EP0998264A1

EP0998264A1 - Composition comprising a lipoaminoacid and a tannin-rich plant extract

Info

Publication number: EP0998264A1
Application number: EP98933685A
Authority: EP
Inventors: Corine Stoltz
Original assignee: Societe dExploitation de Produits pour les Industries Chimiques SEPPIC SA
Current assignee: Societe dExploitation de Produits pour les Industries Chimiques SEPPIC SA
Priority date: 1997-06-25
Filing date: 1998-06-23
Publication date: 2000-05-10
Also published as: WO1999000109A1; JP2002507207A; FR2765109B1; FR2765109A1; US20010002257A1

Abstract

The invention concerns a composition characterised in that it comprises as active principle, at least a compound of formula (I) or its topically acceptable salts, in which: R represents the characterising chain of a fatty acid, saturated or unsaturated, linear or branched, containing 3 to 30 carbon atoms; R1 represents a characterising chain of an aminoacid and m ranges between 1 and 5, and the constituents of at least one extract and/or of at least one dye of plant raw materials rich in tannins (II). The invention is applicable in cosmetics.

Description

COMPOSITION COMPRISING ACID LIPOAMINO AND TANNIN-RICH PLANT EXTRACT

The present invention relates to a new cosmetic composition of compounds with a lipoamino acid structure, with germicidal activity.

Most skin-related problems such as dandruff, blackheads, cysts, "blackheads", or any other manifestation affecting the aesthetics of the human body, are related to the presence of bacterial germs which, in particular due to of their enzymes, induce a reaction thereof such as for example, inflammation.

Among these skin problems, mention may be made of acne, which is a frequent skin condition affecting, as of the filing date of this patent application, approximately five million people in this country; the most common form is juvenile polymorphic acne, which appears at puberty. Acne is triggered in the pilosebaceous follicle by simultaneously causing hyper keratinization of the pilosebaceous canal, sebaceous hypersecretion as well as bacterial proliferation in the pilosebaceous follicle

The hyper keratinization of the pilosebaceous canal leads to its obstruction, which in turn favors the implantation of a germ frequently found in this pathology: Propionibacterium acnes.

Sebaceous hypersecretion is a constant factor during acne; it comes from an increased sensitivity of the sebaceous gland to androgens, which leads to greater secretion of sebum. Due to the hyper keratinization of the pilosebaceous canal, the elimination of sebum is hindered, even prevented, and this induces the formation of closed comedones and microcysts. The sebum thus accumulated in a follicle then becomes a place of bacterial proliferation. The sebum, rich in triglycerides, is then very quickly degraded into free fatty acids (GLA) by lipases from bacterial germs. The free fatty acids thus formed oxidize on contact with oxygen in the air, in particular into peroxides, which maintain, or even aggravate, local inflammation. Whether on healthy or acne-prone skin, the bacterial flora found on the surface or inside the comedones is qualitatively the same: they are yeasts such as Pityrosporum ovale and Pityrosporum orbiculare , staphylococci such as Staphylococus epidermis, Staphylococus capitis or Staphylococus hominis or of propionibacteria such as Propionibacterium acnes.

Propionibacterium acnes produces lipases which are capable of hydrolyzing the triglycerides of sebum into free fatty acids. Free fatty acids are known to be comedogenic, that is, they can cause follicular hyperkeratosis. Thus, colonization of the follicle by these bacteria determines another source of comedogenic material which, subsequently, will cause the development of micro-comedones. Propionibacterium acnes is also responsible for the accumulation of neutrophilic leukocytes and indirectly of mononuclear lymphocytes, thus leading to the development of inflammation and the activation of an immune response.

The previously named staphylococci colonize both healthy skin and acne lesions, in which they are encountered with a frequency comparable to that of Propionibacterium acnes: 70 to 75% of comedones are colonized, either by staphyloccocci, or by propionibacteria with average 10 ⁴ to 10 ⁵ bacteria per blackhead. The fact that the comedones are open (black dots) or closed (microcysts) does not seem to have a qualitative influence on the proliferation of these two types of bacteria. Staphylococus epidermis secretes Pelastase, responsible for lesions of perifollicular elastolysis.

Pityrosporum, such as those previously named, are present in quantities of the same order as staphylococci or as propionibacteria; although aerobic, they can be found in the deep layers of the follicle as well as in closed comedones.

The Applicant has therefore sought to develop a composition effective against the harmful effects caused by the germs present on the skin and in particular against the harmful effects caused by the enzymes which maintain and develop the inflammatory process.

Compounds with a lipoamino acid structure, such as for example those described in the international patent applications published under the numbers WO92 / 20647, WO92 / 21318, WO94 / 26694 and WO94 / 27561, are, because of their amphiphilic structure, particularly biological vectors interesting as regulators of skin physiology and prove to be suitable for multiple applications, in particular in cosmetics. However, the Applicant has found that the compositions comprising as active principles, the association of lipoaminacids with certain natural plant extracts, possessed both a germicidal and antimicrobial activity on the one hand and an anti-microbial activity on the other hand inflammatory by inhibiting lipases, 5-alpha-reductase, responsible in particular for the production of sebum and by inhibiting elastase. The Applicant has also found that this activity is the result of the synergy between these two families of active principles.

The subject of the invention is a composition characterized in that it comprises, as active principle, at least one compound of formula (I):

R— CO— (NH— CH— CO) _m - O— H (I)

or its topically acceptable salts, in which R represents the characterizing chain of a fatty acid, saturated or unsaturated, linear or branched, comprising from 3 to 30 carbon atoms, Ri represents a characterizing chain of an amino acid and m is included between 1 and 5, and the constituents of at least one extract and / or at least one tincture of vegetable raw materials rich in tannins (II). The term “topically acceptable salt” means any salt of the acid of formula (I) which is biologically acceptable for the skin and / or the mucous membranes, ie any salt which can in particular adjust the pH of the composition to a value between 3 and 8 and preferably approximately equal to 5, that is to say at a pH close to that of the skin

They may especially be alkaline salts such as the sodium, potassium or lithium salts, alkaline earth salts such as the calcium, magnesium or strontium salts; it can also be metallic salts such as divalent zinc or manganese salts or also trivalent salts of iron, lanthanum, cerium or aluminum.

The compound of formula (I) present in the composition which is the subject of the present invention, may be in the form of free acid or in the form of partially or totally salified.

The expression “characterizing chain” used within the framework of the present application designates the non-functional main chain of the fatty acid or of the amino acid considered. Thus, for a fatty acid corresponding to the general formula R-COOH, the characterizing chain will be the chain represented by R.

The radical R represents in particular a radical comprising from 5 to 22 carbon atoms chosen from the pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl radicals , unicosyle, docosyle, heptadécènyle, eicosènyle, uneicosènyle, docosènyle ou heptadécadiènyle ou décènyle.

A more particular subject of the invention is the composition as described above for which, in formula (I), the R - CO fragment contains from 7 to 22 carbon atoms and represents in particular one of the hexanoyl, heptanoyl and octanoyl radicals (capryloyl), decanoyl (caproyl), undecylenoyl, dodecanoyl (lauroyl), tetradecanoyl (myristyle), hexadecanoyl (palmitoyle), octadecanoyl (stearyl), eicosanoyle (arachidoyle), docosanoyle (behenoyoy) (behenoyl) , docosènoyl (erucyle), octadécadiènoyl (linolènoyl). In a first preferred variant of the present invention, in formula (I), the R-CO fragment (I) contains from 7 to 12 carbon atoms.

For an amino acid represented by the general formula

H2N-CHR1.-COOH, the characterizing chain will be the chain represented by Ri.

Ri represents in particular the characterizing chain of one of the amino acids chosen from glycine, alanine, serine, aspartic acid, glutamic acid, valine, threonine, arginine, lysine, proline, leucine, phenylalanine, isoleucine, histidine, tyrosine, tryptophan, asparagine, cysteine, cystine, methionine, hydroxyproline, hydroxylysine and ornithine.

A more particular subject of the invention is the composition as described above for which, in formula (I), R 1 represents the characterizing chain of glycine, alanine, glutamic acid or aspartic acid.

By at least one compound of formula (I), it is indicated that the composition according to the invention can contain one or more of these compounds.

In the definition of the composition which is the subject of the present invention, the words extract and tincture are used in their respective meanings as established in the 1997 edition of the European Pharmacopoeia; extracts (extracts) are concentrated preparations, liquids, solids or of intermediate consistency, generally obtained from dried vegetable or animal raw materials. Tinctures (tincturae) are preparations generally obtained from dried vegetable or animal raw materials.

By extracts or tinctures of vegetable raw materials rich in tannins, is meant in particular extracts or tinctures of rathania, tea, cinnamon, willow or witch hazel. These extracts or tinctures are commercially available. Some are registered in the French and / or European pharmacopoeias.

A more particular subject of the invention is the composition as described above in which the extract or tincture of vegetable raw materials rich in tannins is a cinnamon extract; The compounds of formula (I) are generally obtained by acylation of compounds of formula (F)

H— {NH— CH— CO) _m - O— H (F)

or their salts, themselves obtained by total or partial hydrolysis of proteins of all origins. These proteins can be of animal origin, such as, for example, collagen, elastin, fish flesh protein, fish gelatin, keratin or casein, of vegetable origin, such as, for example , those from soy, sunflower, oats, wheat, corn, barley, potato, lupine, horse bean, sweet almond, silk, or obtained from chorelles (unicellular algae), pink algae or yeast.

This hydrolysis can be carried out, for example, by heating at a temperature between 60 and 130 ° C. a protein placed in an acidic or alkaline medium.

This hydrolysis can also be carried out enzymatically with a protease, optionally coupled to an alkaline or acid post-hydrolysis.

When m is greater than 1, Ri represents several of the characterizing chains of amino acids, depending on the hydrolyzed protein and the degree of hydrolysis. In a preferred variant of the present invention, when the composition comprises only one compound of formula (I), m is equal to 1 and when the composition comprises a mixture of compounds of formula (I), the average degree of condensation of N-acylated amino acids in this mixture is less than 2. The acylation reaction allowing the abovementioned compounds of formula (I) to be obtained can be carried out chemically in an alkaline medium (pH 8 to 10) according to the reaction of

Schotten Bauman or by an enzymatic route and a person skilled in the art may refer in particular to the reference Surfactant Science Series, volume 7, Anionic Surfactants, part II, chapter 16, pages 581 to 617 (Marcel Dekker - 1976).

In general, the currently preferred embodiment for the preparation of the lipoamino acid compounds of formula (I) comprises the following steps: a) Acylation in an alkaline medium (pH 8 to 10) of an excess mixture of amino acids (mixture extemporaneous or obtained by complete hydrolysis of a protein) with a fatty acid (or a mixture of fatty acids), in the form of acid chloride or anhydride.

The amino acid / acid chloride ratio is preferably 1.05 to 1.30 equivalents.

The optimal acylation temperature is around 80 ° C but varies from one amino acid to another between 60 and 110 ° C. The duration of acylation depends on the equipment used (size, stirring); it is approximately 2 hours for an acylated mass of 500 kg and approximately 5 hours for an acylated mass of 5,000 kg. b) Breakage of the alkaline acylate by acidification to decant the water-soluble impurities and release the organic acid acylate (optimum pH 0.5 to 3 depending on the amino acids). c) Purification by washing with water or with the addition of electrolytes or co-solvent to promote decantation.

In addition to the active principles, the composition according to the invention comprises mineral or organic vehicles commonly used in the manufacture of compositions intended to be formulated in preparations for cosmetic and / or pharmaceutical use; mention may, for example, be made of water, propylene glycol, butylene glycol, hexylene glycol or glycerin.

The composition - according to the invention can also comprise one or more neutralization bases commonly used in the manufacture of cosmetic products; these are for example tris (tri shydroxyamino methane), triethylamine, lysine or methyl glycine.

In a preferred aspect of the present invention, the composition as described above comprises from 15% to 60% and, more particularly, from 20% to 40% by weight of at least one compound of formula (I) in which the fragment R -CO includes 7 to 12 carbon atoms, or its topically acceptable salts, and from 0.1% to 10% by weight and, more particularly, from 0.5% to 5% by weight of constituents of at least one extract and / or a tincture of vegetable raw materials rich in tannins.

According to the European Pharmacopoeia, the extracts can be in the form of fluid extracts, soft or firm extracts or dry extracts.

In the preceding definition of the composition according to the invention, the percentages by weight of constituents of the extract or of the dye correspond to the percentages by weight of dry residue, said dry residue being obtained by evaporation of the solvent and drying of said extract or of said dye under operating conditions in which the alteration of the constituents is minimal.

The composition as defined above especially comprises from 20% to 40% by weight of a compound of formula (I) in which Rj. represents a hydrogen atom, the R-CO fragment represents an octanoyl radical and m is equal to 1 and from 0.50% to 5% by weight of constituents of a cinnamon extract. As cinnamon, there is for example cinnamon from Ceylon cinnamon

(Cinnamomun zeylanicum).

The composition according to the invention can also comprise from 0.1% to 10% by weight of magnesium and potassium aspartate.

In a preferred aspect of the present invention, the composition as described above comprises from 4% to 20% of lauroyl glutamic acid, from 4% to 20% of lauroyl aspartic acid, from 2% to 8% of lauroyl glycine and from 2% to 8% of lauroyl alanine, from 0.5% to 5% by weight of constituents of a cinnamon extract and from 0.5% to 5% of mixed magnesium and potassium aspartate.

In another preferred aspect of the present invention, the composition as described above further comprises from 0.1% to 10% by weight of zinc gluconate.

The composition which is the subject of the present invention is prepared by methods known to those skilled in the art. In general, there is introduced with stirring, into a composition comprising at least one compound of formula (I), at least one extract and / or one tincture of vegetable raw materials rich in tannins, in an amount suitable for reaching the desired concentration in the solution final component of said extract and / or said tincture. If necessary, or if desired, said extract and / or said tincture are diluted before mixing. The composition according to the invention is used in cosmetics. As the following examples show, the composition according to the invention is unexpectedly characterized by a quadruple activity, anti-elastase, anti-lipase, anti-bacterial and anti-5-α-reductase. This makes it possible to use it in particular, to soothe and / or protect sensitive skin, moisturize dry skin, slow the aging of the skin and / or treat acne prone skin; in this latter indication, the composition according to the invention can be used as a complementary treatment to medical treatment of acne.

The composition according to the invention is also used for disinfecting the skin and mucous membranes. In this case it can be a simple act of personal hygiene or a complementary treatment to the medical treatment of an infection.

The composition according to the invention is also used in the treatment of the scalp, in particular as an anti-dandruff active.

These uses also constitute in themselves an object of the present invention.

Depending on the use, the composition as described above is used at different concentrations and in a formulation suitable for this use; such cosmetic compositions are usually in the form of aqueous solutions, dilute alcoholic solutions, or single or multiple emulsions, such as water in oil (W / O), oil in water (HE) or water in oil in emulsion. water (W / O / W). As cosmetic formulation, mention may be made of creams, milks, lotions, wipes, shower gels, soaps, liquid soaps, probes, intimate hygiene products or shampoos.

Such formulations are known to those skilled in the art; their preparation is described, for example, in the patent applications published under the numbers, WO92 / 06778, WO93 / 28204, WO95 / 13863, WO95 / 35089, or WO96 / 22109. The invention therefore also relates to a cosmetic formulation capable of being obtained by dilution from 1/10 to 1/20000 of the composition as described above, in one or more cosmetically acceptable excipients, and in particular a cosmetic formulation under form of an oil-in-water emulsion having the appearance of a milk having a viscosity of less than lPa.s. comprising as emulsifier a self-emulsifiable composition based on fatty alcohols.

As self-emulsifying preferred composition include MONTANOV 68 ^® marketed by Seppic. The term dilution used in the foregoing includes, in its broadest sense, all the steps making it possible to pass from the composition as defined above to the cosmetic formulation intended to be marketed.

In another preferred embodiment of the present invention, the cosmetic formulation is a lotion for treating skin prone to acne.

In another preferred embodiment of the present invention, the cosmetic formulation is a foaming formula or an anti-dandruff shampoo.

The invention particularly relates to a cosmetic formulation comprising, as active principle, from 0.001% to 6% by weight of at least one compound of formula (I) and from 0.00005%) to 1% by weight of constituents d '' at least one extract (H) and / or at least one tincture of vegetable raw materials rich in tannins chosen from cinnamon, rathania, tea, willow or witch hazel extracts. and if desired up to 1% zinc gluconate.

The invention particularly relates to a cosmetic formulation comprising as active principle from 0.5% to 2% by weight of a compound of formula (I) ι CH ₃ - (CH ₂ ) ₆ -CO-NH-CH ₂ -COOH (I) ι from 0.05% to 0.2% by weight of constituents of an extract of vegetable raw material chosen from cinnamon, rathania, tea, willow or witch hazel extracts. and if desired from 0.025% to 0.2% zinc gluconate, and a cosmetic formulation comprising as active ingredient from 0.001% to

0.005% by weight of at least one compound of formula (I) ι CH ₃ - (CH ₂ ) ₆ -CO-NH-CH ₂ -COOH (I) ι from 0.0001% to 0.005% by weight of constituents d '' an extract of vegetable raw material chosen from cinnamon, rathania, tea, willow or witch hazel extracts. and if desired from 0.0001% to 0.0005% o of zinc gluconate.

The following examples illustrate the invention without, however, limiting it.

EXAMPLES:

A) PREPARATION OF THE COMPOSITIONS ACCORDING TO THE INVENTION 1) Composition A

The following compounds are mixed with stirring:

. Lipacide ^® C8G marketed by SEPPIC, the active ingredient of which is octanoyl glycine

. butylene glycol . glycerin

. Tris (Tris hydroxymethyl aminomethane or tromethamine): sufficient quantity to obtain a pH of approximately 5.0 to 6.0;

. Sepicide ^® HB (sold by the company SEPPIC). Water.

A liquid, stable, odorless and water-soluble solution is thus obtained, the pH of which is approximately 5.6 to which is added with stirring an aqueous solution of a dry cinnamon extract marketed by the company ALBAN JvTULLER INTERNATIONAL; the mixture thus obtained is filtered on a membrane filter (approximately 3 μ) to obtain composition A containing approximately:

- 25% by weight of octanoyl glycine;

- 10% by weight of glycerin;

- 10% by weight of butylene glycol; and

- 3% by weight of constituents of the cinnamon extract.

2) Composition B a) To a mixture consisting of 27.4 kg of L-aspartic acid, 35.3 kg of L-glutamic acid, 7.9 kg of L-alanine, 7.9 kg of glycine and 112 , 5 kg of water are added 96 kg of potassium hydroxide solution (50%) in order to obtain a pH of approximately 10. A co-solvent facilitating subsequent acylation can also be added to this mixture.

The temperature of the mixture thus obtained is brought to 80 ° C., then 110 kg of lauroyl chloride are poured simultaneously with stirring. The reaction lasts 2 hours.

The “acylated mass” of 465 kg thus obtained comprises a mixture of lauroylated amino acids, free amino acids and lauric acid, these compounds being in the form of potassium salt.

The mixture of compounds with a lipoamino acid structure can be extracted from this acylated mass in a very acid medium (pH of approximately 1) and under hot conditions (90 ° C.) for example by implementing the following protocol: - adjustment of the pH to a value of 1 by adding an appropriate quantity (approximately

125 kg) 30% hydrochloric acid, at a temperature of about 80 ° C;

stirring of the mixture thus obtained for 30 minutes at 90 ° C (temperature due to exotherm); - decantation for 30 minutes (the compounds with a lipoamino acid structure remaining in the organic phase);

- withdrawal of acidic water which is rejected after neutralization to thereby eliminate the free non-acylated amino acids, the salt formed and the co-solvent; - washing the organic supernatant phase with saline water (10% NaCl);

- withdrawal of the aqueous phase;

obtaining an organic phase containing more than 70% by weight of the following mixture of compounds with a lipoamino acid structure of formula (I):

. 27% lauroyl glutamic acid. Lauroyl aspartic acid 30%

. Lauroyl glycine acid 6%. 8% lauroyl alanine acid as well as reaction residues, in particular:. Lauric acid 15%. Water 10%

. 1% sodium chloride. Co-solvent (propylene glycol) 3% b) At 155 kg of the organic phase obtained in Example 1, the following compounds are added with stirring:. Propylene glycol: 100 kg;

. Tris (Tris hydroxymethyl aminomethane or tromethamine): sufficient quantity to obtain a pH of approximately 5.0 to 6.0; . Sepicide® HB: 2 kg; . Water: 200 kg. . Mixed potassium and magnesium aspartate: 5 kg;

The mixture thus obtained is filtered on a pocket filter (approximately 3 μ). A liquid, stable, odorless and water-soluble solution is thus obtained, the pH of which is approximately 5.7 to which an aqueous solution of a cinnamon extract is added to obtain composition B containing approximately: - 25% by weight of the mixture of products of formula (I)

- 3% by weight of active ingredient, cinnamon extract

- 1.25% by weight of magnesium and potassium aspartate. The following compositions were also prepared:

B) EVIDENCE OF THE ANTI-ELASTASE PROPERTIES OF THE COMPOSITIONS ACCORDING TO THE INVENTION a) Principle of the test:

We know that human leukocyte elastase (ELH) is involved in a large number of inflammatory pathologies. This enzyme is in particular capable of degrading many macromolecules such as fibrous elastin, certain types of collagen, proteoglycans, glycoproteins.

For this reason, human leukocyte elastase is one of the links in the chain of reactions accompanying an inflammation phenomenon.

The blocking of this enzyme by an anti-elastase effect therefore makes it possible to prevent the degradation of the aforementioned molecules and therefore to inhibit the process of inflammation. The anti-elastatic properties of a given product can be demonstrated by an in vitro test, carried out with a spectrophotometer, using a support substance capable of degrading by coloring, in contact with human leukocyte elastase.

Such a substance can be for example N-methoxysuccinyl-alanine-proline-valine-para-nitroanilide, normally colorless substance which releases, by hydrolysis by human leukocyte elastase, a colored product, para-nitroaniline, whose kinetics d appearance can be followed by spectrophotometry at 410 nm.

The reaction is carried out in a spectrophotometer thermostatically controlled at 25 ° C., having a sample changer. All the kinetics are carried out at least three times, the mean and the standard deviation then being calculated for the three values obtained. The presence of a molecule with anti-elastatic activity results in a limitation of the appearance of the colored product and the anti-elastatic effect can then be calculated relative to a control curve obtained in the absence of said molecule.

There is thus a correlation between the percentage of inhibition of the appearance of the colored product by the test compound and the percentage of inhibition of human leukocyte elastase.

The percentage of inhibition thus calculated is also representative of the soothing activity of the test compound, b) Results obtained

Compositions A and H are diluted in water to get Ai compositions, _A. , A ₃ , Hi, H ₂ and H ₃ having the following active ingredient concentrations:

The elastase inhibition percentages are as follows

These results show that at concentrations for which the C8G lipid has no elastase inhibiting activity, and for which cinnamon has limited activity (from 33% to 60%); the combination of the two unexpectedly exhibits superior activity.

C) EVIDENCE OF THE ANTI-5α-REDUCTASE PROPERTIES OF THE COMPOSITIONS ACCORDING TO THE INVENTION.

a) Principle of the test

Enzymes of the 5-alpha-reductase type transform testosterone into 5-dehydrotestosterone (5-HT). The activity of 5-alpha-reductase is important on the skin, in the perineal areas. It is present in the sebaceous glands and the apocrine glands (sweat), in keratinocytes and fibroblasts. The carbon-14 testosterone is incubated in the presence of microsomes of human skin, prepared according to the method described by VOIGT et al. (1970) J. Biol. Chem., 245, 5594-5599, in the absence and in the presence of the test compound or in the presence of finasteride, used as a reference inhibitor molecule.

After extraction and drying of the steroids, chromatography and quantification of the NADPH-dependent transformation of ¹⁴ C testosterone, the results of the tests are expressed as a percentage inhibition of the 5-alpha-reductase activity. b) results

By carrying out this test with a composition according to the invention containing C8G lipid and a cinnamon extract, a synergy was observed between these two products. By carrying out this test with a combination of C8G lipacid and zinc gluconate, a synergy inherent in the combination of these two compounds for this activity has also been observed.

For this activity, it is therefore advantageous to combine the compounds of formula (I) with extracts of vegetable raw materials rich in tannins and / or zinc gluconate. D) EVIDENCE OF THE ANTI-LIPASE ACTIVITY OF THE COMPOSITIONS ACCORDING TO THE INVENTION.

a) Principle of the test

This is the dosage of free fatty acids obtained by degradation of triglycerides by lipase.

In a tube, a known quantity of triglycerides (“Lipase Substrate” sold by the company SIGMA), a known quantity of lipase (“Enzyme Control 2E” sold by the company SIGMA) are brought into contact with the composition to be tested. After an incubation period of three hours at 37 ° C., the enzymatic reaction is stopped and the free fatty acids formed are assayed by titration with 0.05 M sodium hydroxide. The results are expressed as a percentage of inhibition of the enzyme by the composition considered by comparing it with a control test. b results

Composition A was diluted ^1/15 in water to obtain composition A ₄ having the following active ingredient concentrations:. octanoyl glycine: 1.6%. cinnamon extract: 0.19%. While 1.6% octanoyl glycine leads to a 44% inhibition percentage

% and that the 0.19% cinnamon extract leads to a percentage inhibition of 16%, composition A4 leads to a percentage inhibition of 71%, while the simple addition of the effects would give 60% inhibition.

This clearly demonstrates the synergy existing between the two active ingredients. It was found that under the same operating conditions, a 0.13% solution of zinc gluconate leads to a percentage inhibition of 40% and that the combination octanoylglycine (1.6%) zinc gluconate (0.13% ) leads to a percentage inhibition of 95%.

This test shows the advantage that there are, in using compositions according to the invention containing both compounds of formula (I), extracts of vegetable raw materials rich in tannins and / or zinc gluconate. E) EVIDENCE OF ANTI-MICROBIAL ACTIVITY ACCORDING TO THE INVENTION a) The minimum inhibitory concentration at pH5 in composition according to the invention of the growth of the following strains was determined:

- Propionibacterium acnes

- Staphylococcus aureus

- Staphylococcus epidermis.

The following results are obtained:

These results show a synergy of the antimicrobial activity inherent in the combination of products (I) and (II). b) The minimum inhibitory concentration at pH5 of the growth of the same strains was determined for an octanoyl glycine + zinc gluconate combination.

The following results are obtained:

These results show a synergy of the antimicrobial activity inherent in the combination of products (I) + (lu).

These tests show the advantage that there is in combining in the same formulation a product of formula (I) and an extract of vegetable raw materials rich in tannins and / or zinc gluconate.

F) PREPARATION OF COSMETIC FORMULATIONS Example 1: Care for oily and acne-prone skin. FORMULA

A MONT NOV ^® 202 3.00%

(Arachidyl behenyl alcohols & Arachidylglucoside - SEPPIC)

B Water q.s.p l00% Composition A 4.00%

C Dimethicone 4.00%

Isohexadecane 8.00%

D SEPIGEL ^® 305) 2.00%

(Polyacrylamide / C13-14 isoparaffin / Laureth-7- SEPPIC

E SEPICIDE ^® HB 0.50%

(Phenoxyethanol / Methylparaben / Ethylparaben / Propylparaben / Butylparaben SEPPIC)

Perfume 0.20%

Procedure: Heat phase B to 85 ° C. Add MONTANOV ^® 202 (scales) and stir until it is completely melted. Add phase C without heating it beforehand. Homogenize with the foam concentrate. Start cooling very slowly. At 70 ° C, introduce SEPIGEL. At 60 ° C stop the foam concentrate, evacuate and continue cooling with slow stirring. At around 30 ° C, introduce the constituents of phase E. Example 2: Anti-shine cream gel for oily or combination skin FORMULA:

A SEPIGEL ^® 305 3.50% (Polyacrylamide / C13-14 isoparaffin / Laureth7 - SEPPIC)

PELEMOL ^® 89 (Octyl isononanoate - PHOENIX) 5.00%

MICROPEARL ^® M305 1.00%

((crosslinked polymethyl methacrylate - SEPPIC) Water q.s..p l00%

B Composition A 4.00%

SEPICIDE ^® HB 0.30% (Phenoxyethanol / Methylparaben / Ethylparaben / Propylparaben / Butylparaben SEPPIC)

SEPICIDE ^® CI 0.20%

(Imidazolidinyl urea - SEPPIC)

Perfume 0.10%

C CAPIGEL ^® 98 1.00%

(Acrylates copolymer - SEPPIC) Water 10.00%

Procedure: Introduce the MICROPEARL ^® M305 into the PELEMOL ^® , add the SEPIGEL ^® 305 then mount the gel with water. Then add the composition A and then all other components of Phase B. Add the Capigel ^® 98 previously diluted with water. Adjust the pH to around 7.

Example 3: Purifying cleanser for oily skin prone to acne FORMULA

Water q.s.p 100%

METOLOSE ^® 65SH4000 1.00%

(hydroxypropyl methylcellulose - SEPPIC) NACRANT BASE 9578 10.00% (Sodium laureth sulfate / Cocamide DEA / Glycol Stearate - SEPPIC) PROTEOL ^® OAT

(Sodium lauroyl oat aminoacids - SEPPIC)

Composition A 2.00% CAPIGEL ^® 98 2.00%

(Acrylates copolymer - SEPPIC)

Water 10.00%

Perfume 0.20%

SEPICIDE ^® HB 0.20% (Thenoxyethanol / Methylparaben / Ethylparaben / Propylparaben / Butylparaben -

SEPPIC)

Trometamol qs pH 7.2

Procedure: Disperse METOLOSE in hot water around 70 - 75 ° C and allow to cool. At around 30 ° C., add, with stirring, the pearly base, the OAT proteol and then composition A. Then add the acrylate copolymer previously dispersed in 10% water. Shake then introduce the perfume and the preservative. Neutralize the formula at the desired pH.

Example 4: Moisturizing cream for greasy skin FORMULA Montanov 68 ^® 5% cétylstéaryloctanoate: 8%

Composition A 2 to 4%

Water q.s.p 100%

Compound of Example 1: 0.6% MICROPEARL ^® Ml 00: 3.0%

Mucopolysaccharides 5%

SEPICIDE ^® HB 0.8%

Perfume 0.3%

EXAMPLE 5 Alleviating After-Shave Balm Without Alcohol

FORMULA

Composition A 2 to 4%

LANOL ^® 99 2% sweet almond oil 0.5%) water qs 100% compound of Example 1: 3%

SEPICIDE ^® HB 0.3%

SEPICIDE ^® CI 0.2% perfume 0.4%

(LANOL 99 is isononyl isononanoate marketed by the company SEPPIC)

EXAMPLE 6 AHA Cream for Sensitive Skin FORMULA

Composition A 2% _> magnesium and potassium aspartate 0.002% to 0.5%

LANOL ^® 99 2%

MONTANOV ^® 68 5.0% water qs 100% compound of Example 1 1.50% triethylamine 0.9%

SEPICIDE ^® HB 0.3%

SEPICIDE ^® CI 0.2% perfume 0.4%

Claims

1. Composition characterized in that it comprises, as active principle, at least one compound of formula (I):

R— CO— (NH— CH— CO) _m - O— H (I)

or its topically acceptable salts, in which R represents the characterizing chain of a fatty acid, saturated or unsaturated, linear or branched, comprising from 3 to 30 carbon atoms, Ri represents a characterizing chain of an amino acid and m is included between 1 and 5, and the constituents of at least one extract and / or at least one tincture of vegetable raw materials rich in tannins (II).

2. Composition as defined in claim 1, for which, in formula (I), the R - CO fragment contains from 7 to 22 carbon atoms and represents in particular one of the hexanoyl, heptanoyl, octanoyl (capryloyl) radicals , decanoyl (caproyl), undecylenoyl, dodecanoyl (lauroyl), tetradecanoyl (myristyle), hexadecanoyl (palmitoyl), octadecanoyl (steary), eicosanoyle (dochenoyle (behenenoyle), octosoloyl) erucyle), octadecadienoyl (linolenic).

3. Composition as defined in any one of claims 1 or 2, for which, in formula (I), the R-CO fragment (I) contains from 7 to 12 carbon atoms.

4. Composition defined in any one of claims 1 to 3, for which, in formula (I), Rj _. represents the characterizing chain of glycine, alanine, glutamic acid or aspartic acid.

5. Composition as defined in any one of claims 1 to 4, in which the extract and / or the tincture of vegetable raw materials rich in tannins is chosen from extracts of rathania, tea, cinnamon, willows , witch hazel

6. Composition as defined in any one of claims 1 to 5 in which the extract and / or the tincture of vegetable raw materials rich in tannins is a cinnamon extract.

7. Composition as defined in any one of claims 1 to 6, characterized in that when the composition comprises only one compound of formula (I), m is equal to 1 and when the composition comprises a mixture of compounds of formula (I), the average degree of condensation of the N-acylated amino acids in this mixture is less than 2.

8. Composition as defined in claim 3, comprising from 15% to 60% by weight of at least one compound of formula (I) or one of its topically acceptable salts thereof, and from 0.1% to 10% by weight. weight of constituents of at least one extract and / or tincture of vegetable raw materials rich in tannins.

9. Composition as defined in claim 8, comprising from 20% to 40% by weight of at least one compound of formula (I) in which Ri represents a hydrogen atom, the R-CO fragment represents an octanoyl radical and m is equal to 1 and from 0.50% to 5% by weight of constituents of a cinnamon extract.

10. Composition as defined in one of claims 1 to 9 further comprising from 0.1% to 10% by weight of magnesium and potassium aspartate.

11. Composition as defined in claim 10, comprising from 4% o to 20% of lauroyl glutamic acid, from 4% to 20% of lauroyl aspartic acid, from 2%> to 8% of lauroyl glycine and of 2 % to 8% of lauroyl alanine, from 0.5%> to 5% by weight of constituents of a cinnamon extract and from 0.5% to 5% of mixed magnesium and potassium aspartate.

12. Composition as defined in one of claims 1 to 11, characterized in that it also contains zinc gluconate.

13. Use of the composition as defined in one of claims 1 to 12 in cosmetics.

14. Use according to claim 13 for soothing and / or protecting sensitive skin, for hydrating dry skin, and / or for slowing the aging of the skin, and / or treating the scalp.

15. Use according to claim 13 for disinfecting the skin and mucous membranes.

16. Use according to claim 13 for treating skin prone to acne.

17. Cosmetic formulation capable of being obtained by dilution from 1/10 to 1/20000 of the composition as defined by any one of claims 1 to 12, in one or more cosmetically acceptable excipients.

18. Formulation as defined in claim 17 in the form of an oil-in-water emulsion having the appearance of a milk having a viscosity of less than 1 Pa.s. comprising as emulsifier a self-emulsifiable composition based on fatty alcohols.

19. Formulation as defined in claim 17, in the form of a lotion for treating acne prone skin.

20. Formulation as defined in claim 17 in the form of a foaming formula or an anti-dandruff shampoo.

21. Cosmetic formulation comprising, as active principle, from 0.001 to 6% by weight of at least one compound of formula (I) and from 0.00005%) to 1%> by weight of constituents of an extract (II) vegetable raw materials rich in tannins.

22. Cosmetic formulation as defined in claim 19, comprising as active principle from 0.5% to 2% by weight of a compound of formula (I) ι

CH ₃ - (CH ₂ ) ₆ -CO-NH-CH ₂ -COOH (I). from 0.05% to 0.2% by weight of constituents of an extract of vegetable raw materials chosen from cinnamon, rathania, tea, willow or witch hazel extracts.

23. Cosmetic formulation as defined in claim 22 further comprising 0.025%) to 0.2% zinc gluconate.

24. Cosmetic formulation as defined in claim 21, comprising as active ingredient from 0.001% to 0.005% by weight of a compound of; formula (I) ι

CH ₃ - (CH ₂ ) ₆ -CO-NH-CH ₂ -COOH (I) ι from 0.0001% to 0.005% by weight of constituents of an extract of vegetable raw materials chosen from extracts of cinnamon, rathania , tea, willow, or witch hazel.

25. Cosmetic formulation as defined in claim 24 comprising

0.0001% to 0.0005%) of zinc gluconate.