Classifications

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  • A61K36/13—Coniferophyta (gymnosperms)
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  • A61K36/18—Magnoliophyta (angiosperms)
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  • A61K36/18—Magnoliophyta (angiosperms)
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  • A61K36/896—Liliaceae (Lily family), e.g. daylily, plantain lily, Hyacinth or narcissus
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  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
  • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
  • A61K8/9755—Gymnosperms [Coniferophyta]
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  • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
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  • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
  • A61K8/9783—Angiosperms [Magnoliophyta]
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  • A61Q15/00—Anti-perspirants or body deodorants

Definitions

• the present invention relates to particular extracts obtained from perfume plants, aromatic plants or medicinal plants, which comprise both volatile compounds and phenolic compounds.
• the subject of the invention is also the process for obtaining these extracts, as well as the compositions including them and their uses.
• PPAMs are mainly used to extract:
• these extracts are generally in the form of essential oils or in the form of hydrolats or floral waters;
• phenolic compounds macerates comprising nonvolatile phenolic compounds.
• Terpenes are compounds which have a backbone with at least one isoprenic unit with 5 carbon atoms called isoprene unit (2-methylbut-1,3-adiene).
• the number of carbon atoms constituting the molecules of this group can be distinguished: the hemiterpenes (1 unit: C5), the monoterpenes (2 units: C10), the sesquiterpenes (3 units: C15), the diterpenes (4 units : C20), sesterpenes (5 units: C25), triterpenes (6 units: C30), tetraterpenes (8 units: C40) and polyisoprenes (n units: C5n).
• Phenolic compounds constitute a very diverse set of several thousand molecules classified according to their chemical structure and their biosynthetic pathway. Single phenols, phenolic acids, coumarins, flavonoids, isoflavonoids, xanthones, stilbenes, tannins, lignans and quinones are distinguished.
• the common basic structural element is a benzene ring to which at least one hydroxyl group is directly bonded, free or engaged in another function generally oxide or ester. They are generally obtained by maceration of PPAM in hydroalcoholic solutions.
• Phenolic compounds are plant secondary metabolites known for their important antioxidant properties and are used in the pharmaceutical and cosmetic fields.
• organic solvents conventionally used, mention may be made of glycol ethers, hexane, ether, acetone, methylene chloride, chlorinated and fluorinated solvents for example.
• These solvents make it possible to obtain lipophilic (or strongly apolar) molecules with satisfactory yields, but they have numerous disadvantages. They are particularly highly flammable, dangerous or extremely toxic for humans and their environment.
• Supercritical C0 2 extraction developed from the 1970s as it is non-flammable, non-toxic, available, inexpensive and recyclable. However, because solubilization properties of supercritical CO 2 , the extraction is selective for hydrophobic compounds such as lipids, volatile compounds, carotenoids. The extraction of more polar molecules of phenolic compounds type is possible only by the addition of co-solvent such as ethanol, methanol or water.
• the objective of the invention is to overcome these disadvantages and shortcomings.
• it relates to an extract obtained from at least one plant selected from scented plants, aromatic and medicinal, comprising both volatile compounds and phenolic compounds (non-volatile).
• the subject of the invention is an extract obtained from at least one plant chosen from fragrant, aromatic and medicinal plants, comprising between 0.1% and 5% of volatile compounds by weight of dry matter of extract and between 0.5% and 40% of phenol compounds by weight of dry matter of the extract.
• the process according to the invention makes it possible to obtain extracts rich in water-soluble molecules of a polar nature - phenolic compounds - but surprisingly and unexpectedly, it also makes it possible to simultaneous extraction of apolar molecules - volatile compounds.
• the invention provides a process which consists of a subcritical water extraction from at least one plant chosen from fragrant, aromatic and medicinal plants, carried out at least with the following three conditions:
• the water in the subcritical state circulates through the plant by carrying with it the solubilized compounds, and for a very short time.
• V Volume of the cylinder (extraction tank)
• the passage time of the compounds extracted in the process according to the invention is thus between 11 and 17 minutes, preferentially 15 minutes, ie a shorter contact time. only in the "batch" process described in the prior art, where the contact time is 20 to 30 minutes.
• the method according to the invention in dynamic mode allows a concomitant extraction of volatile compounds and phenolic compounds in significant proportions within the same aqueous extract, with a good yield. It particularly makes it possible to extract certain volatile compounds that are not present in hydrolates or essential oils and / or to eliminate certain troublesome components present in essential oils, in particular allergens.
• the aqueous extracts thus obtained have an aromatic character and antimicrobial properties related to their volatile fraction, and simultaneously antioxidant properties because of their high content of phenolic compounds. They can be used in compositions, such as, in particular, perfume compositions, food compositions, cosmetic compositions, veterinary products, cleaning products and medicaments.
• the subject of the invention is therefore also a composition comprising at least 0.1% of an extract according to the invention, as well as the use of said extract alone or in a composition, as a cosmetic or pharmaceutical or veterinary active ingredient, perfume additive or preservative.
• critical water within the meaning of the invention is meant water brought to temperatures greater than or equal to 100 ° C and less than or equal to the critical point (374 ° C) and at pressures below 221 bar.
• allergenic compounds within the meaning of the invention is meant substances known to cause allergies in humans. These are in particular the substances indicated in the list of ingredients mentioned in 8 ° of Article R.5131-4 of the French Public Health Code. These substances are part of a list of 26 substances, identified as likely to cause allergic contact reactions in sensitized individuals (likely contact allergens).
• extract of at least one plant chosen from fragrant, aromatic and medicinal plants within the meaning of the invention is meant a set of molecules obtained from all or part of one or more chosen plants ( s) among fragrant, aromatic and medicinal plants.
• cosmetic active ingredient within the meaning of the invention is meant a substance having an effect on the skin to improve its appearance and / or its functions and / or to protect it.
• terpenoid means oxygenated derivatives of terpenes.
• a wide variety of structures characterize terpenoids according to the number of carbons present, the saturated or unsaturated nature of the bonds, the spatial configuration and the nature of the functional group. They consist of different functions:
• R1-O-R2 eg eucalyptol
• the subject of the invention is therefore a subcritical water extract obtained from at least one plant chosen from perfume, aromatic and medicinal plants, comprising both volatile compounds and phenolic compounds.
• the volatile compounds are present between 0.1% to 5% by weight of dry matter of the extract, preferably between 0.5 and 3%.
• the volatile compounds present in the extract according to the invention are at least partly terpenes.
• the terpenes may be at least partly oxygenated terpenes and / or at least partly hydrocarbon terpenes.
• the relative share of oxygenated terpenes in the extract according to the invention is at least 95% of the terpenes.
• Oxygenated terpenes are preferably alcohols and / or ketones and / or esters. According to a suitable embodiment:
• the relative part of the alcohols is between 5% and 50% of the oxygenated terpenes, and / or
• the relative part of the ketones is between 5% and 75% of the oxygenated terpenes, and / or
• oxygenated terpenes present in the extracts according to the invention are preferably chosen from one or more of the following oxygenated terpenes: ⁇ -terpineol, linalool, geraniol, citronellol, menthol, eucalyptol, verbenone, italidiones, ⁇ -damascenone, cryptone, nerol, carvacrol, thymol, borneol, eugenol, linalyl acetate, camphor, benzyl benzoate. In particular, they are chosen from:
• Camphor extract - Verbenone for example extracted from Rosemary
• benzyl benzoate for example extracted from YIang-Ylang
• these molecules are known for their antioxidant, anti-inflammatory and antibacterial properties and their presence in large quantities in the extracts according to the invention makes it possible to increase the effectiveness of said extracts in cosmetic or pharmaceutical compositions.
• hydrocarbon terpenes when they are present, their relative share in the extract according to the invention preferably represents less than 5% of the total terpenes.
• the phenolic compounds are present between 0.5% and 40% by weight of dry matter of the extract, preferably between 3% and 20%.
• they are chosen from at least one of the following phenolic compounds: simple phenols, phenolic acids, stilbenoids and flavonoids.
• they may be phenolic compounds chosen from at least one of the following phenolic compounds: quercetin, myricetin, kaempferol and their glycosylated derivatives, catechin, epicatechin and their proanthocyanidol oligomers, anthocyanidins and their glycosylated derivatives arbutin, gallic acid, quinic acid, p-coumaric acid, caffeic acid, caffeoylquinic and di-O-caffeoylquinic acids, rosmarinic acid, resveratrol and its glycosylated derivatives.
• these molecules are known for their antioxidant and anti-inflammatory properties, and their presence in large quantities in the extracts according to the invention makes it possible to increase the effectiveness of said extracts in cosmetic or pharmaceutical compositions.
• the extract according to the invention contains little or no allergenic compounds, that is to say less than 0.002% by weight of dry matter of the extract.
• the extracts according to the invention are obtained from one or more plant (s) chosen from fragrant, aromatic and medicinal plants belonging to the botanical genera. following: Helichrysum, Rosmarinus, Eucalyptus, Inula, Laurus, Rosa, Thymus, Mentha, Citrus, Lavandula, Cupressus, Salvia, Picea, Pinus, Jasmine, Anthemis, Lippia, Myrtus, Lilium, Arnica, Cinnamomum, Crocus, Cananga, Pelargonium.
• Helichrysum Rosmarinus, Eucalyptus, Inula, Laurus, Rosa, Thymus, Mentha, Citrus, Lavandula, Cupressus, Salvia, Picea, Pinus, Jasmine, Anthemis, Lippia, Myrtus, Lilium, Arnica, Cinnamomum, Crocus, Cananga, Pelargonium.
• the extracts according to the invention possess both quantitative and qualitative richness of molecules: volatile compounds and phenolic compounds. In addition, they are obtained from an aqueous solvent which, unlike the extracts obtained with organic solvents, does not contain traces of toxic and carcinogenic residues.
• the extracts according to the invention are preferably obtained by extraction with subcritical water. They can be obtained in particular by the implementation of a method of extraction with subcritical water in "dynamic" mode by percolation.
• the subcritical water extraction process is preferably carried out in a dedicated device consisting in particular of a cylindrical extraction tank, a heating system, a temperature control system, a water pumping system, a pressure control system.
• Subcritical water extraction in dynamic mode preferably comprises the following steps:
• the method according to the invention is particular for the selected parameters. This is a subcritical water extraction process characterized by the following parameters:
• a pumping rate of circulating water of between 1 and 4, preferably between 2 and 3 ml / min,
• a ratio raw material / extract between 1/2 and 1/30 (weight / volume), pressurizing the water between 20 and 60 bar.
• the method according to the invention may comprise the implementation of the following steps:
• the process according to the invention makes it possible to selectively extract both volatile compounds and phenolic compounds in the same extract. It thus brings a real originality in terms of molecular constituents vis-à-vis the hydrolates and essential oils of PPAM, and this with significant yields and the use of a solvent that is environmentally friendly.
• the extracts according to the invention can be used alone or in compositions.
• compositions comprising at least 0.1% of an extract according to the invention.
• These compositions may contain suitable excipients and possibly one or more other extract (s) or active subtances).
• the compositions according to the invention may especially be in the form of cream, oil, ointment, gel, powder, lotion, serum or soap. Because of the molecules that constitute the extracts according to the invention, they have numerous effects.
• ketones are known for their ability to heal and regenerate cutaneous tissues and mucous membranes in the case of burns or wounds, they are also mucolytic.
• Terpenic alcohols and in particular those having an allyl alcohol group have antioxidant activities.
• A-terpineol has antibacterial and anti-cancer properties.
• Borneol is analgesic and anesthetic. It increases the sensitivity of GABA (gamma-aminobutyric acid) receptors to their natural ligand and enhances the activity of low doses of GABA.
• GABA decreases the activity of other neurotransmitters. It therefore modulates the activity of the central nervous system in general.
• Phenolic compounds are known to exhibit antioxidant, anti-collagenase, anti-elastase and anti-inflammatory activities. Especially among flavonoids, myricitrin has analgesic, anxiolytic, antiallergic and hepatoprotective properties. Similarly, the hyperoside has antiviral properties, in particular against the hepatitis B virus, antifungal and antimicrobial agents. In addition, phenolic acids also have important properties, including:
• Quinic acid has an inhibitory activity of the replication of the hepatitis B virus
• the caffeoylquiniques and di-O-caféoylquiniques acids are known for their slimming, antioxidant, skin lightening, antibacterial, antiviral, inhibition of the replication of the HIV virus.
• the extracts according to the invention can be used, alone or in a composition, as a cosmetic active ingredient, perfume, food flavoring, preservative or medicament.
• the subject of the invention is therefore also:
• an extract according to the invention alone or in a composition, as an anti-aging, firming, antiperspirant, anti-stain, antioxidant, antimicrobial, astringent, anti-dandruff, anti-seborrheic cosmetic active ingredient, purifying, soothing, moisturizing, slimming, healing, anti-wrinkle, anti-pollution, etc.
• an extract according to the invention alone or in a composition, as a food flavoring, in natural flavoring preparations to impart odor and taste to foodstuffs (alcohols, non-alcoholic beverages, confectionery, dairy products, meat products , sauces, soups, snacks, bakery products),
• an extract according to the invention alone or in an aromatherapy composition for treating, attenuating or preventing infections by inhalation or by application to the skin through massages for the treatment of stress, cramps rheumatism, pain, blood circulation, cellulitis, etc.
• the extract according to the invention for use in a pharmaceutical composition, especially as an antibacterial and / or antiviral and / or analgesic and / or anxiolytic and / or antiallergic and / or hepatoprotective drug, and / or for the treatment of canker sores, gingivitis, dental neuralgia, sore throat or to fight bad breath.
• the four PPAM species studied are Italian Immortelle (Helichrysum italicum), Myrtle (Myrtus communis), Rosemary (Rosmarinus officinalis), and Eucalyptus (Eucalyptus camaldulensis).
• the plant material was harvested in the wild in Corsica.
• the extraction reactor (volume 34 ml) is filled with 5 g of dried plant and crushed.
• the temperature of the water is set at 150 ° C, the flow rate at 2 ml / min and the pressure at 30 bar.
• a total volume of 150 ml of extract is harvested, an extraction time of 75 minutes.
• the volatile compounds contained in the extracts with subcritical water were analyzed in the following manner: after 3 successive liquid / liquid extractions with 25 ml of diethyl ether (C 4 H 10 O) and then evaporation of the solvent in the open air, the volatile compounds were analyzed qualitatively and quantitatively by GC-FID and GC / MS.
• the phenolic compounds were analyzed by HPLC-DAD and LC-MS / MS.
• Table 1 Concentrations of volatile compounds and phenolic compounds in the extracts with subcritical water (mg / l of aqueous extract).
• Tqblequ 2 Percentage of stoichiometric digits (%) of chemical products in hydrodistillation products (HE: essential oil and HY: hydrolytic) and in subcritical equals (ESC) Essential oils:
• the Myrtle and Roma rin EOs are mainly represented by hydrocarbon compounds (74% and 69.6% respectively), whereas the EO of Italy and Eucalyptus contain oxygenated compounds. In Myrte and Rosemary HEs, oxygenated compounds accounted for 25.2% and 29.6%, respectively, but with a different distribution of chemical families.
• Myrtle's EO contains 17.0% oxides vs. 0% in that of Roma rin, which contains in close proportion alcohols (9.4%), ketones (9.3%) and esters (10.7%) vs. 2.9%, 0.8% and 3.8%, respectively, in Myrte's HE.
• Eucalyptus EO is characterized by a higher proportion of oxygenates (52.4%), mostly represented by alcohols (28.9%) and aldehydes (8.4%).
• Immortelle's HE from Italy consists essentially of oxygenated compounds (73.4%) and in particular ketones (33.4%) and esters (27.1%).
• the chemical compositions of HE obtained from these 4 PPAMs are in agreement with those found in the literature.
• the volatile compound compositions in the hydrolates of the 4 species differ completely from those of the respective HEs. Very logically, very low proportions of hydrocarbon compounds (0 to 0.4%) were measured, so oxygenates (76.3% - 97.8%) are predominant in these solutions. The latter are essentially represented by alcohols (21.2% - 66.1%) and ketones (3.2% - 74.8%) and by oxides (Myrte, 20.1%). The proportions of alcohols and ketones are systematically higher in the hydrolates than in the corresponding HEs. In contrast, the esters are less well represented in the hydrolates of Rosemary, Italian Immortelle and Myrtle than in HE. It is the same for the aldehydes of Eucalyptus.
• Extracts with subcritical water according to the invention Extracts with subcritical water according to the invention:
• the chemical compositions of the volatile fractions of the extracts obtained with subcritical water according to the invention are clearly closer to those of the hydrolates than to those of the HEs.
• the analyzes highlight a true originality in terms of the molecular constituents of the extracts according to the invention with respect to HY and HE.
• the volatile compounds consist essentially of oxygenated compounds, the share of the hydrocarbon compounds being negligible (0% -0.5%).
• the oxygenated compounds the alcohols (5.1% - 47.3%) and the ketones (5.3% - 72.0%) are the predominant families.
• the extracts according to the invention are depleted of oxides, especially in the Myrtle extract where the proportion (9.8%) is lower than in the HY (20.1%) and in the HE ( 17%).
• the proportions of esters (0% - 1.7%) are lower than those found in the HE (3.8% - 27.1%).
• the aldehyde percentages of the Eucalyptus extract according to the invention are lower (1.2%) than in the HE (8.4%) and HY (4.5%).
• Table 3 Volatile compounds composition of Rosemary extracts from hydrodistillation and subcritical water extraction (mg compound / 100 g plant)
• the essential oil of rosemary has the particularity of having a high content of terpenic ketones (verbenone and camphor) and ester (bornyl acetate).
• the process according to the invention makes it possible to extract 2 times more ketones (verbenone and camphor) and 30 times less ester (bornyl acetate) than in the H E resulting from the hydrodistillation.
• the method according to the invention makes it possible to extract from beetol (35.8 mg / 100 g of plant), a bicyclic monoterpene alcohol that is not found in the HE from the hydrodistillation.
• Quantitative analysis by HPLC-DAD showed that the concentration of rosmarinic acid, a molecule of interest present in rosemary, is multiplied by 43 during extraction with subcritical water compared to the extraction method. by hydroalcoholic maceration (Table 4).
• Table 5 Volatile compounds composition of Eucalyptus extracts from hydrodistillgtion and subcritical water extraction (ma compound / 100 g of plant)
• the process according to the invention makes it possible to extract 3 times more volatile phenol (carvacrol, 11.0 mg / 100 g) compared with hydrodistillation (3.8 mg / 100 g).
• the process according to the invention makes it possible to extract 2.7 times more ketone (cryptone), 2 times less aldehydes and 10 times less alcohol (spathulenol) than during the production of HE by hydrodistillation. .
• linalool its content is reduced in the extract according to the invention (3.2 times less than in the H H extract), which is very favorable insofar as this compound is composed of compounds allergens whose content in cosmetics is regulated.
• Table 6 Volatile compound composition of Myrtle extracts from hydrodistillation and subcritical water extraction (mg compound / 100 g plant)
• the green myrtle (Myrtus communis) is a plant whose leaf essential oil contains hydrocarbon monoterpenes ( ⁇ -pinene) and oxides such as 1,8-cineole. While the essential oil has many properties (astringent, laxative, analgesic and tonic), its hydrolate also called “angel water” is highly appreciated for its fresh smell and its astringent properties.
• the Myrtle extract according to the invention contains 1.5 times more alcohols than HE and HY. Of the alcohols, those having an aromatic ring (p-cymene-8-ol and 7-ol) as well as ⁇ -terpineol are better extracted by the process according to the invention than by hydrodistillation. More specifically, ⁇ -terpineol appears to have a high affinity with subcritical water. With regard to the allergens in the extract according to the invention, linalool (4.7 times less extracted than in H E) and geraniol (in the form of traces), their contents very reduced in the extract According to the invention, it is a very favorable advantage insofar as these compounds comprise allergenic compounds the contents of which in cosmetics are regulated.
• the I mmortelle d'Italie is an emblematic plant of the Corsican maquis whose essential oil is very popular in the perfume and cosmetics sectors. It has a real originality vis-à-vis the essential oils produced in the Mediterranean basin since it is rich in esters (acetate and nyl propionate), alcohols (nerol), and ⁇ -diketones also called italidiones.
• the Italian Immortelle extract according to the invention contains a large quantity of dissolved volatile compounds (53.3 mg / L), and the amount of ⁇ -di-ketones (italidiones) extracted according to the process of the invention. (137.0 mg / 100 g) is greater than that of the essential oil obtained by hydrodistillation (110.3 mg / 100 g).
• O-terpineol is also better extracted (19.7 mg / 100g) than in the essential oil (4.9 mg / 100 g).
• the extract according to the invention does not contain esters (acetate and nyl propionate), unlike the essential oil.
• the linalool content is reduced in the extract according to the invention, which is very favorable with regard to the cosmetic regulation with regard to allergens.
• the maceration of the plant material was carried out in a volume of 30 to 40 ml of a water / ethanol mixture (50:50) with the aid of an orbital shaker for 6 to 8 hours depending on the plant material.
• the DPPH test (2,2-diphenyl-1-picrylhydrazyl) makes it possible to estimate the antioxidant potential of plant extracts, based on their ability to trap the free radical DPPH ' .
• the anti-radical activity of the extracts was determined using the test (DPPH). This test defines the ability of an extract to give an H ' radical to a violet-colored DPPH ' to reduce it to the yellow-colored DPPH-H form.
• test extract solution 50 ⁇ l of test extract solution are added to 150 ⁇ l of methanolic solution of DPPH (Sigma-Aldrich, 100 ⁇ l). After 30 minutes of incubation at 37 ° C, in the dark, the absorbance is measured at 520 nm using a microplate reader spectrophotometer. The tests are carried out in triplicate over 5 dilutions. A blank is also analyzed under the same conditions.
• the ORAC test makes it possible to estimate the antioxidant potential of plant extracts, based on their ability to trap free radicals.
• the ORAC method is based on the ability of antioxidants in a plant extract to limit the oxidation of an oxidizable substrate by free radicals.
• a solution of fluorescein (Sigma-Aldrich, 117 nM) is added to 30 ⁇ l of extract previously diluted in phosphate buffer, and the whole is incubated for 25 minutes at 37 ° C. 140 ⁇ l of AAPH solution (Sigma-Aldrich, 40 mM) are added to each well and the fluorescence is measured for 90 minutes.
• a blank (phosphate buffer) and a standard range of Trolox (Sigma-Aldrich, concentrations of 10 to 125 ⁇ ) are analyzed under the same conditions.
• the area under the curve (AUC) of each sample is calculated by the software by integrating the relative fluorescence curve
• the PPAM extracts according to the invention inhibit the DPPH radical in a significantly significant manner than do the PPAM extracts obtained by hydroalcoholic maceration and the values of the ORAC tests confirm the values of the DPPH ' test (Table 9).
• the rosemary extract according to the invention diluted 600 times has a percentage of inhibition 27 times higher than the hydro-alcoholic extract.
• the myrtle extract according to the invention diluted l / 600th, reveals a higher percentage of inhibition (75.4%) than that of the hydro-alcoholic extract diluted to 800 th (50.5 %).
• the ORAC values expressed in Trolox ® equivalents are higher (41.2 - 82.5 mM Trolox ® Eq) than the values calculated for the hydroalcoholic extracts (6.3 - 39.1 mM Trolox ® Eq).
• Subcritical water extracts of twelve aromatic and medicinal plants were prepared according to the method of the invention.
• the assay of the 26 cosmetic allergens was carried out by GC-MS according to the EFFA / IFRA Analytical Working Group method (A. Chaintreau, D. Joulain, C. Ma rin, CO. Schmidt, M. Vey GC-MS Ouantitation of Fragrance Compounds Suspected to Cause Skin Reaction, Part 1, J. Agric., Food Chem., 2003, 51, 6398-6403).

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