FR2891737A1 - Use of C-glycoside compounds in a regime or regimen for de-pigmentation or whitening of skin - Google Patents

Abstract

A regime or regimen for de-pigmentation/whitening or anti-browning of the skin involves administering at least one C-glycoside compound (I), or its salt, solvate, hydrate or isomer. A regime or regimen for de-pigmentation/whitening or anti-browning of the skin involves administering at least one C-glycoside compound of formula S'-CH 2-X-R (I), or its salt, solvate, hydrate or isomer. R : (un)saturated linear 1-20C alkyl, or (un)saturated and branched or cyclic 3-20C alkyl (excluding substituted phenyl), (un)saturated linear 1-20C hydrofluoro- or perfluoroalkyl, or (un)saturated and branched or cyclic 3-20C hydrofluoro- or perfluoroalkyl (hydrocarbon chain optionally interrupted by at least one heteroatom selected from N, O, S and Si atom, and optionally substituted by -OR 4, -SR 4, NR 4R 5, COOR 4, CONHR 4, CN, halo, 1-6C hydrofluoro- or perfluoroalkyl, 3-8C cycloalkyl). R 4, R 5H, (un)saturated linear 1-30C alkyl, perfluoroalkyl or hydrofluoroalkyl, (un)saturated and branched or cyclic 3-30C alkyl, perfluoroalkyl or hydrofluoroalkyl, or 6-10C aryl; X : -C(O)-, CH(NR 1R 2), -CHR 1a-, or C=CHR 3; R 1H, R or 6-10C aryl; R 2, R 3H or R; R 1aH, OH or R; and S' : mono- or poly-saccharide having up to 20 sugar units in a pyranose and/or furanose form and of the L and/or D series (optionally substituted by free hydroxyl and optionally protected amine groups). The S'-CH 2-X bond is a bond of C-anomeric nature which is either alpha or beta . Independent claims are also included for: (1) a cosmetic/pharmaceutical composition (C1) for depigmenting/whitening the skin and/or for the anti-browning comprising (I), and at least one other depigmenting agent other than (I), soothing agent, (in)organic photoprotective agent, formulated into a physiologically acceptable medium; and (2) a food supplement or enriched food comprising (I). ACTIVITY : Dermatological. A double blind comparative single-center clinical study (using a composition comprising C-beta -D-xylopyranoside-n-propan-2-one as active principle, versus placebo composed of the vehicle of the active principle) randomized with regard to its location was carried out on 15 women with an average age of 62 years, exhibiting moderate signs of overall aging of the face with phototype (III) (on scale with 6 levels: with I-always burning, never tanning; III-burning moderately, tanning progressively; and VI-never burning, highly pigmented). The women applied either placebo (vehicle) or a test composition, which comprised C-beta -D-xylopyranoside-n-propan-2-one (10 wt.%) in the vehicle composition. The women applied C-beta -D-xylopyranoside-n-propane-2-one at a concentration of 10 wt.% with respect to the total weight of the composition in a proportion of 2 mg/cm 2> or the placebo (vehicle) twice daily for 98 days to the pre-marked regions. The clinical evaluation of actinic lentigines was carried out at the beginning and at the end of the test study according to the scale with 7 levels, including 4 main levels of 0-absent, 1-few blemishes, 2-many blemishes, 3-great many blemishes, and 3 intermediate levels of 0.5, 1.5 and 2.5. It was observed that the mean score on the treated side treated with C-beta -D-xylopyranoside-n-propane-2-one had decreased from 1.07+-0.62 before treatment to 0.93+-0.68, whereas on the placebo side, the score increased from 1.1+-0.69 to 1.13+-0.67. The results demonstrated that 54% of the subjects exhibited a lower (improved) score on the treated side versus 13% at the beginning of the study. MECHANISM OF ACTION : None given.

Description

(I) The present invention relates to the use of compound

  C-glycoside to depigment and / or whiten the skin. The color of human skin is a function of various factors, including year-round, race, and sex, and is primarily determined by the nature and concentration of melanin produced by melanocytes. Melanocytes are specialized cells that, via particular organelles, melanosomes, synthesize melanin. In addition, at different periods of their life, some people see on the skin and especially on the hands, darker spots and / or more colorful, giving the skin a heterogeneity. These spots are also due to a high concentration of melanin in keratinocytes located on the surface of the skin.

  The use of harmless topical depigmenting substances with good efficacy is particularly sought for treating regional hyperpigmentations by melanocytic hyperactivity such as idiopathic melasmas, occurring during pregnancy ("pregnancy mask" or chloasma) or a oestro-progestative contraception, hyperpigmentations localized by hyperactivity and benign melanocyte proliferation, such as senile pigmentary spots known as actinic lentigo, accidental hyperpigmentations, possibly due to photosensitization or post-injury healing, as well as certain leukoderma, such as vitiligo. For the latter (the scarring may result in a scar giving the skin a whiter appearance), failing to repigment the damaged skin, it completes depigmenting the areas of residual normal skin to give the whole skin a homogeneous white color.

  The mechanism of formation of skin pigmentation, that is to say the formation of melanin is particularly complex and schematically involves the following main steps: Tyrosine ---> Dopa ---> Dopaquinone --- > Dopachrome ---> Melanin

  Tyrosinase (monophenol dihydroxyl phenylalanine: oxygen oxido-reductase EC 1.14.18.1) is the essential enzyme involved in this series of reactions. In particular, it catalyzes the transformation reaction of tyrosine into Dopa (dihydroxyphenylalanine) thanks to its hydroxylase activity and the conversion reaction of Dopa into dopaquinone thanks to its oxidase activity. This tyrosinase only acts when it is maturing under the influence of certain biological factors.

  Depigmenting substances can act directly on the vitality of epidermal melanocytes, where melanogenesis takes place and / or interfere with one of the stages of melanin biosynthesis, either by inhibiting one of the enzymes involved in melanogenesis or by interposing them as structural analogue of one of the chemical compounds of the synthesis chain of melanin, which chain can then be blocked and thus ensure depigmentation.

  The substances most used as depigmenting agents are more particularly hydroquinone and its derivatives, in particular its ethers such as monomethyl ether and hydroquinone monoethyl ether. However, these compounds may cause undesirable effects such as the appearance of skin rashes in particular situations such as use at high concentrations, sensitive skin or dermatological disorder ...

  On the other hand, commonly used as the inhibitor of tyrosinase activation is kojic acid which complexes the copper present in the active site of this enzyme. However, this compound may prove unstable in solution, which complicates its formulation.

  There is still a need for novel whitening agents for human skin that are as effective as those known and non-irritating, non-toxic and / or non-allergenic to the skin, while being stable in a composition, or alternatively having an action. reinforced so that it can be used in a smaller quantity, which considerably reduces the observed side effects.

  In this regard the Applicant has surprisingly and unexpectedly found that certain C-glycoside compounds have good depigmenting activity without exhibiting cytotoxicity.

  C-glycosides have already been described in EP 1 345 919 as having the property of inducing the synthesis of proteoglycans and glycosaminoglycans thus contributing to reinforcing the extracellular matrix of the dermis. More precisely, the subject of the invention is therefore the cosmetic or pharmaceutical use, in particular dermatological use, of at least one compound of formula (I) below: ## STR2 ## in which

  S represents a monosaccharide or a polysaccharide up to 20 sugar units, in pyranose and / or furanose form, and of L and / or D series, said mono- or polysaccharide having at least one hydroxyl function which is necessarily free and, optionally, one or several amine functions optionally protected, the S-CH2X bond represents a bond of C-anomeric nature, X represents a group chosen from: -CO-, -CH (NR, R2) -, -CHR'-, -C ( = CHR ') -, - R represents a linear or branched, saturated or unsaturated alkyl, perfluoroalkyl, hydrofluoroalkyl chain, a cycloalkyl, cycloperfluoroalkyl, cyclohydrofluoroalkyl ring, comprising from 1 to 18 carbon atoms, a benzyl radical, the said chain, the said cycle or said radical may be optionally interrupted by one or more heteroatoms selected from oxygen, sulfur, nitrogen, silicon, and optionally substituted with at least one radical chosen from -OR ',, -SR ", , -NR "'1R'2, -COOR 2, -CONHR "2, -CN, halogen, perfluoroalkyl, hydrofluoroalkyl and / or at least one optionally substituted cycloalkyl, aryl, heterocyclic radical, it being understood that the benzyl radical can not be substituted, -R ', R ,, R 2, which are identical or different, have the same definition as that given for R, and may also represent a hydrogen and a hydroxyl radical, R '1, R' 2, R "1, R" 2, R "', R" 12, identical or different, represent a hydro-gene atom, a radical chosen from a linear or branched, saturated or unsaturated alkyl, hydroxyl, perfluoroalkyl and / or hydrofluoroalkyl radical comprising from 1 to 30 carbon atoms; . The C-anomeric bond may be a or R.

  According to a preferred form of the invention, C-glycoside derivatives corresponding to formula (I) are used for which R ', R ,, R2, identical or different, have the same definition as that given for R, and may also represent a hydroxyl radical.

  According to a preferred form of the invention, C-glycoside derivatives corresponding to formula (I) are used, for which S represents a monosaccharide or a polysaccharide containing up to 6 sugar units, in the pyranose and / or furanose form, and in series. L and / or D, the so-called mono- or polysaccharide having at least one hydroxyl function necessarily free and / or optionally one or more amine functions compulsorily protected, X and R otherwise retaining all of the previously given definitions.

  Advantageously, the preferred monosaccharides are chosen from D-glucose, D-galactose, D-mannose, D-xylose, D-lyxose, L-fucose, L-arabinose and L-rhamnose. D-glucuronic acid, D-galacturonic acid, D-iduronic acid, N-acetyl-D-glucosamine, N-acetyl-D-galactosamine and advantageously denotes D-glucose, D-xylose, N-acetyl-D-glucosamine or L-fucose, and very preferentially D-xylose.

  Advantageously, the preferred polysaccharides containing up to 6 sugar units are chosen from D-maltose, D-lactose, D-cellobiose and D-maltotriose, a disaccharide associating a uronic acid chosen from D-iduronic acid. or D-glucuronic acid with a hexosamine selected from D-galactosamine, D-glucosamine, N-acetyl-D-galactosamine, N-acetyl-D-glucosamine, an oligosaccharide containing at least one xylose, advantageously chosen from xylobiose, methyl-13-xylobioside, xylotriose, xylotetraose, xylopentaose and xylohexaose and preferably xylobiose which is composed of two xylose molecules linked by a 1-4 bond.

  According to another preferred form of the invention, C-glycoside derivatives corresponding to formula (I) are used for which X represents a group chosen from -CO-, -CH (OH) -, -CH (NR, R2) -, -CH2-, -C (= CHR ') - and very advantageously represents a group -CO-, -CH (OH) -, -CH (NH2) -, S and R also preserving all the definitions previously given.

  Among the C-glycoside derivatives of formula (I) used according to the invention, C- [3-D-xylopyranoside-n-propan-2-one; 2. C-α-D-xylopyranoside-n-propan-2-one; 3. 1-phenyl-2- (C- [3-D-xylopyranoside) -ethane-1-one; 4. 1-phenyl-2- (C-α-D-xylopyranoside) -ethane-1-one; 5. 1- [2- (3-Hydroxypropylamino) propyl] -C- [3-D-xylopyranose; 6. 1- [2- (3-Hydroxypropylamino) propyl] -C-α-D-xylopyranose; 7. C- [3-D-xylopyranoside-2-hydroxypropane; 8. C-α-D-xylopyranoside-2-hydroxypropane; 9. C- [3-D-xylopyranoside-2-amino-propane; 10. C-α-D-xylopyranoside-2-aminopropane; 11. C- [3-D-xylopyranoside-2-phenylamino propane; 12. C-α-D-xylopyranoside-2-phenylamino propane; 13. 3-methyl-4- (C- [3-D-xylopyranoside) -butyric acid ethyl ester; 14. ethyl ester of 3-methyl-4- (C-α-D-xylopyranoside) -butyric acid; 15. 6- (C- [3-D-xylopyranoside) -5-keto hexanoic acid; 16. 6- (C-α-D-xylopyranoside) -5-keto hexanoic acid; 17. 6- (C- [3-D-xylopyranoside) -5-hydroxy-hexanoic acid; 18. 6- (C-α-D-xylopyranoside) -5-hydroxy-hexanoic acid; 19. 6- (C- [3-D-xylopyranoside) -5-aminohexanoic acid; 20. 6- (C-α-D-xylopyranoside) -5-aminohexanoic acid; 21. 6- (C- [3-D-xylopyranoside) -5-phenylaminohexanoic acid; 22. 6- (C-α-D-xylopyranoside) -5-phenylamino-hexanoic acid; 23. 1- (C- [3-D-xylopyranoside) -hexane-2,6-diol; 24. 1- (C-α-D-xylopyranoside) -hexane-2,6-diol; 25. 5- (C- [3-D-xylopyranoside) -4-keto-pentanoic acid; 26. 5- (C-α-D-xylopyranoside) -4-keto-pentanoic acid; 27. 5- (C- [3-D-xylopyranoside) -4-hydroxy-pentanoic acid; 28. 5- (C-α-D-xylopyranoside) -4-hydroxy-pentanoic acid; 29. 5- (C- [3-D-xylopyranoside) -4-amino-pentanoic acid; 30. 5- (C-α-D-xylopyranoside) -4-amino-pentanoic acid; 31. 5- (C- [3-D-xylopyranoside) -4-phenylaminopentanoic acid; 32. 5- (C-α-D-xylopyranoside) -4-phenylaminopentanoic acid; 33. 1- (C- [3-D-xylopyranoside) -pentane-2,5-diol; 34. 1- (C-α-D-xylopyranoside) -pentane-2,5-diol; 35. 1- (C- (3-D-fucopyranoside) -propan-2-one; 36. 1- (CaD-fucopyranoside) -propan-2-one; 37. 1- (C- (3-L-fucopyranoside) ) -propan-2-one; 38. 1- (CaL-fucopyranoside) -propan-2-one; 39. 1- (C- (3-D-fucopyranoside) -2-hydroxypropane; CaD-fucopyranoside) -2-hydroxy-propane 41. 1- (C- (3-L-fucopyranoside) -2-hydroxy-propane, 42. 1- (CaL-fucopyranoside) -2-hydroxypropane; 1- (C- (3-D-fucopyranoside) -2-amino-propane, 44. 1- (CaD-fucopyranoside) -2-amino-propane, 45. 1- (C- (3-L-fucopyranoside) - 2-amino-propane, 46. 1- (CaL-fucopyranoside) -2-amino-propane, 47. 1- (C- (3-D-fucopyranoside) -2-phenylamino-propane, 48. 1- (Ca fucopyranoside) -2-phenylamino-propane; 49. 1- (C- (3-L-fucopyranoside) -2-phenylamino-propane; 50. 1- (CaL-fucopyranoside) -2-phenylamino-propane; 51. ethyl ester 3-methyl-4- (C- (3-D-fucopyranoside) -butyric acid, 52. 3-methyl-4- (CaD-fucopyranoside) -butyric acid ethyl ester, 53. ethyl ester, 3-methyl-4- (C- (3-Lf ucopyranoside) -butyric acid; 54. 3-methyl-4- (C-α-L-fucopyranoside) -butyric acid ethyl ester; 55. 6- (C- (3-D-fucopyranoside) -5-keto hexanoic acid, 56. 6- (CaD-fucopyranoside) -5-keto hexanoic acid, 57. 6- (C- (3- L-fucopyranoside) -5-keto hexanoic acid, 58. 6- (α-L-fucopyranoside) -5-keto hexanoic acid, 59. 6- (C- (3-D-fucopyranoside) -5-hydroxy-hexanoic acid; 60. 6- (CaD-fucopyranoside) -5-hydroxy-hexanoic acid, 61. 6- (C- (3-L-fucopyranoside) -5-hydroxy-hexanoic acid, 62. 6- (CaL-fucopyranoside) acid; 5-hydroxyhexanoic acid, 63. 6- (C- (3-D-fucopyranoside) -5-aminohexanoic acid, 64. 6- (CaD-fucopyranoside) -5-aminohexanoic acid, 65. 6- (C- (3-L-fucopyranoside) -5-aminohexanoic acid, 66. 6- (α-L-fucopyranoside) -5-aminohexanoic acid, 67. 1- (C- (3-D-fucopyranoside) -hexane 2,6-diol; 68. 1- (CaD-fucopyranoside) -hexane-2,6-diol; 69. 1- (C-13-L-fucopyranoside) -hexane-2,6-diol; 70. 1 - (α-L-fucopyranoside) -hexane-2,6-diol, 71. 5- (C- (3-D-fucopyranoside) -4-keto-pentanoic acid, 72. 5- (CaD-fucopyranoside) acid; keto-pentanoic 73. aci 5- (C- (3-L-fucopyranoside) -hexane-2,6-diol) -4-keto-pentanoic; 74. 5- (C-α-L-fucopyranoside) -hexane-2,6-diol) -4-keto-pentanoic acid; 75. 5- (C- (3-D-fucopyranoside) -4-hydroxy-pentanoic acid, 76. 5- (CaD-fucopyranoside) -4-hydroxy-pentanoic acid, 77. 5- (C- (3- L-fucopyranoside) -4-hydroxy-pentanoic acid, 78. 5- (α-L-fucopyranoside) -4-hydroxy-pentanoic acid, 79. 5- (C- (3-D-fucopyranoside) -4-amino-pentanoic acid; 80. 5- (CaD-fucopyranoside) -4-amino-pentanoic acid 81. 5- (C- (3-L-fucopyranoside) -4-amino-pentanoic acid, 82. 5- (CaL-fucopyranoside) acid -4 amino-pentanoic; 83. 1- (C- (3-D-fucopyranoside) -pentane-2,5-diol; 84. 1- (CaD-fucopyranoside) -pentane-2,5-diol; (1- (3-L-fucopyranoside) -pentane-2,5-diol, 86. 1- (CaL-fucopyranoside) -pentane-2,5-diol, 87. 1- (C-13-D-Glucopyranosyl) 2-hydroxyl-propane, 88. 1- (CaD-Glucopyranosyl) -2-hydroxylpropane, 89. 1- (C- (3-D-Glucopyranosyl) -2-amino-propane, 90. 1- (CaD 2-Amino propane, 91. 1- (C- (3-D-Glucopyranosyl) -2-phenylaminopropane, 92. 1- (CaD-Glucopyranosyl) -2-phenylamino-propane; 3-m acid ethyl ethyl-4- (C- (3-D-Glucopyranosyl) butyric acid; 94. 3-methyl-4- (C-α-D-Glucopyranosyl) -butyric acid ethyl ester; 95. 6- (C- (3-D-Glucopyranosyl) -5-keto-hexanoic acid, 96. 6- (CaD-Glucopyranosyl) -5-keto-hexanoic acid, 97. 6- (C- (3- D-Glucopyranosyl) -5-hydroxy-hexanoic acid, 98. 6- (CaD-Glucopyranosyl) -5-hydroxy-hexanoic acid, 99. 6- (C- (3-D-Glucopyranosyl) -5-aminohexanoic acid; 6- (C-Glucopyranosyl) -5-aminohexanoic acid, 101. 6- (C- (3-D-Glucopyranosyl) -5-phenylaminohexanoic acid, 102. 6- (CaD-Glucopyranosyl) - acid. 5-phenylamino-hexanoic acid, 103. 1- (C- (3-D-Glucopyranosyl) -hexane-2,6-diol, 104. 1- (CaD-Glucopyranosyl) -hexane-2,6-diol; 6- (C- (3-D-Glucopyranosyl) -5-keto-pentanoic acid; 106. 6- (CaD-Glucopyranosyl) -5-keto-pentanoic acid; 107. 6- (C- (3-D-Glucopyranosyl) acid; ) -5-hydroxy-pentanoic acid, 108. 6- (CaD-Glucopyranosyl) -5-hydroxy-pentanoic acid, 109. 6- (C- (3-D-Glucopyranosyl) -5-amino-pentanoic acid, 110. acid. 6- (CaD-Glucopyranosyl) -5-hydroxy-pentanoic acid, 111. 6- (C- (3-D-Glucopyranosyl) -5-phenylamino-pentanoic acid; 6- (C-α-D-Glucopyranosyl) -5-phenylaminopentanoic acid; 113. 1- (C- (3-D-Glucopyranosyl) -pentane-2,6-diol; 114. 1- (CaD-Glucopyranosyl) -pentane-2,6-diol; 115. 1- (C- (3 -D-galactopyranosyl) -2-hydroxylpropane; 116. 1- (C-α-D-galactopyranosyl) -2-hydroxylpropane; 117. 1- (C- (3-D-galactopyranosyl) -2-amino-propane; 118. 1- (Ca-Galactopyranosyl) -2-amino-propane; 119. 1- (C- (3-D-galactopyranosyl) -2-phenylamino-propane; 120. 1- (CaD-galactopyranosyl) -2- phenylamino-propane, 121. 3-methyl-4 - ((3-D-galactopyranosyl) -butyric acid ethyl ester, 122. 3-methyl-4- (α-D-galactopyranosyl) -butyric acid ethyl ester; 123. 6- (C- (3-D-galactopyranosyl) -5-ketohexanoic acid; 124. 6- (CaD-galactopyranosyl) -5-ketohexanoic acid; 125. 6- (C- (3)) acid; -D-galactopyranosyl) -5-hydroxy-hexanoic acid, 126. 6- (CaD-galactopyranosyl) -5-hydroxy-hexanoic acid, 127. 6- (C- (3-D-galactopyranosyl) -5-aminohexanoic acid; 128. 6- (Ca-Galactopyranosyl) -5-aminohexanoic acid; 129. 6- (C-13-D-galactopyranosyl) -5-phenylaminohe xanoic; 130. 6- (C-α-D-galactopyranosyl) 5-phenylaminohexanoic acid; 131. 1- (C- (3-D-galactopyranosyl) -hexane-2,6-diol; 132. 1- (CaD-galactopyranosyl) -hexane-2,6-diol; 133. 6- (C- 3-D-galactopyranosyl) -5-keto-pentanoic acid, 134. 6- (Ca-galactopyranosyl) -5-keto-pentanoic acid, 135. 6- (C- (3-D-galactopyranosyl) -5-hydroxy-acid, pentanoic acid, 136. 6- (CaD-galactopyranosyl) -5-hydroxy-pentanoic acid, 137. 6- (C- (3-D-galactopyranosyl) -5-amino-pentanoic acid, 138. 6- (CaD-galactopyranosyl) acid; 5-amino-pentanoic acid, 139. 6- (C- (3-D-galactopyranosyl) -5-phenylaminopentanoic acid, 140. 6- (CaD-galactopyranosyl) -5-phenylaminopentanoic acid, 141. 1 - (C- (3-D-galactopyranosyl) -pentane-2,6-diol; 142. 1- (CaD-galactopyranosyl) -pentane-2,6-diol; 143. 1- (C- (3-D- fucofuranosyl) -propan-2-one; 144. 1- (CaD-fucofuranosyl) -propan-2-one; 145. 1- (C-13-L-fucofuranosyl) propan-2-one; CaL-fucofuranosyl) -propan-2-one; 147. 3 '- (acetamido-C- (3-D-glucopyranosyl) propan-2'-one; 148. 3' - (acetamido-CaD-glucopyranosyl) -propane -2 ' -one; 149. 1- (C- (3-D-galactopyranosyl) -2-hydroxylpropane, 150. 1- (CaD-galactopyranosyl) -2-amino-propane, 151. 1- (acetamido-C- (3-D) 2-phenylamino-propane, 152. 1- (acetamido-CaD-glucopyranosyl) -2-phenylamino-propane, 153. ethyl ester of 3-methyl-4- (acetamido-C-13-D) Glucopyranosyl) -butyric acid, 154. 3-methyl-4- (acetamido-CaD-glucopyranosyl) butyric acid ethyl ester, 155. 6- (acetamido-C- (3-D-glucopyranosyl) -5-keto acid) -hexanoic acid, 156. 6- (acetamido-CaD-glucopyranosyl) -5-keto hexanoic acid, 157. 6- (acetamido-C- (3-D-glucopyranosyl) -5-hydroxy-hexanoic acid; - (acetamido-CaD-glucopyranosyl) -5-hydroxy-hexanoic acid, 159. 6- (acetamido-C- (3-D-glucopyranosyl) -5-aminohexanoic acid, 160. 6- (acetamido-CaD-glucopyranosyl acid) 5-amino-hexanoic acid, 161. 6- (acetamido-C-13-D-glucopyranosyl) 5-phenylaminohexanoic acid, 162. 6- (acetamido-CaD-glucopyranosyl) 5-phenylaminohexanoic acid; 1- (acétamid o-C- (3-D-glucopyranosyl) hexane-2,6-diol; 164. 1- (acetamido-C-α-D-glucopyranosyl) hexane-2,6-diol; 165. 6- (acetamido-C- (3-D-glucopyranosyl) -5-keto-pentanoic acid, 166. 6- (acetamido-C-α-D-glucopyranosyl) -5-keto-pentanoic acid, 167. 6- (acetamido-C- (3-D-glucopyranosyl) -5-hydroxy-pentanoic acid, 168. 6- (acetamido-CaD-glucopyranosyl) -5-hydroxy-pentanoic acid, 169. 6- (acetamido-C-) -D-glucopyranosyl) -5-aminopentanoic acid, 170. 6- (acetamido-CaD-glucopyranosyl) -5-aminopentanoic acid, 171. 6- (acetamido-C- (3-D-glucopyranosyl) -5 acid) phenylamino-pentanoic acid, 172. 6- (acetamido-CaD-glucopyranosyl) -5-phenylaminopentanoic acid, 173. 1- (acetamido-C- (3-D-glucopyranosyl) -pentane-2,6-diol; 1- (acetamido-CaD-glucopyranosyl) -pentane-2,6-diol, C- (3-D-xylopyranoside-n-propan-2-one is preferably used. C-glycoside derivatives of formula (I) may be used alone or in admixture and in any proportion.

  According to the invention, the C-glycoside derivatives corresponding to formula (I) may be of natural or synthetic origin, totally or partially purified or any preparation containing them.

  By natural origin is meant a derivative extracted from natural material in which it is present, for example plants. By synthetic origin is meant a derivative prepared by chemical synthesis or by biotechnology.

  The term "totally or partially purified" herein means that, during its synthesis or relative to its natural state (fresh or dried plant or cells), the C-glycoside derivative having the formula (I) in the composition of the present invention. the invention has been concentrated and / or has been freed, respectively from at least a part of the secondary reaction products resulting from its synthesis or from at least a part of the other constituents of the natural material in which it is present. The C-glycoside derivatives may in particular be obtained by the synthesis method described in document EP 1 345 919.

  The compounds of formula (I) according to the invention make it possible to effectively depigment and / or lighten the skin of human beings.

  Skin pigmentation is a normal physiological process resulting from exposure of the skin to sunlight. It may, for aesthetic purposes, be desirable to beautify the appearance of the skin by limiting the pigmentation and thus reduce the appearance of darker skin areas. It is also possible that the pigmentation results from cutaneous disorders which may, for example, be related to a local proliferation of active melanocytes.

  The C-glycosides are intended, in particular, to be applied to the skin of individuals with brownish pigmentation spots, senescence spots, or on the skin of individuals wishing to combat the appearance of a brownish color coming from the skin. melanogenesis, for example following exposure to ultraviolet radiation.

  Thus, the compounds of formula (I) may be used as a whitening agent for the skin and / or as an anti-browning agent, in particular for preventing the formation and / or reducing pigment spots, ephelides, senescence spots and / or to lighten and / or whiten and / or uniformize the color of a burnished skin.

  These compounds are particularly effective in preventing and / or treating actinic spots. Actinic spots, also called senile lentigo, are characterized by circumscribed brown macules corresponding to a greater local production of melanin induced by chronic sun exposure. They are usually found on the face, back of the hands, forearms, upper back and décolleté, even the scalp areas of the scalp devoid of hair.

  The invention also relates to the use of a compound of formula (I) as described above for the manufacture of a dermatological composition for treating pigmentary disorders of the skin.

  The compounds of formula (I) may also be useful for treating regional hyperpigmentations by melanocytic hyperactivity such as melasma of the forearms, idiopathic melasmas, occurring during pregnancy ("pregnancy mask" or chloasma) or a estrogen-progestative contraception, puva-lentigines, post-inflammatory hyperpigmentation, accidental hyperpigmentations, possibly due to photosensitization or post-lesion scarring, as well as certain leukoderma, such as vitiligo.

  Depigmenting substances also find application in the bleaching of superficial body growths, in particular hairs which may be desirable to lighten in order to make them less visible.

  That the compounds of formula (I) are used for cosmetic or pharmaceutical purposes, their administration can be carried out by different routes, for example, the oral route, these compounds will then be formulated in compositions adapted to this mode of administration. For ingestion, many embodiments of oral compositions and especially dietary supplements are possible. Their formulation is carried out by the usual methods for producing dragees, capsules, gels, emulsions, tablets, capsules. In particular, the active (s) according to the invention can be incorporated into any other form of food supplements or fortified foods, for example food bars, or compacted powders or not. The powders can be diluted with water, in soda, dairy products or soy derivatives, or incorporated into food bars.

  The subject of the invention is therefore also a cosmetic process for bleaching human skin and / or scalp and / or mucous membranes, comprising ingestion or application to the skin and / or the scalp and / or mucous membranes. at least one C-glycoside compound. In the case of a topical application, the C-glycoside compound may be left in contact with the skin and / or the scalp and / or mucous membranes, and then possibly rinsed.

  The method is particularly suitable for removing brownish pigment spots and / or senescence spots, and / or for lightening browned skin.

  For topical use, the compounds of formula (I) may be formulated in a composition comprising a physiologically acceptable medium.

  In particular the composition is suitable for topical application to the skin. The physiologically acceptable medium will preferably be a cosmetically or dermatologically acceptable medium, that is to say without any unpleasant appearance, and which does not generate tingling, tightness or redness that is unacceptable to the user.

  By physiologically acceptable medium, an environment compatible with keratin materials of human beings such as the skin, the mucous membranes, the nails, the scalp and / or the hair is understood.

  The composition according to the invention may be intended for a cosmetic or pharmaceutical application, particularly dermatological.

  The quantity of compounds of formula (I) that can be used in the context of the invention obviously depends on the desired effect. By way of example and for topical administration, this amount may range, for example, from 0.0001% to 25% by weight, 0.001% to 10% by weight, preferably from 0.01% to 5% by weight. , in particular from 0.1 to 2% by weight, relative to the total weight of the composition. In the case of oral administration, the amount of compound of formula (I) may be between 10 and 1000 mg weight / kg body weight / day, preferably 100 mg weight / kg body weight / day.

  In the case of oral administration, the composition may be in the form of tablets, capsules, dragees, syrups, suspensions, solutions, powders, granules, emulsions, suspensions of microspheres or nanospheres or lipid or polymeric vesicles for controlled release. Preferably, the composition is in the form of complement.

  In the case of topical administration, the composition may comprise the constituents usually employed in the intended application.

  It may especially be mentioned water, solvents, oils of mineral, animal and / or vegetable origin, waxes, pigments, fillers, surfactants, cosmetic or dermatological active agents, UV filters, polymers, gelling agents, preservatives.

  Of course, the person skilled in the art will take care to choose this or these optional compounds and / or their quantity, in such a way that the advantageous properties of the compounds according to the invention are not, or not substantially, impaired by the addition envisaged.

  The composition according to the invention may be in any galenical form normally used in the cosmetic and dermatological fields; it may especially be in the form of an aqueous solution, hydroalcoholic, optionally gelled, a dispersion of the lotion type possibly two-phase, an oil-in-water or water-in-oil or multiple emulsion, an aqueous gel , an oil dispersion in an aqueous phase using spherules, these spherules may be polymeric nanoparticles such as nanospheres and nanocapsules or lipid vesicles of ionic and / or nonionic type.

  When the composition of the invention is an emulsion, the proportion of the fatty phase may range from 5 to 80% by weight, and preferably from 5 to 50% by weight relative to the total weight of the composition. The oils, the emulsifiers and any coemulsifiers used in the composition in emulsion form are chosen from those conventionally used in the field under consideration. The emulsifier and the coemulsifier are present in the composition in a proportion ranging from 0.3 to 30% by weight, and preferably from 0.5 to 20% by weight relative to the total weight of the composition.

  This composition may be more or less fluid and have the appearance of a white or colored cream, an ointment, a milk, a lotion, a serum, a paste, a mousse . It can optionally be applied to the skin in the form of an aerosol. It can also be in solid form, and for example in the form of a stick. It can be used as a care product and / or as a makeup product.

  This composition may constitute a cream for cleaning, protecting, treating or caring for the face, for the hands, for the feet, for large anatomical folds or for the body (for example, day creams, night creams, creams). make-up removers, foundation creams, sunscreen creams); a fluid foundation, a decaffeinated milk, a protective or care body milk, an anti-sun milk; a lotion, gel or mousse for the care of the skin, such as a cleaning lotion. In an advantageous aspect of the invention, the compositions used may also comprise at least one depigmenting agent and / or a desquamating agent, and / or at least one soothing agent, and / or at least one organic photoprotective agent and / or at least one an inorganic photoprotective agent.

  The use of at least one C-glycoside compound in combination with another de-pigmenting agent may in particular make it possible to use a smaller amount of each of the depigmenting agents. By depigmenting agent is meant, for example, depigmenting or anti-pigmenting agents the following compounds: kojic acid; ellagic acid; arbutin and its derivatives such as those described in EP-895,779 and EP-524,109; hydroquinone; aminophenol derivatives such as those described in WO 99/10318 and WO 99/32077, and in particular N-cholesteryloxycarbonyl-para-aminophenol and N-ethyloxycarbonyl-para-aminophenol; iminophenol derivatives, in particular those described in application WO 99/22707; L-2-oxothiazolidine-4-carboxylic acid or procysteine, as well as its salts and esters; calcium d-panthétéine sulfonate, ascorbic acid and its derivatives, in particular ascorbyl glucoside; and plant extracts, in particular licorice, mulberry, skullcap and Bacopa monnieri, without this list being limiting.

  By "desquamating agent" is meant any compound capable of acting: either directly on desquamation by promoting exfoliation, such as [3-hydroxy acids, in particular salicylic acid and its derivatives (of which octyl 5- salicylic); α-hydroxy acids, such as glycolic, citric, lactic, tartaric, malic or mandelic acids; urea; gentisic acid; oligofucoses; cinnamic acid; Saphora japonica extract; resveratrol; or on the enzymes involved in the desquamation or degradation of corneodesmosomes, glycosidases, stratum corneum chymotryptic enzyme (SCCE) or even other proteases (trypsin, chymotrypsin-like). Mention may be made of the chelating agents for mineral salts: EDTA; N-acyl-N, N ', N', ethylene diaminetriacetic acid; aminosulfonic compounds and in particular (N-2-hydroxyethylpiperazine-N-2-ethane) sulfonic acid (HEPES); 2-oxothiazolidine-4-carboxylic acid derivatives (procysteine); glycine-type alpha amino acid derivatives (as described in EP 0 852 949, as well as sodium methyl glycine diacetate marketed by BASF under the trade name TRILON M); honey ; sugar derivatives such as O-octanoyl-6-D-maltose and N-acetyl glucosamine.

  As soothing agents that can be used in the composition according to the invention, mention may be made of: pentacyclic triterpenes and plant extracts (for example Glycyrrhiza glabra) containing them, for instance [3-glycyrrhetinic acid and its salts and / or derivatives thereof glycyrrhetinic acid monoglucuronide, stearyl glycyrrhetinate, 3-stearoyloxy glycyrrhetic acid), ursolic acid and its salts, oleanolic acid and its salts, betulinic acid and its salts, an extract of Paeonia suffruticosa and / or lactiflora, salicylic acid salts and in particular zinc salicylate, Codif's phycosaccharides, Laminaria saccharina extract, Canola oil, bisabolol and chamomile extract, allantoin, Sepivital EPC (Seppic Vitamin E and C) diesterphosphoric acid, unsaturated omega 3 oils such as rosehip musk, black currant, ecchium, fish, plankton extract, capryloyl glycine, Seppicalm VG (sodium palmitoylproline and nymphea alba) of Seppic, an extract of Pygeum, an extract of Boswellia serrata, an extract of Centipeda cunnighami, an extract of Helianthus annuus, an extract of Linum usitatissimum, tocotrienols, extracts of Cola nitida, piperonal, clove extract, Epilobium Angustifolium extract, aloe vera, Bacopa moniera extract, phytosterols, cortisone, hydrocortisone, indomethacin and beta methasone.

  The organic photoprotective agents are in particular chosen from anthranilates; cinnamic derivatives; dibenzoylmethane derivatives; salicylic derivatives, camphor derivatives; triazine derivatives such as those described in US 4,367,390, EP 0 863 145, EP 0 517 104, EP 0 570 838, EP 0 796 851, EP 0 775 698, EP 0 878 469, EP 0 933 376, EP 0 507 691, EP 0 507 692, EP 0 790 243, EP 0 944 624; benzophenone derivatives; X3,13-diphenylacrylate derivatives; benzotriazole derivatives; benzalmalonate derivatives; benzimidazole derivatives; imidazolines; bis-benzoazolyl derivatives as described in patents EP 0 669 323 and US 2,463,264; derivatives of p-aminobenzoic acid (PABA); methylene bis (hydroxyphenyl benzotriazole) derivatives as described in US applications 5,237,071, US 5,166,355, GB 2303549, DE 197 26 184 and EP 0 893 119; and filter polymers and silicone filters such as those described in particular in the application WO-93/04665; dimers derived from α-alkylstyrene such as those described in patent application DE 198 55 649.

  The inorganic photoprotective agents are chosen from pigments or even nanopigments (average size of the primary particles: generally between 5 nm and 100 nm, preferably between 10 nm and 50 nm) of coated or uncoated metal oxides such as, for example, nanopigments titanium oxide (amorphous or crystallized in rutile and / or anatase form), iron, zinc, zirconium or cerium which are all UV photoprotective agents well known per se. Conventional coating agents are, moreover, alumina and / or aluminum stearate. Such nanopigments of metal oxides, coated or uncoated, are in particular described in patent applications EP 0 518 772 and EP 0 518 773.

  The photoprotective agents are generally present in the composition according to the invention in proportions ranging from 0.1 to 20% by weight relative to the total weight of the composition, and preferably ranging from 0.2 to 15% by weight relative to to the total weight of the composition.

  Preferably, the C-glycoside derivative (s) will be associated with at least one depigmenting agent and / or at least one photoprotective agent.

  The examples which follow illustrate the invention without limiting its scope. The compounds are, as the case may be, listed in chemical names or CTFA names (International Cosmetic Ingredient Dictionary and Handbook). EXAMPLE 1 Demonstration of the depigmenting activity of C-R-D-xylopyranoside-2-hydroxy-propane

  A single-center, comparative (placebo-active active vehicle-based, see detailed formula below) double-blind randomized site-specific clinical study (the subject being its own control) was conducted in 15 elderly women. average 62 years, phototype Ill (on a scale of 6 levels: I - always burns, never tans, He - always burns, little bronze, III - moderately burns, progressively bronze, IV - lightly burns, bronze very easily, V - rarely burns, intensely bronze, VI - never burns, strongly pigmented) with moderate signs of global aging of the face. A clinical evaluation of actinic lentigines was performed by a dermatologist at the beginning and the end of the study on a 7-level scale with 4 main levels: 20 o 0 o absent; o 1 - few spots; o 2 - many spots; o 3 - very numerous spots and 3 intermediate levels (0.5, 1.5, 2.5). The women applied C- (3-D-xylopyranoside-2-hydroxypropane) twice daily for 3 months (98 days) at a concentration of 10% by weight relative to the total weight of the composition at 2 mg / cm2 or placebo Composition of the vehicle: Chemical Name WHITE VASELINE 4 SORBITANE TRI-STEARATE 0.9 POLYETHYLENE GLYCOL STEARATE (40 0E) 2 PERFUME 0.25 MYRISTYL MYRISTATE 2 METHYL P-HYDROXYBENZOATE MIXTURE , BUTYL, ETHYL, 0.35 PROPYL, ISOBUTYL (7/57/22/14) MONO / DISTEARATE MIXTURE (36/64) OF GLYCERYLE / STEARATE OF 3 POTASSIUM ISOPARAFFIN (6-8 MOLDS OF ISOBUTYLENE) HYDROGENATED 8.5 PURE SODIUM HYDROXIDE 0.05 GLYCEROL 3 WATER DESIONIZED MICROBIOLOGICALLY CLEAN 35.84 CHLORHEXIDINE DIGLUCONATE IN SOLUTION 0.25 CYCLOPENTA DIMETHYLSILOXANE 5 PURE BIDISTILATED 4-CELLALLIC ALKOLIC ACID FATTY ACID (MAJORITY STEARIC ACID) OF PLANT ORIGIN 1.2 ACETYLENE ETHYLENE DIAMINE TETRACETIC, SALT DISODIUM, 2 H2O 0.15 ACETATE OF DL-ALPHA -TOCOPHER YLE (VITAMIN E ACETATE) 0.3 4-METHOXYCINNAMATE OF 2-ETHYL HEXYL PROTECTED 0.52 1.5-ANHYDRO-6.8-DIDEOXY-L-GLUCO-OCTITOL AT 30% IN WATER 28.74 The mean score on the side treated with C- ( 3-D-xylopyranoside-2-hydroxy-propane decreases from 1.07 +/- 0.62 before treatment to 0.93 +/- 0.68 (p = 0.08) whereas on the placebo side, this score increases from 1.10 +/- 0.69 to 1.13 +/- 0.67 (NS).

  Thus, 54% of the subjects presented a less severe score on the treated side compared to 13% at the beginning of study. Example 2 Example of a Topical Composition An oil-in-water emulsion facial cream, comprising (% by weight), is prepared: C- (3-D-xylopyranoside-2-hydroxy-propane 0.005% stearate glycerol 2% polysorbate 60 (ICI Tween 60) 1% stearic acid 1.4% triethanolamine 0.7% carbomer 0.4% liquid fraction of shea butter 12% perhydrosqualene 12% antioxidant 0.05% perfume, preservative qs water EXAMPLE 3 Example of Topical Composition A depigmenting gel for the skin comprising (% by weight): -C- (3-D-xylopyranoside-2-hydroxypropane 2% - hydroxypropylcellulose (Klucel H from Hercules) 1 % - antioxidant 0.05% - isopropanol 40% - perfume, preservative qs - water gsp100% Example 4: example of oral composition Dreads are prepared comprising (% by weight): active ingredients mg / dragée C- (3-D- xylopyranoside-2-hydroxy-propane 300 Excipient of Dragee Core Minocrystalline Cellulose 70 EncompressTM 60 Magnesium Stearate 3 S colloid anhydrous ilice 1 Coating agent Shellac 5 Talc 61 Polyvidone 6 This type of sugar can be taken 1 to 4 times a day.

Claims (174)

  1. Use of at least one C-glycoside derivative corresponding to the following formula (I): ## STR3 ## in which: S represents a monosaccharide or a polysaccharide up to 20 sugar units, in pyranose and / or furanose form; and L and / or D series, said mono- or polysaccharide having at least one hydroxyl function necessarily free and / or possibly one or more optionally protected amine functions, - the bond S-CH2X represents a bond of C-anomeric nature, X represents a group chosen from: -CO-, -CH (NR, R2) -, -CHR'-, -C (= CHR ') -, - R represents an alkyl, perfluoroalkyl, linear or branched hydrofluoroalkyl chain, saturated or unsaturated, a cycloalkyl, cycloperfluoroalkyl, cyclohydrofluoroalkyl ring, comprising from 1 to 18 carbon atoms, a benzyl radical, the said chain, the said ring or said radical possibly being interrupted by one or more heteroatoms chosen from oxygen , the sulfur, the nitrogen, silicon, and optionally substituted, with the exception of the benzyl radical, with at least one radical chosen from -OR ',, -SR ",, -NR"' 1R'2, -COOR "2, -CONHR" 2, -CN, halogen, perfluoroalkyl, hydro-fluoroalkyl and / or at least one optionally substituted cycloalkyl, aryl, heterocyclic radical, it being understood that the benzyl radical can not be substituted, - R ', R ,, R2, identical or different have the same definition as that given for R, and may also represent a hydrogen and a hydroxyl radical, -R'1, R'2, R "1, R" 2, R "',, R" 12, identical or different, represent a hydrogen atom, a radical chosen from a linear or branched, saturated or unsaturated alkyl, hydroxyl, perfluoroalkyl and / or hydrofluoroalkyl radical, comprising from 1 to 30 carbon atoms, as bleaching agent; skin and / or anti-browning agent.   2. Use according to claim 1 for lightening and / or whitening and / or uniforming the color of burnished skin, preventing the formation and / or eliminating brownish pigment spots and / or senescence spots and / or ephelides. .   3. Use of at least one C-glycoside derivative corresponding to the following formula (I): ## STR5 ## in which: S represents a monosaccharide or a polysaccharide up to 20 sugar units, in pyranose and / or furanose form; and L and / or D series, said mono- or polysaccharide having at least one hydroxyl function necessarily free and / or possibly one or more optionally protected amine functions, - the bond S-CH2X represents a bond of C-anomeric nature, X represents a group chosen from: -CO-, -CH (OH) -, -CH (NR, R2) -, -CHR'-, -C (= CHR ') -, - R represents an alkyl chain, perfluoroalkyl, linear or branched, saturated or unsaturated hydrofluoroalkyl, a cycloalkyl, cycloperfluoroalkyl or cyclohydrofluoroalkyl ring, comprising 1 to 18 carbon atoms, a benzyl radical, the said chain, the said ring or the said radical possibly being interrupted by one or more heteroatoms; chosen from oxygen, so uffre, nitrogen, silicon, and optionally substituted, with the exception of the benzyl radical, by at least one radical chosen from - OR ',, -SR ",, -NR"' 1R'2, -COOR "2 -CONHR "2, -CN, halogen, perfluoroalkyl, hydrofluoroalkyl and / or at least one optionally substituted cycloalkyl, aryl, heterocyclic radical, it being understood that the benzyl radical can not be substituted, -R ', R ,, R2, which are identical or different, have the same definition as that given for R, and may also represent a hydrogen and a hydroxyl radical, R'1, R'2, R "1, R" 2, R "', R" 12 , identical or different, represent a hydrogen atom, a radical chosen from a linear or branched, saturated or unsaturated alkyl, hydroxyl, perfluoroalkyl and / or hydrofluoroalkyl radical, comprising from 1 to 30 carbon atoms, for the preparation of a composition for the treatment of disorders of pigmentation.   4. Use according to claim 3, characterized in that the composition is intended to treat melasma forearms, idiopathic melasmas, hyperpigmentations associated with pregnancy or estrogen-progestative contraception, puva-lentigines, hyperpigmentations accidental hyperpigmentation due to leukoderma, vitiligo.   5. Use according to any one of claims 1 to 4, characterized in that said derivative is such that S represents a monosaccharide chosen from D-glucose, D-galactose, D-mannose, D-xylose, D-lyxose, L-fucose, L-arabinose, L-rhamnose, D-glucuronic acid, D-galacturonic acid, D-iduronic acid, N-acetyl-D-glucosamine, N acetyl-D-galactosamine or a polysaccharide containing up to 6 sugar units chosen from D-maltose, D-lactose, D-cellobiose and D-maltotriose, a disaccharide associating a uronic acid chosen from D-iduronic acid or D-glucuronic acid with a hexosamine selected from D-galactosamine, D-glucosamine, N-acetyl-D-galactosamine, N-acetyl-D-glucosamine or an oligosaccharide containing at least one xylose.   6. Use according to any one of the preceding claims, characterized in that said derivative is such that X represents a group chosen from -CO-, -CH (OH) -, -CH (NR, R2) -, -CH2- or -C (= CHR ') -.   7. Use according to any one of the preceding claims, characterized in that said derivative is chosen from: 1. C- [3-D-xylopyranoside-n-propan-2-one; 2. C-α-D-xylopyranoside-n-propan-2-one; 3. 1-phenyl-2- (C- [3-D-xylopyranoside) -ethane-1-one; 4. 1-phenyl-2- (C-α-D-xylopyranoside) -ethane-1-one; 5. 1- [2- (3-Hydroxypropylamino) propyl] -C- [3-D-xylopyranose; 6. 1- [2- (3-Hydroxypropylamino) propyl] -C-α-D-xylopyranose; 7. C- [3-D-xylopyranoside-2-hydroxypropane;   8. C-α-D-xylopyranoside-2-hydroxypropane;   9. C- [3-D-xylopyranoside-2-amino-propane;   10. C-α-D-xylopyranoside-2-aminopropane;   11. C- [3-D-xylopyranoside-2-phenylamino propane;   12. C-α-D-xylopyranoside-2-phenylamino propane; 13. 3-methyl-4- (C- [3-D-xylopyranoside) -butyric acid ethyl ester;   14. 3-methyl-4- (C-α-D-xylopyranoside) -butyric acid ethyl ester   15. 6- (C- [3-D-xylopyranoside) -5-keto hexanoic acid;   16. 6- (C-α-D-xylopyranoside) -5-keto hexanoic acid;   17. 6- (C- [3-D-xylopyranoside) -5-hydroxy-hexanoic acid;   18. 6- (C-α-D-xylopyranoside) -5-hydroxy-hexanoic acid;   19. 6- (C- (3-D-xylopyranoside) -5-aminohexanoic acid;   20. 6- (C-α-D-xylopyranoside) -5-aminohexanoic acid;   21. 6- (C- (3-D-xylopyranoside) -5-phenylaminohexanoic acid;   22. 6- (C-α-D-xylopyranoside) -5-phenylamino-hexanoic acid;   23. 1- (C- (3-D-xylopyranoside) -hexane-2,6-diol;   24. 1- (C-α-D-xylopyranoside) -hexane-2,6-diol;   25. 5- (C- (3-D-xylopyranoside) -4-keto-pentanoic acid;   26. 5- (C-α-D-xylopyranoside) -4-keto-pentanoic acid;   27. 5- (C- (3-D-xylopyranoside) -4-hydroxy-pentanoic acid;   28. 5- (C-α-D-xylopyranoside) -4-hydroxy-pentanoic acid;   29. 5- (C- (3-D-xylopyranoside) -4-amino-pentanoic acid;   30. 5- (C-α-D-xylopyranoside) -4-amino-pentanoic acid;   31. 5- (C- (3-D-xylopyranoside) -4-phenylaminopentanoic acid;   32. 5- (C-α-D-xylopyranoside) -4-phenylaminopentanoic acid;   33. 1- (C- (3-D-xylopyranoside) -pentane-2,5-diol;   34. 1- (C-α-D-xylopyranoside) -pentane-2,5-diol;   35. 1- (C- (3-D-fucopyranoside) propan-2-one;   36. 1- (C-α-D-fucopyranoside) -propan-2-one;   37. 1- (C- (3-L-fucopyranoside) -propan-2-one;   38. 1- (C-α-L-fucopyranoside) -propan-2-one;   39. 1- (C- (3-D-fucopyranoside) -2-hydroxypropane;   40. 1- (C-α-D-fucopyranoside) -2-hydroxypropane;   41. 1- (C- (3-L-fucopyranoside) -2-hydroxypropane;   42. 1- (C-α-L-fucopyranoside) -2-hydroxypropane;   43. 1- (C- (3-D-fucopyranoside) -2-amino-propane;   44. 1- (C-α-D-fucopyranoside) -2-amino-propane;   45. 1- (C- (3-L-fucopyranoside) -2-amino-propane;   46. 1- (C-α-L-fucopyranoside) -2-amino-propane;   47. 1- (C- (3-D-fucopyranoside) -2-phenylamino propane;   48. 1- (C-α-D-fucopyranoside) -2-phenylaminopropane;   49. 1- (C- (3-L-fucopyranoside) -2-phenylamino propane;   50. 1- (C-α-L-fucopyranoside) -2-phenylamino propane; 51. 3-methyl-4- (C- (3-D-fucopyranoside) -butyric acid ethyl ester;   52. 3-methyl-4- (C-α-D-fucopyranoside) -butyric acid ethyl ester; 53. 3-methyl-4- (C- (3-L-fucopyranoside) -butyric acid ethyl ester;   54. 3-methyl-4- (C-α-L-fucopyranoside) -butyric acid ethyl ester;   55. 6- (C- (3-D-fucopyranoside) -5-keto hexanoic acid;   56. 6- (C-α-D-fucopyranoside) -5-keto hexanoic acid;   57. 6- (C- (3-L-fucopyranoside) -5-keto hexanoic acid;   58. 6- (C-α-L-fucopyranoside) -5-keto hexanoic acid;   59. 6- (C- (3-D-fucopyranoside) -5-hydroxy-hexanoic acid;   60. 6- (C-α-D-fucopyranoside) -5-hydroxy-hexanoic acid;   61. 6- (C- (3-L-fucopyranoside) -5-hydroxy-hexanoic acid;   62. 6- (C-α-L-fucopyranoside) -5-hydroxy-hexanoic acid;   63. 6- (C- (3-D-fucopyranoside) -5-aminohexanoic acid;   64. 6- (C-α-D-fucopyranoside) -5-aminohexanoic acid;   65. 6- (C- (3-L-fucopyranoside) -5-aminohexanoic acid;   66. 6- (C-α-L-fucopyranoside) -5-aminohexanoic acid;   67. 1- (C- (3-D-fucopyranoside) -hexane-2,6-diol;   68. 1- (C-α-D-fucopyranoside) -hexane-2,6-diol;   69. 1- (C- (3-L-fucopyranoside) -hexane-2,6-diol;   70. 1- (C-α-L-fucopyranoside) -hexane-2,6-diol;   71. 5- (C- (3-D-fucopyranoside) -4-keto-pentanoic acid;   72. 5- (C-α-D-fucopyranoside) -4-keto-pentanoic acid;   73. 5- (C- (3-L-fucopyranoside) -hexane-2,6-diol) -4-keto-pentanoic acid;   74. 5- (C-α-L-fucopyranoside) -hexane-2,6-diol) -4-keto-pentanoic acid;   75. 5- (C- (3-D-fucopyranoside) -4-hydroxy-pentanoic acid;   76. 5- (C-α-D-fucopyranoside) -4-hydroxy-pentanoic acid;   77. 5- (C- (3-L-fucopyranoside) -4-hydroxy-pentanoic acid;   78. 5- (C-α-L-fucopyranoside) -4-hydroxy-pentanoic acid;   79. 5- (C- (3-D-fucopyranoside) -4-amino-pentanoic acid;   80. 5- (C-α-D-fucopyranoside) -4-amino-pentanoic acid   81. 5- (C- (3-L-fucopyranoside) -4-amino-pentanoic acid;   82. 5- (C-α-L-fucopyranoside) -4-amino-pentanoic acid;   83. 1- (C- (3-D-fucopyranoside) -pentane-2,5-diol;   84. 1- (C-α-D-fucopyranoside) -pentane-2,5-diol;   85. 1- (C- (3-L-fucopyranoside) -pentane-2,5-diol;   86. 1- (C-α-L-fucopyranoside) -pentane-2,5-diol;   87. 1- (C-13-D-Glucopyranosyl) -2-hydroxylpropane;   88. 1- (C-α-D-Glucopyranosyl) -2-hydroxylpropane;   89. 1- (C- (3-D-Glucopyranosyl) -2-amino-propane;   90. 1- (C-α-D-Glucopyranosyl) -2-amino-propane;   91. 1- (C- (3-D-Glucopyranosyl) -2-phenylamino propane;   92. 1- (C-α-D-Glucopyranosyl) -2-phenylamino propane; 93. 3-methyl-4- (C- (3-D-Glucopyranosyl) -butyric acid ethyl ester;   94. 3-methyl-4- (C-α-D-Glucopyranosyl) -butyric acid ethyl ester;   95. 6- (C- (3-D-Glucopyranosyl) -5-keto hexanoic acid;   96. 6- (C-α-D-Glucopyranosyl) -5-keto hexanoic acid;   97. 6- (C- (3-D-Glucopyranosyl) -5-hydroxy-hexanoic acid;   98. 6- (C-α-D-Glucopyranosyl) -5-hydroxy-hexanoic acid;   99. 6- (C- (3-D-Glucopyranosyl) -5-aminohexanoic acid;   6- (C-α-D-Glucopyranosyl) -5-aminohexanoic acid;   101. 6- (C- (3-D-Glucopyranosyl) -5-phenylamino-hexanoic acid;   102. 6- (C-α-D-Glucopyranosyl) -5-phenylamino-hexanoic acid;   103. 1- (C- (3-D-Glucopyranosyl) hexane-2,6-diol;   104. 1- (C-α-D-Glucopyranosyl) -hexane-2,6-diol;   105. 6- (C- (3-D-Glucopyranosyl) -5-keto-pentanoic acid;   106. 6- (C-α-D-Glucopyranosyl) -5-keto-pentanoic acid;   107. 6- (C- (3-D-Glucopyranosyl) -5-hydroxy-pentanoic acid;   108. 6- (C-α-D-Glucopyranosyl) -5-hydroxy-pentanoic acid;   109. 6- (C- (3-D-Glucopyranosyl) -5-amino-pentanoic acid;   110. 6- (C-α-D-Glucopyranosyl) -5-hydroxy-pentanoic acid;   111. 6- (C- (3-D-Glucopyranosyl) -5-phenylaminopentanoic acid;   112. 6- (C-α-D-Glucopyranosyl) -5-phenylaminopentanoic acid;   113. 1- (C- (3-D-Glucopyranosyl) -pentane-2,6-diol;   114. 1- (C-α-D-Glucopyranosyl) -pentane-2,6-diol;   115. 1- (C- (3-D-galactopyranosyl) -2-hydroxylpropane;   116. 1- (C-α-D-galactopyranosyl) -2-hydroxylpropane;   117. 1- (C- (3-D-galactopyranosyl) -2-amino-propane;   118. 1- (C-α-D-galactopyranosyl) -2-amino-propane;   119. 1- (C- (3-D-galactopyranosyl) -2-phenylamino propane;   120. 1- (C-α-D-galactopyranosyl) -2-phenylamino propane; 121. 3-methyl-4 - ((3-D-galactopyranosyl) -butyric acid ethyl ester; 122. 3-methyl-4- (α-D-galactopyranosyl) -butyric acid ethyl ester;   123. 6- (C- (3-D-galactopyranosyl) -5-keto hexanoic acid;   124. 6- (C-α-D-galactopyranosyl) -5-keto hexanoic acid;   125. 6- (C- (3-D-galactopyranosyl) -5-hydroxy-hexanoic acid;   126. 6- (C-α-D-galactopyranosyl) -5-hydroxy-hexanoic acid;   127. 6- (C- (3-D-galactopyranosyl) -5-aminohexanoic acid;   128. 6- (C-α-D-galactopyranosyl) -5-aminohexanoic acid;   129. 6- (C- (3-D-galactopyranosyl) 5-phenylaminohexanoic acid;   130. 6- (C-α-D-galactopyranosyl) 5-phenylaminohexanoic acid;   131. 1- (C- (3-D-galactopyranosyl) hexane-2,6-diol;   132. 1- (C-α-D-galactopyranosyl) -hexane-2,6-diol;   133. 6- (C- (3-D-galactopyranosyl) -5-keto-pentanoic acid;   134. 6- (C-α-D-galactopyranosyl) -5-keto-pentanoic acid;   135. 6- (C- (3-D-galactopyranosyl) -5-hydroxy-pentanoic acid;   136. 6- (C-α-D-galactopyranosyl) -5-hydroxy-pentanoic acid;   137. 6- (C- (3-D-galactopyranosyl) -5-amino-pentanoic acid;   138. 6- (C-α-D-galactopyranosyl) -5-amino-pentanoic acid;   139. 6- (C- (3-D-galactopyranosyl) -5-phenylaminopentanoic acid;   140. 6- (C-α-D-galactopyranosyl) -5-phenylaminopentanoic acid;   141. 1- (C- (3-D-galactopyranosyl) -pentane-2,6-diol;   142. 1- (C-α-D-galactopyranosyl) -pentane-2,6-diol;   143. 1- (C- (3-D-fucofuranosyl) propan-2-one;   144. 1- (C-α-D-fucofuranosyl) propan-2-one;   145. 1- (C-13-L-fucofuranosyl) propan-2-one;   1-6. (1- (L-fucofuranosyl) propan-2-one;   147. 3 '- (acetamido-C- (3-D-glucopyranosyl) propan-2'-one;   148. 3 '- (acetamido-C-α-D-glucopyranosyl) propan-2'-one;   149. 1- (C- (3-D-galactopyranosyl) -2-hydroxylpropane;   150. 1- (C-α-D-galactopyranosyl) -2-amino-propane;   151. 1- (acetamido-C- (3-D-glucopyranosyl) -2-phenylamino propane;   152. 1- (acetamido-C-α-D-glucopyranosyl) -2-phenylaminopropane; 153. 3-methyl-4- (acetamido-C- (3-D-glucopyranosyl) -butyric acid ethyl ester; 154. 3-methyl-4- (acetamido-C-α-D-glucopyranosyl) -butyric acid ethyl ester;   155. 6- (acetamido-C- (3-D-glucopyranosyl) -5-keto hexanoic acid;   156. 6- (acetamido-C-α-D-glucopyranosyl) -5-keto hexanoic acid;   157. 6- (acetamido-C- (3-D-glucopyranosyl) -5-hydroxy-hexanoic acid;   158. 6- (acetamido-C-α-D-glucopyranosyl) -5-hydroxy-hexanoic acid;   159. 6- (acetamido-C- (3-D-glucopyranosyl) -5-aminohexanoic acid;   160. 6- (acetamido-C-α-D-glucopyranosyl) -5-aminohexanoic acid;   161. 6- (acetamido-C- (3-D-glucopyranosyl) 5-phenylamino-hexanoic acid;   162. 6- (acetamido-C-α-D-glucopyranosyl) 5-phenylaminohexanoic acid;   163. 1- (acetamido-C- (3-D-glucopyranosyl) hexane-2,6-diol;   164. 1- (acetamido-C-α-D-glucopyranosyl) hexane-2,6-diol;   165. 6- (acetamido-C- (3-D-glucopyranosyl) -5-keto-pentanoic acid;   166. 6- (acetamido-C-α-D-glucopyranosyl) -5-keto-pentanoic acid;   167. 6- (acetamido-C- (3-D-glucopyranosyl) -5-hydroxypentanoic acid;   168. 6- (acetamido-C-α-D-glucopyranosyl) -5-hydroxypentanoic acid;   169. 6- (acetamido-C- (3-D-glucopyranosyl) -5-aminopentanoic acid;   170. 6- (acetamido-C-α-D-glucopyranosyl) -5-aminopentanoic acid;   171. 6- (acetamido-C- (3-D-glucopyranosyl) -5-phenylaminopentanoic acid;   172. 6- (acetamido-C-α-D-glucopyranosyl) -5-phenylaminopentanoic acid;   173. 1- (acetamido-C- (3-D-glucopyranosyl) -pentane-2,6-diol;   174. 1- (acetamido-C-α-D-glucopyranosyl) -pentane-2,6-diol. 8. Use according to any one of the preceding claims, characterized in that said derivative is used in an amount representing from 0.0001% to 25% of the total weight of the composition. 9. Use according to claim 8, characterized in that said derivative is used in an amount representing from 0.001% to 10% of the total weight of the composition. 10. Use according to any one of the preceding claims, characterized in that said C-glycoside derivative is associated with at least one depigmenting agent and / or at least one organic photoprotective agent and / or at least one inorganic photoprotective agent. Cosmetic method for bleaching the skin and / or the scalp and / or the mucous membranes, comprising ingestion or application to the skin and / or the scalp and / or the mucous membranes of at least one C-glycoside compound responding in the formula (I) as defined in any one of the preceding claims.