEPILIFT ™ DPHP 00.50%

Dimethicone 02.00%

Cyclomethicone 02.00%

Arbutin 0.3% SEPICIDE ™ HB 00.30% SEPICIDE ™ Cl 00.20%

Perfume 00.10%

Example 7 Gel-cream lightening with alpha-hydroxyacids

Hydroxyethylcellulose 0.80%

Ethylhexyl octanoate 05.00%

Sodium lactate 60% 14.00%

Water QSP 100%

Composition (B) 03.00% SEPIGEL ™ 305 04.20% SEPICIDE ™ HB 02.00% SEPICIDE ™ Cl 03.00%

Perfume 00.10%

Example 8: Emulsion - Lightening care MONTANOV ™ L 01.00%

Cetyl alcohol 02.00%

Isodecyl neopentanoate 12.00%

Cetearyl octanoate 10.00%

Glycerin 03.00%

Water QSP 100%

Composition (A) 01.00% SIMULGEL ™ EG 02.00%

Kojic Acid 01.00% SEPICIDE ™ HB 00.30% SEPICIDE ™ Cl 00.20%

Perfume 00.10%

Example 9: Lightening Lotion ORAMIX ™ CG110 05.00% KATHON ™ CG 00.08%

Water QSP 100%

Composition (A) 01.00%

Perfume 00.10%

This lotion can be sold in bottles or impregnated on wipes.

The definitions of the commercial products used in the examples are the following: SEPILIFT ™ DPHP: (INCI name: Dipalmitoyl hydroxyproline), sold by the company SEPPIC; SEPICIDE ™ Cl: imidazoline urea (preservative) sold by the company ESPIC; SEPICIDE ™ HB: Mixture of phenoxyethanol, methylparaben, ethylparaben, propyl paraben and butylparaben (preservative) sold by the company ESPIC; KATHON ™ CG (INCI name: methyl isothiazolinone / methylchloroisothiazolinone); SIMULGEL ™ EG: self-invertible inverse copolymer latex such as those described in the international publication WO 99/36445 (INCI name: Sodium acrylate / Sodiumacryloyldimethyl taurate copolymer and Isohexadecane and Polysorbate 80) marketed by the company SEPPIC; SIMULGEL ™ NS: self-invertible inverse copolymer latex such as those described in the international publication WO 99/36445 (INCIhydroxyethylacrylate / Sodium acryloyldimethyltaurate copolymer and squalane and Polysorbate 60) marketed by the company SEPPIC; SEPIGEL ™ 305: Self-Invertible Inverse Latex (INCI Name: Polacrylamide / C13-14 Isoparaffin / Laureth-7); LANOL ™ 1688: cetearyl ethylhexanoate marketed by the company SEPPIC, MONTANOV ™ L: emulsifying agent based on C14-C22 alcohol and C12-C20 alkylpolyglucoside such as those described in the European patent application EP 0995 487; MONTANOV ™ 202 is an emulsifier based on arachidyl alcohol of alkenyl alcohol and arachidyl polyglucoside. Lanol ™ 1688 is cetearyl ethylhexanoatel marketed by the company SEPPIC. MONTANOV ™ 68 is an emulsifier based on cetearyl alcohol and cetearyl polyglucoside. ORAMIX ™ CG110 is a foaming agent based on octyl polyglucosides and decylpolyglucosides.

Bibliography: (1) Karleskind A., 1992. Manual of fatty substances, Lavoisier, Vol. 1 and 2: 65-78, 115-241, 1072-1089, 1433-1459.

Claims (5)

claims 1. Use of a compound of formula (I): R'-O-CH 2 -CH (OH) - [CH 2 -O-CH 2] s - [CH (OH)] p -CH 2 -OR "(I) (I) wherein s is 0 or 1 and p is 0, 1, 2 or 3 and R 'and R ", which are identical or different, represent either a hydrogen atom or a monovalent radical of formula ( II): wherein R1 (OO) is an acyl radical selected from octanoyl, decanoyl, dodecanoyl, tetradecanoyl and optionally hexadecanoyl, octadecanoyl, 9-octadecenoyl and octadeca-9,12-dienoyl, it being understood that in said formula ( I), at least one of the radicals R 'or R "does not represent a hydrogen atom and that when none of the radicals R' and R" is present at a hydrogen atom, R 'and R "are identical, or a mixture of compounds of formula (I), said use being for the purpose of lightening human skin and said use being in a cosmetic composition. 2. Use as defined in the claim, of a composition (C1) comprising for 100% of its mass: from 99% by mass to 20% by weight of at least one compound of formula (Ia): in which s is 0 or 1 and p is 0, 1, 2 or 3 and wherein R 'is a monovalent radical of formula (ii): formula (H) in which the group R 1 (C = O) represents an acyl radical chosen from among the radicals octanoyie, decanoyte, dodecanoyie, tetradecanoyl, hexadecanoyl, octadecanoyl, 9-octadecenoyl and octadeca-9,12-dienoyl; and from 1% by weight to 80% by weight of at least one compound of formula (Ib): formula (Ib) wherein s is 0 or 1 and p is 0, 1, 2 or 3, wherein R is a monovalent radical of formula (II): formula (II) in which the group R 1 (C = O) represents an acyl radical chosen from among the octanoyl, decanoye, dodecanoyl, tetradecanoyl, and optionally hexadecanoyl, octadecanoyl, 9-octadecenoyl and octadeca-9,12-dienoyl radicals. 3. Use as defined in any one of claims 1 or 2, wherein in the formula (l), s and p are equal to 0. 4. A process for the purpose of lightening human skin, comprising at least one step of applying to human skin, a topical cosmetic formulation comprising at least one cosmetically acceptable excipient and an effective amount of the compound of formula (I): formula (I) in which s is 0 or 1 and p is 0, 1, 2 or 3 and R 'and R ", which are identical or different, represent either a hydrogen atom or a monovalent radical of formula (II): formula (Ii) in which the group R1 (C = O) represents an acyl radical chosen from octanoyl, decanoyl radicals. dodecanoyl, tetradecanoyl, hexadecanoyl, octadecanoyl, 9-octadecenoyl and octadeca-9,12-dienoyl, or a decomposed mixture of formula (I), it being understood that in said formula (I), at least one of the radicals R 'or R "does not represent a hydrogen atom and when none of the radicals R 'and R" is hydrogen, R' and R "are the same. 5. A method for lightening human skin comprising at least one step of applying to the human skin a cosmetic topical formulation comprising at least one cosmetically acceptable excipient and an effective amount of the composition (C1) comprising at least 100 % of its mass: from 99% by weight to 20% by weight of at least one compound of formula (Ia): R'-O-CH 2 -CH (OHHCH 2 -O-CH 2) s- [CH (OH)] p -CH 2 -OH (la) wherein s is 0 or 1 and ρ is 0, 1, 2 or 3 and wherein R 'is a monovalent radical of formula (II): formula (II) in which the group R 1 (C = O) represents an acyl radical chosen from the radicals octanoyie, decanoyte, dodecanoyie, tetradecanoyl, hexadecanoyl, octadecanoyl, 9-octadecenoyl and octadeca-9,12-dienoyl; and from 1% by weight to 80% by weight of at least one compound of formula (Ib): formula (Ib) wherein s is 0 or 1 and p is 0, 1, 2 or 3, wherein R is a monovalent radical of formula (II): formula (II) in which the group R1 (C ~ O) represents an acyl radical selected from the radicals octanoyie, decanoyte, dodécanoyie, tetradecanoyl, and optionally the radicals hexadecanoyl, octadecanoyl, 9-octadecenoyl and octadeca-9,12-dienoyl.