New compounds derived from CNSL and their application in cosmetics

Abstract

The invention relates in particular to new compounds of the following general formula (I): wherein A is in particular a group A0 following: wherein R1, R2 and R3, identical or different, are selected from a hydrogen atom and B is in particular a hydrogen atom. (No figure)

Description

Title of the invention: New compounds derived from CNSL and their application in cosmetics

[0001] The invention relates to new compounds derived from CNSL, their preparation process and their application in cosmetics. CONTEXT OF THE INVENTION

[0002] Cashew nuts comprise 55 to 65% by weight of shells and 35 to 45% by weight of kernel weight. Cashew nut shells are therefore an agricultural waste generated by cashew processing plants and thus a starting material inexpensive. Cashew nut shells in particular contain a dark reddish-brown caustic oil, in the order of 15 to 40% by weight, rich in phenolic lipids and have potential for the production of high-value fuels and chemicals, providing an eco-responsible and local alternative to products from the petroleum industry.

[0003] Cashew Nut Shell Liquid or CNSL is a natural oil derived from cashew nut shells. The main components of raw (natural) CNSL are phenolic compounds: anacardic acid, cardol and cardanol. Methyl cardol is also present, but in trace amounts (<5%).

[0004] Each of these compounds is itself a mixture of products, comprising an alkyl or alkenyl chain, said alkenyl chain having 1, 2 or 3 double bonds (Scheme 1):

[0005] [Chem.l] OH O Gold! OH OH anacardic acid cardd 65% ' 15 to 20% methy! cardol cardanol trace 10%

[0006] Scheme 1 - chemical structures of the main constituents of natural CNSL.

[0007] To date, the valorization of CNSL oil remains to be done given the potential presented by the components that constitute it.

[0008] There is a need to valorize CNSL compounds.

[0009] There is a need for new cosmetic molecules.

[0010] There is a need for new cosmetic molecules of natural origin or derived of natural substances such as cinnamic derivatives.

[0011] One of the aims of the invention is to provide compounds derived from plant and natural sources as cosmetic molecules.

[0012] Another aim of the invention is the recovery of CNSL compounds, derived from agricultural production waste, in the cosmetic field.

[0013] Another object of the invention is to provide compounds derived from anacardic acid esterified with a natural product, preferably an alcohol or a natural acid such as ferulic, caffeic or sinapic acids and sinappylic, cou-maryl and coniferyl alcohols.

[0014] Another aim of the invention is the use of said esterified derivative compounds in a progressive release of anacardic acid and the natural cinnamic derivative (acid or alcohol) involved in the esterification, making it possible to release at least two natural molecules on the skin which can present a synergy.

[0015] A first subject of the present invention relates to a compound of the following general formula (I):

[0016] [Chem.2] HAS ■O a DJ

[0017] in which: - A is chosen from: • a hydrogen atom, or • a linear or branched alkyl group of 1 to 12 carbon atoms, preferably a methyl or ethyl group, or • a linear or branched -CO-alkyl group of 1 to 12 carbon atoms, preferably a -CO-CH3 group, or • an A0 group:

[0018] [Chem.3]

[0019] in which Rb R2 and R3, identical or different, are chosen from: • a hydrogen atom, or • an alkoxy group of 1 to 8 carbon atom(s), preferably a methoxy group, or • an -OH group,

[0020] preferably the group A0 is chosen from the following groups:

[0021] [Chem. 4] as A4 AS HAS / ©H A7 AS AS B is chosen from: • a hydrogen atom, or • a linear or branched alkyl group of 1 to 12 carbon atoms, preferably a methyl or ethyl group, or • a B0 group:

[0022]

[0023] in which R4, R5 and R6, identical or different, are chosen from: • a hydrogen atom, or • an alkoxy group of 1 to 8 carbon atoms, preferably a methoxy group -O-CH3, or • an -OH group,

[0024] preferably the group B0 is chosen from the following groups:

[0025] [Chem.6]

[0026] provided that A represents the group A0

[0027] [Chem.7]

[0028] and / or B represents the group B0

[0029] [Chem. 8] "5 BO

[0030] The ester or diester compounds of the present invention have the advantage of a progressive release of anacardic acid and at least one cinnamate synthon of the A and / or B groups after application to the skin by the action of esterases present on the skin.

[0031] Advantageously, the groups A0 and B0 are derived from natural products.

[0032] Advantageously, the A0 and B0 groups are derivatives of cinnamic acids. or cinnamic alcohols.

[0033] Advantageously, the A0 group is a derivative of cinnamic acids.

[0034] Advantageously, the B0 group is a derivative of cinnamic alcohols.

[0035] Advantageously:

[0036] - Al is a derivative of cinnamic acid,

[0037] - A2 is a derivative of caffeic acid,

[0038] - A3 is a derivative of ferulic acid,

[0039] - A4 is a derivative of 2,4,5 trihydroxycinnamic acid, in particular derived from tea rooibos or Alisma orientale seeds,

[0040] - A5 is a derivative of 3,4,5 trihydroxycinnamic acid (IUP Name AC: (2E)-3-(3,4,5-trihydroxyphenyl)-2-propenoic acid),

[0041] - A6 is a derivative of sinapic acid,

[0042] - A7 is a derivative of ort / zo-coumaric acid,

[0043] - A8 is a derivative of meta-coumaric acid,

[0044] - A9 is a derivative of para-coumaric acid.

[0045] Advantageously:

[0046] - B1 is a derivative of cinnamic alcohol,

[0047] - B2 is a derivative of caffeic alcohol,

[0048] - B3 is a derivative of coniferulic alcohol,

[0049] - B4 is a derivative of sinapyl alcohol,

[0050] - B5 is a derivative of ort / zo-coumaryl alcohol

[0051] - B6 is a derivative of meta-coumaryl alcohol

[0052] - B7 is a derivative of para-coumaryl alcohol

[0053] According to a particular embodiment, the invention relates to a compound as defined above, of formula chosen from the following formulas (II), (III) and (IV):

[0054] [Chem.9] R. = H, CH,3 or C2H5

[0055] in which Rb R2, R3, R4, R5 and R6 have the meanings defined above.

[0056] According to a particular embodiment, the invention relates to a compound as defined above of formula (I), in which

[0057] group A is chosen from: - a hydrogen atom, or - a linear or branched alkyl group of 1 to 12 carbon atoms, preferably a methyl or ethyl group, or - a linear or branched -CO-alkyl group of 1 to 12 carbon atoms, preferably a -CO-CH3 group, or - a group chosen from the following formulas: AS A4 At 5 A6

[0059] group B is chosen from: - a hydrogen atom, or - a linear or branched alkyl group of 1 to 12 carbon atoms, preferably a methyl or ethyl group, - a group chosen from the following formulas:

[0061] According to a particular embodiment, the invention relates to a compound as defined above, of formula (I), in which A and B are chosen from the formulas of Table 1 below: AB Compound Cl Al H Compound C2 A2 H Compound C3 A3 H Compound C4 A4 H Compound C5 A5 H Compound C6 A6 H Compound C7 A7 H Compound C8 A8 H Compound C9 A9 H Compound CIO Al ch3 Compound Cil A2 ch3 Compound C12 A3 ch3 Compound C13 A4 ch3 Compound C14 A5 ch3 Compound C15 A6 ch3 Compound C16 A7 ch3 Compound C17 A8 ch3 Compound Cl8 A9 ch3 Compound C19 Al c2h5 Compound C20 A2 c2h5 Compound C21 A3 c2h5 Compound C22 A4 c2h5 Compound C23 A5 c2h5 Compound C24 A6 c2h5 Compound C25 A7 c2h5 Compound C26 A8 c2h5 Compound C27 A9 c2h5 Compound C28 H B1 Compound C29 H B2 Compound C30 H B3 Compound C31 H B4 Compound C32 H B5 Compound C33 H B6 Compound C34 H B7 Compound C35 ch3 B1 Compound C36 ch3 B2 Compound C37 ch3 B3 Compound C38 ch3 B4 Compound C39 ch3 B5 Compound C40 ch3 B6 Compound C41 ch3 B7 Compound C42 Al B1 Compound C43 A2 B1 Compound C44 A3 B1 Compound C45 A4 B1 Compound C46 A5 B1 Compound C47 A6 B1 Compound C48 A7 B1 Compound C49 A8 B1 Compound C50 A9 B1 Compound C51 Al B2 Compound C52 A2 B2 Compound C53 A3 B2 Compound C54 A4 B2 Compound C55 A5 B2 Compound C56 A6 B2 Compound C57 A7 B2 Compound C58 A8 B2 Compound C59 A9 B2 Compound C60 Al B3 Compound C61 A2 B3 Compound C62 A3 B3 Compound C63 A4 B3 Compound C64 A5 B3 Compound C65 A6 B3 Compound C66 A7 B3 Compound C67 A8 B3 Compound C68 A9 B3 Compound C69 Al B4 Compound C70 A2 B4 Compound C71 A3 B4 Compound C72 A4 B4 Compound C73 A5 B4 Compound C74 A6 B4 Compound C75 A7 B4 Compound C76 A8 B4 Compound C77 A9 B4 Compound C78 Al B5 Compound C79 A2 B5 Compound C80 A3 B5 Compound C81 A4 B5 Compound C82 A5 B5 Compound C83 A6 B5 Compound C84 A7 B5 Compound C85 A8 B5 Compound C86 A9 B5 Compound C87 Al B6 Compound C88 A2 B6 Compound C89 A3 B6 Compound C90 A4 B6 Compound C91 A5 B6 Compound C92 A6 B6 Compound C93 A7 B6 Compound C94 A8 B6 Compound C95 A9 B6 Compound C96 Al B7 Compound C97 A2 B7 Compound C98 A3 B7 Compound C99 A4 B7 Compound Cl00 A5 B7 Compound C101 A6 B7 Compound Cl02 A7 B7 Compound Cl03 A8 B7 Compound Cl04 A9 B7

[0063] Table 1: Compounds of formula (I)

[0064] According to a particular embodiment, the invention relates to a compound as defined above, of formula (I), in which

[0065] group A is chosen from: - a hydrogen atom, or - a linear or branched alkyl group of 1 to 12 carbon atoms, preferably a methyl or ethyl group, or - a linear or branched -CO-alkyl group of 1 to 12 carbon atoms, preferably a -CO-CH3 group, or - a grouping of the following formula Al:

[0066] [Chem. 12]

[0067] group B is chosen from: - a hydrogen atom, or - a linear or branched alkyl group of 1 to 12 carbon atoms, preferably a methyl or ethyl group, or - a grouping of the following formula B1:

[0069] provided that A represents the grouping

[0070] [Chem. 14]

[0071] and / or B represents the group

[0072] [Chem. 15]

[0073] According to a particular embodiment, the invention relates to a compound such as defined above, of the following formulas: Hs = H or CH - or -COCH

[0075] According to a particular embodiment, the invention relates to a compound as defined above, corresponding to one of the following formulas:

[0077] A second subject of the present invention relates to a cosmetic composition comprising at least one compound of formula (I) as defined above in a cosmetically acceptable medium.

[0078] By “cosmetic composition” is meant any composition for cosmetic purposes, in particular a composition which can be brought into contact with the superficial parts of the human body, the skin, in particular the epidermis, the mucous membranes and the scalp.

[0079] For the purposes of the present invention, the term "cosmetic composition" means a non-pharmaceutical composition, i.e. intended for skin which does not require therapeutic treatment, i.e. intended for any area of ​​healthy skin.

[0080] By "a cosmetically acceptable medium" is meant, within the meaning of the invention, a medium compatible with use in cosmetics.

[0081] According to one embodiment, the invention relates to a cosmetic composition as defined above, in which the compound(s) of formula (I) represents 0.00003 to 10% by total mass of the composition, in particular 0.005 to 10%.

[0082] The range of 0.00003% to 10% includes the ranges: from 0.00003 to 0.00005%; from 0.00005 to 0.0001%; ​​from 0.0001 to 0.0003%; from 0.0003 to 0.0005%; from 0.0005% to 0.001%; ​​from 0.001 to 0.003%; from 0.003 to 0.005%; from 0.005% to 0.01%; from 0.01 to 0.1%; from 0.1 to 1%; from 1 to 2%; from 2 to 3%; from 3 to 4%; from 4 to 5%; from 5 to 6%; from 6 to 7%; from 7 to 8%; from 8 to 9%; from 9 to 10%.

[0083] According to one embodiment, the invention relates to a cosmetic composition as defined above, said composition comprising at least one cosmetic adjuvant or excipient, in particular chosen from: fatty substances, organic solvents, ionic or non-ionic thickeners, softeners, preservatives, emulsifiers, hydrophilic or lipophilic gelling agents, opacifiers, stabilizers, emollients, α-hydroxy acids, anti-foam agents, moisturizing agents, vitamins, perfumes, preservatives, surfactants, fillers, sequestrants, polymers, propellants, alkalizing or acidifying agents, and colorants.

[0084] According to one embodiment, the invention relates to a cosmetic composition as defined above, said cosmetic composition being formulated for topical application, in particular topical application to the skin, said composition being in particular in the form of an aerosol, an emulsion, a microemulsion, a lamellar emulsion, liposomes, encapsulated forms, a cream, a gel, a dispersion, a serum, a mousse, a body milk or an anhydrous balm, preferably in the form of a body milk or a cream.

[0085] A third subject of the present invention relates to a cosmetic composition as defined above for its use as an antioxidant cream on healthy skin.

[0086] The term “healthy skin” means an area of ​​skin to which the combination or composition according to the invention is applied, deemed “non-pathological” by a dermatologist, i.e. not presenting any infection, disease, or wounds or injuries and / or other dermatoses.

[0087] Cinnamic acid and its derivatives are known to exhibit, among other things, antioxidant activity. Similarly, CNSL derivatives, in particular anacardic acid derivatives, also exhibit antioxidant properties. The compounds of the invention as defined above are capable of releasing onto healthy skin both an anacardic acid derivative and a cinnamic acid or cinnamic alcohol derivative, and thus of providing an antioxidant action on healthy skin.

[0088] Another subject of the present invention relates to a cosmetic composition as defined above for its use on healthy skin as a UV absorber, in particular as a sunscreen.

[0089] Advantageously, the compounds of the invention as defined above have UV absorption properties, particularly UVB, and exhibit photostability allowing them to be used as a new sunscreen.

[0090] Another subject of the present invention relates to a cosmetic composition as defined above for its use on healthy skin as a keratolytic agent.

[0091] CNSL derivatives, in particular anacardic acid, are known for their keratolytic property, namely to dissolve or soften the horny layer of the epidermis. The compounds of the invention as defined above are capable of releasing an anacardic acid derivative onto healthy skin, and thus providing a keratolytic action.

[0092] Advantageously, the cytotoxicity analyses indicate that the compounds of the invention do not exhibit a cytotoxic effect, unlike anacardic acid which exhibits cytotoxicity for human keratinocyte cells beyond 0.003% by mass of the composition tested.

[0093] Another subject of the present invention relates to the use of a compound as defined above for the release on healthy skin, in the presence of esterase, of a molecule of anacardic acid and at least one molecule of natural substance of formula:

[0094] [Chem. 18] WHAT

[0095] in which Rb R2, R3, R4, R5 and R6 have the meanings defined above.

[0096] Advantageously, the use of a compound as defined above releases onto healthy skin, one molecule of anacardic acid and at least one molecule of natural substance, said molecule of natural substance being the cinnamic acid derivative corresponding to the A0 group or the cinnamic alcohol derivative corresponding to the B0 group of said compound.

[0097] Another subject of the present invention relates to a dermatological composition, comprising as active substance, a compound of the invention as defined above- above, with a pharmaceutically acceptable excipient,

[0098] said composition being in particular formulated for topical application, in particular topical application to the skin,

[0099] said composition being in particular in the form of an emulsion, a cream, a gel, a dispersion, a serum, a mousse, a body milk or an anhydrous balm.

[0100] By “dermatological composition” is meant any composition for pharmaceutical purposes which can be brought into contact with the superficial parts of the human body, the skin, in particular the epidermis.

[0101] According to a particular embodiment, the invention relates to a composition as defined above for its use in the prevention or treatment of pathologies linked to oxidative stress.

[0102] According to a particular embodiment, the invention relates to a composition as defined above for its use for photoprotection against solar radiation.

[0103] According to a particular embodiment, the invention relates to a composition as defined above for its use for the prevention and treatment of epidermal conditions produced by an excess of keratin, in particular the treatment of warts, psoriasis or acne.

[0104] Another subject of the present invention relates to a process for preparing a compound of formula (I) according to the invention, as defined above from hydrogenated anacardic acid, comprising:

[0105] a) a step of esterification or etherification of the phenol function of hydrogenated anacardic acid,

[0106] and / or

[0107] b) a step of esterification of the acid function of hydrogenated anacardic acid.

[0108] According to a particular embodiment, the invention relates to a method as defined above comprising:

[0109] a) a step of esterification or etherification of the phenol function of hydrogenated anacardic acid,

[0110] or

[0111] b) a step of esterification of the acid function of hydrogenated anacardic acid.

[0112] According to a particular embodiment, the invention relates to a method as defined above comprising:

[0113] a) a step of esterification or etherification of the phenol function of hydrogenated anacardic acid,

[0114] and

[0115] b) a step of esterification of the acid function of hydrogenated anacardic acid.

[0116] According to a particular embodiment, the invention relates to a method as defined above comprising:

[0117] a) a step of esterification of the phenol function of hydrogenated anacardic acid,

[0118] and / or

[0119] b) a step of esterification of the acid function of hydrogenated anacardic acid.

[0120] According to a particular embodiment, the invention relates to a method as defined above comprising:

[0121] a) a step of esterification of the phenol function of hydrogenated anacardic acid,

[0122] or

[0123] b) a step of esterification of the acid function of hydrogenated anacardic acid.

[0124] According to a particular embodiment, the invention relates to a method as defined above comprising:

[0125] a) a step of esterification of the phenol function of hydrogenated anacardic acid,

[0126] and

[0127] b) a step of esterification of the acid function of hydrogenated anacardic acid.

[0128] According to a particular embodiment, the invention relates to a method as defined above comprising:

[0129] a) a step of etherification of the phenol function of hydrogenated anacardic acid,

[0130] and

[0131] b) a step of esterification of the acid function of hydrogenated anacardic acid.

[0132] Hydrogenated anacardic acid corresponds to the anacardic acid compound in which the C15 alkyl chain is saturated and has the following formula:

[0133] [Chem. 19] OH 0

[0134] Hydrogenated anacardic acid comprises two -OH functions, corresponding to the phenol function and the carboxylic acid function.

[0135] According to a particular embodiment, the invention relates to a process as defined above in which step a) of esterification of the phenol function of hydrogenated anacardic acid is followed by step b) of esterification of the acid function of hydrogenated anacardic acid.

[0136] According to a particular embodiment, the invention relates to a process as defined above in which step b) of esterification of the acid function of hydrogenated anacardic acid is followed by step a) of esterification of the phenol function of hydrogenated anacardic acid.

[0137] According to a particular embodiment, the invention relates to a process as defined above in which step a) of esterification of the phenol function of hydrogenated anacardic acid is carried out with an anhydride.

[0138] Advantageously, said acid anhydride is an acid anhydride corresponding to the group A as defined above, preferably acetic anhydride.

[0139] According to a particular embodiment, the invention relates to a process as defined above in which step a) of esterification of the phenol function of hydrogenated anacardic acid is carried out with an acid chloride.

[0140] Advantageously, said acid chloride is an acid chloride corresponding to group A as defined above, in particular of formula A-COCl, preferably cinnamoyl chloride.

[0141] According to a particular embodiment, the invention relates to a process as defined above in which step a) of esterification of the phenol function of hydrogenated anacardic acid is carried out by a Steglish reaction.

[0142] Advantageously, the acid used in the Steglish reaction is an acid corresponding to the group A as defined above, in particular of formula A-COOH, preferably cinnamic acid.

[0143] According to a particular embodiment, the invention relates to a process as defined above in which step b) of esterification of the acid function of hydrogenated anacardic acid is carried out with an alcohol.

[0144] Advantageously, said alcohol used is the alcohol corresponding to group B as defined above, in particular of formula B-OH, preferably cinnamic alcohol.

[0145] According to a particular embodiment, the invention relates to a process as defined above in which step b) of esterification of the acid function of hydrogenated anacardic acid is carried out with an alkyl bromide.

[0146] Advantageously, said alkyl bromide is the alkyl bromide corresponding to the group B as defined above, in particular of formula B-Br, preferably cinnamyl bromide.

[0147] According to a particular embodiment, the invention relates to a process as defined above in which step b) of esterification of the acid function of hydrogenated anacardic acid is carried out by a Steglish reaction.

[0148] Advantageously, the acid used in the Steglish reaction is an acid corresponding to the group B as defined above, in particular of formula B-COOH, preferably cinnamic acid.

[0149] According to a particular embodiment, the invention relates to a process as defined above for the preparation of a compound of the following formula:

[0150] [Chem.20]

[0151] comprising:

[0152] - a step of esterification of the acid function of hydrogenated anacardic acid by ethanol, to form ethyl anacardate,

[0153] - followed by a step of esterification of the phenol function of ethyl anacardate by cinnamoyl chloride, particularly in the presence of 4-dimethylaminopyridine (DMAP), optionally in the presence of another amine base such as triethylamine.

[0154] Advantageously, the amine-type base such as triethylamine makes it possible to trap the hydrochloric acid (HCl) formed during the esterification reaction of the phenol function by the acid chloride.

[0155] According to a particular embodiment, the invention relates to a process as defined above for the preparation of a compound of the following formula:

[0156] [Chem.21]

[0157] comprising:

[0158] - a step of esterification of the acid function of hydrogenated anacardic acid by ethanol, to form ethyl anacardate

[0159] - followed by a step of esterification of the phenol function of ethyl anacardate by a Steglish reaction in the presence of cinnamic acid, particularly in the presence of 4-dimethylaminopyridine (DMAP) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC).

[0160] According to a particular embodiment, the invention relates to a process as defined above for the preparation of a compound of the following formula:

[0161] [Chem.22] O

[0162] comprising:

[0163] - a step of esterification of the phenol function of hydrogenated anacardic acid by acetic anhydride, to form the O-acetylated anacardic acid derivative,

[0164] - followed by a step of esterification of the acid function of said derivative by bromide of cinnamyl.

[0165] According to a particular embodiment, the invention relates to a process as defined above for the preparation of a compound of the following formula:

[0166] [Chem.23]

[0167] comprising:

[0168] - a step of esterification of the phenol function of hydrogenated anacardic acid by cinnamoyl chloride, to form the cinnamoyl ester, in particular in the presence of 4-dimethylaminopyridine (DMAP), optionally in the presence of triethylamine,

[0169] - followed by a step of esterification of the acid function of said cinnamoyl ester by cinnamyl bromide.

[0170] The following examples and figures illustrate the invention, without limiting its scope. LIST OF FIGURES

[0171] [Fig.l] represents the percentage of cell viability of solutions at different mass concentrations of compound (4).

[0172] [Fig.2] represents the percentage of cell viability of solutions at different mass concentrations of compound (2).

[0173] [Fig.3] represents the percentage of cell viability of solutions at different mass concentrations of compound (3).

[0174] [Fig.4] represents the percentage of cell viability of solutions at different mass concentrations of anacardic acid.

[0175] [Fig.5] represents the UV absorption spectrum, before and after irradiation, of compound (4) and compound (2).

[0176] [Fig.6] represents the percentage of light stopped, before and after irradiation, of compound (4) and compound (2).

[0177] EXAMPLES

[0178] Example 1: General description of the synthesis processes

[0179] In the context of the examples presented, three diesters (2), (3) and (4) based on anacardic acid were prepared from hydrogenated anacardic acid (1):

[0180] [Chem.24] P) AA <4)« ani a4hOH

[0181] Each of these diesters (2), (3) and (4) was synthesized in two steps (esterification of the acid function, then of the phenol, or vice versa depending on the desired molecule). In the following, the following naming system to identify the intermediates and final products (here are some examples) was adopted:

[0182] - AA-OH-COOH: hydrogenated anacardic acid (starting reagent), with OH = phenol function and COOH = acid function.

[0183] - AA-acetate-COOH: anacardic acid derivative (intermediate), with acetate = acetate group at the phenol level and COOH = acid function.

[0184] - AA-OH-EtOH: anacardic acid derivative (intermediate), with OH = phenol and EtOH = acid function esterified by ethanol.

[0185] - AA-double-cinnamic: final product of interest, both functions (phenol and acid) have been esterified by a reagent carrying the cinnamic group.

[0186] The expression "anacardic acid derivative" identifies the different intermediates indifferently. Thus, the same expression can concern AA-OH-EtOH or AA-cinnamic-COOH.

[0187] The diesters of interest based on anacardic acid were obtained in two stages: • Either an esterification of the phenol function, followed by that of the acid function. • Either an esterification of the acid function, followed by that of the phenol function.

[0188] Examples 2, 3 and 4 below describe the different esterification methods which were implemented on the phenol function in order to synthesize the diesters of interest.

[0189] The following examples 5, 6, and 7 describe the different esterification methods which were implemented on the acid function in order to synthesize the diesters of interest.

[0190] Example 2: Protocol for esterification of the phenol function by an anhydride

[0191] In a container, 1 equivalent of hydrogenated anacardic acid was solubilized in a solvent at room temperature (20 to 30 °C). The medium was then immersed in an ice bath. Then 2 equivalents of pyridine, with 0.1 equivalent of 4-dimethylaminopyridine (DMAP) and 2 equivalents of anhydride of interest corresponding to the A group of the molecule, were then added to the medium. The latter was left stirring in the cold for 30 minutes, then at 30 °C until the desired conversion was reached (monitored by thin layer chromatography (TLC) and / or by 'H NMR spectrometry). The product of interest was obtained after liquid-liquid (L / L) extractions in an acidic medium.

[0192] Example 3: Protocol for esterification of the phenol function by an acid chloride

[0193] In a container, 1 equivalent of hydrogenated anacardic acid (or anacardic acid derivative, corresponding to the intermediate compound obtained by esterification of the acid function of anacardic acid) and 0.1 equivalent of DMAP were dissolved in an anhydrous solvent, in the cold. From 1 to 1.2 equivalents of alkyl chloride, dissolved in the same solvent and from 1 to 1.2 equivalents of triethylamine, dissolved in the same solvent, were gradually and jointly added to the medium via two addition funnels. The reaction medium was left stirring at room temperature (30°C) until the desired conversion was reached. The product of interest was obtained after liquid-liquid (L / L) extractions in acidic medium (and by purification on a silica column).

[0194] Example 4: Protocol for esterification of the phenol function by a Steglish reaction

[0195] In a container, 1 equivalent of acid of interest (corresponding to the acid of the group A), as well as 2 equivalents of l-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) and 0.5 equivalents of 4-dimethylaminopyridine (DMAP) were mixed in a flask in the presence of a solvent. The medium was left stirring at 30°C for 15 minutes. In parallel, 1 equivalent of anacardic acid derivative was dissolved in the same solvent. The solution thus obtained was introduced into the reaction medium. The latter was left stirring at 30°C until the desired conversion was reached. The crude reaction product was purified by liquid-liquid extractions (L / L), then the product of interest was recovered after purification on a silica column.

[0196] Example 5: Protocol for esterification of the acid function by an alcohol

[0197] In a two-necked flask equipped with a MgSO4 guard placed between the flask and the condenser, 1 equivalent of hydrogenated anacardic acid was mixed with sulfuric acid (catalyst) and the alcohol of interest (corresponding to group B) in large excess (and with a solvent if necessary). The reaction medium was left stirring at reflux until the desired conversion to alkyl anacardate was reached. The crude reaction product was concentrated, then analyzed by 'H NMR in order to determine the residual mass quantity of anacardic acid. If necessary, the latter was removed by precipitation with calcium hydroxide. The product of interest was obtained after liquid-liquid (L / L) extractions.

[0198] Example 6: Protocol for esterification of the acid function by an alkyl bromide

[0199] In a flask, 1 equivalent of an anacardic acid derivative (corresponding either to the acid-acetate-COOH compound or to the acid-cinnamic-COOH compound) and 1.2 equivalents of anhydrous K2CO3 were dissolved in a hot solvent. 1.2 equivalents of alkyl bromide (previously dissolved in the same solvent) were then added to the medium. The suspension was left stirring while hot until the desired conversion to the product of interest was reached. The final product was obtained after filtration, L / L extractions, then purification on a silica column.

[0200] Example 7: Esterification of the acid function by a Steglish reaction

[0201] In a flask, 1 equivalent of an anacardic acid derivative (corresponding to the cinnamic acid compound COOH), 2 equivalents of EDC and 0.5 equivalents of DMAP were mixed in a flask in the presence of a solvent. The medium was left stirring at 30°C for 15 minutes. In parallel, 5 equivalents of the alcohol of interest (corresponding to group B) were solubilized in the same solvent. The solution thus obtained was introduced into the reaction medium. The latter was left stirring at 30°C until the desired conversion was reached. The reaction crude was purified by L / L extractions.

[0202] Example 8: Synthesis of the compound cinnamic acid-EtOH

[0203] [Chem.25]

[0204] A) Esterification of hydrogenated anacardic acid by ethanol (sample CB 160822-55)

[0205] The operating setup consists of a two-necked flask, a condenser and a guard of MgSO4 placed between the flask and the condenser. In the flask, 1 equivalent of hydrogenated anacardic acid (1) was solubilized in 62.9 equivalents of ethanol at room temperature. 1.25 equivalents of sulfuric acid were then added to the medium. The latter was left stirring at reflux (80°C) until the desired conversion to ethyl anacardate was reached (monitored by *H NMR). The solvent was removed under reduced pressure at 50°C, then the residual mass quantity (if any) of anacardic acid was determined by 'H NMR. The oily residue was then solubilized in a 1 / 0.05 V / V ethanol / water mixture, then 2 equivalents of Ca(OH) 2 were added to the medium. The latter was left stirring at RT (20-30°C) for 20 minutes. The suspension was then filtered, the solid was rinsed on a frit with 2x10 mL of ethanol.The filtrate was collected, and the solvent removed under reduced pressure at 50°C. The solid residue was solubilized in 20 mL of ethyl acetate, then the organic phase was washed with 3x20 mL of NaCl-saturated water and dried over MgSO4. After removal of the solvent under reduced pressure at 50°C, the product of interest was obtained in the form of a beige solid (yield r = 41.2%).

[0206] 1H NMR (400 MHz, CDC13): 11.23 (1H, s), 7.28 (1H, m), 6.83 (1H, dd, J1 = 8.3 Hz, J2 = 1.2 Hz), 6.71 (1H, dd, J1 = 7.5 Hz, J2 = 1.3 Hz), 4.44 (2H, q, J = 7.1 Hz), 2.90 (2H, m), 1.54 (2H, m), 1.43 (3H, t, J = 7.1 Hz), 1.26 (24H, solid), 0.87 (3H, m).

[0207] Bl) O-esterification of ethyl anacardate by cinnamoyl chloride (sample AR4172-58)

[0208] The operating setup consists of a three-necked flask, a condenser and two addition funnels. 1 equivalent of ethyl anacardate and 0.10 equivalents of DM AP were solubilized in 36 equivalents of ethyl acetate (previously dried on 3 Å molecular sieve). The medium was then immersed in an ice bath, then 1.21 equivalents of cinnamoyl chloride (solubilized in 9 equivalents of ethyl acetate) and 1.20 equivalents of triethylamine (solubilized in 9 equivalents of ethyl acetate) were added gradually (drop by drop) to the reaction medium. The reaction medium was then heated to 30°C with stirring for 4 h (appearance of a solid in the medium). The suspension was filtered, then the filtrate was washed with 20 mL of a 3% mass HCl solution and 3x20 mL of a saturated NaCl solution. The organic phase was dried over MgSO4, then the solvent was removed under reduced pressure at 50°C. The product was then purified on a silica column (eluent: cyclohexane / ethyl acetate 95 / 5). Obtaining a white-yellow solid (mass yield r = 47.8%).

[0209] 1H-NMR, (400 MHz, CDC13): 7.86 (1H, d, J = 16 Hz), 7.58 (2H, m), 7.43 (3H, massive), 7.37 (1H, t, J = 7.9 Hz), 7.14 (1H, m), 7.06 (1H, m), 6.60 (1H, d, J = 16 Hz), 4.32 (2H, q, J = 7.1 Hz), 2.69 (2H, m), 1.61 (2H, m), 1.30 (3H, m, J = 7.1 ppm), 1.26 (24H, m), 0.88 (3H, m).

[0210] B2) Steglish O-esterification of ethyl anacardate by cinnamic acid (sample CB 100622-27)

[0211] 1.13 equivalents of cinnamic acid are solubilized in 39 equivalents of acetate of ethyl acetate at room temperature. 2.20 equivalents of EDC and 0.55 equivalents of DMAP were then added to the medium. The latter was left stirring at 30°C for 15 minutes. In parallel, 1 equivalent of ethyl anacardate was dissolved in 34.6 equivalents of ethyl acetate. The solution thus obtained was introduced into the reaction medium. The latter was left stirring at 30°C overnight. The reaction medium was diluted in ethyl acetate, then washed with 2x150 mL of saturated NaCl solution. The organic phase was dried over MgSO4, then the solvent was removed under reduced pressure at 50°C. Part of the product was then purified on a silica column (eluent: cyclohexane / ethyl acetate, elution gradient 98 / 2 - 95 / 5). Obtaining a white-yellow solid (purification mass yield r = 40%).

[0212] 1H NMR (400 MHz, CDC13): 7.86 (1H, d, J = 16 Hz), 7.58 (2H, m), 7.43 (3H, m), 7.37 (1H, m), 7.14 (1H, dd, J1 = 7.7 Hz, J2 = 1 Hz), 7.05 (1H, dd, J1 = 8.1 Hz, J2 = 1 Hz), 6.60 (1H, d, J = 16 Hz), 4.32 (2H, q, J = 7.1 Hz), 2.69 (2H, m), 1.58 (2H, m), 1.30 (3H, t, J = 7.1 Hz), 1.26 (24H, solid), 0.87 (3H, m).

[0213] Example 9: Synthesis of the compound cinnamic acid-acetate

[0214] [Chem.26] ToAscelate-dnn amic

[0215] A) O-acetylation of hydrogenated anacardic acid (sample AR4172-59)

[0216] 1 equivalent of hydrogenated anacardic acid was solubilized in 35.1 equivalents of ethyl acetate at room temperature. The medium was then immersed in an ice bath. 1.98 equivalents of pyridine, 0.11 equivalents of DMAP and 1.99 equivalents of acetic anhydride were then added to the medium. The latter was left to stir in the cold for 30 minutes, then at 30°C for 17 h. The medium was transferred into a separating funnel. The organic phase was washed with 20 mL of a 5% mass HCl solution, then 2x20 mL of a saturated NaCl solution before being dried over MgSO4. The solvent was removed under reduced pressure at 50°C. A beige solid was obtained (yield r = 96.9%).

[0217] 1H-NMR, (400 MHz, CDC13): 7.40 (1H, t, J = 7.9 Hz), 7.16 (1H, dd, J1 = 7.8 Hz, J2 = 1 Hz), 6.99 (1H, dd, J1 = 8.1 Hz, J2 = 1.1 Hz), 2.78 (2H, m), 2.29 (3H, s), 1.61 (2H, m), 1.26 (24H, solid), 0.88 (3H, m).

[0218] B) Esterification of the O-acetylated anacardic acid derivative by cinnamyl bromide (sample AR4172-63)

[0219] 1 equivalent of the compound anacardic acid - acetate - COOH and 1.20 equivalents of K2CO3 (previously dried in an oven at 60°C) were dissolved in 21.2 equivalents of 2-butanone at 61°C. 1.20 equivalents of cinnamyl bromide (previously dissolved in 21.2 equivalents of 2-butanone) were then added to the medium. The suspension was left stirring at 61°C for 3h45. The suspension was filtered, and the solvent was removed under reduced pressure at 50°C. The solid obtained was resolubilized in 20 mL of ethyl acetate, then the organic phase was washed with 3x20 mL of saturated NaCl solution. The organic phase was then dried over MgSO4, then, after filtration, the solvent was removed under reduced pressure at 50°C. The product was purified by a silica column (eluent: cyclohexane / AcOEt 95 / 5). The fraction of interest was dried with MgSO4 then the solvent was removed under reduced pressure at 50°C. The solid obtained was dried under vacuum at RT for 7 h.Obtaining a white-yellow solid (yield r = 61.6%, purity p £ 90. %).

[0220] 1H-NMR, (400 MHz, CDC13): 7.25 - 7.41 (6H, massive), 7.12 (1H, dd, J1 = 7.8 Hz, J2 = 1 Hz), 6.97 (1H, dd, J1 = 8.1 Hz, J2 = 1 Hz), 6.75 (1H, d, J = 15.8 Hz), 6.38 (1H, dt, J1 = 15.9 Hz, J2 = 6.5 Hz), 4.95 (2H, dd, J1 = 6.5 Hz, J2 = 1.3 Hz), 2.69 (2H, m), 2.18 (3H, s), 1.57 (2H, m), 1.26 (24H, solid), 0.88 (3H, m).

[0221] Example 10: Synthesis of the compound cinnamic acid-cinnamic acid

[0222] [Chem.27] (4)

[0223] A) O-esterification of anacardic acid with cinnamoyl chloride (sample CB050722-38) to form cinnamoyl ester (the intermediate compound AA-cinnamic-COOH).

[0224] 1 equivalent of hydrogenated anacardic acid (1) and 0.10 equivalent of DMAP were solubilized in 35.5 equivalents of ethyl acetate, previously dried over 3Â molecular sieve, cold (ice bath). 0.99 equivalent of cinnamoly chloride (solubilized in 12.4 equivalents of anhydrous ethyl acetate) and 0.99 equivalent of triethylamine (solubilized in 3.6 equivalents of anhydrous ethyl acetate) were added gradually (drop by drop) and jointly into the medium. At the end of the additions, the ice bath was removed, then the reaction medium was left stirring at room temperature for 4 h. The solvent was removed under reduced pressure at 50°C, and the residue was resolubilized in 20 mL of chloroform. The organic phase was then washed with 2x60 mL of NaCl-saturated water, 60 mL of a 3% mass HCl solution, then 60 mL of NaCl-saturated water before being dried over MgSO4. The solvent was removed under reduced pressure at 50°C. An orange solid was obtained (yield r = 84.9%, purity p 2 90%).

[0225] 1H-NMR, (400 MHz, CDC13): 7.86 (1H, d, J = 16 Hz), 7.55 (2H, massive), 7.40 (4H, massive), 7.15 (1H, dd, J1 = 7.9 Hz, J2 = 1 Hz), 7.07 (1H, dd, J1 = 8.1 Hz, J2 = 1 Hz), 6.61 (1H, d, J = 16 Hz), 2.75 (2H, m), 1.60 (2H, q, J = 7.3 Hz), 1.26 (24H, solid), 0.87 (3H, m).

[0226] B) Esterification of cinnamoyl ester by cinnamyl bromide (sample AR4172-56) to form compound (4)

[0227] 1 equivalent of the compound AA-cinnamic-COOH and 1.20 equivalents of K2CO3 (previously dried in an oven at 60°C) were dissolved in 33 equivalents of 2-butanone at 61°C. 1.20 equivalents of cinnamyl bromide (previously dissolved in 17.7 equivalents of 2-butanone) were then added to the medium. The suspension was left stirring at 61°C for 3h45. The suspension was filtered, and the solvent was removed under reduced pressure at 50°C. The solid obtained was resolubilized in 20 mL of chloroform, then the organic phase was washed with 3x20 mL of saturated NaCl solution. The organic phase was then dried over MgSO 4, then, after filtration, the solvent was removed under reduced pressure at 50°C. The product was purified by a silica column (eluent: cyclohexane / AcOEt 98 / 2). The fraction of interest was dried with MgSO4 and then the solvent was removed under reduced pressure at 50°C. The solid obtained was dried under vacuum at RT for 7 h.Obtaining a white-yellow solid (yield r = 57.8%, purity p - 90%).

[0228] 1H-NMR, (400 MHz, CDC13): 7.79 (1H, d, J = 16 Hz), 7.19-7.43 (11H, massive), 7.14 (1H, m), 7.06 (1H, m), 6.65 (1H, d, J = 15.9 Hz), 6.53 (1H, d, J = 16 Hz), 6.31 (1H, dt, J1 = 15.9 Hz, J2 = 6.5 Hz), 4.91 (2H, dd, J1 = 6.5 Hz, J2 = 1.3 Hz), 2.72 (2H, m), 1.61 (2H, q, J = 7.5 Hz), 1.24 (24H, m), 0.87 (3H, m).

[0229] Example 11: Cytotoxicity study

[0230] a) Objective of the study

[0231] The cytotoxicity of 3 products of the invention, namely compounds (2), (3) and (4), and that of hydrogenated anacardic acid (1) as reference molecule, were evaluated on human keratinocyte cells (cells constituting the majority of the human epidermis) placed in contact with the products to be evaluated for 24 hours.

[0232] b) Material and method

[0233] The cell culture medium was used to dilute the products to be evaluated to the targeted concentrations from the maximum solubility of each compound tested:

[0234] For compounds (2), (3) and (4), the following mass concentrations were prepared: 0.005% (solubility limit), 0.003%, 0.001%, 0.0005%, 0.0003%, 0.0001%, 0.00005%, 0.00003%

[0235] For the reference molecule (1), the following mass concentrations were prepared: 0.1% (solubility limit), 0.05%, 0.03%, 0.01%, 0.005%, 0.003%, 0.001%, 0.0005%

[0236] The solutions were prepared by serial dilutions (from the initial concentrations) and transferred into the cell-seeded wells.

[0237] c) Treatment of cells

[0238] The cells are of the HaCat type, namely human keratinocyte cells, with n=6 per condition. The seeding is 30,000 cells per well in plates of tissue culture.

[0239] Cells were conditioned at 37°C (5% CO2) in DMEM GlutaMax + 2% FBS culture medium.

[0240] The cells were then placed in contact with the compound to be analyzed at the desired concentration for 24 hours.

[0241] The toxicity control is a 10 mM H2O2 solution.

[0242] The evaluation was carried out by MTS reduction tests at an optical density absorbance measured at 490 nm.

[0243] d) Evaluation of cell viability

[0244] Cell viability was measured using the MTS assay protocol at a wavelength of 490 nm.

[0245] The MTS assay protocol is based on the reduction of the tetrazolium compound MTS by viable mammalian cells (and cells of other species) to generate a colored formazan dye that is soluble in cell culture media. This conversion is carried out by NAD(P)H-dependent dehydrogenase enzymes in metabolically active cells. The formazan dye is quantified by measuring the absorbance at 490-500 nm.

[0246] After an incubation period with the product to be analyzed, the Optical Density (OD) of each well was read at a wavelength of 490 nm by a fluorescence-luminescence reader. The results obtained for the wells treated with the product to be evaluated were compared to those of the untreated control wells (CTRL, 100% viability) and converted into percentage values. • Calculation of the percentage of cell viability

[0247] The percentages of cell viability were expressed as a percentage relative to the control:

[0248] [Math.l] Percentage of cellular vsabHdé = 100 x (OD of test well — DG of blank) CTRL DO—White DD

[0249] Example 12: Cytotoxicity of compound (4)

[0250] The results for compound (4), named PI (reference AR4172-56) are expressed in Table 2 and [Fig.l] as mean percentage of cell viability normalized to the control condition (untreated) and standard deviation of the mean (Std. Dev.). The toxicity threshold is set at 70% cell viability (%) and visualized in [Fig.l] as a dotted line. [0251 ] [T ableaux2] Concentrations Cell viability (%) Std. Dev CTRL 100 3 PI 0.005% 99 3 PI 0.003% 104 5 PI 0.001% 105 3 PI 0.0005% 108 5 PI 0.0003% 109 5 PI 0.0001% 106 4 PI 0.00005% 106 6 PI 0.00003% 105 3 H2O2 (toxicity) 2 1

[0252] Table 2: Results of cell viability analysis after contact with compound (4) at different mass concentrations.

[0253] These results in Table 2 and [Fig. 1] show that compound (4) does not exhibit cytotoxicity on keratinocyte cells at the concentrations tested.

[0254] The highest non-toxic concentration tested is 0.005% by mass.

[0255] Example 13: Cytotoxicity of compound (2)

[0256] The results for compound (2), named P2 (reference AR4172-58) are expressed in Table 3 and [Fig.2] as the mean of percentage of cell viability normalized to the control condition (untreated) and the standard deviation of the mean (Std. Dev.). The toxicity threshold is set at 70% cell viability (%) and visualized in [Fig.2] as a dotted line.

[0257] [Tables3] Concentrations Cell Viability (%) Std. Dev CTRL 100 2 P2 0.005% 103 3 P2 0.003% 104 3 P2 0.001% 103 6 P2 0.0005% 105 5 P2 0.0003% 105 4 P2 0.0001% 105 3 P2 0.00005% 105 4 P2 0.00003% 104 3 H2O2 (toxicity) 2 1

[0258] Table 3: Results of cell viability analysis after contact with compound (2) at different mass concentrations.

[0259] These results in Table 3 and [Fig.2] show that compound (2) does not exhibit cytotoxicity on keratinocyte cells at the concentrations tested.

[0260] The highest non-toxic concentration tested is 0.005% by mass.

[0261] Example 14: Cytotoxicity of compound (3)

[0262] The results for compound (3), named P3 (reference AR4172-63) are expressed in Table 4 and [Fig.3] as mean percentage of cell viability normalized to the control (untreated) condition and standard deviation of the mean (Std. Dev.). The toxicity threshold is set at 70% cell viability (%) and visualized in [Fig.3] as a dotted line.

[0263] [Tables4] Concentrations Cell Viability (%) Std. Dev CTRL 100 1 P3 0.005% 106 4 P3 0.003% 111 4 P3 0.001% 108 6 P3 0.0005% 109 6 P3 0.0003% 110 6 P3 0.0001% 111 5 P3 0.00005% 108 6 P3 0.00003% 110 3 H2O2 (toxicity) 2 1

[0264] Table 4: Results of cell viability analysis after contact with compound (3) at different mass concentrations.

[0265] These results in Table 4 and [Fig.3] show that compound (3) does not exhibit cytotoxicity on keratinocyte cells at the concentrations tested.

[0266] The highest non-toxic concentration tested is 0.005% by mass.

[0267] Example 15: Cytotoxicity of hydrogenated anacardic acid

[0268] The results for the reference compound (1), named P4 (hydrogenated anacardic acid) are expressed in Table 5 and [Fig.4] as the mean of percentage of cell viability normalized to the control condition (untreated) and the standard deviation of the mean (Std. Dev.). The toxicity threshold is set at 70% cell viability (%) and visualized in [Fig.3] as a dotted line.

[0269] [Tables5] Concentrations % Viability Std. Dev CTRL 100 2 P4 0.1% 10 2 P4 0.05% 8 3 P4 0.03% 9 2 P4 0.01% 10 3 P4 0.005% 51 5 P4 0.003% 105 8 P4 0.001% 103 7 P4 0.0005% 101 7 H2O2 (toxicity) 3 1

[0270] Table 5: Results of cell viability analysis after contact with hydrogenated anacardic acid (1) at different mass concentrations.

[0271] These results in Table 5 and [Fig.4] show that anacardic acid exhibits cytotoxicity on keratinocyte cells at the concentrations tested.

[0272] The highest non-toxic concentration tested is 0.003% by mass.

[0273] Example 16: Method for evaluating sun protection Principle

[0274] The level of protection of a cosmetic product containing sunscreens can be evaluated by an in vitro spectrophotometric method.

[0275] The method allows you to provide information on:

[0276] - the protection coefficient “SPF”,

[0277] - the UVA protection factor “PF-UVA”, and

[0278] - the Critical Wavelength “LOC”, which must not be less than 370 nm, so that formulated products can claim conformity of their UVA protection value, by a UVA logo.

[0279] To determine the effectiveness of sunscreens, their ability to prevent erythema that appears on the surface of the skin if it is exposed for a certain time to a source of UV energy is assessed. UVB rays represent only about 5% of the total UV energy received (UVA + UVB), but given their energy, they have a predominant effect on the appearance of this erythema. UVA rays, for their part, are involved in the appearance of sunburn to the tune of about 16%.

[0280] The method used consists of measuring the UV energy flux passing through the cream, expressed in energy transmission and to compare this flux to the initial flux according to the principle of any spectrophotometric method:

[0281] [Math.2] Or ; - X asi the wavelength; - I is the UV energy flux; - 10 is your energy flow Mat

[0282] However, the comparison of these two curves is not sufficient to express the level of protection of the product spread on the skin. Indeed, two other wave functions are involved: • The source wave function: In practice, this is the sun whose spectrum has been defined by the International Commission on Illumination as a wave function S(X). • The wave function concerning the skin: Cutaneous or subcutaneous reactions depend on the energy of the excitation light and are expressed in the form of a wave function E(X).

[0283] By integrating each of these 3 curves over the entire UVB and UVA range and taking the product of the 3 integrals, we will obtain the expression of the SPF In Vitro.

[0284] This method was originally described by B. Diffey and J. Robson (JSCC 40. 127-133 - 1989). It is now widely used and recognized by international bodies. Materials and methods

[0285] Laboratory equipment - A UV spectrophotometer, Kontron 933 (BIO-TEK Kontron instruments) equipped with a UV source and a monochromator as well as an integrating sphere capable of delivering a UV energy flux between 290 and 400 nm. The wavelength increment is 1 nm. - A solar simulator, Suntest CPS+ (Atlas) allowing to reproduce sunlight and to take into account the possible photodegradation of the tested sample.

[0286] The sample is spread on Sunplate (Helioscience) polymethyl methacrylate (PMMA) plates, measuring 5x5 cm, having a rough phase obtained by sandblasting.

[0287] The tested product is spread according to the quantity recommended by the standards, i.e. 1.3 mg / cm 2 for PMMA.

[0288] The sample is exposed to 2 minimal erythemal doses “MED”.

[0289] The MED value was chosen at 550 W / m2, this value corresponding to exposure to zenithal sunlight. With this standard sunlight, while receiving 2 MED, the product will therefore receive: 400 J / m2.

[0290] The measuring device is pre-calibrated with PMMA plates.

[0291] The tests are carried out on 3 PMMA plates on which the product is deposited. 4 plate measurements were carried out with the spectrometer. Determination of SPF value

[0292] The in vitro SPF is expressed from the entire residual UVB and UVA spectrum having passed through the layer of cream spread on the plate. However, this wave function T(X) must be multiplied by: - A first wave function which expresses the spectral characteristic of the sun S(X). - A second wave function which expresses the reactivity of the skin as a function of the wavelength (and therefore of the dissipated energy): the erythematous function E(X).

[0293] [Math.3] this

[0294] With: - E(X) is the action spectrum of erythema - S(X) is the standard solar spectrum - T(X) is the average transmission of the test product layer spread on a suitable support - d(X) is the wavelength interval (1 nm) Determination of PF-UVA value

[0295] In vitro UVA protection is expressed from the entire residual UVA spectrum having passed through the same layer of cream.

[0296] [Math.4] SS ZU)-d W PFUVA= SS Z. P (>0. LU). T W- d (X)

[0297] With: - P(X) is the action spectrum of PPD - L(X) is the spectrum of the Xenon arc lamp - T(X) is the average transmission of the test product layer spread on a suitable support - d(X) is the wavelength interval (1 nm) Determination of LOC value

[0298] In the calculation, Xc corresponds to the wavelength for which the area under the absorption curve reaches 90% of the total area from 290 nm to 400 nm. The critical wavelength will therefore be determined according to the formula:

[0299] [Math.5] fAc ftoonm LOC = IA(l) * d(Â) = 0.9 x IA(A) xd(À) '• 290 nm 2290 nm

[0300] With: - The corresponds to the critical wavelength - A(X) corresponds to absorption - d(X) corresponds to the wavelength interval between measurements

[0301] The critical wavelength Le of the tested product is obtained by calculating the arithmetic mean of the different measurements: all the selected measurements are taken into account for the calculation of the statistical dispersion. Statistical expression of results

[0302] The average protection index of the preparation studied is obtained by calculating the arithmetic mean of the protection indices of each test.

[0303] The calculations are obtained using specific software which allows immediate access, without any manipulation, to all the calculations necessary to obtain the values. Analysis under irradiation

[0304] All of these analyses can be carried out after irradiation of the sample.

[0305] After measuring the absorbance of the plate, it is irradiated using a solar simulator delivering a dose of 4 DEM (800 J / m2).

[0306] The PMMA plate containing the spread product is analyzed using a UV spectrophotometer to determine the absorbance of the sample in the 290-400 nm range after irradiation.

[0307] Example 17

[0308] The analyses according to Example 16 were carried out on the 3 compounds (2), (3) and (4) of the invention from solutions diluted to 1g / L in ethanol and prepared with the compounds in powder form. The results are reported in Table 6. The results after irradiation are reported in Table 7.

[0309] [Tableauxô] Tested Compound SPF Measured UVA LOC (nm) Compound (4) 12.5 1.3 330 Compound (2) 13.0 1.3 331 Compound (3) 3.1 1.2 358

[0310] Table 6: Results of sun protection analysis

[0311] [Tables?] Compound tested after irradiation SPF Measured UVA LOC (nm) Compound (4) 9.8 1.2 330 Compound (2) 11.2 1.2 328 Compound (3) 2.7 1.2 353

[0312] Table 7: Results of analysis of sun protection after irradiation

[0313] Example 18: Method for analyzing photosatibility

[0314] Photo stability is calculated using the following equation:

[0315] [Math.6] SPE-,, PliotostabOîté = —— x ÎOD SFR

[0316] Where:

[0317] - SPFir corresponds to the SPF after irradiation,

[0318] - SPFi corresponds to the initial SPF before irradiation.

[0319] Irradiation is carried out using a solar simulator delivering a dose of 4 DEM (800 J / m2).

[0320] There is no standard that defines what a photostable product is. However, if this value is greater than or equal to 70%, the product is considered to be photostable. It would not be reasonable to expect or demand that the product be 100% photostable.

[0321] According to this method, the solar product is qualified as follows:

[0322] - Average photo stability < 70%: photo-unstable

[0323] - 70% < Average photo stability < 80%: photostable

[0324] - Average photo stability > 80%: very photostable.

[0325] Example 19: Analysis of photo stability

[0326] The photostabilities of compounds (2), (3) and (4) were carried out according to example 18 and reported in the following table 8.

[0327] [Tables8] Compound tested Photostability (%) Compound (4) 78% Compound (2) 86% Compound (3) 87%

[0328] Table 8: photo stability

[0329] The compounds of the invention are photostable. In particular, compounds (2) and (3) are considered to be very photostable.

[0330] Example 20: Percentage of light stopped

[0331] The measured UV spectra of [Fig.5] for compounds (4) and (2) make it possible to extract the percentage of light stopped.

[0332] The results in percentage of light stopped for compounds (4) and (2), before and after irradiation (noted after IR) are reported in table 9 and [Fig.6].

[0333] [Tables9] Compound tested after irradiation Irradiation UVA UVB Total UV Compound (4) Without 48 99 29 After IR 45 97 25 Compound (2) Without 50 99 31 After IR 46 99 26

[0334] Table 9: Percentage of light stopped

[0335] The spectra of [Fig.5] reveal that compounds (4) and (2) absorb in the UV range at a maximum wavelength which is shifted towards UVB.

[0336] The results in Table 9 and [Fig.6] show that protection in UVB is improved for compounds (4) and (2) with UVB absorption of the order of 99%.

Claims

1. Claims Compound of the following general formula (I): [Chem.28] (tj in which: - A is chosen from: • a hydrogen atom, or • a linear or branched alkyl group of 1 to 12 carbon atoms, preferably a methyl or ethyl group, or • a linear or branched -CO-alkyl group of 1 to 12 carbon atoms, preferably a -CO-CH3 group, or • an AO group: [Chem.29] O AO in which R2 and R3, identical or different, are chosen from: • a hydrogen atom, or • an alkoxy group of 1 to 8 carbon atom(s), preferably a methoxy group, or • an -OH group, preferably the AO group is chosen from the following groups: A3 A7 A® B is chosen from: • a hydrogen atom, or • a linear or branched alkyl group of 1 to 12 carbon atoms, preferably a methyl or ethyl group, or • a B0 group: in which R4, R5 and R6, identical or different, are chosen from: • a hydrogen atom, or • an alkoxy group of 1 to 8 carbon atoms, preferably a methoxy group -O-CH3, or • an -OH group, preferably the BO group is chosen from the following groups: [Chem. 32] 86 Bï provided that A represents the grouping and / or B represents the group [Chem. 34]

2. Compound according to claim 1, of formula chosen from formulas (II), (III) and (IV): Rg — H, CH i or CgH Rp = H or CH 3 or -COCH3 (III) O

3. (IV) wherein RB R2, R3, R4, R5 and R6 have the meanings defined in claim 1. A compound of formula (I) according to claim 1, wherein Group A is chosen from: - a hydrogen atom, or - a linear or branched alkyl group of 1 to 12 carbon atoms, preferably a methyl or ethyl group, or - a linear or branched -CO-alkyl group of 1 to 12 carbon atom(s), preferably a -CO-CH3 group, or a grouping chosen from the following formulas: [Chem.36] Al A5 Group B is chosen from: a hydrogen atom, or a linear or branched alkyl group of 1 to 12 carbon atoms, preferably a methyl or ethyl group, or a group chosen from the following formulas: [Chem.37]

4. Compound of formula (I) according to one of claims 1 to 3, in which Group A is chosen from: - a hydrogen atom, or - a linear or branched alkyl group of 1 to 12 carbon atoms, preferably a methyl or ethyl group, or - a linear or branched -CO-alkyl group of 1 to 12 carbon atoms, preferably a -CO-CH3 group, or - a grouping of the following formula Al: Group B is chosen from: - a hydrogen atom, or - a linear or branched alkyl group of 1 to 12 carbon atoms, preferably a methyl or ethyl group, or - a grouping of the following formula B1: [Chem. 39] provided that A represents the group [Chem. 40] and / or B represents the group [Chem.41] in particular, of the following formulas: R_ = H or CH 3 su - COCH r' w' notably

5. Cosmetic composition comprising at least one compound of formula (I) according to one of claims 1 to 4 in a cosmetically acceptable medium.

6. Cosmetic composition according to claim 5, in which the compound(s) of formula (I) represents 0.00003 to 10% by total mass of the composition, in particular from 0.005 to 10%.

7. Cosmetic composition according to one of claims 5 or 6, said composition comprising at least one cosmetic adjuvant or excipient, in particular chosen from: fatty substances, organic solvents, ionic or non-ionic thickeners, softeners, preservatives, emulsifiers, hydrophilic or lipophilic gelling agents, opacifiers, stabilizers, emollients, α-hydroxy acids, anti-foaming agents, moisturizing agents,

8.

9.

10.

11.

12. vitamins, perfumes, preservatives, surfactants, fillers, sequestrants, polymers, propellants, alkalizing or acidifying agents, and colorants. Cosmetic composition according to one of claims 5 to 7, said cosmetic composition being formulated for topical application, in particular topical application to the skin, said composition being in particular in the form of an aerosol, an emulsion, a microemulsion, a lamellar emulsion, liposomes, encapsulated forms, a cream, a gel, a dispersion, a serum, a mousse, a body milk or an anhydrous balm, preferably in the form of a body milk or a cream. Cosmetic composition according to one of claims 5 or 8 for its use as an antioxidant cream on healthy skin. Cosmetic composition according to one of claims 5 to 9 for its use on healthy skin as a UV absorber, in particular as a sunscreen. Cosmetic composition according to one of claims 5 to 8 for its use on healthy skin as a keratolytic agent. Use of a compound according to one of claims 1 to 4 for the release on healthy skin, in the presence of esterase, of a molecule of anacardic acid and at least one molecule of natural substance of formula: [Chem. 44] WHAT

13. in which Rb R2, R3, R4, R5 and R6 have the meanings defined in claim 1. Dermatological composition, comprising as active substance, a compound according to one of claims 1 to 4, with a pharmaceutically acceptable excipient, said composition being in particular formulated for topical application, in particular topical application to the skin, said composition being in particular in the form of an emulsion, a cream, a gel, a dispersion, a serum, a mousse, a body milk or an anhydrous balm.

14. Composition according to claim 13 for its use in the prevention or treatment of pathologies linked to oxidative stress.

15. Composition according to claim 13 for its use for photoprotection against solar radiation.

16. Composition according to claim 13 for its use for the prevention and treatment of conditions of the epidermis produced by an excess of keratin, in particular the treatment of warts, psoriasis or acne.

17. Process for the preparation of a compound of formula (I) according to claim 1 from hydrogenated anacardic acid, comprising: a) a step of esterification or etherification of the phenol function of the hydrogenated anacardic acid, and / or b) a step of esterification of the acid function of the hydrogenated anacardic acid.

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