Pomegranate extract formulations with enhanced stability and their applications

Abstract

The present disclosure relates to a formulation in a cosmetically acceptable medium comprising: a) a pomegranate extract; b) at least one stabilizing agent comprising sodium thiosulfate; c) water; and d) at least one organic solvent. The present disclosure also relates to a kit comprising said formulation and to a method for cosmetically treating keratin materials using said formulation.

Description

Invention Field

[0001] This disclosure relates to the field of cosmetics. This disclosure particularly relates to pomegranate (which has enhanced stability) Punica granatum The formulation of the extract. It further relates to a method of cosmetically treating keratin materials using said formulation. Background of the Invention Antioxidants are key active ingredients in cosmetics targeting keratin materials, especially skin. Many antioxidants are already available, such as tocopherol (vitamin E) or its derivatives, vitamin C or its derivatives, carotenoids, ubiquinone, etc. In particular, consumers prefer products containing antioxidants derived from natural sources compared to synthetic antioxidants. Plant extracts are a major natural source of antioxidants used in cosmetics. Pomegranate extract is known in the art as an antioxidant active agent. FR3031901 describes a pomegranate extract obtained from a mixture of 70% w / w ethanol / 30% w / w water, containing no more than 1.93% ellagic acid, and a weight ratio [ellagic acid / punicalin A and B] equal to 0.2. WO2021064034A1 describes a pomegranate extract containing at least 10% by weight of punicalin and at least 10% by weight of ellagic acid, wherein the weight ratio [ellagic acid / punicalin] ranges from 0.5 to 2. The antioxidant activity of such extracts needs to remain stable in the formulation over time, especially after storage at room temperature for 2 weeks, 1 or 2 months. For pomegranate extract in particular, stability can be measured by the stability of pungentin content; if this content is greater than 91% after 2 weeks, 1 or 2 months of storage at room temperature, the formulation is considered stable. In some cases, it is also expected that the pomegranate extract in the formulation will be stable even under accelerated testing conditions, such as 45°C for 2 months or 55°C for 2 weeks.

[0003] Therefore, it is necessary to develop a cosmetic formulation in which the source of natural antioxidants remains stable under environmental conditions throughout the entire shelf life of the formulation without impairing its aesthetic and sensory aspects. In particular, a cosmetic formulation containing pomegranate extract is needed that remains stable for at least 2 weeks, 1 or 2 months at room temperature, wherein the content of punicin after storage is greater than 91% compared to the unstored content. A cosmetic formulation containing pomegranate extract is also needed that is further expected to be stable even under accelerated testing conditions, such as 45°C for 2 months or 55°C for 2 weeks.

[0004] The applicant has surprisingly demonstrated that formulations containing a) a pomegranate extract, preferably comprising at least 10% by weight of punicalin as a percentage of the total weight of the dry extract; and at least 10% by weight of ellagic acid as a percentage of the total weight of the dry extract; wherein the weight ratio [ellagic acid / punicalin] ranges from 0.5 to 2; b) at least one stabilizer comprising sodium thiosulfate; c) water; and d) at least one organic solvent are stable after storage at room temperature for 2 weeks, 1 or 2 months, i.e., the content of punicalin in such formulations after storage is greater than 91% compared to the content before storage. Invention Overview In one aspect of this disclosure, a formulation in a cosmetically acceptable medium is provided, comprising: a) a pomegranate extract; b) at least one stabilizer comprising sodium thiosulfate; c) water; and d) at least one organic solvent.

[0006] In another aspect of this disclosure, a kit is provided comprising (a) a formulation as disclosed herein; (b) a container; and (c) optionally, an applicator.

[0007] In another aspect of this disclosure, a cosmetic treatment method for a keratin material is provided, comprising applying an agent as disclosed herein to the keratin material, preferably to the skin.

[0008] These and other features, aspects, and advantages of the subject matter will be better understood by referring to the following description and appended claims. This overview is provided to introduce the concept in a simplified form. This overview is not intended to identify key or essential features of the claimed subject matter, nor is it intended to limit the scope of the claimed subject matter. Invention Details Those skilled in the art will recognize that variations and modifications are possible with respect to these specific descriptions. It should be understood that this disclosure includes all such variations and modifications. This disclosure also includes all such steps, features, compositions, and compounds individually or collectively mentioned or indicated in this specification, and any and all combinations of any one or more such steps or features.

[0010] definition For convenience, certain terms used in the specification and embodiments are detailed herein before further description of this disclosure. These definitions should be read in conjunction with the remainder of this disclosure and understood by those skilled in the art. The terms used herein have meanings recognized and known to those skilled in the art; however, for convenience and completeness, specific terms and their meanings are described below.

[0011] The articles “a”, “an”, and “the” are used to refer to one or more of the grammatical objects of the article (i.e., at least one).

[0012] The terms “comprise” or “contain” and “comprising” or “containing” are used in an open sense of inclusion, meaning that they may include additional elements. They are not intended to be interpreted as “consisting of only…”.

[0013] The term "at least one" is used to mean one or more, and therefore includes individual components as well as mixtures / combinations.

[0014] The term "polyol" is used to refer to an organic compound containing at least two hydroxyl groups, such as two, three, four, five, or six hydroxyl groups.

[0015] Throughout this specification, unless the context otherwise requires, the word “comprise” and variations such as “comprises” and “comprising” shall be understood to imply inclusion of the said element or step or group of elements or steps, but not to exclude any other element or step or group of elements or steps.

[0016] The term "including" is used to mean "including but not limited to". "Including" and "including but not limited to" are used interchangeably.

[0017] The term "INCI" is an abbreviation for International Nomenclature of Cosmetic Ingredients, which is a naming system provided by the International Nomenclature Committee of the Personal Care Products Committee for identifying cosmetic or personal care ingredients.

[0018] As used herein, the term "keratin material" refers to skin, hair, eyelashes, eyebrows, and nails, with skin being preferred.

[0019] As used herein, the term "cosmetically acceptable medium" means a medium that is compatible with "keratinous materials," preferably skin and / or its superficial body growths, exhibits a pleasant color, odor, and feel, and does not cause unacceptable discomfort (tingling or tightness) that might prevent a consumer from using the formulation for cosmetic application. Examples of cosmetically acceptable media include, but are not limited to, water, glycols, water-diol monocultures, water-in-oil or oil-in-water emulsions to form creams, serums, or lotions, and surfactant-based shampoos or facial cleansers or hair care products, water-surfactant mixtures for cleansing products, etc.

[0020] As used herein, the term "treatment" refers to any action designed to improve an individual's comfort or well-being. Therefore, the term encompasses reducing, alleviating, or suppressing symptoms of aging / damaged skin, but is limited to cosmetic treatments.

[0021] As used in this article, the term "room temperature" refers to a temperature between 18°C ​​and 25°C.

[0022] Unless otherwise stated, all percentages, parts, and ratios are based on the total weight of the formulations disclosed herein. Ratios, concentrations, amounts, and other numerical data may be presented herein in a range format. It should be understood that such range format is used for convenience and brevity only and should be flexibly interpreted to include not only the values ​​explicitly listed as range limits but also all individual values ​​or subranges covered within the range, as if each value and subrange were explicitly listed. For example, a percentage range of about 10% to 70% should be interpreted to include not only the explicitly listed limit of about 10% to about 70% but also subranges such as 20% to 30%, 30% to 45%, etc., and individual amounts within the specified range, including fractional amounts such as 28.4% and 64%.

[0023] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains. While any methods and materials similar to or equivalent to those described herein may be used in the practice or testing of this disclosure, preferred methods and materials are described hereafter. All publications referenced herein are incorporated by way of citation.

[0024] This disclosure should not be limited in scope to the specific embodiments described herein, which are intended for illustrative purposes only. As described herein, functionally equivalent products, compositions, and methods are clearly within the scope of this disclosure.

[0025] The embodiments described herein provide formulations in cosmetically acceptable media for skin treatment. The disclosed embodiments include formulations, kits containing said formulations, and methods for treating keratin materials by applying said formulations. In various embodiments herein, the formulations are in the form of an essence with improved stability of pomegranate extract. Cosmetics containing pomegranate extract have shown advantages in treating damaged skin and treating / preventing skin aging. Polyphenols, such as punicin and ellagic acid, are key active compounds present in the extract that contribute to skin treatment. However, due to the sensitivity of its phenolic antioxidants in water-based formulations, pomegranate extract exhibits poor stability in such cosmetics, which affects overall product stability. Therefore, it is necessary to select formulation components that favor the stability of the extract, a key active ingredient in the formulation. Therefore, formulations according to embodiments herein contain at least one stabilizer, namely sodium thiosulfate, which improves the stability of pomegranate extract to over 91% when stored at room temperature. Furthermore, the use of additional stabilizers, such as N-acetylcysteine, improves the stability of pomegranate extract to over 91% when stored under accelerated testing conditions.

[0026] preparation The embodiments described herein provide formulations for treating keratin materials, preferably skin. In one embodiment of this disclosure, a formulation for use in a cosmetically acceptable medium is provided, comprising: a) pomegranate extract; b) at least one stabilizer comprising sodium thiosulfate; c) water; and d) at least one organic solvent. In other embodiments, the formulation further comprises additives selected from pH adjusters, surfactants, thickeners, or mixtures thereof.

[0027] Pomegranate extract The formulations according to the embodiments described herein include pomegranate extract.

[0028] The pomegranate is a fruit-bearing deciduous shrub or small tree belonging to the Lythraceae family, growing to a height of 5 to 10 meters (16-30 feet). Bright red, white, or variegated flowers bloom at the tips of its branches, either singly or in clusters of up to five. The pomegranate fruit is nearly round, but with a prominent calyx at the base forming a crown. It has a tough, leathery outer skin or pericarp, and is generally yellow, covered with light pink, dark pink, or deep red. The interior is divided into compartments by membranous walls and white, spongy tissue, each compartment filled with a transparent aril containing a tart, palatable, fleshy, juicy pulp (aril). Within each aril is a white or red, angular, soft or hard seed. The aril accounts for approximately 52% of the total fruit weight.

[0029] In the preferred embodiment, the pomegranate fruits are harvested from near the Ramban district (kanga village) in Jammu and Kashmir, India, between September and December, more specifically at a latitude and longitude of approximately 32°N, 74°E.

[0030] The pomegranate extract is preferably an ethanolic or dry extract of the fruit, particularly the pomegranate peel. As used herein, the term "dry extract" refers to an extract containing no more than 7% by weight of solvent relative to the total weight of the dry extract, preferably no more than 5%, and more preferably no more than 3% by weight of solvent relative to the total weight of the dry extract. In a preferred embodiment of this disclosure, the dry extract contains no more than 1% by weight of solvent relative to the total weight of the dry extract. In another preferred embodiment, the dry extract is free of any solvent (i.e., 0%), wherein the solvent may be water or a C2-C5 monohydric alcohol selected from ethanol, propanol, isopropanol, butanol, and pentanol, and mixtures thereof.

[0031] In a preferred embodiment, the method for preparing pomegranate extract includes at least the following steps: i. providing pomegranate peel; ii. extracting at least pungentin and ellagic acid from the peel with ethanol of at least 99.5% degree for 2 to 5 hours at a temperature in the range of 37°C to 45°C; iii. filtering and repeating step (ii) at least twice; iv. optionally, vacuum drying the filtrate obtained at the end of step (iii) at a temperature in the range of 35°C to 40°C.

[0032] Advantageously, the ethanol in step (ii) has a water content of less than 0.5%, more preferably less than 0.2%.

[0033] Preferably, the pomegranate extract contains pungentin and ellagic acid.

[0034] As used herein, the term "arugula glycoside" refers to a mixture of two diastereomers, arugula glycoside A and B. They belong to the polyphenol family and, in particular, are complex ellagitannins formed by the linkage of glucose with ellagic acid and polygallic acid, with a molar mass of about 1084 gmol-1, formed from isomers of 2,3-(S)-hexahydroxybiphenyldicarboxyloyl-4,6-(S,S)-galloyl-D-glucose of formula (I).

[0035] As used in this article, the term “ellagic acid” refers to the polyphenol of formula (II).

[0036] In a preferred embodiment, the weight ratio of [peel / anhydrous ethanol] is 1:5.

[0037] Advantageously, the temperature range of extraction step (ii) is 40°C to 43°C, more preferably 42°C.

[0038] The filtration step (iii) is performed according to conventional filtration methods known to those skilled in the art, such as by means of a Buchner funnel.

[0039] Preferably, the temperature range of the drying step (iv) is 37°C to 39°C, more preferably 38°C.

[0040] Preferably, the method for preparing pomegranate extract comprises: i. providing pomegranate peel; ii. extracting at least pungentin and ellagic acid from the peel with ethanol of at least 99.5% degree for 2 to 5 hours at a temperature in the range of 37°C to 45°C; iii. filtering and repeating step (ii) at least twice; iv. optionally, vacuum drying the filtrate obtained at the end of step (iii) at a temperature in the range of 35°C to 40°C.

[0041] According to the embodiments described herein, the pomegranate extract comprises i) at least 10% by weight of punicalin, which is the total weight of the dry extract; and ii) at least 10% by weight of ellagic acid, which is the total weight of the dry extract; wherein the weight ratio [ellagic acid / punicalin] is in the range of 0.5 to 2.

[0042] The extract according to the invention may further contain 1% to 5% by weight of pomegranate tannin, preferably 2% to 4.5%, and even more preferably 3% to 4%, of the total weight of the dry extract.

[0043] Advantageously, the weight ratio of [ellagic acid / punicin] ranges from 0.6 to 1.6, more preferably from 0.7 to 1.3, and even more preferably from 0.7 to 1.

[0044] In a preferred embodiment, the extract according to the invention comprises: i) 11.7% to 14.6% by weight of punicalin, and ii) 11.2% to 14.5% by weight of ellagic acid, wherein the weight ratio [ellagic acid / punicalin] ranges from 0.6 to 1.6, more preferably from 0.7 to 1.3, and even more preferably from 0.7 to 1.

[0045] In another preferred embodiment, the extract according to the invention comprises: i) 11.7% to 14.6% by weight of punicalin, ii) 11.2% to 14.5% by weight of ellagic acid, and iii) 3% to 4% by weight of punical tannin, wherein the weight ratio [ellagic acid / punicalin] ranges from 0.6 to 1.6, more preferably from 0.7 to 1.3, and even more preferably from 0.7 to 1.

[0046] According to the embodiments described herein, the amount of pomegranate extract present in the formulation can vary. According to the embodiments described herein, the pomegranate extract may be present in the formulation at a weight range of 0.01% to 10% relative to the total weight of the formulation, preferably at a weight range of 0.02% to 5%, and more preferably at a weight range of 0.05% to 3% relative to the total weight of the formulation.

[0047] In some further embodiments herein, the formulation comprises a pomegranate extract comprising i) at least 0.001% by weight of punicalin, preferably in the weight range of 0.001% to 1% relative to the total weight of the formulation; and ii) at least 0.001% by weight of ellagic acid, preferably in the weight range of 0.001% to 1% relative to the total weight of the formulation; and wherein the weight ratio [ellagic acid / punicalin] ranges from 0.5 to 2.

[0048] stabilizer The formulation according to the embodiments described herein includes at least one stabilizer.

[0049] As used herein, the term "stabilizer" refers to those substances used to maintain the function and activity of active ingredients, such as plant extracts in cosmetic formulations. Furthermore, stabilizers are also necessary to maintain the functionality and aesthetics of formulations when stored under appropriate conditions.

[0050] According to the embodiments described herein, the formulation comprises at least one stabilizer containing sodium thiosulfate.

[0051] Examples of optional additional stabilizers that may be used in the formulations disclosed herein include, but are not limited to, N-acetylcysteine.

[0052] According to the present invention, the amount of sodium thiosulfate present in the formulation can vary. Sodium thiosulfate may be present in the formulation at a weight range of 0.01% to 2% relative to the total weight of the formulation, preferably at a weight range of 0.03% to 1%, more preferably at a weight range of 0.05% to 0.8%, such as 0.2%.

[0053] According to the present invention, the amount of one or more optional additional stabilizers present in the formulation may vary. The total amount of optional additional stabilizers present in the formulation is in the weight range of 0% to 2% relative to the total weight of the formulation, preferably in the weight range of 0% to 1%, more preferably in the weight range of 0% to 0.8%, such as 0.1%.

[0054] According to the embodiments described herein, the amount of stabilizer (i.e., sodium thiosulfate and optionally additional stabilizer, preferably N-acetylcysteine) present in the formulation can vary. According to the embodiments described herein, the stabilizer can be present in the formulation at a weight range of 0.01% to 4% relative to the total weight of the formulation, preferably at a weight range of 0.03% to 1%, such as 0.3%.

[0055] water According to the present invention, the formulation comprises water. In a preferred embodiment, the formulation comprises water at a weight of greater than 10% and less than 70% relative to the total weight of the formulation.

[0056] In a more preferred embodiment, the formulation contains water in the following weight range relative to the total weight of the formulation: preferably 10% to 70% by weight, more preferably 40% to 60% by weight.

[0057] organic solvents According to the embodiments described herein, the formulation includes at least one organic solvent.

[0058] According to the embodiments described herein, the organic solvent is selected from C1-C4 monohydric alcohols (ethanol or isopropanol or 2-ethoxyethanol), or polyhydric alcohols such as C2-C8 polyhydric alcohols (triols, such as glycerol; hexahydric alcohols, such as sorbitol; diols, such as octyl ethylene glycol, 1,2-pentanediol, propylene glycol, butanediol, ethylene glycol, propylene glycol, butanediol, dipropylene glycol, diethylene glycol, 1,2-propanediol, 1,3-butanediol, pentanediol, hexanediol, diethylene glycol monomethyl ether or triethylene glycol monomethyl ether), or mixtures thereof.

[0059] In one embodiment, the formulation comprises a mixture of at least one C1-C4 monohydric alcohol (preferably ethanol) and at least one polyol, preferably with a total weight ratio of polyol / total C1-C4 monohydric alcohol >1, more preferably >5.

[0060] In one embodiment, the formulation comprises at least one polyol selected from pentylene glycol, glycerol, butylene glycol, hexanediol, dipropylene glycol, propylene glycol, or mixtures thereof, more preferably selected from glycerol, pentylene glycol, butylene glycol, or mixtures thereof.

[0061] According to the embodiments described herein, the amount of organic solvent present in the formulation may vary. According to the embodiments described herein, the formulation contains organic solvents comprising more than 30% and less than 90% by weight relative to the total weight of the formulation.

[0062] In a preferred embodiment, the formulation comprises an organic solvent in the range of 34% to 80% by weight relative to the total weight of the formulation, preferably in the range of 35% to 60% by weight, and more preferably in the range of 37% to 50% by weight.

[0063] UV filter The formulations according to this disclosure may additionally include a UV filter. The terms "UV filter," "UV shield," and "shield" should be used interchangeably. In a preferred embodiment of this disclosure, the formulation comprises one or more UV filters selected from hydrophilic, lipophilic, insoluble organic UV filters, one or more inorganic pigments, or combinations thereof. In a more preferred embodiment, the UV filter is selected from at least one hydrophilic, lipophilic, or insoluble organic UV filter.

[0064] The term "hydrophilic UV filter" should be understood to mean any cosmetic or dermatological organic or inorganic compound that shields against UV radiation and is completely soluble in a liquid aqueous phase in a molecular state or in a colloidal form (e.g., micelles).

[0065] The term "lipophilic UV filter" should be understood to mean any cosmetic or dermatological organic or inorganic compound that shields against UV radiation and is completely soluble in a liquid fat phase in a molecular state or in a colloidal form (e.g., micelles).

[0066] The term "insoluble UV filter" should be understood to mean any cosmetic or dermatological organic or inorganic compound that shields against UV radiation and has a solubility of less than 0.5% by weight in water and less than 0.5% by weight in most organic solvents, such as liquid paraffin, fatty alcohol benzoates, and fatty acid triglycerides, for example, Miglyol 812. ® (Dynamit Nobel). This solubility is determined at 70°C and is defined as the amount of product in the solvent that is in equilibrium with the suspended excess solid after the solution has returned to ambient temperature.

[0067] Organic UV filters are particularly selected from cinnamic acid compounds; anthranilic acid compounds; salicylic acid compounds; benzoylmethane compounds; benzyl camphor compounds; benzophenone compounds; β,β-diphenyl acrylate compounds; triazine compounds; benzotriazole compounds; benzyl malonate compounds, especially those referenced in patent US 5,624,663; benzimidazole derivatives; imidazoline compounds; bisbenzoazole compounds, such as those described in patents EP 669,323 and US 2,463,264; methylene bis(hydroxyphenylbenzotriazole) compounds, such as those described in applications US 5,237,071, US 5,166,355, GB 2,303,549, DE 197,261,84 and EP 893,119; benzoxazole compounds, such as those in patent applications EP 0,832,642, EP 1, EP 1 The following are included: those described in 300 137 and DE 101 62 844; shielding polymers and shielding silicones, such as those particularly described in application WO 93 / 04665; dimers derived from α-alkylstyrene, such as those described in patent application DE 198 55 649; 4,4-diarylbutadiene compounds, such as those described in applications EP 0967 200, DE 197 46 654, DE 197 55 649, EP-A-1 008 586, EP 1 133 980 and EP 133 981; and mixtures thereof.

[0068] Examples of organic UV filters include, but are not limited to, the following list: Cinnamic acid compounds: Ethylhexyl methoxycinnamate, particularly under the trade name Parsol ® MCX (DSM Nutritional Products) sells; and isoamyl paramethoxycinnamate, under the trade name Neo Heliopan E 1000. ® (Symrise) sales.

[0069] Benzoylmethane compounds: Butylmethoxydibenzoylmethane, particularly under the trade name Parsol ® 1789 (DSM Nutritional Products) is sold.

[0070] Salicylic acid compounds: Humosalt, under the name Parsol ® HMS (DSM nutritional products) products are sold; as well as ethylhexyl salicylate, under the name Neo Heliopan. ® OS (Symrise) sales.

[0071] β,β-diphenylacrylate compounds: Octocrylene, especially under the brand name Uvinul ® N 539 T (BASF) for sale.

[0072] Benzophenone compounds: Benzophenone-3 or hydroxybenzophenone, marketed under the trade name Uvinul ® M 40 (BASF) sells: Diethylaminohydroxybenzoyl benzoate, under the trade name Uvinul ® A Plus is sold, or as a mixture with ethylhexyl methoxycinnamate under the trade name Uvinul. ® A Plus B (BASF) sells 1,1'-(1,4-piperazinidyl)bis[1-[2-[4-(diethylamino)-2-hydroxybenzoyl]phenyl]methyl ketone] (CAS 919803-06-8), as described in application WO2007 / 071584; the compound is advantageously used in micronized form (average size 0.02 to 2 µm), which can be obtained, for example, by the micronization methods described in applications GB-A-2 303 549 and EP-A-893 119, and particularly in the form of an aqueous dispersion.

[0073] benzyl camphor compounds: 4-Methylbenzylidene camphor, under the name Eusolex ® 6300 (Merck) for sale; terephthalic acid, methylene dicamphor sulfonic acid, under the name Mexoryl ® Manufactured by SX (Noveal).

[0074] Phenylbenzimidazole compounds: Phenylenic acid, specifically under the trade name Eusolex® 232 (Merck) for sale.

[0075] Bibenzoazole compounds: Sodium phenyl dibenzimidazole tetrasulfonate, marketed under the trade name Neo Heliopan ® AP (Symrise) sales.

[0076] Phenylbenzotriazole compounds: Mexoryl cresoltrazol trisiloxane ® Manufactured by XL (Noveal).

[0077] Methylene bis(hydroxyphenylbenzotriazole) compounds: Methylenebis-benzotriazolyltetramethylbutylphenol, particularly in solid form, such as under the trade name Mixhim BB / 100 ® Products sold by Fairmount Chemical, or in the form of aqueous dispersions of micronized particles having an average particle size of 0.01 to 5 µm, more preferably 0.01 to 2 µm, and more particularly 0.020 to 2 µm, wherein the particles contain at least one structure C n H 2n+10 (C6H 10 The alkyl polyglycoside surfactant (O5)xH is used in the presence of n, which is an integer from 8 to 16, and x is (C6H) 10 The average degree of polymerization of the O5 unit varied from 1.4 to 1.6, as described in patent GB-A-2 303 549, specifically under the trade name Tinosorb. ® M (BASF) is sold; or in the form of an aqueous dispersion of micronized particles having an average particle size of 0.02 to 2 µm, more preferably 0.01 to 1.5 µm, and more particularly varying from 0.02 to 1 µm, in at least one polyglycerol mono(C8-C) with a degree of polymerization of at least 5. 20 Used in the presence of alkyl esters, such as the aqueous dispersions described in application WO2009 / 063392, particularly products sold under the name Tinosorb WPGL (BASF).

[0078] Triazine compounds: 3,3'-(1,4-phenylene)bis(5,6-diphenyl-1,2,4-triazine), its INCI name is phenylene bis(diphenyltriazine); bis-ethylhexyloxyphenol methoxyphenyltriazine, traded under the name Tinosorb ®S (BASF) sells it, and its aqueous dispersion form has the INCI name bis-ethylhexyloxyphenol methoxyphenyl triazine (and) acrylate / C12-22 alkyl methacrylate copolymer, under the trade name TINOSORB. ® S LiteAqua (BASF) sells ethylhexyl triazine, especially under the trade name Uvinul. ® T 150 (BASF) sold; Diethylhexylbutyramidotriazinone, produced by 3V (Sigma) under the trade name Uvasorb ® HEB Sales; Naphthyl or polyphenyl substituted symmetrical triazine shielding agents, described in patent US 6 225 467, application WO2004 / 085412 (see compounds 6 and 9) or literature "Symmetrical Triazine Derivatives", IP.COMIPCOM000031257 Journal, INC West Henrietta, NY, US (20 September 2004), particularly 2,4,6-tris(biphenyl)triazine and 2,4,6-tris(biphenyl)triazine, under the name TINOSORB ® A2B (BASF) is also mentioned in patent applications WO06 / 035000, WO06 / 034982, WO06 / 034991, WO06 / 035007, WO2006 / 034992 and WO2006 / 034985. These compounds are advantageously used in micronized form (average particle size 0.02 to 3 µm), which can be obtained, for example, according to the micronization process described in applications GB-A-2 303 549 and EP-A-893 119, and especially in the form of aqueous dispersions.

[0079] o-aminobenzoic acid compounds: Menthyl anthranilate, marketed under the trade name Neo Heliopan ® MA (Symrise) Sales.

[0080] benzyl malonate compounds: Polyorganosiloxanes containing benzylmalonic acid functional groups, such as polysiloxane-15, are marketed under the trade name ParsolSLX. ® (Hoffmann-La Roche) for sale.

[0081] Benzoxazole compounds: The INCI name for the UV filter is 2,2'-(1,4-phenylene)bis(1,3-benzoxazole), and it is provided under the name DBO(DSM).

[0082] Preferred organic UV filters are selected from: ethylhexyl methoxycinnamate, ethylhexyl salicylate, humosasulfate, butyl methoxydibenzoylmethane, octocrylene, phenylbenzimidazole sulfonic acid, benzophenone-3, hexyl diethylaminohydroxybenzoyl benzoate, 4-methylbenzyl camphor, terephthalimide dicamphor sulfonic acid, disodium phenyl dibenzimidazole tetrasulfonate, methylene bis-benzotriazolyl tetramethylbutylphenol, bis-ethylhexyloxyphenol methoxyphenyl triazine, ethylhexyl triazine ketone, diethylhexylbutamidotriazine ketone, 2,4,6-tris(biphenyl)triazine, 2,4,6-tris(biphenyl)triazine, cresoltrazol trisiloxane, polysiloxane-15, bis-(diethylaminohydroxybenzoylbenzoyl)piperazine, or mixtures thereof.

[0083] The particularly preferred organic UV filter is selected from: ethylhexyl salicylate, homosalate, butyl methoxydibenzoylmethane, octocrylene, diethylaminohydroxybenzoylhexyl benzoate, terephthalic acid dicamphor sulfonic acid, bis-ethylhexyloxyphenol methoxyphenyl triazine, ethylhexyl triazine ketone, diethylhexylbutamidotriazine ketone, bis-(diethylaminohydroxybenzoylbenzoyl)piperazine, cresoltrazol trisiloxane, 2,4,6-tris(biphenyl)triazine, or mixtures thereof.

[0084] The inorganic UV filter used according to this disclosure is a metal oxide pigment. More preferably, the inorganic UV filter of this disclosure is a metal oxide particle or pigment with an average basic particle size of less than or equal to 0.5 µm, more preferably between 0.005 and 0.5 µm, more preferably still between 0.01 and 0.2 µm, even more preferably still between 0.01 and 0.1 µm, and more particularly between 0.015 and 0.05 µm. Metal oxide pigments are specifically described in Annex VI of European Cosmetics Regulation No. 1223 / 2009, updated on 22 September 2021, but are not limited to this list.

[0085] Metal oxide pigments may be specifically selected from titanium oxide, zinc oxide, iron oxide, zirconium oxide, cerium oxide, or mixtures thereof.

[0086] Such coated or uncoated metal oxide pigments are specifically described in patent application EP-A-0 518 773. As commercial pigments, products sold by Croda, Tayca, and Merck may be mentioned.

[0087] Metal oxide pigments can be coated or uncoated.

[0088] Coated pigments are pigments that have undergone one or more chemical, electronic, mechanochemical and / or mechanical surface treatments using compounds such as amino acids, beeswax, fatty acids, fatty alcohols, anionic surfactants, lecithin, sodium, potassium, zinc, iron or aluminum salts of fatty acids, metal alkoxides (titanium or aluminum), polyethylene, silicone, proteins (collagen, elastin), alkanolamines, silicon oxides, metal oxides or sodium hexametaphosphate.

[0089] The coating pigment is more specifically applied to titanium dioxide coated with the following: - Use hydrated silica, such as the Tayca product MT-100WP; - Using silicon dioxide and iron oxide, such as Sunveil F from Ikeda. ® ; - Using silica and alumina, such as the Tayca MT-500SA product. ® and MT-100SA ® And Tioveil™ AQ-N from Croda; - Use alumina, such as TTO-55 (A) from Ishihara. ® ; - Using alumina and aluminum stearate, such as the Tayca MT-100TV product. ® MT-100Z ® and MT-01 ® The Solaveil™ CT100 from Croda and the Eusolex T-AVO from Merck ® ; - Using silica, alumina, and alginate, such as the Tayca MT-100AQ product. ® ; - Using alumina and aluminum lauryl; - Using iron oxide and ferric stearate; - Using zinc oxide and zinc stearate; - Made with silica and alumina and treated with silicone, such as the Tayca product MTY-500SAS. ® Or micro titanium dioxide MT-100SAS ® ; - Treated with silica, alumina and aluminum stearate with silicone; - Use silicon dioxide and treat with silicone; - Made with alumina and treated with silicone, such as TTO-55(S) from Ishihara. ® ; - Use triethanolamine; - Use stearic acid, such as TTO-55 (C) from Ishihara. ® ; - Use sodium hexametaphosphate; - TiO2 treated with octyltrimethylsilane; - TiO2 treated with polydimethylsiloxane; - Anatase / rutile TiO2 treated with polydimethylsiloxane; - TiO2 coated with glyceryl tri(ethylhexanoate), aluminum stearate and alumina, sold by Croda under the trade name Solaveyil™ CT-200; - TiO2 coated with aluminum stearate, aluminum oxide and silicone, sold by Croda under the trade name Solaveyil™ CT-12W; - TiO2 coated with lauroyl lysine; or - TiO2 coated with C9-C15 fluorophosphate and aluminum hydroxide.

[0090] It may also be mentioned that TiO2 pigments doped with at least one transition metal (such as iron, zinc, or manganese, and more particularly manganese). Preferably, the doped pigment is in the form of an oily dispersion. The oil present in the oily dispersion is preferably selected from triglycerides, including triglycerides of decanoic acid / caprylic acid. The oily dispersion of the titanium dioxide particles may additionally contain one or more dispersants, such as, for example, sorbitan ester, such as sorbitan isostearate; polyoxyalkylene glycerol fatty acid esters, such as tri(PPG-3 myristyl ether) citrate and polyglycerol-3 polyricinoleate. Preferably, the oily dispersion of the titanium dioxide particles contains at least one dispersant selected from polyoxyalkylene glycerol fatty acid esters. More specifically, an oily dispersion of manganese-doped TiO2 particles in decanoic acid / caprylic acid triglyceride in the presence of tri(PPG-3 myristyl ether) citrate, polyglycerol-3 polyricinoleate, and sorbitan isostearate may be mentioned, with the INCI name: Titanium dioxide (and) tri(PPG-3 myristyl ether) citrate (and) polyglycerol-3 polyricinoleate (and) sorbitan isostearate, or a product sold by Croda under the trade name Optisol™ OPT-1.

[0091] Uncoated titanium dioxide pigments, for example, are produced by Tayca under the trade names MT-500B or MT-600B. ® Sold by Evonik under the name Degussa P 25.

[0092] Uncoated zinc oxide pigment, for example, is produced by BASF under the name Z-COTE ®Those sold; or by Nanophase Technologies under the name NanoArc ® Those sold by Zinc Oxide.

[0093] The zinc oxide pigments used for coating are, for example: ZnO coated with polymethylhydrosiloxane; Solaveil™ CZ-100 (INCI: zinc oxide (and) C12-15 alkylbenzoate (and) polyhydroxystearic acid (and) isostearic acid) dispersed in C12-15 alkylbenzoate from Croda; and Daito Kasei under the name Daitopersion Zn-60VA. ® Those sold (dispersions containing dispersants in C9-12 alkanes); manufactured by Shin-Etsu under the name SPD-Z5 ® Those sold (ZnO coated with silicone-grafted acrylic polymer and dispersed in cyclodimethylsiloxane).

[0094] Uncoated cerium oxide pigments can be, for example, produced by Solvay under the name Rhodigard. ® Those sold under the W185 brand.

[0095] Mixtures of metal oxides may also be mentioned, particularly mixtures of titanium dioxide and cerium dioxide, including mixtures of titanium dioxide and cerium dioxide coated with silica in equal weight, and mixtures of titanium dioxide and zinc dioxide coated with alumina, silica and silicone or with alumina, silica and glycerin.

[0096] According to this disclosure, coated or uncoated titanium dioxide pigments are particularly preferred.

[0097] According to this disclosure, the UV filter may be present in the formulation at a weight range of 0.1% to 60% relative to the total weight of the formulation, preferably at a weight range of 5% to 30%.

[0098] Cosmetic preparations This disclosure also relates to a cosmetic formulation comprising, as defined above, a cosmetically acceptable medium.

[0099] Cosmetically acceptable media are generally suited to the properties of the carrier to which the formulation is to be applied and the appearance to which the formulation will be packaged. According to embodiments herein, a cosmetically acceptable media is a media compatible with keratinous materials (preferably skin). The cosmetically acceptable media of the formulation may more particularly comprise water and optionally a cosmetically acceptable water-soluble organic solvent as described herein.

[0100] additive Formulations according to this disclosure may additionally contain additives commonly used in cosmetics, such as ascorbic acid, Tinogard Q or active ingredients other than pomegranate extract, pH adjusters, surfactants, thickeners and mixtures thereof.

[0101] In one embodiment of this disclosure, the formulation comprises one or more active ingredients different from pomegranate extract. In one embodiment, the formulation comprises ascorbic acid as an additional active ingredient different from pomegranate extract. In another embodiment, the formulation comprises Tinogard Q as an additional active ingredient different from pomegranate extract. In yet another embodiment, the formulation comprises ascorbic acid and Tinogard Q as additional active ingredients different from pomegranate extract.

[0102] pH adjuster According to the embodiments described herein, the formulation includes at least one pH adjuster.

[0103] As used herein, the term "pH adjuster" refers to those substances that establish the pH of a formulation and maintain it within the desired range.

[0104] pH adjusters can be “acidifiers”, which can be inorganic acids such as hydrochloric acid, phosphoric acid or sulfuric acid; or organic acids, preferably carboxylic acids such as acetic acid, tartaric acid, citric acid or lactic acid, or sulfonic acid, and mixtures thereof.

[0105] pH adjusters can be "alkalizing agents," which can be organic, such as arginine, lysine, amines such as monoethanolamine, diethanolamine, and triethanolamine; or inorganic, such as ammonia, alkali metal carbonates, sodium hydroxide, potassium hydroxide, or mixtures thereof.

[0106] In one embodiment of this disclosure, the pH adjuster is one or more alkalizing agents selected from arginine, triethanolamine, sodium hydroxide, or mixtures thereof.

[0107] The amount of pH adjuster present in the formulation can vary and is determined based on the required pH that the formulation is to maintain.

[0108] surfactants According to the embodiments described herein, the formulation includes one or more surfactants selected from amphoteric surfactants, anionic surfactants, cationic surfactants, nonionic surfactants, or mixtures thereof.

[0109] According to a preferred embodiment, the surfactant is an anionic surfactant selected from polyglycerol-2-laurate, sodium cocoyl sarcosinate, isopropyl lauroyl sarcosinate, or mixtures thereof.

[0110] According to the embodiments described herein, the amount of surfactant present in the formulation can vary. According to the embodiments described herein, the surfactant can be present in the formulation at a weight range of 0.1% to 20% relative to the total weight of the formulation, preferably at a weight range of 0.5% to 15%, and more preferably at a weight range of 1% to 10%.

[0111] Thickener According to the embodiments described herein, the formulation includes one or more thickeners that provide the desired viscosity to the formulation.

[0112] Examples of thickeners include, but are not limited to, carboxyl polymers, acrylate / C10-C30 alkyl acrylate crosspolymers, polyacrylamide and its derivatives, polysaccharides, water-soluble or water-dispersible silicone derivatives or mixtures thereof.

[0113] Examples of carboxyvinyl polymers suitable for use in this disclosure are Carbopols® (Carbomers) and Pemulens, such as Pemulen TR1® and Pemulen TR2® (acrylate / C10-C30 alkyl acrylate crosspolymers).

[0114] Examples of polyacrylamides and derivatives applicable to this disclosure include crosslinked copolymers sold by SEPPIC under the names Sepigel 305® (CTFA name: polyacrylamide / C13-14 isoparaffin / laurate polyether-7) or Simulgel 600 (CTFA name: acrylamide / sodium acryloyl dimethyl taurate copolymer / isohexadecane / polysorbate 80); optionally crosslinked and / or neutralized 2-acrylamido-2-methylpropanesulfonic acid polymers and copolymers, such as poly(2-acrylamido-2-methylpropanesulfonic acid) sold by Hoechst under the trade name Hostacerin AMPS® (CTFA name: ammonium polyacrylamide dimethyl taurate) or Simulgel 800® (CTFA name: sodium polyacrylamide dimethyl taurate / polysorbate 80 / sorbitol oleate) sold by SEPPIC; copolymers of 2-acrylamido-2-methylpropanesulfonic acid and hydroxyethyl acrylate, such as Simulgel NS® and Sepinov sold by SEPPIC. EMT 10®.

[0115] Examples of polysaccharides applicable to this disclosure are gums, such as xanthan gum and chitosan; linear polysaccharides, such as chitosan and β-glucan; and cellulose derivatives, such as hydroxyethyl cellulose; water-soluble or water-dispersible silicone derivatives, such as acrylic silicone, polyether silicone and cationic silicone, and mixtures thereof.

[0116] In one embodiment of this disclosure, the thickener is preferably selected from polysaccharides, more preferably from cellulose derivatives, gums, linear polysaccharides, or mixtures thereof.

[0117] According to the embodiments described herein, the amount of thickener present in the formulation can vary. According to the embodiments described herein, the thickener can be present in the formulation at a weight range of 0.1% to 10% relative to the total weight of the formulation, preferably at a weight range of 0.2% to 8%, and more preferably at a weight range of 0.5% to 5%.

[0118] Other additives The formulation may further include other additives commonly used in the cosmetic and / or dermatological fields, such as fragrances, preservatives, fillers, oils, and colorants. It should be understood that those skilled in the art will take care to select optional additives and / or their amounts such that the advantageous properties of the formulation used according to this disclosure are not adversely affected or substantially unaffected by the contemplated addition. All such embodiments including optional additives are to be understood as being included within the scope of this disclosure.

[0119] In one embodiment of this disclosure, the formulation does not contain trisodium ethylenediaminedisuccinate or contains less than 0.2% trisodium ethylenediaminedisuccinate. In another embodiment of this disclosure, the formulation contains less than 0.2%, less than 0.1%, or less than 0.05% trisodium ethylenediaminedisuccinate by weight relative to the total weight of the formulation.

[0120] Preparation of formulations according to this disclosure The formulations according to this disclosure can be prepared using known methods commonly used in the cosmetic or dermatological fields. Typically, the method includes mixing water, a pH adjuster, at least one surfactant, and at least one stabilizer to obtain a first mixture. Pomegranate and at least one organic solvent are then mixed to obtain a clear, transparent solution. This clear, transparent solution is then added to the first mixture along with one or more additives and mixed to obtain a homogeneous, transparent or translucent formulation (cosmetic formulation).

[0121] application The formulations according to the embodiments herein are more particularly formulations for treating keratinous materials such as skin. Preferably, the formulations according to the embodiments herein are formulations for treating skin. Therefore, in the various embodiments herein, the formulations may be in the form of an essence.

[0122] In one embodiment of this disclosure, the pH of the formulation is in the range of 2 to 8, preferably in the range of 3 to 7.

[0123] In one embodiment of this disclosure, the formulation exhibits greater than 91% stability of the punicalin marker after being stored at room temperature for at least 2 months. In another embodiment of this disclosure, the formulation exhibits greater than 91% stability of the punicalin marker after being stored at room temperature for 4, 6, 8, 10, or 12 months.

[0124] In one embodiment of this disclosure, the formulation exhibits greater than 91% stability of the punicalin marker when stored at room temperature for 2 weeks, 1 month, or 2 months, such as 2 weeks.

[0125] In one embodiment of this disclosure, when the formulation contains N-acetylcysteine ​​as an additional stabilizer, it exhibits greater than 91% punicin marker stability when stored under accelerated testing conditions for 2 weeks, 1 month, or 2 months, such as 2 weeks.

[0126] The formulation according to the embodiments described herein may optionally be applied to the skin using an applicator, and then the formulation may be rubbed into the skin.

[0127] Although this disclosure has been described in considerable detail with reference to certain embodiments and their implementations, other embodiments may cover modifications and variations of this disclosure. Example

[0128] This disclosure will now be illustrated by working examples, which are intended to illustrate how the disclosure works and are not intended to restrictively imply any limitation on the scope of the disclosure. Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains. Although similar or equivalent methods and materials may be used in the practice of the disclosed methods and compositions, exemplary methods, apparatus, and materials are described herein. It should be understood that this disclosure is not limited to the specific methods and experimental conditions described, as such methods and conditions may be applicable.

[0129] The amounts of the components in the following examples are expressed as a percentage of the weight of the active material.

[0130] Example 1 Preparation of pomegranate extract Dried pomegranate peel (1 kg) was extracted briefly at 42 °C with 5 L of ethanol (99.5% purity) at 800 rpm for 4 hours with stirring. The obtained ethanol extract was filtered through a Buchner funnel lined with cotton cloth (mesh size: 20 μm). The filtered extract was evaporated under vacuum at 38 °C to obtain a brown amorphous powder. The extraction was repeated twice under the above conditions. The combined dried extracts consisted mainly of phenolic compounds, namely ellagic acid and punicalin.

[0131] The specifications of the extracts are shown in Tables 1a and 1b below: Table 1a parameter With % w / w value Anshijigan 14.44 % pomegranate peel tannins 3.28 % Total polyphenols (punical tannin, punical glycoside, ellagic acid, gallic acid, epicatechin gallate, polygallic acid, ellagic acid hexoside / glycoside) 42 % Total fat 2.6 % Total protein 0.73 % Total sugar 19.1 % Moisture 6.5 % .

[0132] Table 1b

[0133] Example 2: Preparation of formulation The formulations listed in Tables 2a and 2b are prepared as follows.

[0134] Phase A (pH adjuster, at least one surfactant, and at least one stabilizer) is weighed and added to a first container along with water, and mixed at 400 rpm. Phase B (pomegranate extract according to Example 1 and at least one organic solvent) is weighed and added to a second container, and mixed at 300 rpm in a magnetic stirrer at 45 to 50°C to obtain a clear, transparent solution, which is then added to the first container while mixing at 400 rpm. Phase C (at least one thickener) is added to the first container and dispersed by stirring at 600 rpm for 10 minutes. Phase D (another surfactant) and Phase E (another organic solvent) are added to the first container and mixed for 10 minutes to obtain a uniform, clear, or translucent gel.

[0135] Table 2a

[0136] Table 2b

[0137] Example 3 Evaluation of formulation stability The stability of formulations PK01 to PK07 (Table 2a) and formulations PP1 to PP4 (Table 2b) prepared in Example 2 above was evaluated under room temperature and accelerated testing conditions.

[0138] The formulations were stored at room temperature for 2 weeks or 2 months, and the content of the biomarker punicalin was analyzed at the initial time point (T0) and after 2 weeks (T2W) or 2 months (T2M) at room temperature (using ultra-high performance liquid chromatography (UPLC)). For some formulations, the content of the biomarker punicalin was analyzed at the initial time point (T0) and under accelerated testing conditions (i.e., after 2 weeks at 55°C (T2W 55°C)) (using ultra-high performance liquid chromatography (UPLC)).

[0139] Preparation of punicalin (a mixture of punicalin A and punicalin B) standard: In a 10 mL volumetric flask, dissolve punicalin standard (5 mg, >93.4% purity, CAS NO.: 65995-63-3, Chromadex) in methanol (10 mL) and sonicate (10 min). To prepare a calibration curve, prepare serially diluted solutions (at least 6 calibration points) from the standard stock solution using methanol as the diluent.

[0140] Separation was achieved by reversed-phase liquid chromatography (LC) on a Nexera Ultra Performance LC system equipped with a photodiode array detector (Shimadzu). Details of the method are described below.

[0141] (i)Column Agilent Zorbax Eclipse XDB-C18, 5 µm, 4.6 X 150 mm (ii) Mobile phase A: 0.1% orthophosphoric acid in water (iii) Mobile phase B: 0.1% phosphoric acid in acetonitrile (iv) Gradient:

[0142] (v) Flow rate: 1 mL / min (vi) Running time: 25 minutes (vii) Column temperature: 30℃ (viii) Detector: PDA (ix) Detection wavelength: Punicin - 258 nm (x) Injection volume: 10 µL (xi) Retention time: Punicantin A - 3.5 minutes; Punicantin B - 4.8 minutes The percentage decrease in pungent glycoside content was calculated using the following formula: A decrease of less than 9% in the percentage of the marker punicalin relative to the initial content is acceptable.

[0143] result Table 3a preparation The % stability of punicalin T0 relative to room temperature after 2 weeks PK01 (This invention) 98.7 PK02 (This invention) 97.9 PK03 (Excluded in this invention) 75.4 PK04 (This invention) 98.3 PK05 (This invention) 95.7 PK06 (This invention) 95.8 PK07 (Excluded in this invention) 84 .

[0144] As is evident from Table 3a, formulations lacking sodium thiosulfate as a stabilizer (PK03 and PK07) exhibited poorer marker stability (below 91%) after 2 weeks of storage at room temperature.

[0145] Similar results were observed in formulations PP1 and PP2 that do not contain sodium thiosulfate, as shown in Table 3b.

[0146] Furthermore, it was observed that using N-acetylcysteine ​​as an additional stabilizer improved the stability of the punicin marker to over 91% under accelerated testing conditions, as shown in Table 3c for samples PK01 and PP4, respectively.

[0147] Table 3b preparation The % stability of punicalin T0 relative to room temperature after 2 weeks PP1 (without any solution) is excluded from this invention. 84 PP2 (PP1 + 0.1% N-acetylcysteine) is excluded in this invention. 75.4 PP3 (PP1 + 0.2% sodium thiosulfate) This invention 98.3 PP4 (PP1 + 0.2% sodium thiosulfate + 0.1% N-acetylcysteine) This invention 98.7 .

[0148] Table 3c

[0149] Example 4 Effects of water and organic solvent (polyol) content on formulation stability The stability of formulations containing varying amounts of organic solvent was tested. The different amounts tested are mentioned in Table 4a. The tested formulations P4 to P5 contained water, various polyols as organic solvents, and 0.5% by weight of the extract described in Example 1, 0.2% by weight of sodium thiosulfate, and 0.1% by weight of N-acetylcysteine ​​(Table 4b). Phase A components (at least one stabilizer) were weighed and added to a first container along with water, and mixed at 400 rpm. Phase B components (the pomegranate extract according to Example 1 and at least one organic solvent) were weighed and added to a second container, and mixed at 300 rpm in a magnetic stirrer at 45 to 50°C to obtain a clear, transparent solution. This clear, transparent solution was then added to the first container while mixing at 400 rpm to obtain formulations P1 and P2. It was observed that the presence of more than 30% organic solvent relative to the total weight of the formulation improved the dispersibility (or solubility) of the extract in the formulation, and thereby improved the stability of the extract in the formulation (see the results shown in Table 4c for formulations P1 and P2).

[0150] Table 4a describe P1 P2 Polyol portion (organic solvent) ~40% ~50% Water (qs) ~60% ~50% .

[0151] Table 4b

[0152] Table 4c preparation The % stability of pungent glycoside T0 relative to T2W after 2 weeks at room temperature P1 98.40 P2 96.80 .

[0153] Example 5 Furthermore, after one month of storage at room temperature, no other stabilizer other than sodium thiosulfate produced similar levels of punicalin marker stability (Table 5a). Formulations PR1, PR2, and PR3 containing sodium thiosulfate, sodium metabisulfite, or sodium sulfite were prepared using the method described in Example 2. For example, the use of sodium metabisulfite and sodium sulfite produced marker stability of less than 91% compared to the formulation containing sodium thiosulfate (PR1) (Table 5b).

[0154] Table 5a

[0155] Table 5b preparation The stability of pungent glycoside T0 relative to 1 month at room temperature (%) PR1 formulation containing 0.2% sodium thiosulfate (this invention) 98.61 PR2 formulation using 0.2% sodium metabisulfite instead of sodium thiosulfate (excluded in this invention) 90.84 PR3 formulation using 0.2% sodium sulfite instead of sodium thiosulfate (excluded in this invention) 87.3 .

[0156] Advantages of this disclosure This disclosure provides a formulation in a cosmetically acceptable medium comprising a) pomegranate extract; b) at least one stabilizer comprising sodium thiosulfate; c) water; and d) at least one organic solvent. The use of sodium thiosulfate as a stabilizer provides over 91% stability to pungent glycoside, a marker of the pomegranate extract in the formulation. Furthermore, the use of N-acetylcysteine ​​as an additional stabilizer provides further stability of the formulation under accelerated testing conditions.

Claims

1. A formulation in a cosmetically acceptable medium, comprising: a) Pomegranate extract; b) At least one stabilizer containing sodium thiosulfate; c) Water; and d) At least one organic solvent.

2. The formulation of claim 1, wherein the pomegranate extract comprises: i. Punicin comprising at least 10% by weight of the total dry extract; and ii. Ellagic acid comprising at least 10% by weight of the total weight of the dry extract; and The weight ratio of [ellagic acid / punicaloside] is in the range of 0.5 to 2.

3. The formulation as claimed in any of the preceding claims, wherein the pomegranate extract is present in a weight range of 0.01% to 10% relative to the total weight of the formulation, preferably in a weight range of 0.05% to 5%.

4. The formulation as described in any one of the preceding claims, comprising: i. Punicanthin, comprising at least 0.001% by weight of the total weight of the formulation, preferably in the range of 0.001% to 1% by weight relative to the total weight of the formulation; and ii. Ellagic acid comprising at least 0.001% by weight of the total weight of the formulation, preferably in the range of 0.001% to 1% by weight relative to the total weight of the formulation; and The weight ratio of [ellagic acid / punicaloside] ranges from 0.5 to 2.

5. The formulation as claimed in any of the preceding claims, wherein sodium thiosulfate is present in a weight range of 0.01% to 2% relative to the total weight of the formulation, preferably in a weight range of 0.03% to 1%.

6. The formulation of any one of the preceding claims, wherein the stabilizer further comprises N-acetylcysteine.

7. The formulation of claim 6, wherein N-acetylcysteine ​​is present in a weight range of 0.01% to 2% relative to the total weight of the formulation, preferably in a weight range of 0.03% to 1%.

8. The formulation of any one of the preceding claims, wherein the formulation comprises at least one organic solvent selected from C1-C4 monohydric alcohols (ethanol, isopropanol, or 2-ethoxyethanol), or polyhydric alcohols such as C2-C8 polyhydric alcohols (triols, such as glycerol; hexahydric alcohols, such as sorbitol; diols, such as octyl ethylene glycol, 1,2-pentanediol, propylene glycol, butanediol, ethylene glycol, propylene glycol, butanediol, dipropylene glycol, diethylene glycol, 1,2-propanediol, 1,3-butanediol, pentanediol, hexanediol, diethylene glycol monomethyl ether, or triethylene glycol monomethyl ether), or mixtures thereof.

9. The formulation of claim 8, wherein the at least one organic solvent comprises more than 30% and less than 90% of the total weight of the formulation.

10. The formulation as claimed in any of the preceding claims, wherein water accounts for more than 10% and less than 70% of the total weight of the formulation.

11. The formulation as claimed in any of the preceding claims, further comprising at least one UV filter, said UV filter comprising 0.1% to 60% of the total weight of the formulation, preferably 5% to 30% by weight.

12. The formulation as claimed in any of the preceding claims, further comprising an additive selected from pH adjusters, surfactants, thickeners, or mixtures thereof.

13. The formulation of claim 12, wherein the pH adjuster is selected from acidifiers (hydrochloric acid, phosphoric acid, sulfuric acid, carboxylic acid, acetic acid, tartaric acid, citric acid or lactic acid, sulfonic acid), alkalizers (arginine, lysine, ammonia, alkali metal carbonates, monoethanolamine, diethanolamine and triethanolamine and their derivatives, sodium hydroxide, potassium hydroxide) or mixtures thereof, preferably one or more alkalizers, more preferably selected from arginine, triethanolamine, sodium hydroxide or mixtures thereof.

14. The formulation as claimed in any of the preceding claims, wherein the formulation has a pH in the range of 2 to 8, preferably in the range of 3 to 7.

15. The formulation of claim 12, wherein the surfactant is selected from amphoteric surfactants, anionic surfactants, cationic surfactants, nonionic surfactants, or mixtures thereof.

16. The formulation of claim 15, wherein the surfactant is in the range of 0.1% to 20% by weight relative to the total weight of the formulation, preferably in the range of 0.5% to 15% by weight.

17. The formulation of claim 12, wherein the thickener is selected from carboxyl polymers, acrylate / C10-C30 alkyl acrylate crosspolymers, polyacrylamide and its derivatives, polysaccharides (cellulose derivatives, gums), water-soluble or water-dispersible silicone derivatives, or mixtures thereof.

18. The formulation of claim 17, wherein the thickener is in the range of 0.1% to 10% by weight relative to the total weight of the formulation, preferably in the range of 0.2% to 8% by weight.

19. The formulation as claimed in any of the preceding claims, wherein the formulation does not contain trisodium ethylenediamine disuccinate or contains less than 0.2% trisodium ethylenediamine disuccinate.

20. The formulation as claimed in any of the preceding claims, wherein the formulation is provided in an essence form.

21. The formulation as claimed in any of the preceding claims, wherein the formulation has greater than 91% stability of the punicin marker when stored at room temperature for at least 2 months.

22. A kit comprising (a) a formulation according to any one of claims 1 to 21; (b) a container; and (c) optionally, an applicator.

23. A cosmetic treatment method for a keratin material, comprising applying the preparation according to any one of claims 1 to 21 to the keratin material, preferably to the skin.

24. Use of the formulation according to any one of claims 1 to 21 for treating the skin.

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