FR3029104A1 - USE OF ESTERS OF ALPHA, OMEGA DIOLS AND N-ACYL DERIVATIVES OF AMINO ACIDS AS A BROWNING AND / OR TANNING AGENT OF HUMAN SKIN - Google Patents

Abstract

Use of a compound of formula (I): in which n is an integer greater than or equal to 3 and less than or equal to 12 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 a radical chosen from octanoyl, decanoyl, ω-undecylenoyl, dodecanoyl, tetradecanoyl, hexadecanoyl, octadecanoyl, 9- octadecenoyl or 9,12-octadecadienoyl and R2 represents a radical chosen from methyl, isopropyl, isobutyl and 1-methylpropyl radicals, and benzyl, it being understood that when the R1-C (= O) - group represents the ω-undecylenoyl radical; R2 represents neither the methyl radical nor the isobutyl radical, that 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" represents an atom of hydrogen, R 'and R "are identical, or a mixture of s of formula (I), or of a composition (C1) comprising: - from 99% by weight to 20% by weight of at least one compound of formula (Ia): formula (I) in which n is a higher integer or equal to 3 and less than or equal to 12 and R 'represents a monovalent radical of formula (II): from 1% by mass to 80% by weight of at least one compound of formula (Ib): formula (Ib) in which n is an integer greater than or equal to 3 and less than or equal to 12 and R represents either a hydrogen atom or a monovalent radical of formula (II), as defined above for the compound of formula (Ia); to brown and / or tan human skin or maintain natural hair pigmentation. New composition, cosmetic process and drug implementing them.

Description

The present invention relates to the use of esters of N-acyl derivatives of amino acids and α, β-alkanediol as a coloring agent for the skin of the human body, as well as non-therapeutic treatment methods. for tanning and / or browning the skin of the human body employing cosmetic compositions for topical use comprising said esters of N-acyl derivatives of amino acids and α, β-alkanediol. Human skin is the first image offered in the eyes of others, and therefore, 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. Thus, a tanned complexion and tanned skin are signs of good health and people are attaching more and more importance to this appearance of "good looks". The color of the skin results 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 quantities of melanins and carotenes present in human skin. Melanins are produced by specific epidermal cells: 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 come into contact with the surrounding keratinocytes, which can be up to two superior cell layers, to transmit the melanin grouped in melanosomes. Epidermal Unit of Melanization (EMU), the group of melanocytes and keratinocytes, interacting together to give color to the skin. An EMU comprises in particular a melanocyte and forty keratinocytes. The process of melanogenesis itself includes melanin synthesis by melanocytes, their transfer and distribution to neighboring keratinocytes. The color of the hair and hair is determined by the presence in proportions and in variable quantity of two types of melanins: the pheomelanines (red and yellow pigments) and the eumelanines (brown and black pigments). Hair pigmentation requires the presence of melanocytes in the bulb of the hair follicle which, when active, synthesize melanins. It is known in the literature that natural hair whitening, or canitie, is associated with decreased melanin in the hair follicle hair shaft. It has been proposed that the cause of this decrease could be related to a decrease in melanogenic activity by analogy to the pigmentation mechanism of the skin, but also to a melanin transfer deficiency or a decrease in the proportion of melanin. melanocytes in the bulb (3). Melanin synthesis 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. There are two main groups of melanins: eumelanins (brown or black) and phaeomelanines (yellow-orange). The maturation of melanosomes goes through four stages in order to be mature and able to be transferred to keratinocytes. During their maturation, melanosomes migrate to the end of the dendrites through a system of microtubules and microfilaments. The transfer between melanocytes and keratinocytes is done by a more or less detailed system of phagocytosis / endocytosis / pinocytosis, via in particular a PAR-2 membrane receptor. The pigmentation of the skin can either be constitutive or induced. The constitutive pigmentation 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. Indirect action on keratinocytes also comes into play to promote the process of melanogenesis by the secretion of soluble factors. An increase in the synthesis and / or activity of melanogenic enzymes allowing an increase in the amount of melanins produced by melanocytes, and more generally in the biogenesis of melanosomes, their transport and transfer to keratinocytes, will lead to their visible manifestation. know the coloring and / or natural browning of human skin. Natural tanning is not always recommended because it requires prolonged exposures to sunlight, and more particularly to ultra-violet radiation from the sun, and more particularly to UV-A and UV-B radiation from the sun that generates heat. browning of human skin, but which also cause unwanted reactions and alteration of human skin, especially for sensitive skin. Among these reactions and alterations, mention may be made of erythema, burning, the external signs of aging of the skin, such as, for example, alteration or loss of elasticity, lack of tone, lack of firmness, s 0071 the appearance or deepening of wrinkles or fine lines in human skin. The Ministry of Health and Social Protection, in collaboration with INPES and the Health Insurance, under the cancer plan, recently drafted recommendations on these exposures in order to limit the risk of developing skin cancers.

To combine tanned skin and unaltered skin, there are products for tanning and / or artificial browning of the skin, such as carbonyl-containing chemical substances which, by interaction with the amino acids of human skin, allow the formation of colored products on the surface of the skin. For example, mono- or polycarbonyl compounds such as dihydroxyacetone (DHA), erythrulose, mesotartaric aldehyde, glutaraldehyde, glyceraldehyde, alloxane, ninhydrin. DHA is the most commonly used self-tanning agent for the preparation of cosmetic compositions intended to brown and / or artificially tan human skin as it provides an external tanning or browning effect of human skin similar to the one that can result from exposure to sunlight. However, the DHA has disadvantages: its effectiveness is not universal, the color generated by its application to the skin depends on the type of skin, and the consumer may encounter problems of unevenness in the coloring obtained on the skin. DHA has the disadvantage of degrading over time, depending on the cosmetic medium in which it is formulated, partially oxidizing during storage, which manifests itself in the eventual appearance of a color yellowish or even orange of the cosmetic composition comprising it. To overcome the disadvantages of DHA as a self-tanning agent for human skin, the cosmetics industry has over the last twenty years deployed numerous solutions, in particular to combine DHA with other cosmetically acceptable ingredients. The European patent published under the number EP 0 425 324 B1, which discloses the combination of DHA with an indole derivative for coloring human skin in an intense and rapid manner over time, can be cited. In addition, academic studies have highlighted the possibility of long-term genotoxicity of DHA (1). To achieve a tanned skin, there are also specific technologies for exposure to ultraviolet radiation, such as cabins called "UV cabins", which are closed spaces in which the subject is subjected for a variable duration to radiation. UV-A (320400 nm). Their regular use is, however, harmful to human health. There are also chemical substances and compositions, more particularly plant or bacterial extracts, which are disclosed as a coloring agent for human skin. There may be mentioned the French patent application published under the number FR 2 973 697 A1 which discloses the use of a hydroglycolic extract of Tribulus terrestris and of chaulmoogra oil in cosmetic compositions for pigmenting the skin.

The use of plant extracts, bacteria, however, has the disadvantage of showing unreliable and non-repetitive performance over time due to the variability of the content of the raw materials used to obtain them. There are also synthetic active principles, for example peptides and polypeptides, which are described as coloring agents for human skin. The French patent application published under the number FR 2 970 968 A1 discloses the increase of the amount of melanin in biopsies of human skin, treated with peptide compounds. The French patent published under the number FR 2 913 685 B1 discloses the use, as agents for treating disorders of skin pigmentation, of unsaturated fatty amino acid derivatives of formula (A): NH 2 -CH 2 [CH (Rn)] - CH2 = CH (R1) -COOR (A) The French patent application published under the number FR 2 827 511 A1 discloses self-tanning compositions comprising self-tanning agents and N-acyl esters of amino acids of general formula (B): R'1- (C = O) -N (R'2) -CH (R'3) (CH2) n (C = O) OR'4 (B) French patent application published under the number FR 2 827 511 A1 specifically discloses self-tanning compositions comprising self-tanning agents and isopropyl N-lauroyl sarcosinate, and the use of the compounds of formula (B) for to improve the stability and the coloration of the compositions comprising a self-tanning agent. Japanese Patent Application No. 2000-229121 describes the use of N-acylamino acid-based polyols as high performance surfactants. The international publication VVO 201/0034917 discloses the mono-esters and di-esters of polyols of N- (w-undecylenoyl) phenylalanine, and more particularly the mono-esters and diesters resulting from the reaction of glycerol and N - (w-undecylenoyl) phenylalanine, and their uses as lightening agents of human skin.

In the context of their search for new active agents intended to color and / or brown the skin of the human body, the inventors have endeavored to develop a new technical solution based on the use of products resulting from the esterification reaction between a α,--alkanediol and N-acyl derivatives of amino acids. This is why, in a first aspect, the subject of the invention is the use of a compound of formula (I): ## STR2 ## I) wherein n is an integer greater than or equal to 3 and less than or equal to 12 and R 'and R ", which are identical or different, represent either a hydrogen atom or a monovalent radical of formula (II): Wherein R1-C (= O) - represents a radical selected from octanoyl, decanoyl, w-undecylenoyl, dodecanoyl, tetradecanoyl, hexadecanoyl, octadecanoyl, 9 octadecenoyl or 9,12-octadecadienoyl and R2 is a radical selected from methyl, isopropyl, isobutyl, 1-methylpropyl, and benzyl; it being understood that when the group R 1 -C (= O) - represents the radical w-undecylenoyl, R2 represents neither the methyl radical nor the isobutyl radical, that at least one of the radicals R 'or R "does not represent a a hydrogen atom and when none of the radicals R 'and R "represents a hydrogen atom, R' and R" are identical, or a mixture of compounds of formula (I), said use being in the purpose of browning and / or tanning human skin and / or maintaining the natural pigmentation of hair and / or hair, and / or limiting and / or stopping the development of canities in humans, and said use being in a cosmetic composition.

By "browning and / or tanning of human skin" is meant, in the sense of the invention, a modification of the external appearance of the skin resulting in the appearance and development of a brown color, more or less intense, from the surface of human skin. According to a first particular aspect, the subject of the invention is the use as defined above, of a composition (Cl) comprising for 100% of its mass: from 99% by weight to 20% by mass, plus particularly from 99% by weight to 50% by mass, and even more particularly from 95% to 75% by weight of at least one compound of formula (Ia): R'-O- [CH 2] -OH (la) formula (I) in which n is an integer greater than or equal to 3 and less than or equal to 12 and R 'represents a monovalent radical of formula (II): ## STR5 ## wherein R1-C (= O) - represents a radical chosen from the octanoyl, decanoyl, w-undecylenoyl, dodecanoyl, tetradecanoyl, hexadecanoyl, octadecanoyl, 9-octadecenoyl or 9,12-octadecadienoyl radicals and R2 represents a radical selected from the group consisting of methyl, isopropyl, isobutyl, 1-methylpropyl and benzyl radicals; it being understood that when the group R 1 -C (= O) - represents the radical w-undecylenoyl, R2 represents neither the methyl radical nor the isobutyl radical; From 1 wt% to 80 wt%, more particularly from 1 wt% to 50 wt%, and even more particularly from 5 wt% to 25 wt% of at least one compound of formula (Ib): R-O- [ CH2] -OR (Ib) wherein n is an integer greater than or equal to 3 and less than or equal to 12 and R represents either a hydrogen atom or a monovalent radical of formula (II), such as as defined above for the compound of formula (Ia).

According to a more particular aspect, the subject of the invention is the use as defined above, for which, in the formula (II), when the group R 1 -C (= O) - represents the radical w-undecylenoyl, R2 represents the isopropyl radical or the 1-methylpropyl radical, when the R1-C (= O) - represents the octanoyl radical, R2 represents the 1-methylpropyl radical or the benzyl radical.

According to another particular aspect, the subject of the invention is the use as defined above, for which, in the formulas (I), (Ia) and (Ib), n represents an integer greater than or equal to 3 and less than or equal to 8. According to this particular aspect, when n represents an integer equal to 8, the compounds of formulas (I), (Ia) and (Ib) are 1,8-octanediol esters.

According to this particular aspect, when n represents an integer equal to 6, the compounds of formulas (I), (Ia) and (Ib) are 1,6-hexanediol esters. According to this particular aspect, when n represents an integer equal to 4, the compounds of formulas (I), (Ia) and (Ib) are 1,4-butanediol esters. According to this particular aspect, when n represents an integer equal to 3, the compounds of formulas (I), (Ia) and (Ib) are 1,3-propanediol esters. In a more particular aspect, the subject of the invention is the use as defined above, which in formulas (I), (Ia) and (Ib), n is an integer equal to 3. Examples of compounds of formula (I) or mixtures of compounds of formula (I) used in the context of the present invention are the following: - 3-hydroxypropyl N- (w-undecylenoyl) valinate, 3-hydroxypropyl N-octanoyl phenylalaninate, 3-hydroxypropyl N-octanoyl isoleucinate, 3-hydroxypropyl N- (w-undecylenoyl) isoleucinate, 3-hydroxy N-cocoyl valinate propyl.

Examples of compositions (C1) used in the context of the present invention are those in which: the compound of formula (Ia) is 3-hydroxypropyl N- (w-undecylenoyl) valinate and the compound of formula (Ib) 1,3-propanediyl bis [N- (--undecylenoyl) valinate]; The compound of formula (Ia) is 3-hydroxypropyl N-octanoyl phenylalaninate and the compound of formula (1b), 1,3-propanediyl bis [N-octanoyl phenylalaninate]; The compound of formula (Ia) is 3-hydroxypropyl N-octanoyl isoleucinate and the compound of formula (1b), 1,3-propanediyl bis [N-octanoyl isoleucinate]; The compound of formula (Ia) is 3-hydroxypropyl N- (w-undecylenoyl) isoleucinate and the compound of formula (1b), 1,3-propanediyl bis [N- (w-undecylenoyl) isoleucinate] ; or alternatively - The compound of formula (Ia) is 3-hydroxypropyl N-cocoyl valinate and the compound of formula (1b), 1,3-propanediyl bis (N-cocoyl valinate). By N-cocoyl valine is meant the mixture of N-acyl derivatives of valine, obtained by reaction of valine the mixture of fatty acid chloride derived from coconut oil comprising 100 mol%, about 11 mol% octanoyl chloride, about 9.5 mol% decanoyl chloride, about 51 mol% lauroyl chloride, about 15.5 mol% myristoyl chloride, about 6.5 mole percent palmitoyl chloride, about 2 mole percent stearoyl chloride, about 3 mole percent oleolyl chloride, and about 1.5 mole percent linoleoyl chloride.

The compound of formula (I) as defined above may be prepared according to a preparation process comprising: - a step a) of esterification of a compound of formula (IV): Si 0071 8 0 R1 N 0 with a compound of formula (V): H-O- [CH 2], -O-H (V), wherein (n) is an integer greater than or equal to 3 and less than or equal to 12, in the appropriate molar proportions for obtaining either the compound of formula (Ia), 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 if desired, - a step b) of separating the compounds of formula (Ia) and formula (Ib), from said mixture (M) obtained in step (a).

The compounds of formulas (IV) 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 molar ratio of compound of formula (IV) to 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 separation methods known to those skilled in the art. The compound of formula (I) as defined above may also be prepared according to a preparation method comprising: - a step a1) of esterification of a compound of formula (IV) ## STR2 ## with an alcohol of formula (VI): R 5 -OH (VI), in which R 5 represents a linear aliphatic radical containing from 1 to 4 carbon atoms, to form a compound of formula (VII): ## STR1 ## A step a2) of trans-esterification of the compound of formula (VII) obtained in step a1), by reaction with the compound of formula (V), to obtain either the compound of formula (Ia) or compound of formula (Ib), that is a mixture (M) of the compound of formula (Ia) and the compound of formula (Ib); and if necessary or if 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, trifluoromethanesulfonic acid, or acidic ion exchange resins. In step a1) of the variant of the process as described above, the molar ratio of compound of formula (IV) to 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 (VII) obtained in step a1) is generally carried out at a temperature of 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 inert gas, and in the presence of a system catalytic acid as described above, and with vacuum distillation of the alcohol of formula (VI) formed insitu.Dans step a2) of this variant of the process for preparing the compounds of formula (I) as described above , the compound molar ratio of formula (Vila) 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 (C1) 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 (C1) consists in 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 for preparing the composition (Cl) consists of carrying out 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 layer of formula (IV) or a mixture of compounds of formula (IV). A third route of preparation of the composition (Cl) consists in carrying out 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 (VII) or a mixture of compounds of formula (VII). The subject of the invention is also a composition (Cl ') comprising for 100% of its mass: from 99% by weight to 20% by weight of at least one compound of formula (a): R'-O- [ CH2], -O-H (a), formula (a) in which n represents an integer greater than or equal to 3 and less than or equal to 12, more particularly an integer greater than or equal to 3 and lower or equal to 8, especially greater than or equal to 3 and less than or equal to 6, for example greater than or equal to 3 and less than or equal to 4 and R 'represents a monovalent radical of formula (II "): O R2 R1 / Wherein R1-C (= O) - represents an acyl radical selected from octanoyl, decanoyl, dodecanoyl, tetradecanoyl and optionally hexadecanoyl, octadecanoyl, 9-octadecenoyl radicals. and octadeca-9,12-dienoyl, and R2 is the isopropyl radical: 1% by weight to 80% by weight of at least one compound of formula (11D): R-O- [CH2] In which n represents an integer greater than or equal to 3 and less than or equal to 12, and R represents a monovalent radical of formula (II ") as defined above for the formula (a): said composition (Cl ') being obtained by the process comprising the following steps: s1 0071 - A step A of acylation of valine with a mixture of acid chlorides comprising for 100 mol% from 40 mol% to 60 mol% of dodecanoyl chloride, from 10 mol% to 20 mol% of tetradecanoyl chloride, from 5 mol% to 15 mol% of decanoyl chloride, and from 5 mol% to 15 mol% of octanoyl chloride, and optionally up to 100 mol%, hexadecanoyl chloride and / or octadecanoyl chloride and / or 9-octadecenoyl chloride and / or octadecahloride chloride. 9,12-dienoyl, to obtain a mixture of compounds of formula (IV '): ## STR2 ## rification of the mixture of compounds of formula (IV ') obtained in step A, with the diol of formula (V): H-O- [CH2] -O-H (V) formula (V) in which n represents a an integer greater than or equal to 3 and less than or equal to 12, in the appropriate molar proportions. The subject of the invention is also a composition (Cl ') as defined above, obtained by a variant of the process comprising: - an esterification step A1, of the mixture of compounds of formula (IV') obtained in step A, with an alcohol of formula (VI): R 5 -OH (VI), in which R 5 represents a linear aliphatic radical containing from 1 to 4 carbon atoms, to form a mixture of compounds of formula (VII ') : CH C1-13 0 CH R1 NH'e1 / 4:) R5 0 (VIII and - A step B1 of trans-esterification of the mixture of compounds of formula (VII ') obtained in stage Al), with the diol of formula (V) in the appropriate proportions. According to a more particular aspect of the present invention, the composition (Cl ') as defined above is characterized in that the mixture of acid chloride used in step A of the process for obtaining it comprises for 100% 45 mol% to 55 mol% of dodecanoyl chloride, from 10 mol% to 20 mol% of tetradecanoyl chloride, from 5 mol% to 10 mol% of decanoyl chloride, and from 5 mol% to 15 mol%. mol% of octanoyl chloride, from 5 mol% to 10 mol% hexadecanoyl chloride and from 5 mol% to 10 mol% octadecanoyl chloride and / or 9-octadecenoyl chloride and / or 'octadeca-9,12-diènoyle. According to another particular aspect the composition (Cl ') as defined above is caracterized in that, in the formulas (a) or (I'b), n is equal to 3. The invention also relates to a process for the preparation of the composition (Cl ') as defined in any one of claims 5 to 7, comprising the following steps: a step A of acylation of leucine with a mixture of acid chlorides comprising, for 100 mol%, from 40 mol% to 60 mol% of dodecanoyl chloride, from 10 mol% to 20 mol% of tetradecanoyl chloride, from 5 mol% to 15 mol% of decanoyl chloride, and 5 mol% 15% molar octanoyl chloride, and optionally up to 100% molar, hexadecanoyl chloride and / or octadecanoyl chloride and / or 9-octadecenoyl chloride and / or octadeca-9,12-dienoyl, to obtain a mixture of compounds of formula (IV '): ## STR1 ## An esterification step B of the mixture of compounds of formula (IV ') obtained in step A, with the diol of formula (V): 1-1-04C1-12], - 0-11 ( V) formula (V) wherein n represents an integer greater than or equal to 3 and less than or equal to 12, in the appropriate molar proportions; as well as the variant of the process as defined above, comprising: - an esterification step A1, of the mixture of compounds of formula (IV ') obtained in step A, with an alcohol of formula (VI): R5 -OH (VI), formula (VI) wherein R5 represents a linear aliphatic radical having 1 to 4 carbon atoms, to form a mixture of compounds of formula (VII '): Si 0071 CH C1-13 0 CH R1 NH R5 0 (VIII and - A step B1 of trans-esterification of the mixture of compounds of formula (VII ') obtained in step A1), with the diol of formula (V) in the appropriate proportions, to obtain said composition (C1 ').

The compound of formula (I), the composition (C1) and the composition (C1 ') as defined above can be administered orally, topically or parenterally, and more particularly topically. As will be shown in the experimental part of the present patent application, the compound of formula (I), the composition (C1) and the composition (C1 ') as defined above make it possible to increase the production of melanin by melanocytes. This is why the invention also relates to a method for the purpose of browning and / or tanning the human skin and / or to maintain the natural pigmentation of the hair and / or the hair, and / or to limit and / or or to stop the development of canitia in humans, comprising at least one step A of application to human skin or hair or hair, a cosmetic formulation for topical use comprising at least one cosmetically acceptable excipient and an effective amount of at least one compound of formula (I), composition (C1) or composition (C1 ') as defined above.

The expression "for topical use" used in the definition of the cosmetic formulation used in step A) of the cosmetic process that is the subject of the present invention means that said formulation is implemented by application to the skin, that it is a direct application in the case of a cosmetic formulation or an indirect application when the cosmetic formulation according to the invention is impregnated on a support intended to be placed in contact with the skin (paper, wipe, textile, transdermal device, etc ...). The expression "cosmetically acceptable" used in the definition of the cosmetic formulation for topical use, used in step A) of the cosmetic process that is the subject of the present invention, means according to the directive of the Council of the European Economic Community No. 76/768 / EEC of 27 July 1976 as amended by Regulation (EEC) No 93/35 / EEC of 14 June 1993, that the said wording for topical use includes any substance or preparation intended to be placed in contact with the various parts of the body. human (epidermis, hair and hair system, nails, lips and genitals) or with oral teeth and mucous membranes with a view, exclusively and mainly, to clean, perfume, modify the appearance and / or to correct body odor and / or to protect or maintain them in good condition. By effective amount of the compound of formula (I), of the composition (Cl) or of the composition (Cl ') as defined above, is meant for 100% of the mass of said cosmetic formulation for topical use, the amount between 0.1% and 5% by weight, more particularly between 0.1% and 3% by mass, and even more particularly between 0.5% and 2% by weight of compound of formula (I), of composition (Cl) or of composition (Cl '). In a particular aspect, the method as defined above further comprises a step B of exposure to sunlight or ultraviolet radiation generated by an artificial light device, said human skin or said hair. or bristles having undergone said step A. Among artificial light devices capable of generating ultraviolet radiation and can be used in step B) of the cosmetic tanning or browning process of the human skin that is the subject of the present invention. For example, ultraviolet lamps, consisting of one or more fluorescent lamps emitting ultraviolet radiation, of which 95% are ultraviolet-A radiation (wavelength of 400 to 315 nanometers) and 5% are ultraviolet-B radiation (wavelength 315 to 280 nanometers) (with a margin of error of ± 3%).

Advantageously, the cosmetic process as defined above, makes it possible to obtain a tan or a browning of the skin treated after a short period, characterized by a greater intensity of the coloration and a prolonged duration of persistence after the end of step B), and by a protective effect against characteristic histological alterations of sunburn or against the consequences of abusive exposures to ultraviolet radiation. Cosmetic processes of the canitie intended to maintain the natural pigmentation of the hair and / or hair as described above, may consist of an application of the cosmetic formulations used on the surface to be treated followed by a rinsing step with water. 'water. These methods may also consist of the application of the cosmetic formulations used on the surfaces to be treated, followed by storage on the treated surface overnight and then followed by a rinsing step in the morning. These methods may also consist of a preliminary step of washing the zones to be treated by a separate cleaning formulation of the surface to be treated (such as, for example, a shampoo), followed by an application step on said surface to be treated with a formulation. topical application comprising an effective amount of at least one compound of formula (I) of a composition (Cl) or (Cl '), as defined above, followed by a rinsing step. The cosmetic formulations for topical use used in stage A) of the cosmetic process which is the subject of the present invention are generally in the form of aqueous or hydro-alcoholic or hydro-glycolic solutions, in the form of a suspension, of an emulsion, a microemulsion or a nanoemulsion, whether of the water-in-oil, oil-in-water, water-in-oil-in-water or oil-in-water-in-oil type or in the form of a powder.

The topical cosmetic formulations used in the cosmetic process which is the subject of the present invention may be packaged in a bottle, in a device of the 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 provided with a ball applicator (called "roll-on").

In general, the compound of formula (I) or the compositions (Cl) or (Cl '), present in the topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, is associated with chemical additives usually used in the field of formulations for topical use, such as foaming and / or detergent surfactants, thickening and / or gelling surfactants, thickening and / or gelling agents, stabilizing agents, film-forming compounds, solvents and co-polymers. solvents, hydrotropic agents, thermal or mineral waters, plasticizers, emulsifiers and co-emulsifiers, opacifying agents, pearlescent agents, superfatting agents, sequestering agents, chelating agents, oils, waxes, antioxidants, fragrances, essential oils, preservatives, conditioners, deodorants, bleaching agents ants intended for hair and skin discoloration, active principles intended to provide a treating and / or protective action against the skin or hair, sunscreens, mineral fillers or pigments, particles providing a visual effect or s1 0071 for encapsulation of actives, exfoliating particles, texture agents, optical brighteners, repellents for insects. Examples of foaming and / or detergent surfactants which can be combined with the compound of formula (I) or compositions (Cl) or (Cl ') in topical cosmetic formulations used in the cosmetic process object of the present invention, there may be mentioned foaming surfactants and / or anionic, cationic, amphoteric or nonionic detergents. Among the foaming and / or detergent anionic surfactants which can be combined with the compound of formula (I) or with the compositions (Cl) or (Cl '), in the cosmetic formulations for topical use used in the cosmetic process The subject of the present invention is the alkali metal, alkaline earth metal, ammonium, amine or aminoalcohol salts of alkyl ether sulfates, alkyl sulphates, alkyl amido ether sulphates, alkylaryl polyether sulphates, sulphate monoglycerides, alpha-olefin sulphonates, paraffin sulfonates, alkyl phosphates, alkyl ether phosphates, alkyl sulphonates, alkyl amide sulphonates, alkyl aryl sulphonates, alkyl carboxylates, alkyl sulphosuccinates, alkyl ether sulphosuccinates, alkyl amide sulphosuccinates, alkylsulfoacetates, alkylsarcosinates, acylisethionates, N-acyltaurates, acyllactylates, N-acyl derivatives of amino acids, N-acyl derivatives of peptides, N-acyl derivatives of protein s, N-acyl derivatives of fatty acids.

Among the foaming and / or detergent amphoteric surfactants which can be combined with the compound of formula (I) or with the compositions (Cl) or (Cl '), in the cosmetic formulations for topical use used in the cosmetic process The object of the present invention is alkylbetaines, alkylamidobetaines, sultaines, alkylamidoalkylsulfobetaines, imidazoline derivatives, phosphobetaines, amphopolyacetates and amphopropionates. Among the foaming and / or detergent cationic surfactants that can be combined with the compound of formula (I) or with the compositions (Cl) or (Cl '), in the cosmetic formulations for topical use implemented in the cosmetic process object of the present invention, there may be mentioned particularly quaternary ammonium derivatives. Among the foaming and / or detergent nonionic surfactants that can be combined with the compound of formula (I) or with the compositions (Cl) or (Cl '), in the cosmetic formulations for topical use used in the cosmetic process object of the present invention, there may be mentioned more particularly alkylpolyglycosides s1 0071 comprising a linear or branched, 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 which can be combined with the compound of formula (I) or with compositions (Cl) or (Cl ') in cosmetic formulations for topical use used in the cosmetic process object of the present invention include fatty esters of alkylpolyglycosides optionally alkoxylated, such as ethoxylated methylpolyglucoside esters such as PEG 120 methyl glucose trioleate and PEG 120 methyl glucose dioleate respectively marketed under the names GLUCAMATETm LT and GLUMATETm DOE120; fatty alcohols such as PEG 150 pentaerythrityl tetrastearate sold 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 dicarbamate marketed under the name ELFACOSTM T211, PPG-14 palmeth-60 hexyl dicarbamate sold under the name ELFACOSTM GT2125. As examples of thickening and / or gelling agents that can be combined with the compound of formula (I) or compositions (Cl) or (Cl '), in the cosmetic formulations for topical use used in the cosmetic process object of the present invention, mention may be made of polyelectrolytes polymers, linear or branched or crosslinked, such as homopolymer of partially or totally salified acrylic acid, homopolymer of partially or totally salified methacrylic acid, homopolymer partially or completely salified acid-2-methyl-[(1-oxo-2-propenyl) amino] -1-propanesulfonic acid (AMPS), copolymers of acrylic acid and AMPS, copolymers of acrylamide and AMPS, copolymers of vinylpyrolidone and AMPS, copolymers of AMPS and (2-hydroxyethyl) acrylate, copolymers of AMPS and methacrylate of 2-hydroxyethyl), copolymers of AMPS and hydroxyethylac copolymers of AMPS and N, N-dimethylacrylamide, the copolymers of AMPS and tri, oxy-aminoylmethyl methacrylate (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 N, N-dimethyl acrylamide, terpolymers of acrylic or methacrylic acid, AMPS and acrylate; (2-hydroxyethyl), 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-dimethyl acrylamide, terpolymers of acrylic or methacrylic acid, AMPS and acrylamide, copolymers of acrylic acid or methacrylic acid and alkyl acrylates having a carbon chain of between four and four; thirty carbon atoms and more particularly between ten and thirty carbon atoms, copolymers of AMPS and alkyl acrylates whose carbon chain comprises between four and thirty carbon atoms and more particularly between ten and thirty carbon atoms the linear, branched or crosslinked terpolymer of at least one monomer having a strong, free, partially salified or totally salified acid function, with at least one neutral monomer, and at least one monomer of formula (VIII): CH 2 = C ( R7) -C (= O) - [CH2-CH2-OH-R8 (VIII) in which R7 represents a hydrogen atom or a methyl radical, R8 represents a linear or branched alkyl radical containing from eight to thirty carbon atoms and n represents a name greater than or equal to one and less than or equal to fifty. Polymers of polyelectrolytic type, linear or branched or crosslinked that can be associated with the compound of formula (I) or compositions (Cl) or (Cl '), in cosmetic formulations for topical use implemented in the cosmetic process of the present invention may be in the form of a solution, an aqueous suspension, a water-in-oil emulsion, an oil-in-water emulsion, a powder. Polymers of polyelectrolytic type, linear or branched or crosslinked that can be associated with the compound of formula (I) or compositions (Cl) or (Cl '), in cosmetic formulations for topical use implemented in the cosmetic process of the present invention, may be selected from the products marketed under the names SIMULGELTm EG, SIMULGELTmEPG, SEPIGELTM 305, SIMULGELTm 600, SIMULGELTm NS, SIMULGELTm INS 100, SIMULGELTm FL, SIMULGELTm A, SIMULGELTm SMS 88, SEPINOVTmEMT 10 , SEPIPLUSTm400, SEPIPLUSTm265, SEPI- s1 0071 PLUSTmS, SEPIMAXTmZen, ARISTOFLEXTmAVC, ARISTOFLEXTmAVS, NOVEMERTmEC1, NOVEMERTmEC 2 ARISTOFLEXTmHMB, COSMEDIATmSP, FLOCARETmET 25 FLOCARETmET 75, FLOCARETmET 26 FLOCARETmET 30 FLOCARETmET 58, FLOCARETmPSD 30 VISCOLAMTmAT 64, VISCOLAMTmAT 100.

As examples of thickening and / or gelling agents that can be combined with the compound of formula (I) or compositions (Cl) or (Cl '), in the cosmetic formulations for topical use used in the cosmetic process object of the present invention, mention may be made of polysaccharides consisting solely of monosaccharides, such as glu-canes or homopolymers of glucose, glucomannoglucans, xyloglycans, and lactamannans 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 cassia gum (DS = 1/5), locust bean gum (DS = 1/4), tara gum (DS = 1/3), guar gum (DS = 1/2), fenugreek gum (DS = 1).

As examples of thickening and / or gelling agents that can be combined with the compound of formula (I) or compositions (Cl) or (Cl '), in the cosmetic formulations for topical use used in the cosmetic process object of the present invention, mention may be made of polysaccharides consisting of monosaccharides, such as sulphated galactans and more particularly carrageenans and agar, uronans and more particularly alginines, 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 agents and / or gelling agents that can be combined with the compound of formula (I) or compositions (Cl) or (Cl '), in the cosmetic formulations for topical use implemented in the process cosmetic object of the present invention, mention may be made of cellulose, cellulose derivatives such as methylcellulose, ethylcellulose, hydroxypropylcellulose, silicates, starch, hydrophilic derivatives of starch, polyurethanes. As examples of stabilizing agents which can be combined with the compound of formula (I) or compositions (Cl) or (Cl '), in the topical cosmetic formulations used in the cosmetic process object of the the present invention include microcrystalline waxes, and more particularly ozokerite, inorganic salts such as sodium chloride or magnesium chloride, silicone polymers such as polysiloxane polyalkyl polyether copolymers. Examples of solvents which can be combined with the compound of formula (I) or with compositions (Cl) or (Cl '), in topical cosmetic formulations used in the cosmetic process which is the subject of the present invention. mention may be made of water, organic solvents such as glycerol, diglycerol, glycerol oligomers, ethylene glycol, propylene glycol, butylene glycol, 1,3-propanediol, 1,2-propanediol, hexylene glycol, diethylene glycol, xylitol, 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 compositions (Cl) or (Cl ') in topical cosmetic formulations used in the cosmetic process object of the present invention, mention may be made of thermal or mineral waters having a mineralization of at least 300 mg / l, in particular Avene water, Vittel water, Vichy basin water, water Uriage, the water of the Roche Posay, the water of the Bourboule, the water of Enghien-les-bains, the water of Saint-Gervais-the baths, the water of Néris-les-bains , Allevard-les-Bains water, Digne water, Maizieres water, Neyrac-les-bains water, Lons le Saunier water, Rochefort water, water of Saint Christau, the water of Fumades and the water of Tercis-les-bains. As examples of hydrotropic agents that can be combined with the compound of formula (I) or with compositions (Cl) or (Cl ') in topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, mention may be made of xylenesulfonates, cumenesulfonates, hexylpolyglucoside, 2-ethylhexylpolyglucoside and n-heptylpolyglucoside. Examples of emulsifying surfactants that can be combined with the compound of formula (I) or compositions (Cl) or (Cl '), in cosmetic formulations for topical use used in the cosmetic process object of the present invention may include nonionic surfactants, anionic surfactants, cationic surfactants. Examples of emulsifying nonionic surfactants which can be combined with the compound of formula (I) or compositions (Cl) or (Cl ') in cosmetic formulations for topical use used in the cosmetic process object of the present invention, mention may be made of esters of fatty acids and of sorbitol, such as the products sold under the names MONTANET ™ 40, MONTANET ™ 60, MONTANET ™ 70, MONTANET ™ 80 and MONTANET ™ 85; compositions comprising glycerol stearate and ethoxylated stearic acid between 5 moles and 150 moles of ethylene oxide, such as the composition comprising stearic acid ethoxylated with 135 moles of ethylene oxide and stearate glycerol marketed under the name SIMULSOL ™ 165; mannitan esters; ethoxylated mannitan esters; sucrose esters; methylglucoside esters; alkylpolyglycosides having a saturated or unsaturated, linear or branched, aliphatic radical having from 14 to 36 carbon atoms, such as tetradecyl polyglucoside, hexadecyl polyglucoside, octadecylpolyglucoside, hexadecylpolyxyloside, octadecylpolyxyloside, eicosyl polyglucoside, dodecosyl polyglucoside, 2-octyldodecyl polyxyloside, 12-hydroxystearyl polyglucoside; linear or branched fatty alcohol compositions, saturated or unsaturated, and comprising from 14 to 36 carbon atoms, and alkylpolyglycosides as described previously, such as, for example, the compositions sold under the tradename MONTANOVTm68, MONTANOVTm82, MONTANOVTm14, MONTANOVTm202, MONTANOVTmS, MONTANOVTmVVO 18, FLUIDANOVTm2OX and EASYNOVTM. As examples of anionic surfactants which can be combined with the compound of formula (I) or with compositions (Cl) or (Cl ') in the topical cosmetic formulations used in the cosmetic process which is the subject of the present invention, it is possible to mention may be made of glyceryl stearate citrate, cetearyl sulphate, soaps such as sodium stearate or triethanolammonium stearate, N-acyl derivatives of salified amino acids, for example stearoyl glutamate.

As examples of emulsifying cationic surfactants which can be combined with the compound of formula (I) or with compositions (Cl) or (Cl ') in topical cosmetic formulations used in the cosmetic process which is the subject of the present invention, mention may be made of the aminoxides, the quaternium-82 and the surfactants described in the international application published under the number VVO 96/00719 and mainly those whose fatty chain comprises at least 16 carbon atoms. Examples of opacifying and / or pearling agents which can be combined with the compound of formula (I) or with compositions (Cl) or (Cl ') in topical cosmetic formulations used in the cosmetic process which is the subject of the present invention may be mentioned sodium palmitate, sodium stearate, sodium hydroxystearate, magnesium palmitate, magnesium stearate, magnesium hydroxystearate, ethylene glycol monostearate, distearate. ethylene glycol, 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 compositions (Cl) or (Cl ') in cosmetic formulations for topical use implemented in the cosmetic process object of the the present invention includes N-acylated amino acid derivatives, such as lauroyl lysine marketed under the name AMINOHOPETmLL, octenyl starch succinate marketed under the name DRYFLOTM, myristyl polyglucoside marketed under the name MONTANOVTm 14, cellulose fibers, cotton fibers, chitosan fibers, talc, sericite, mica. As examples of deodorant agents that can be combined with the compound of formula (I) or with compositions (Cl) or (Cl ') in topical cosmetic formulations used in the cosmetic process that is the subject of the present invention, there may be mentioned alkali silicates, zinc salts such as zinc sulfate, zinc gluconate, zinc chloride, zinc lactate; quaternary ammonium salts such as cetyltrimethylammonium salts, cetylpyridinium salts; glycerol derivatives such as glycerol caprate, glycerol caprylate, polyglycerol caprate; 1,2 decanediol; 1,3 propanediol; salicylic acid; sodium bicarbonate; cyclodextrins; metallic zeolites; TRICLOSANTm; aluminum bromohydrate, aluminum chlorohydrates, aluminum chloride, aluminum sulphate, aluminum and zirconium hydrochlorides, aluminum and zirconium trihydrochloride, aluminum zirconium tetrachlorohydrate , aluminum and zirconium pentachlorohydrate, aluminum and zirconium octochlorhydrate, aluminum sulphate, sodium and aluminum lactate, aluminum and glycol hydrochloride complexes, as well as propylene glycol aluminum dihydrochloride complex, aluminum and propylene glycol sesquichlorohydrate complex, polyethylene glycol aluminum aluminum and polyethylene glycol, the complex of aluminum sesquichlorohydrate and polyethylene glycol. As examples of oils which can be combined with the compound of formula (I) or with the compositions (Cl) or (Cl ') in the topical cosmetic formulations used in the cosmetic process which is the subject of the present invention, it is possible to mention may be made of mineral oils such as liquid paraffin, petroleum jelly, isoparaffins or mineral white oils; oils of animal origin, such as squalene or squalane, vegetable oils, such as phytosqualane, sweet almond oil, coconut oil, castor oil, jojoba, olive oil, rapeseed oil, peanut oil, sunflower oil, wheat germ oil, corn germ oil, soybean oil, cottonseed oil, alfalfa oil, poppy oil, pumpkin oil, evening primrose oil, millet oil, barley oil, rye oil, safflower oil, bancoulin oil, passionflower oil, hazelnut oil, palm oil, shea butter, shell oil, oil of calophyllum, 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 myristate, propyl myristate, isopropyl myristate, cetyl myristate, isopropyl palmitate, octyl palmitate, butyl stearate, hexadecyl stearate, isopropyl stearate, octyl stearate, isocetyl stearate, dodecyl oleate, hexyl laurate, propylene glycol dicaprylate, esters derived from lanolic 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 such as isohexadecane, isododecane, perfluorinated oils; silicone oils such as dimethylpolysiloxanes, methylphenylpolysiloxanes, amine-modified silicones, fatty acid-modified silicones, alcohols-modified silicones, alcohol-modified silicones and fatty acids, modified silicones, polyether groups, modified epoxy silicones, silicones modified with fluorinated groups, cyclic silicones and silicones modified with alkyl groups. By "oils" is meant herein the compounds and / or the mixtures of water-insoluble compounds having a liquid appearance at a temperature of 25 ° C.

As examples of waxes that can be combined with the compound of formula (I) or with compositions (Cl) or (Cl ') in the topical cosmetic formulations used in the cosmetic process which is the subject of the present invention, it is possible to beeswax, camauba wax, candelilla wax, ouricoury wax, Japan wax, cork fiber wax, sugar cane wax, paraffin waxes, lignite, microcrystalline waxes, lanolin wax; ozokerite; polyethylene wax; silicone waxes; vegetable waxes; fatty alcohols and solid fatty acids at room temperature; glycerides solid at room temperature. By "waxes" is meant in the present application the compounds and / or mixtures of compounds insoluble in water, 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 compositions (C1) or (C1 ') in topical cosmetic formulations used in the cosmetic process which is the subject of the present invention. mention may be made of vitamins and their derivatives, in particular their esters, such as retinol (vitamin A) and its esters (retinyl palmitate, for example), ascorbic acid (vitamin C) and its esters, the derivatives of ascorbic acid sugar (such as ascorbyl glucoside), tocopherol (vitamin E) and its esters (such as tocopherol acetate), vitamins B3 or B10 (niacinamide and its derivatives); compounds showing a lightening or depigmenting action of the skin, such as w-undecelynoyl phenylalanine marketed under the name SEPIVVHITETmMSH, SEPICALMTmVG, the mono ester and / or the glycerol diester of w-undecelynoyl phenylalanine, the w-undecelynoyl dipeptides, l arbutin, kojic acid, hydroquinone; the compounds showing a soothing action, especially SEPICALM ™ S, allantoin and bisabolol; anti-inflammatory agents; compounds showing a moisturizing action such as urea, hydroxyureas, glycerol, polyglycerols, glycerolglucoside, diglycerolglucoside, polyglycerylglucosides, xylityl-plucoside; 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 ™, ADIPOLES ™, fucoxanthin; N-acylated proteins; N-acylated peptides such as MATRIXIL ™; N-acyl amino acids; partial hydrolyzers of N-acyl proteins; amino acids; peptides; total hydrolysts of protein; soy extracts, for example Raffermine TM; wheat extracts, for example TENSINETm or GLIADINETM; plant extracts, such as tannin-rich plant extracts, plant extracts rich in isoflavones or plant extracts rich in terpenes; freshwater algae 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 LIPACIDETM C8G, LIPACIDETM UG, SEPICONTROL ™ A5; OCTOPIROXTm or SENSIVATM SC50; compounds showing an energizing or stimulating property such as PHYSIOGENYL ™, panthenol and its derivatives such as SEPICAP ™ MP; anti-aging actives like SEPILIFTTm DPHP, LIPAdDETM PVB, SEPIVINOLTM, SEPIVITALTm, MANOLIVATM, PHYTO-AGETm, TIMECODETm; SURVICODETM; anti-aging photo active ingredients; the active ingredients protecting the integrity of the dermal-epidermal junction; the active agents enhancing S1 0071 synthesis of extracellular matrix components such as collagen, elastins, glycosaminoglycans; assets acting favorably on chemical cellular communication such as cytokines or physical ones such as integrins; actives that create a sensation of "heating" on the skin, such as cutaneous microcirculation activators (such as nicotinic acid derivatives) or products that create a sensation of "coolness" on the skin (such as menthol and derivatives); the active agents improving cutaneous microcirculation, for example the venotonic ones; draining assets; decongestant active ingredients such as extracts of ginko biloba, ivy, horse chestnut, bamboo, ruscus, holly, centalla asiatica, fucus, rosemary, willow; agents for tanning or browning the skin, such as, for example, dihydroxyacetone (DHA), erythrulose, mesotartaric aldehyde, glutaraldehyde, glyceraldehyde, alloxane, ninhydrin, plant extracts, for example the red wood extracts of the genus Pterocarpus and of the genus Baphia such as Pteropcarpus santalinus, Pterocarpus osun, Pterocarpus soyauxii, Pterocarpus erinaceus, Pterocarpus indi- CuS or Baphia nitida, such as those described in the European patent application EP 0 971 683; ; the agents known for their action of facilitating and / or accelerating the tanning and / or browning of human skin, and / or for their action of coloring human skin, such as, for example, caratenoids (and more particularly beta carotene and gamma carotene), the product marketed under the tradename "Carrot oil" (INCI name: Daucus Carota, helianthus annuus sunflower oil) by Provital, which contains carotenoids, vitamin E and vitamin K ; tyrosine and / or its derivatives, known for their effect on the tanning acceleration of human skin in association with exposure to ultraviolet radiation, such as for example the product marketed under the brand name "SunTan AcceleratorTM" by the Provital company which contains tyrosine and riboflavins (vitamin B), the tyrosine and tyrosinase complex marketed under the trademark "Zymo Tan Complex" by Zymo Line, the product marketed under the brand name MelanoBronze TM ( INCI name: Acetyl Tyrosine, Monk's pepper extract (Vitex Agnus-castus)) by the company Mibelle which contains acetyl tyrosine, product sold under the brand name Unipertan VEG-24/242/2002 (INCI name: butylene glycol and Acetyl Tyrosine and Hydrolyzed Vegetable Protein and Adenosine Triphosphate) by the company UNIPEX, the product marketed under the brand name "Try-ExcellTm" (INCI name: Oleoyl Tyrosine and Luffa Cylindr ica (Seed) Oil and Oleic acid) by Sederma Company which contains extracts of pumpkin seed (or Loofah oil), the product sold under the name s1 0071 trademark "ActibronzeTM" (INCI name: hydrolyzed wheat protein and acetyl tyrosine and copper gluconate) by the company Alban Muller, the product sold under the brand name TyrostanTm (INCI name: potassium caproyl tyrosine) by Synerga, the product sold under the trade name Tyrosinol (INCI name: Sorbitan Isostearate, glyceryl oleate, caproyl Tyrosine) by the company Synerga, the product sold under the brand name lnstaBronzeTM (INCI name: Dihydroxyacetone and acetyl tyrosine and copper gluconate) marketed by Alban Muller, the product sold under the trade name Tyrosilane (INCI name : methylsilanol and acetyl tyrosine) by Exymol; peptides known for their effect of activating melanogenesis, for example the product marketed under the brand name Bronzing SF Peptide Powder (INCI name: Dextran and Octapeptide-5) by the company Infinitec Activos, the product marketed under the name brand name Melitane (INCI name: Glycerin and Aqua and Dextran and Acetyl hexapeptide-1) including acetyl hexapeptide-1 known for its alpha-MSH agonist action, the product marketed under the brand name Melits SolutionsTM (INCI name: Butylene glycol, Palmitoyl Tripeptide-40) by LI-POTEC, sugars and sugar derivatives such as for example the product sold under the brand name TanositolTm (INCI name: inositol) by the company Provital, the product sold under the trademark Thalitan TM (or PhycosaccharideTM AG) by CODIF International (INCI name: Aqua and hydrolyzed algin (Laminaria Digitata) and magnesium sulfate and manganese sulfate) a oligosaccharide of marine origin (guluronic acid and mannuronic acid chelated with magnesium and manganese ions), the product sold under the trade name Melactiva TM (INCI name: Maltodextrin, Mucuna Pruriens Seed extract) by Alban Muller, compounds rich in flavonoids, for example the product marketed under the trade name BioTanning (INCI name: Hydrolyzed citrus Aurantium dulcis fruit extract) by the company Silab and known to be rich in flavonoids of lemon (of the hesperidin type). As examples of antioxidants that can be combined with the compound of formula (I) or compositions (Cl) or (Cl ') in cosmetic formulations for topical use implemented in the cosmetic process object of the present invention, mention may be made of EDTA and its salts, citric acid, tartaric acid, oxalic acid, BHA (butylhydroxyanisole), BHT (butylhydroxytoluene), tocopherol derivatives such as tocopherol acetate, mixtures of antioxidant compounds such as DISSOLVINETM GL 47S marketed by Akzo Nobel under the name INCI: Tetrasodium Glutamate Diacetate. Examples of sunscreens that can be combined with the compound of formula (1) or with compositions (Cl) or (Cl ') in topical cosmetic formulations used in the cosmetic process which is the subject of the present invention all those listed in the Cosmetic Directive 76/768 / EEC as amended Annex VII.

Among the solar organic filters which can be combined with the compound of formula (1) or with the compositions (Cl) or (Cl ') in the topical cosmetic formulations used in the cosmetic process which is the subject of the present invention, it is possible to mention may be made of the family of benzoic acid derivatives such as para-aminobenzoic acids (PABA), in particular the monoglycerol esters of PABA, the ethyl esters of N, N-propoxy PABA and the ethyl esters of N, N-diethoxy PABA ethyl esters of N, N-dimethyl PABA, methyl esters of N, N-dimethyl PABA, butyl esters of N, N-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 and p-methoxyisopropyl cinnamate; p-methoxyisoamyl cinnamate, pmethoxyoctyl cinnamate (p-methoxy-2-ethylhexyl cinnamate), p-methoxy-2-ethoxyethyl cinnamate, p-methoxycyclohexyl cinnamate, ethyl-a-cyano cinnamate Phenyl, 2-ethylhexyl-ia-cyano-6-phenyl cinnamate, glyceryl diparamethoxy mono-2-ethylhexanoyl 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-hydroxy-4-methoxy-4'-methylbenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonate, 4-phenylbenzophenone, 2-ethylhexyl-4'-phenylbenzophenone-2-carboxylate, 2-hydroxy-2-hydroxybenzophenone, 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) benzoic acid ethyl ester, 2-phenyl-5-methylbenzoxazole, 2,2'-s-hydroxy-5-methylphenylbenzotriazole, 2- (2'-hydroxy-5'-t-octylphenyl) benzotriazole 2- (2'-hydroxy-5'-methylphenyl) benzotriazole; dibenzazine; dianisoylmethane, 4-methoxy-4 "-t-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 combined with the compound of formula (1) or with compositions (Cl) or (Cl ') in topical cosmetic formulations used in the cosmetic process which is the subject of the present invention, mention may be made of titanium oxides, zinc oxides, cerium oxide, zirconium oxide, yellow, red or black iron oxides, chromium oxides These inorganic screens may or may not be micronised. undergoes or not surface treatments and may be presented in the form of aqueous or oily pre-dispersions.

The subject of the invention is also the compound of formula, the composition (C1) or the composition (Cl ') as defined above, for their use in a therapeutic treatment method intended to stimulate the production of melanins to prevent and / or treat diseases of human skin and / or hair or hair. The following examples illustrate the invention without limiting it.

EXAMPLE 1 Preparation of a Composition (C18) According to the Invention 400.5 grams of valine is introduced, ie one molar equivalent in a mixture of hydroalcoholic consisting of 1439.8 grams of water and 160.0 grams of water. isopropanol at a temperature of 20 ° C. The pH of the medium is adjusted to 10 by addition of a 30% sodium hydroxide solution. 555.5 grams of undecylenoyl chloride, ie 0.8 molar equivalents, are then gradually added to the mixture maintained between 20 ° C. and 40 ° C., and at a pH of between 10 and 10.5. The reaction medium is then stirred for two hours and then heated to 70 ° C, then added 994.3 grams of a 75% phosphoric acid acid solution 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 washed several times with 10% brine at 80 ° C. with stirring. After washing and then drying by distillation of the residual water under vacuum, the organic phase comprising 758.2 grams of desired N-undecylenoyl valine is obtained. 33.7 grams of 1,3-propanedioll, ie one molar equivalent, are introduced into the reactor comprising 125.4 grams of the dried reaction medium obtained in the preceding step. The temperature is raised to 120 ° C. 0.37 grams of 98% sulfuric acid and 0.39 grams of 50% hypophosphorous acid are then added and the resulting mixture is brought to a temperature of 125 ° C. under partial vacuum with bubbling. 'nitrogen. The reaction mixture is then maintained for 24 hours with stirring 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 number (according to NFT 60-204) = 38.6 pH 5% of the composition (C1A) in water (according to the method NFT 73-206) = 5.7 Hydroxyl number (according to US Pharmacopeia XXI NF XVI 01/011985) = 189.7 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) = 135.1 Saponification number (according to NFT 60-206) = 173.7 mg KOH / g. EXAMPLE 2: E aration of a Composition C1B According to the Invention The procedure of the process described in Example 1 is carried out by replacing the molar equivalent of valine with one molar equivalent of phenylalanine and replacing the 0.8 molar equivalent of undecylenoyl chloride per 0.8 molar equivalents of octanoyl chloride, to obtain the composition (C1B), the analytical characteristics of which are as follows: acid number (according to NFT 60-204) = 8.1 pH 5% of the composition (C1B) in water (according to the method NFT 73-206) = 5.1 Hydroxyl number (according to US Pharmacopeia XXI NF XVI 01/011985) = 152.9 Ester number ( calculated by 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) = 152.3 Saponification index (according to NFT 60-206) = 160.4 mg KOH / g.

EXAMPLE 3 Preparation of a Composition (Cl) According to the Invention The procedure of the process described in Example 1 is carried out by replacing the molar equivalent of valine with one molar equivalent of isoleucine and replacing the 0.8 molar equivalent of undecylenoyl chloride with 0.8 molar equivalents of octanoyl chloride, to obtain the composition (C10), the analytical characteristics of which are as follows: Acid value (according to NFT 60-204) = 52 4 pH 5% of the composition (C1 c) in water (according to the method NFT 73-206) = 4.3 Hydroxyl number (according to US Pharmacopeia XXI NF XVI 01/011985) = 112.5 Index d ester (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) = 161.8 saponification number (according to NFT 60 -206) = 214.2 mg KOH / g.

Example 4: CID Compression According to the Invention The procedure of the method described in Example 1 is carried out by replacing the molar equivalent of valine with one molar equivalent of isoleucine to obtain the composition. (CID) whose analytical characteristics are as follows: Acid value (according to NFT 60-204) = 38.5 pH 5% of the composition (CID) in water (according to the NFT 73-206 method) = 6.1 Hydroxyl number (according to US Pharmacopeia XXI NF XVI 01/011985) = 193.5 Ester number (calculated as the difference between the saponification number measured according to the method NFT 60-110 and the index of acid measured according to the method NFT 60-204) = 134.8 Saponification number (according to NFT 60-206) = 173.3 mg KOH / g. EXAMPLE 5 Preparation of a Composition (CIE) According to the Invention The procedure of the process described in Example 1 is carried out by replacing the 0.8 molar equivalent of undecylenoyl chloride by 0.8 equivalents. mole of cocoyl chloride, comprising, for 100% of its mass, 8% by weight of octanoyl chloride, 8% by weight of decanoyl chloride, 50% by weight of lauroyl chloride, 17% by mass of myristoyl chloride, 8% by mass 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), to obtain the composition (CI E ) whose analytical characteristics are as follows: Acid value (according to NFT 60-204) = 29.3 pH 5% of the composition (CIE) in water (according to the NFT 73-206 method) = 5.6 d Hydroxyl (according to US Pharmacopeia XXI NF XVI 01/011985) = 163.1% ester ester (calculated by the difference between e the saponification number measured according to the NFT 60-110 method and the acid number measured according to the NFT 60-204 method) = 139.8 Saponification number (according to NFT 60-206) = 169.1 mg KOH /boy Wut.

Example 6 (comparative): preparation of a composition (A) comprising the mono- ester of N- (3-undecylenoyl) leucine and 1,3-propanediol and the di-ester of N- (wundecylenoyl) leucine and of 1 , 3-propanediol. The procedure of the method described in Example 1 is carried out by replacing the molar equivalent of valine with a molar equivalent of leucine to obtain the composition (A), the analytical characteristics of which are as follows: Acidic index (according to NFT 60-204) = 14.5 pH 5% of the composition (A) in water (according to the method NFT 73-206) = 6.5 Hydroxyl number (according to US Pharmacopeia XXI NF XVI 01/011985) = 164.6 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) = 148.8 Index saponification (according to NFT 60-206) = 163.3 mg KOH / g. Example 7 (comparative): preparation of a composition (B) comprising the N- (--undecylenoyl) alanine mono-ester and 1,3-propanediol and the N- (--undecylenoyl) alanine di-ester and 1,3-propanediol. The procedure of the method described in Example 1 is carried out by replacing the molar equivalent of valine with one molar equivalent of alanine to obtain the composition (B), the analytical characteristics of which are as follows: NFT 60-204) = 12.5 pH 5% of the composition (B) in water (according to the method NFT 73-206) = 4.8 Hydroxyl number (according to US Pharmacopeia XXI NF XVI 01/011985) = 188.3 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) = 177.7 Index saponification (according to NFT 60-206) = 190.2 mg KOH / g.

Demonstration of the human skin staining activity of the compounds and compositions according to the invention by a study of the production of melanin on a line of murine melanocytes B16 / F1 s1 0071 The demonstration of the activity staining was performed by the implementation of a study model of the production of melanin on a line of murine melanocytes B16 / F1. This test is commonly used in the cosmetics and pharmaceutical sector.

Protocol: B16F1 murine melanocytes were amplified in T75 culture flask, then seeded at 5000 cells / well in 96-well culture plates in a specific culture medium, at 37 ° C. in a humid atmosphere containing 5% CO 2. After 24 hours of plaque amplification, the cells were treated with the compositions according to the invention or culture medium alone (control) and then incubated for 72 hours at 37 ° C. under 5% CO 2. Each condition has been realized in triplicate. Evaluation of the effects: After the incubation, the supernatants were recovered and the melanin secreted by the cells in the (extracellular) culture medium was quantified by spectrophotometric measurement at 450 nm of these culture supernatants, against a standard range of melanin. The results were expressed in μg of melanin / ml of culture medium. The cell mats were lysed in PBS using a sonication rod and 2 evaluations were performed on these: Evaluation of the amount of melanin by spectrophotometric measurement at 450 nm of the lysates against a standard range of melanin; Evaluation of the amount of protein by assay according to the method of Bradford. The results of melanin production by (intracellular) cells were expressed relative to the amount of protein present in the carpets. Thus the final result is given as μg of melanin per mg of protein. Statistical analysis using the Student's test was performed to compare each condition with the control condition. The results obtained are recorded in the following Table 1: Table 1 Products tested Intracellular melanin (μg / mg of proteins) Culture control 88 +/- 3 Composition (C1A) (50 μg / ml) 123 +/- 8 Composition (CIE ) (10 μg / ml) 102 +/- 1 Composition (CI E) (50 μg / ml) 110 +/- 5 s1 0071 Composition (C1B) (10 μg / ml) 116 +/- 8 Composition (Cl o) (10 μg / ml) 110 +/- 5 Composition (Cl D) (10 μg / ml) 115 +/- 7 Composition (B) (10 μg / ml) 90 +/- 7 Composition (A) (10 μg / ml) ml) 71 +/- 2 Compared to controls, the use of compositions (C1A), (C1B), (C10), (CID) and (CIE) induce an increase in the production of intracellular melanin at the dose of 10 μg / ml or 50 μg / ml, while the composition (A) induces a decrease thereof and that the composition (B) induces no significant change. Bibliography (1): Petersen et al., "Dihydroxyacetone, the active browning ingredient in sunless tanning lotions, DNA damage digests, cell-cycle block and apoptosis in cultured HaCaT keratinocytes", 2004, Mutat Res, Jun 13; 560 (2) : 173-86. Examples of cosmetic formulations In the following examples, the proportions are expressed in percentages by weight.

Non-greasy tanning machine for face and body LANOLTM 2681: 3.0% SEPIMAXTmZen: 2.5% Water: q.s. 100% Composition (C1B): 1.0% Perfume: 0.2% SEPICIDETM HB: 0.8% Soda: q.s. pH = 5 Bronzing emulsion without sun LANOLTM 99: 15% MONTANOVTm 68: 5.0% PARSOLTM MCX: 3.0% Water: qsp100 ° / 0 Composition (CIA) 3.0% Monosodium phosphate: 0.2% s1 0071 SEPIMAXTm Zen: 0.5% Perfume: 0.3% SEPICIDETM HB: 0.8% Soda: qs pH = 5.

Pressed clay powder SIMULGELTmEG: 2.00% LANOLTM 99: 12.00% Composition (C1B): 1.00% Talc: 33.00% MICROPEARLTM M310: 3.00% Iron oxide yellow: 0.80% Oxide red iron: 0.30% Black iron oxide: 0.05% Mica: qs 100% self-tanning gel SIMULGELTmEG: 5.0% Ethanol: 30% Composition (CIA) 5% Menthol: 0.1% Caffeine: 2.5% Ivry extract: 2% SEPICIDETm HB: 1% Water: q.s. 100% Sunblock and self-tanning gel MONTANOVTm 5: 3.0% Glyceryl triheptanoate: 10.0% LIPACIDETM PVB: 1.05% SIMULGELTmEG: 2.2% Water: q.s. 100% Composition (Cl 5% Fragrance: 0.1% SEPICIDETM HB: 0.3% SEPICIDETM Cl: 0.1% PARSOLTM MCX: 4.0% Si 0071 Self-tanning cream with α-hydroxy acids MONTANOVTm 68: 5.0% LIPACIDETM PVB: 1.05% LANOLTM 99: 10.0% Water: qs 100% Gluconic acid: 1.5% Composition (C1B): 3% Triethanolamine: 0.9% SEPIMAXTmZen: 1.5% Fragrance: 0.4 % SEPICIDETM HB: 0,2% SEPICIDETM Cl: 0,4% Self-tanning cream with a-hydroxy acids for sensitive skin Mixture of N-lauroyl amino acids: 0,1% to 5% Aspartate of magnesium and potassium: 0,002% at 0 , 5% MONTANOVTm 68: 5.0% LANOLTM 99: 2.0% Water: qs 100% Lactic acid: 1.5% Composition (CID) 3.5% Triethanolamine: 0.9% SIMULGELTmINS 100: 1.5% Fragrance: 0.4% SEPICIDETM HB: 0.3% SEPICIDETM Cl: 0.2% SIMULSOLTm 165 self-tanning moisturizing emulsion: 5.0% LANOLTM 1688: 8.5% Galam butter: 2% Liquid paraffin: 6 , 5% LANOLTM 14M: 3% LANOLTM S: 0.6% Water: 66.2% Composition (Clc) 3% s1 0071 MICROPEARLTM M100: SIMULGELTmNS: AQUAXYL TM Acetate tamine E: Sodium pyrolidinonecarboxylate: Fragrance: SEPICIDETM HB: SEPICIDETM CI: Satin self-tanning moisturizing emulsion A Water Disodium EDTA Sodium Benzoate Soda (12%) 5% 3% 5% 0.20% 0.20% 0.2% 0.5% 0.3% Up to 100% 0.10% 0.30% 0.07% B MONTANOVTm L 1.00% SIMULSOLTm 165 2.00% LANOLTM P 2.00% Caprylic / Capric Triglyceride 5.00% Neopentyl Glycol 8.00% Dimethicone 1.00% Composition (C1B) 1.00% C SEPIMAXTm ZEN 1.50% SOLAGUM TM AX 0.50% D Phenoxyethanol and Ethylhexylglycerin 1.00% Suncare lotion - SPF15 A Aqua / VVater SOLAGUM TM AX TriEthanolAmine (99%) B SENSANOVTm VVR MONTANOVTm S C12-15 Alkyl Benzoate Ethylhexylmethoxycinnamate and BHT Butylmethoxydibenzoylmethane Up to 100% 0.50% 0.40% 3.00% 1.00% 10.00% 5.00% 2.50% s1 0071 C Cyclopentasiloxane and cyclohexasiloxane 2.50% D AQUAXYL TM 3.00% Phenoxyethanol and Ethylhexylglycerin 1.00% Composition (C1B) 1.00% Fragrance / Fragrance 0.10% Lactic Acid (25%) 0.09 % Activator Sun Cream Gel with DHA A Aqua / VVater Qs 100% B SIMULG ELTm SMS 88 3.00% C12-15 Alkyl Benzoate 10.00% Dimethicone 5.00% C Glycerin 3.00% Monopropylene Glycol 2.00% Phenoxyethanol and Ethylhexylglycerin 1.00% Tocopherol 0.05% D Aqua / VVater 40.00% Dihydroxyacetone 3.00% E Composition (C1B) 1.00% Perfume / Fragrance 0.10% Citric acid Qs pH Body lotion after solar A Water Up to 100 ° A SEPIMAXTm ZEN 0.50% B AQUAXYL TM 2.00% SEPICALMTm S VVP 1.00% C Butylene Glycol 3.00% SEPICLEARTM G7 1.30% Fragrance / Fragrance 0.03% Phenoxyethanol and Ethylhexyl Glycerin 0.80 % Composition (C1B) 1.00% The commercial products used in the examples are defined as follows: s1 0071 - LANOLTM 2681 is a caprylate mixture, copra caprate, marketed by the company SEPPIC; SEPIMAXTmZen (INCI name: polyacrylate crosspolymer-6) is a thickening, emulsifying and stabilizing agent; LANOL ™ 99 is isononyl isononanoate marketed by the company SEPPIC; MONTANOV-68 (cetearyl glucoside), is a self-emulsifiable composition as described in VVO 92/06778, sold by the company SEPPIC; SEPICIDETM HB (INCI name: Phenoxyethanol / Methylparaben / Ethylparaben / Propylparaban / Butylparaben) is a preserving agent marketed by the company SEPPIC; PARSOL ™ MCX is octyl para-methoxy cinnamate; marketed by GIVAUDAN; MICROPEARL ™ M310 is an ultra fine powder with a very soft feel and a mattifying action marketed by MATSUMO; SIMULGELTmEG (INCI name: sodium acryloyldimethyltaurate / sodium acrylate, and isohexadecane and polysorbate 80) is a thickening, emulsifying and stabilizing agent marketed by the company SEPPIC; MONTANOV ™ S is a pearlescent agent marketed by the company SEPPIC, based on a mixture of alkyl polyglucosides such as those described in VVO 95/13863; LIPACIDETM PVB, is a hydrolysate of acyl wheat proteins marketed by the company SEPPIC; SEPICIDETM C1, imidazolidine urea, is a preserving agent marketed by the company SEPPIC; SIMULGELTMINS 100 (INCI name: sodium acryloyldimethyltaurate / hydroxy ethyl acrylate, and isohexadecane and polysorbate 60) is a thickening, emulsifying and stabilizing agent marketed by the company SEPPIC; SIMULSOL ™ 165 is self-emulsifiable glycerol stearate marketed by the company SEPPIC; - LANOLTM 1688 is an emollient non-fat ester marketed by the company SEPPIC - LANOLTM 14M and LANOLTM S are consistency factors marketed by the company SEPPIC; - SIMULGELTmNS (INCI name: sodium acryloyldimethyltaurate / hydroxy ethyl acrylate, and squalane and polysorbate 60) is a thickening, emulsifying and stabilizing agent marketed by the company SEPPIC; Si 0071 - AQUAXYLTM (INCI name: Xylitylglucoside and Anhydroxylitol and Xylitol): Moisturizing composition marketed by the company SEPPIC; MONTANOV ™ L (INCI name: C14-22 Alkyl Alcohol C12-20 Alkyl Glucoside) is an emulsifying composition marketed by the company SEPPIC; LANOL ™ P is an emollient ester of palmitic acid and ethylene glycol; SOLAGUMTm AX is a mixture of acacia gum and xanthan gum used as an emulsifier; SENSANOV ™ VVR (INCI name: C20-22 Alkyl Phosphate & C20-22 Alcohols) is an anionic surfactant mixture sold by the company SEPPIC; SIMULGEL ™ SMS 88 (INCI name: Sodium acrylate / Acryloyldimethyl tau- rate / Dimethylacrylamide crosspolymer & Isohexadecane & Polysorbate 60) is a thickening and emulsifying agent marketed by the company SEPPIC; SEPICALMTM S VVP (INCI name: Sodium Cocoyl Amino Acids & Sarcosine & Potassium Aspartate & Magnesium) is a soothing agent marketed by the company SEPPIC; SEPICLEARTM G7 (INCI name: heptyl glucoside) is a solubilizing agent marketed by the company SEPPIC.

Claims (14)

CLAIMS1 Use of a compound of formula (I): R'-O- [CH2] -OR "(I), formula (I) in which n is an integer greater than or equal to 3 and less than or equal to 12 and R 'and R ", which may be identical or different, represent either a hydrogen atom or a monovalent radical of formula (II): ## STR3 ## in which formula R1-C (= 0) - represents a radical chosen from the octanoyl, decanoyl, w-undecylenoyl, dodecanoyl, tetradecanoyl, hexadecanoyl, octadecanoyl, 9-octadecenoyl or 9,12-octadecadienoyl radicals and R2 represents a radical chosen from methyl radicals, isopropyl, isobutyl, 1-methylpropyl, and benzyl, it being understood that when the group R1-C (= O) - represents the w-undecylenoyl radical, R2 represents neither the methyl radical nor the isobutyl radical, 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 an atom of h ydrogen, R 'and R "are identical, or a mixture of compounds of formula (I); said use being for the purpose of browning and / or tanning the human skin and / or maintaining the natural pigmentation of the hair and / or hair, and / or limiting and / or stopping the development of the canitie at the human being, and said use being in a cosmetic composition. 2. Use as defined in claim 1, of a composition (Cl) comprising for 100% of its mass: from 99% by weight to 20% by weight of at least one compound of formula (Ia): R'- 0- [CH2] -OH (la) formula (I) wherein n is an integer greater than or equal to 3 and less than or equal to 12 and R 'represents a monovalent radical of formula (II): ## STR2 ## Wherein R1-C (= O) - represents a radical selected from octanoyl, decanoyl, w-undecylenoyl, dodecanoyl, tetradecanoyl, hexadecanoyl, octadecanoyl, 9-octadecenoyl or 9,12- octadecadienoyl and R2 represents a radical selected from methyl, isopropyl, isobutyl, 1-methylpropyl and benzyl radicals; it being understood that when the group R 1 -C (= O) - represents the radical w-undecylenoyl, R2 represents neither the methyl radical nor the isobutyl radical; - from 1 wt.% To 80 wt.% Of at least one compound of formula (Ib): R-O- [CH2] -OR (lb) formula (lb) wherein n is an integer greater than or equal to 3 and less than or equal to 12 and R represents either a hydrogen atom or a monovalent radical of formula (11), as defined above for the compound of formula (Ia). 3. Use as defined in any one of claims 1 or 2, wherein, in the formula (11), when the group R1-C (= O) - represents the w-undecylenoyl radical, R2 represents the isopropyl radical or the 1-methylpropyl radical, when the group R1-C (= O) - represents the octanoyl radical, R2 represents the 1-methylpropyl radical or the benzyl radical. 4. Use as defined in any one of claims 1 to 3, wherein in the formulas (1), (la) and (lb), n is an integer equal to 3. 5. Composition (Cl ') comprising for 100% of its mass: from 99% by weight to 20% by weight of at least one compound of formula (a): R'-O- [CH 2] -O-H (a), formula (a) in which n represents an integer greater than or equal to 3 and less than or equal to 12, and R 'represents a monovalent radical of formula (In: 0 R2 NI 1 1-1 Wherein R1-C (= O) - represents an acyl radical selected from octanoyl, decanoyl, dodecanoyl, tetradecanoyl and optionally hexadecanoyl, octadecanoyl, 9-octadecenoyl and octadeca-9 radicals. , 12-dienoyl, and R2 represents the isopropyl radical. 0071 - From 1 wt% to 80 wt% of at least one compound of formula (I'b): R-04C1-12], -O-R (I b), formula (I'b) wherein n represents an integer greater than or equal to 3 and less than or equal to 12, and R represents a monovalent radical of formula (II ") as defined above for the formula (a): said composition (Cl ') and obtained by the process comprising the following steps: a step A of acylation of valine with a mixture of acid chlorides comprising for 100 mol%, from 40 mol% to 60 mol% of dodecanoyl chloride, of 10% molar to 20 mol% of tetradecanoyl chloride, from 5 mol% to 15 mol% of decanoyl chloride, and from 5 mol% to 15 mol% of octanoyl chloride, and optionally up to 100 mol%, hexadecanoyl chloride and / or octadecanoyl chloride and / or 9-octadecenoyl chloride and / or octadeca-9,12-dienoyl chloride, to obtain a mixture of compounds of formula (IV '): CH3 C1-1 0 C 3 1-1 R1 NHOH O (IV), - A step B of esterification of the mixture of compounds of formula (IV ') obtained in step A, with the diol of formula (V): Wherein n represents an integer greater than or equal to 3 and less than or equal to 12, in the molar proportions requested. 6. Composition (Cl ') as defined in claim 5, obtained by a variant of the process comprising: - an esterification step A1, of the mixture of compounds of formula (IV') obtained in step A, with a alcohol of formula (VI): R5-OH (VI), in which R5 represents a linear aliphatic radical containing from 1 to 4 carbon atoms, to form a mixture of compounds of formula (VII '): Si 0071 CH C1-13 ## STR2 ## and a transesterification step B1 of the mixture of compounds of formula (VII ') obtained in step A1), with the diol of formula (V) in the appropriate proportions. 7. Composition (C1 ') as defined in any one of claims 5 or 6, for which the mixture of acid chloride used in step A of the process for obtaining it, comprises for 100 mol%, from 45 mol% to 55 mol% of dodecanoyl chloride, from 10 mol% to 20 mol% of tetradecanoyl chloride, from 5 mol% to 10 mol% of decanoyl chloride, and from 5 mol% to 15 mol% of chloride. octanoyl, from 5 mol% to 10 mol% hexadecanoyl chloride and from 5 mol% to 10 mol% octadecanoyl chloride and / or 9-octadecenoyl chloride and / or octadeca-9 chloride 12-diènoyle. 8. Composition (C1 ') as defined in any one of claims 5 to 7, for which, in formulas (a) or (I'b), n is equal to 3. 9. Process for the preparation of the composition (C1 '), as defined in any one of claims 5 to 7, comprising the following steps: a step A of acylation of leucine with a mixture of acid chlorides comprising from 100 mol%, from 40 mol% to 60 mol% dodecanoyl chloride, from 10 mol% to 20 mol% tetradecanoyl chloride, from 5 mol% to 15 mol% decanoyl chloride, and from 5 mol% to mol% to 15 mol% of octanoyl chloride, and optionally and up to 100 mol%, hexadecanoyl chloride and / or octadecanoyl chloride and / or 9-octadecenoyl chloride and / or octadeca-9,12-dienoyl chloride, to obtain a mixture of compounds of formula (IV '): ## STR2 ## A step B of esterifying the mixture of compounds of formula (IV ') obtained in step A with the diol of formula (V): ## STR2 ## in which n represents a ## STR2 ## whole number greater than or equal to 3 and less than or equal to 12, in the appropriate molar proportions. 10. A variant of the preparation process as defined in claim 9, comprising: an esterification step A1, of the mixture of compounds of formula (IV ') obtained in stage A, with an alcohol of formula ( VI): R 5 -OH (VI), formula (VI) wherein R 5 represents a linear aliphatic radical having from 1 to 4 carbon atoms, to form a mixture of compounds of formula (VII '): CH C1-13 0 CH R1 NH R5 0 (VIII and - A step B1 of trans-esterification of the mixture of compounds of formula (VII ') obtained in step A1), with the diol of formula (V) in the appropriate proportions, to obtain said composition (C1 '). 11. A method for the purpose of browning and / or tanning human skin and / or maintaining the natural pigmentation of hair and / or hair, and / or limiting and / or stopping the development of canities in the human being, comprising at least one step A of application to human skin of a cosmetic formulation for topical use comprising at least one cosmetically acceptable excipient and an effective amount of at least one compound of formula (I): I), formula (I) wherein n is an integer greater than or equal to 3 and less than or equal to 12 and R 'and R ", which are identical or different, represent either a hydrogen atom or a monovalent radical of formula (II): wherein R1-C (= O) - represents a radical chosen from octanoyl, decanoyl, w-undecylenoyl, dodecanoyl radicals, tetradecanoyl, hexadecanoyl, octadecanoyl, 9-octadecenoyl or 9,12-octadecadienoyl and R2 rep discloses a radical selected from methyl, isopropyl, isobutyl, 1-methylpropyl, and benzyl radicals; it being understood that when the group R 1 -C (= O) - represents the radical w-undecylenoyl, R2 represents neither the methyl radical nor the isobutyl radical, that at least one of the radicals R 'or R "does not represent a a hydrogen atom and when none of the radicals R 'and R "represents a hydrogen atom, R' and R" are identical, or a mixture of compounds of formula (I); 12. Process for the purpose of browning and / or tanning human skin and / or maintaining the natural pigmentation of hair and / or hair, and / or limiting and / or stopping the development of canities in the human being, comprising at least one step A of application to said human skin of a cosmetic formulation for total use comprising at least one cosmetically acceptable excipient and an effective amount of a composition (Cl) comprising for 100% of its mass: from 99% by weight to 20% by weight of at least one compound of formula (Ia): R'-O- [CH2] -OH (la) formula (I) in which n is a higher whole number or equal to 3 and less than or equal to 12 and R 'represents a monovalent radical of formula (II): ## STR2 ## wherein R1-C (= O) represents a radical selected from octanoyl, decanoyl, w-undecylenoyl, dodecanoyl, tetradecanoyl, hexadecanoyl, octadecanoyl, 9-octadecenoyl or 9,12-octadecadienoyl and R2 is a radical selected from methyl, isopropyl, isobutyl, 1-methylpropyl and benzyl; it being understood that when the group R 1 -C (= O) - represents the radical w-undecylenoyl, R2 represents neither the methyl radical nor the isobutyl radical; s1 0071 - From 1 wt% to 80 wt% of at least one compound of formula (Ib): R-O- [CH2] -OR (Ib) formula (Ib) wherein n is an integer greater than or equal to 3 and less than or equal to 12 and R represents either a hydrogen atom or a monovalent radical of formula (II), as defined above for the compound of formula (Ia); or a composition (Cl ') as defined in any one of claims 5 to 8. 13. Compound of formula (I): R'-O- [CH2] -O-R "(I), formula (I) wherein n is an integer greater than or equal to 3 and less than or equal to 12 and R and R ", which may be identical or different, represent either a hydrogen atom or a monovalent radical of formula (II): ## STR3 ## in which formula (II) in which R 1 -C (= O) represents a radical chosen from among the octanoyl, decanoyl, w-undecylenoyl, dodecanoyl, tetradecanoyl, hexadecanoyl, octadecanoyl, 9-octadecenoyl or 9,12-octadecadienoyl radicals, and R2 represents a radical chosen from methyl, isopropyl and isobutyl radicals. methyl propyl, and benzyl; it being understood that when the group R 1 -C (= O) - represents the radical w-undecylenoyl, R2 represents neither the methyl radical nor the isobutyl radical, that 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 a hydrogen atom, R' and R" are identical, or a mixture of compounds of formula (I), for its use in a therapeutic treatment method for stimulating the production of melanins for preventing and / or treating skin diseases. 14. Composition (Cl) 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] -OH (la) I) wherein n is an integer greater than or equal to 3 and less than or equal to 12 and R 'represents a monovalent radical of formula (II): ## STR2 ## wherein the group R1-C (= O) - represents a radical selected from octanoyl, decanoyl, w-undecylenoyl, dodecanoyl, tetradecanoyl, hexadecanoyl, octadecanoyl, 9-octadecenoyl or 9,12-octadecadienoyl and R2 represents a radical selected from dical selected from methyl, isopropyl, isobutyl, 1-methylpropyl and benzyl radicals; it being understood that when the group R 1 -C (= O) - represents the radical w-undecylenoyl, R2 represents neither the methyl radical nor the isobutyl radical; - from 1 wt.% To 80 wt.% Of at least one compound of formula (Ib): R-O- [CH2] -OR (lb) formula (lb) wherein n is an integer greater than or equal to 3 and less than or equal to 12 and R represents either a hydrogen atom or a monovalent radical of formula (II), as defined above for the compound of formula (Ia), or composition (Cl '), as defined in one of claims 5 to 8 for use in a therapeutic treatment method for stimulating the production of melanins to prevent and / or treat diseases of human skin.