A formulation of punica granatum extract with enhanced stability and applications thereof

A formulation with Punica granatum extract and sodium thiosulphate stabilizer maintains punicalagin stability above 91% in cosmetic products, addressing stability issues and ensuring product efficacy.

WO2025141605A1PCT designated stage expired Publication Date: 2025-07-03LOREAL SA +1
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Patent Information

Application Number
PCT/IN2024/052427
Authority / Receiving Office
WO · WO
Patent Type
Applications
Current Assignee / Owner
Priority Date
2024-03-07
Filing Date
2024-12-24
Publication Date
2025-07-03

AI Technical Summary

Technical Problem

Cosmetic formulations containing Punica granatum extract suffer from poor stability, particularly in water-based formulations, leading to a decrease in punicalagin content over time, which affects the product's efficacy.

Method used

A formulation comprising Punica granatum extract with a specific weight ratio of ellagic acid to punicalagins (0.5 to 2) and sodium thiosulphate as a stabilizer, along with water and an organic solvent, enhances stability by maintaining punicalagin content above 91% even after storage at room temperature and accelerated conditions.

Benefits of technology

The formulation ensures that the punicalagin content remains stable at over 91% for extended periods, including at room temperature and accelerated conditions, thereby maintaining the product's effectiveness.

✦ Generated by Eureka AI based on patent content.

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Abstract

The present disclosure relates to a formulation in a cosmetically acceptable medium, comprising, a) an extract of Punica granatum; b) at least one stabilizer comprising sodium thiosulphate; c) water; and d) at least one organic solvent. The present disclosure also relates to a kit comprising the formulation and a method for cosmetic treatment of keratin material, using the formulation.
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Description

A FORMULATION OF PUNICA GRANATUM EXTRACT WITH ENHANCED STABILITY AND APPLICATIONS THEREOFFIELD OF INVENTION

[0001] The present disclosure relates to the field of cosmetics. The present disclosure particularly relates to a formulation comprising Punica granatum extract with enhanced stability. It further relates to a method for cosmetic treatment of keratin material using the formulation.BACKGROUND OF INVENTION

[0002] Antioxidants are key active ingredients in cosmetic products targeted towards keratin material, especially the skin. Many antioxidants already exist, such as tocopherol (vitamin E) or derivatives thereof, vitamin C or derivatives thereof, carotenoids, ubiquinone, etc. In particular, products comprising antioxidants derived from natural sources are favoured by consumers over synthetic antioxidants. Extracts of plants are major natural sources of antioxidants that are used in cosmetic products. Punica granatum extracts are known from the prior art as an antioxidant active agent, FR3031901 describes a Punica granatum extract obtained with a mixture of 70% w / w ethanol / 30% w / w water, comprising no more than 1.93% of ellagic acid, with a weight ratio [ellagic acid / punicalagins A and B] equal to 0.2. W02021064034A1 describes a Punica granatum extract comprising at least 10% by weight of the total weight of the dry extract, of punicalagins and at least 10% by weight of the total weight of the dry extract, of ellagic acid wherein the weight ratio [ellagic acid / punicalagins] is ranging from 0.5 to 2. The antioxidant activity of such extracts needs to be stable over time in the formulations, especially after storage at room temperature for 2 weeks, 1 or 2 months. Especially for Punica granatum extract, the stability can be measured by the stability of the punicalagin content, and a formulation is considered stable if this content is more than 91% after storage at room temperature for 2 weeks, 1 or 2 months. In certain cases, the Punica granatum extracts in the formulation are additionally expected to be stable even at accelerated conditions, such as 45 °C for 2 months or 55 °C for 2 weeks.

[0003] Therefore, it is essential to develop a cosmetic formulation wherein the natural antioxidant sources remain stable throughout the shelf life of the formulation under ambient conditions without compromising the aesthetics and sensorial aspects of the formulation. Particularly, there is a need for a cosmetic formulation containing Punica Granatum extract, which remains stable at least during storage at room temperature for 2 weeks, 1 or 2 months, in which the punicalagins content is more than 91% after storage compared to the content without storage. There is also a need for a cosmetic formulation containing Punica Granatum extract that are additionally expected to be stable even at accelerated conditions, such as 45 °C for 2 months or 55 °C for 2 weeks.

[0004] The Applicant has surprisingly demonstrated that a formulation containing a) a Punica granatum extract and preferably comprising at least 10% by weight of the total weight of the dry extract, of punicalagins ; and at least 10% by weight of the total weight of the dry extract, of ellagic acid ; wherein the weight ratio [ellagic acid / punicalagins] is ranging from 0.5 to 2 and b) at least one stabilizer comprising sodium thiosulphate and; c) water; and d) at least one organic solvent is stable after storage at room temperature for 2 weeks, 1 or 2 months i.e., than in a such formulation the punicalagins content is more than 91% after storage compared to the content without storage.SUMMARY OF THE INVENTION

[0005] In an aspect of the present disclosure, there is provided a formulation in a cosmetically acceptable medium, comprising: a) an extract of Punica granatum; b) at least one stabilizer comprising sodium thiosulphate; c) water; and d) at least one organic solvent.

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

[0007] In another aspect of the present disclosure, there is provided a method for cosmetic treatment of keratin material, comprising applying said formulation as disclosed herein onto the keratin material, preferably skin.

[0008] These and other features, aspects, and advantages of the present subject matter will be better understood with reference to the following description and appended claims. This summary is provided to introduce a selection of concepts in a simplified form. This summary is not intended to identify key features or essential features of the claimed subject matter, nor is it intended to be used to limit the scope of the claimed subject matter.DETAILED DESCRIPTION OF THE INVENTION

[0009] Those skilled in the art will be aware that the present disclosure is subject to variations and modifications other than those specifically described. It is to be understood that the present disclosure includes all such variations and modifications. The disclosure also includes all such steps, features, compositions, and compounds referred to or indicated in this specification, individually or collectively, and any and all combinations of any or more of such steps or features. Definitions

[0010] For convenience, before further description of the present disclosure, certain terms employed in the specification, and examples are delineated here. These definitions should be read in light of the remainder of the disclosure and understood as by a person of skill in the art. The terms used herein have the meanings recognized and known to those of skill in the art, however, for convenience and completeness, particular terms and their meanings are set forth below.

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

[0012] The terms “comprise” or “contain” and “comprising” or “containing” are used in the inclusive, open sense, meaning that additional elements may be included. It is not intended to be construed as “consists of only”.

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

[0014] The term “polyol” is used to mean an organic compound, which contains at least 2 hydroxy radicals such as 2 or 3 or 4 or 5 or 6 hydroxy radicals.

[0015] Throughout this specification, unless the context requires otherwise the word “comprise”, and variations such as “comprises” and “comprising”, will be understood to imply the inclusion of a stated element or step or group of element or steps but not the exclusion of any other element or step or group of element 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 of International Nomenclature of Cosmetic Ingredients, which is a system of names provided by the International Nomenclature Committee of the Personal Care Products Council to identify cosmetic or personal care ingredients.

[0018] The term “keratin material” as used herein means skin, hair, eyelashes, eyebrows, and nails, preferably skin.

[0019] The term “cosmetically acceptable medium” as used herein means being a medium that is compatible with the “keratin materials” preferably skin and / or its superficial body growths, which exhibits a pleasant color, odor and feel, and which does not cause unacceptable discomfort (stinging or tautness) liable to discourage the consumer from using this formulation for cosmetic applications. Examples of cosmetically acceptable medium include but are not limited to water, glycols, water- glycol simplex, water in oil or oil in water emulsions to form creams, serums or lotion and surfactant-based shampoos or face wash or hair wash, water-surfactant mix for cleansing products etc.

[0020] The term “treatment” as used herein refers to any action that aims to improve the comfort or the well-being of an individual. This term therefore covers attenuating, relieving, or suppressing the symptoms of aged / damaged skin, but is limited to a cosmetic treatment.

[0021] The term “room temperature” as used herein refers to a temperature between 18 °C to 25 °C.

[0022] All percentages, parts and ratios are based upon the total weight of the formulation of the present disclosure unless otherwise indicated. Ratios,concentrations, amounts, and other numerical data may be presented herein in a range format. It is to be understood that such range format is used merely for convenience and brevity and should be interpreted flexibly to include not only the numerical values explicitly recited as the limits of the range, but also to include all the individual numerical values or sub-ranges encompassed within that range as if each numerical value and sub-range is explicitly recited. For example, a percentage range of about 10% to 70% should be interpreted to include not only the explicitly recited limits of about 10 % to about 70%, but also to include sub-ranges, such as 20% to 30%, 30% to 45%, and so forth, as well as individual amounts, including fractional amounts, within the specified ranges, such as 28.4%, and 64%, for example.

[0023] Unless defined otherwise, 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 belongs. Although any methods and materials similar or equivalent to those described herein can be used in the practice or testing of the disclosure, the preferred methods and materials are now described. All publications mentioned herein are incorporated herein by reference.

[0024] The present disclosure is not to be limited in scope by the specific embodiments described herein, which are intended for the purposes of exemplification only. Functionally equivalent products, compositions, and methods are clearly within the scope of the disclosure, as described herein.

[0025] Embodiments herein provide a formulation in a cosmetically acceptable medium for skin treatment. The disclosed embodiments include a formulation, a kit comprising the formulation, and a method for treating keratin material by applying said formulation. In various embodiments herein, the formulation is in the form of a serum having improved stability of the Punica granatum extract. Cosmetic products comprising Punica granatum extract have been shown to be advantageous in treating damaged skin and treating / preventing skin aging. Polyphenols, such as punicalagins and ellagic acid are the key active compounds present in the extract that contribute to the skin treatment. However, the Punica granatum extract suffers from poor stability in such cosmetic products owing to the sensitivity of its phenolicantioxidants in a water-based formulation, which affects the overall product stability. Therefore, it is necessary to choose the ingredients of the formulation such that it favors the stability of the extract, the key active of the formulation. Hence, the formulation according to embodiments herein comprises at least one stabilizer, i.e., sodium thiosulphate, which improves the stability of the Punica granatum extract to over 91% when stored at room temperature. Further, the use of additional stabilizer, such as N-acetyl cysteine improves the stability of the Punica granatum extract to over 91% when stored at accelerated conditions.Formulation

[0026] Embodiments herein provide the formulation for treating a keratin material, preferably the skin. In an embodiment of the present disclosure, there is provided a formulation in a cosmetically acceptable medium, comprising: a) an extract of Punica granatum; b) at least one stabilizer comprising sodium thiosulphate; c) water; and d) at least one organic solvent. In other embodiments, the formulation further comprises additives selected from pH adjusters, surfactants, thickening agents, or mixtures thereof.Extract of Punica granatum

[0027] The formulation according to embodiments herein includes an extract of Punica granatum.

[0028] Punica granatum is a fruit-bearing deciduous shrub or small tree in the family Lythraceae that grows between five and 10 m (16-30 feet) tall. Showy red, white, or variegated flowers are found on the branch tips, singly or in clusters of up to five flowers. Nearly round, but crowned at the base by the prominent calyx, the pomegranate fruit has a tough, leathery skin or rind, and is basically yellow overlaid with light or deep pink or rich red. The interior is separated by membranous walls and white spongy tissue into compartments packed with transparent sacs filled with tart, flavourful, fleshy, juicy pulp (the aril). In each sac, there is one white or red, angular, soft, or hard seed. The arils represent about 52% of the weight of the whole fruit.

[0029] In a preferred embodiment, the fruit of Punica granatum is collected from the Indian state of Jammu and Kashmir around the Ramban district (kanga village) during the period of September to December, more particularly at the latitude and longitude around 32° N, 74° E.

[0030] The extract of Punica granatum is preferably an ethanolic extract or a dry extract of the fruit, in particular the pericarp of Punica granatum. The term “dry extract” as used herein refers to an extract, which comprises no more than 7% by weight of solvents relative to the total weight of the dry extract, preferably no more than 5%, more preferably no more than 3% by weight of solvents relative to the total weight of the dry extract. In a preferred embodiment of the present disclosure, the dry extract comprises no more than 1% by weight of solvents relative to the total weight of the dry extract. In another preferred embodiment, the dry extract does not contain any solvent (i.e., 0%), wherein the solvent may be water or C2 - C5 monoalcohols selected from ethanol, propanol, isopropanol, butanol and pentanol, and their mixtures.

[0031] In a preferred embodiment, the method of preparation of the extract of the Punica granatum comprises at least the following steps of: i. providing a Punica granatum pericarp; ii. extracting from the said pericarp, at least punicalagins and ellagic acid, with ethanol of at least 99.5% degree at a temperature ranging from 37°C to 45°C during 2 to 5 hours; iii. filtering and repeating the step (ii) at least two more times; iv. optionally drying the filtrate obtained at the end of the step (iii) at a temperature ranging from 35 °C to 40°C under vacuum.

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

[0033] Preferably, the Punica granatum extract comprises punicalagins and ellagic acid.

[0034] The term “punicalagins” as used herein refers to a mixture of two diastereoisomers, punicalagin A and B. They belong to the polyphenol family, and especially are complex ellagitannins formed of glucose linked to ellagic acid andgallagic acid of molar mass about 1084 gmol-1 formed by the isomers of 2,3-(S)- hexahydroxydiphenoyl- 4,6-(S,S)-gallagyl-D-glucose of chemical formula (I).

[0035] The term “ellagic acid” as used herein refers to a polyphenol of formula (II).

[0036] In a preferred embodiment, the weight ratio [pericarp / absolute ethanol] is1:5.

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

[0038] The step (iii) of filtering is made according to conventional method of filtration well known by the skilled person of the art, for example by a Buchner funnel.

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

[0040] Preferably, the method of preparation of the extract of Punica granatum comprises: i. providing a Punica granatum pericarp; ii. extracting from the said pericarp, at least punicalagins and ellagic acid, with ethanol of at least 99.5% degree at a temperature ranging from 37°C to 45°C during 2 to 5 hours ; iii. filtering and repeating the step (ii) at least two more times; iv. optionally drying the filtrate obtained at the end of the step (iii) at a temperature ranging from 35 °C to 40°C under vacuum.

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

[0042] The extract according to the invention can further comprise 1% to 5% by weight of the total weight of the dry extract, of punicalins, preferably 2% to 4.5%, even more preferably 3% to 4%.

[0043] Advantageously, the weight ratio [ellagic acid / punicalagins] is ranging from 0.6 to 1.6, more preferably from 0.7 to 1.3, even more preferably from 0.7 to 1.

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

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

[0046] The amount of the extract of Punica granatum present in the formulation, according to embodiments herein, may vary. The extract of Punica granatum, according to embodiments herein, may be present in the formulation in a weight range of 0.01% to 10%, preferably in a weight range of 0.02% to 5% relative to the total weight of the formulation, more preferably in a weight range of 0.05% to 3% relative to the total weight of the formulation.

[0047] In some more embodiments herein, the formulation comprises the extract of Punica granatum comprising i) at least 0.001% by weight of the total weight of the formulation, of punicalagins preferably in a weight range of 0.001% to 1% relative to the total weight of the formulation; and ii) at least 0.001% by weight of the total weight of the formulation, of ellagic acid preferably in a weight range of 0.001% to 1% relative to the total weight of the formulation; and wherein the weight ratio [ellagic acid / punicalagins] is ranging from 0.5 to 2.Stabilizer

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

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

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

[0051] Examples of optional additional stabilizers which can be used in the formulation of the present disclosure include but are not limited to N-acetyl cysteine.

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

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

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

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

[0056] In a more preferred embodiment, the formulation comprises water in a weight range of preferably in a weight range of 10% to 70%, more preferably in a weight range of 40% to 60% relative to the total weight of the formulation.Organic solvent

[0057] The formulation, according to embodiments herein, includes at least one organic solvent.

[0058] According to embodiments herein, the organic solvent is selected from Cl- C4 monoalcohols (ethanol or isopropanol or 2-ethoxy ethanol), or polyols such as C2-C8 polyols, (triol, such as glycerol; hexols, such as sorbitol; diols, such as caprylyl glycol, 1,2-pentanediol, propanediol, butanediol, ethylene glycol, propylene glycol, butylene glycol, dipropylene glycol, diethylene glycol, 1,2- propylene glycol, 1,3-butylene glycol, pentylene glycol, hexylene glycol, diethylene glycol monomethyl ether, or triethylene glycol monomethyl ether), or mixtures thereof.

[0059] In an embodiment, the formulation comprises a mixture of at least one Cl- C4 monoalcohol preferably ethanol and at least one polyol, preferably in a total weight ratio of polyols / total weight of C1-C4 monoalcohol > 1, more preferably > 5.

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

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

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

[0063] The formulations according to the present disclosure may additionally comprise UV-filters. The terms “UV-filter”, “UV-screening agent” and “screeningagents” shall be used interchangeably. In a preferred embodiment of the present disclosure, the formulation comprises one or more UV-filters, selected from hydrophilic, lipophilic, insoluble organic UV-filter, 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" is understood to mean any cosmetic or dermatological, organic or inorganic, compound which screens out UV radiation and which is capable of being completely dissolved in the molecular state in a liquid aqueous phase or else of being dissolved in colloidal form (for example in micellar form) in a liquid aqueous phase.

[0065] The term "lipophilic UV-filter" is understood to mean any cosmetic or dermatological, organic or inorganic, compound which screens out UV radiation and which is capable of being completely dissolved in the molecular state in a liquid fatty phase or else of being dissolved in colloidal form (for example in micellar form) in a liquid fatty phase.

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

[0067] The organic UV-filters in particular, are selected from cinnamic compounds; anthranilate compounds; salicylic compounds; dibenzoylmethane compounds; benzylidenecamphor compounds; benzophenone compounds; P,[3- diphenylacrylate compounds; triazine compounds; benzotriazole compounds; benzalmalonate compounds, in particular those cited in Patent US 5 624 663; benzimidazole derivatives; imidazoline compounds; bis-benzazolyl compounds,such as described in Patents EP 669 323 and US 2 463 264; methylenebis(hydroxyphenylbenzotriazole) compounds, such as described in Applications US 5 237 071, US 5 166 355, GB 2 303 549, DE 197 26 184 and EP 893 119; benzoxazole compounds, such as described in Patent Applications EP 0 832 642, EP 1 027 883, EP 1 300 137 and DE 101 62 844; screening polymers and screening silicones, such as those described in particular in Application WO 93 / 04665; dimers derived from a-alkylstyrene, such as those described in Patent Application DE 198 55 649; 4, 4 -diarylbutadiene compounds, such as described in Applications EP 0 967 200, DE 197 46 654, DE 197 55 649, EP-A-1 008 586, EP 1 133 980 and EP 133 981, and their mixtures.Examples of organic UV-filters, include but are not limited to the list below:Cinnamic compounds:

[0068] Ethylhexyl methoxycinnamate, sold in particular under the trade name Parsol® MCX (DSM Nutritional Products); and Isoamyl p-Methoxycinnamate, sold under the trade name Neo Heliopan E 1000® (Symrise).Dibenzoylmethane compounds:

[0069] Butyl methoxy dibenzoylmethane, sold in particular under the trade name Parsol® 1789 (DSM Nutritional Products).Salicylic compounds:

[0070] Homosalate, sold under the name Parsol® HMS (DSM nutritional products), and ethylhexyl Salicylate, sold under the name Neo Heliopan® OS (Symrise).-Diphenylacrylate compounds :

[0071] Octocrylene, sold in particular under the trade name Uvinul® N 539 T (BASF).Benzophenone compounds:

[0072] Benzophenone- 3 or oxybenzone, sold under the trade name Uvinul® M 40 (BASF), diethylamino hydroxybenzoyl hexyl benzoate, sold under the trade name Uvinul® A Plus or, as a mixture with ethylhexyl methoxycinnamate, under the trade name Uvinul® A Plus B (BASF), l,l'-(l,4-piperazinediyl)bis[l-[2-[4- (diethylamino)-2-hydroxybenzoyl]phenyl]methanone] (CAS 919803-06-8), asdescribed in application W02007 / 071584; this compound advantageously being used in micronized form (mean size of 0.02 to 2 pm), which can be obtained, for example, according to the micronization process described in Applications GB-A- 2303 549 and EP-A-893 119, and in particular in the form of an aqueous dispersion. Benzylidenecamphor compounds'.

[0073] 4-Methylbenzylidene camphor, sold under the name Eusolex® 6300 (Merck), Terephthalylidene dicamphor sulfonic acid, manufactured under the name Mexoryl® SX (No veal).Phenylbenzimidazole compounds'.

[0074] Phenylbenzimidazole sulfonic acid, sold in particular under the trade name Eusolex® 232 (Merck).Bis-benzazolyl compounds'.

[0075] Disodium phenyl pibenzimidazole tetrasulfonate, sold under the trade name Neo Heliopan® AP (Symrise).Phenylbenzotriazole compounds'.

[0076] Drometrizole trisiloxane, manufactured under the name Mexoryl® XL (Noveal).Methylenebis(hydroxyphenylbenzotriazole} compounds'.

[0077] Methylene bis-benzotriazolyl tetramethylbutylphenol, in particular in solid form, such as the product sold under the trade name Mixxim BB / 100® (Fairmount Chemical), or in the form of an aqueous dispersion of micronized particles having a mean particle size which varies from 0.01 to 5 pm, more preferentially from 0.01 to 2 pm and more particularly from 0.020 to 2 pm, with at least one alkylpoly glyco side surfactant having the structure CnH2n+io(C6Hio05)xH, in which n is an integer from 8 to 16 and x is the mean degree of polymerization of the (CeHioOs) unit and varies from 1.4 to 1.6, such as described in Patent GB-A-2 303 549, sold in particular under the trade name Tinosorb® M (BASF), or in the form of an aqueous dispersion of micronized particles having a mean particle size which varies from 0.02 to 2 pm, more preferentially from 0.01 to 1.5 pm and more particularly from 0.02 to 1 pm, in the presence of at least one polyglyceryl mono(Cs-C2o)alkyl ester having a degree of glycerol polymerization of at least 5,such as the aqueous dispersions described in application W02009 / 063392, in particular the product sold under the name Tinosorb WPGL (BASF).

[0078] Triazine compounds'.

[0079] 3,3'-(l,4-phenylene)bis(5,6-diphenyl-l,2,4-triazine), with the INCI name phenylene bis-diphenyltriazine, bis-ethylhexyloxyphenol methoxyphenyl triazine, sold under the trade name Tinosorb® S (BASF), and in its hydrodispersible form with the INCI name bis-ethylhexyloxyphenol methoxyphenyl triazine (and) acrylates / C 12-22 alkyl methacrylate copolymer, under the trade name TINOSORB® S LiteAqua (BASF), ethylhexyl triazone, sold in particular under the trade name Uvinul® T 150 (BASF), diethylhexyl butamido triazone, sold under the trade name Uvasorb® HEB by 3V (Sigma), symmetrical triazine screening agents substituted by naphthalenyl groups or polyphenyl groups described in Patent US 6 225 467, Application W02004 / 085412 (refer, compounds 6 and 9) or the document "Symmetrical Triazine Derivatives", IP.COM IPCOM000031257 Journal, INC West Henrietta, NY, US (20 September 2004), in particular 2,4,6- tris(biphenyl)triazine and 2,4,6-tris(terphenyl)triazine sold under the name TINOSORB® A2B (BASF), also mentioned in Patent Applications W006 / 035000, WO06 / 034982, W006 / 034991, W006 / 035007, W02006 / 034992 andW02006 / 034985, these compounds advantageously being used in micronized form (mean particle size of 0.02 to 3 pm), 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 in particular in aqueous dispersion form.Anthranilic compounds'.

[0080] Menthyl anthranilate, sold under the trade name Neo Heliopan® MA (Symrise).Benzalmalonate compounds'.

[0081] Polyorganosiloxane comprising benzalmalonate functional groups, such as Polysilicone-15, sold under the trade name Parsol SLX® (Hoffmann-La Roche). Benzoxazole compounds'.

[0082] The UV filter with the INCI name 2,2'-(l,4-phenylene)bis(l,3-benzoxazole offered under the name DBG (DSM).

[0083] The preferential organic UV filters are selected from: ethylhexyl methoxycinnamate, ethylhexyl salicylate, homosalate, butyl methoxydibenzoylmethane, octocrylene, phenylbenzimidazole sulfonic acid, benzophenone-3, diethylamino hydroxybenzoyl hexyl benzoate, 4- methylbenzylidene camphor, terephthalylidene dicamphor sulfonic acid, disodium phenyl dibenzimidazole tetrasulfonate, methylene bis-benzotriazolyl tetramethylbutylphenol, bis-ethylhexyloxyphenol methoxyphenyl triazine, ethylhexyl triazone, diethylhexyl butamido triazone, 2,4,6-tris(biphenyl)triazine, 2,4,6-tris(terphenyl)triazine, drometrizole trisiloxane, polysilicone-15, bis- (diethylaminohydroxybenzoyl benzoyl) piperazine, or their mixtures.

[0084] The particularly preferred organic UV-filters are selected from: ethylhexyl salicylate, homosalate, butyl methoxydibenzoylmethane, octocrylene, diethylamino hydroxybenzoyl hexyl benzoate, terephthalylidene dicamphor sulfonic acid, bis-ethylhexyloxyphenol methoxyphenyl triazine, ethylhexyl triazone, diethylhexyl butamido triazone, bis-(diethylaminohydroxybenzoyl benzoyl) piperazine, drometrizole trisiloxane, 2,4,6-tris(biphenyl)triazine, or their mixtures.

[0085] The inorganic UV-filters used in accordance with the present disclosure are metal oxide pigments. More preferentially, the inorganic UV-filters of the present disclosure are metal oxide particles or pigments having a mean elementary particle size of less than or equal to 0.5 pm, more preferentially of between 0.005 and 0.5 pm, more preferentially still of between 0.01 and 0.2 pm, better still between 0.01 and 0.1 pm and more particularly between 0.015 and 0.05 pm. Metal oxide pigments are described in particular in annexure VI updated on 22 / 09 / 2021 of the European regulation on cosmetic products number 1223 / 2009, but are not limited to this list.

[0086] Metal oxide pigments may be chosen in particular from titanium oxide, zinc oxide, iron oxide, zirconium oxide, cerium oxide or their mixtures.

[0087] Such coated or non-coated metal oxide pigments are described in particular in Patent Application EP-A-0 518 773. Mention may be made, as commercial pigments, of the products sold by Croda, Tayca and Merck.

[0088] The metal oxide pigments can be coated or non-coated.

[0089] The coated pigments are pigments which have undergone one or more surface treatments of chemical, electronic, mechanochemical and / or mechanical nature with compounds such as amino acids, beeswax, fatty acids, fatty alcohols, anionic surfactants, lecithins, sodium, potassium, zinc, iron or aluminium salts of fatty acids, metal alkoxides (of titanium or aluminium), polyethylene, silicones, proteins (collagen, elastin), alkanolamines, silicon oxides, metal oxides or sodium hexametapho sphate .

[0090] The coated pigments are more particularly titanium oxides coated:- with hydrated silica, such as the product MT-100WP from Tayca,- with silica and iron oxide, such as the product Sunveil F® from Ikeda,- with silica and alumina, such as the products MT-500SA® and MT- 100SA® from Tayca and Tioveil™ AQ-N from Croda,- with alumina, such as the products TTO-55 (A)® from Ishihara,- with alumina and aluminium stearate, such as the products MT-100TV®, MT-100Z® and MT-01® from Tayca, the product Solaveil™ CT100 from Croda and the product Eusolex T-AVO® from Merck,- with silica, alumina and alginic acid, such as the product MT-100AQ® from Tayca,- with alumina and aluminium laurate,- with iron oxide and iron stearate,- with zinc oxide and zinc stearate,- with silica and alumina and treated with a silicone, such as the products MTY-500SAS® or microtitanium dioxide MT-100SAS® from Tayca,- with silica, alumina and aluminium stearate and treated with a silicone,- with silica and treated with a silicone,- with alumina and treated with a silicone, such as the products TTO-55(S)® from Ishihara,- with triethanolamine,- with stearic acid, such as the product TTO-55 (C)® from Ishihara,- with sodium hexametaphosphate,- TiC treated with octyltrimethylsilane,- TiC treated with a polydimethylsiloxane,- anatase / rutile TiC treated with a polydimethylhydrosiloxane,- TiC coated with triethylhexanoin, aluminium stearate and alumina, sold under the trade name Solaveil™ CT-200 by Croda,- TiCh coated with aluminium stearate, alumina and silicone, sold under the trade name Solaveil™ CT-12W by Croda,- TiCh coated with lauroyl lysine, or- TiCh coated with C9-C15 fluoroalcohol phosphate and aluminium hydroxide.

[0091] Mention may also be made to TiCh pigments doped with at least one transition metal, such as iron, zinc or manganese and more particularly manganese. Preferably, said doped pigments are in the form of an oily dispersion. The oil present in the oily dispersion is preferably chosen from triglycerides, including those of capric / caprylic acids. The oily dispersion of titanium oxide particles can additionally comprise one or more dispersing agents, such as, for example, a sorbitan ester, such as sorbitan isostearate, a polyoxyalkylenated glycerol fatty acid ester, such as Tri-PPG-3 Myristyl Ether Citrate and Polyglyceryl-3 Polyricinoleate. Preferably, the oily dispersion of titanium oxide particles comprises at least one dispersing agent chosen from polyoxyalkylenated glycerol fatty acid esters. Mention may more particularly be made to the oily dispersion of TiCh particles doped with manganese in capric / caprylic acid triglyceride in the presence of Tri- PPG-3 Myristyl Ether Citrate and of polyglyceryl-3 polyricinoleate and of sorbitan isostearate with the INCI name: titanium dioxide (and) Tri-PPG-3 myristyl ethercitrate (and) polyglyceryl-3 ricinoleate (and) sorbitan isostearate or the product sold under the trade name Optisol™ OPT-1 by Croda.

[0092] The non-coated titanium oxide pigments are sold, for example, by Tayca under the trade names MT-500B or MT-600B®, by Evonik under the name Degussa P 25.

[0093] The non-coated zinc oxide pigments are, for example, those sold under the name Z-COTE® by BASF; or those sold under the name NanoArc® Zinc Oxide by Nanophase Technologies.

[0094] The coated zinc oxide pigments are, for example: ZnO coated with poly methylhydro siloxane; Solaveil™ CZ-100 from Croda dispersed in C12-15 alkyl benzoate (INCI: Zinc Oxide (and) C 12-15 alkyl benzoate (and) poly hydroxy stearic acid (and) isostearic Acid); those sold under the name Daitopersion Zn-60VA® by Daito Kasei (dispersions in C9-12 alkane with a dispersing agent); those sold under the name SPD-Z5® by Shin-Etsu (ZnO coated with silicone-grafted acrylic polymer, dispersed in cyclodimethylsiloxane).

[0095] The non-coated cerium oxide pigments can, for example, be those sold under the name Rhodigard® W185 by Solvay.

[0096] Mention may also be made of mixtures of metal oxides, in particular of titanium dioxide and cerium dioxide, including the mixture in equal weights of titanium dioxide and cerium dioxide coated with silica, and also the mixture of titanium dioxide and zinc dioxide coated with alumina, silica and silicone or coated with alumina, silica and glycerol.

[0097] According to the present disclosure, coated or non-coated titanium oxide pigments are particularly preferred.

[0098] The UV-filters may be present in the formulation according to the present disclosure in a weight range of 0.1% to 60%, preferably in a weight range of 5% to 30% relative to the total weight of the formulation.Cosmetic formulations

[0099] The present disclosure also relates to a cosmetic formulation comprising, in a cosmetically acceptable medium, a formulation as defined above.

[0100] The cosmetically acceptable medium is generally adapted to the nature of the support to which the formulation is to be applied, as well as to the appearance in which the formulation is to be packaged. According to embodiments herein, the cosmetically acceptable medium is a medium that is compatible with the keratin material, preferably the skin. The cosmetically acceptable medium of the formulation may more particularly comprise water and optionally a cosmetically acceptable water-soluble organic solvent as described herein.Additives

[0101] The formulations according to the present disclosure may additionally comprise additives commonly used in cosmetic products such as, ascorbic acid, Tinogard Q, or actives different from Punica granatum extract, pH adjusters, surfactants, thickening agents, and their mixtures.

[0102] In an embodiment of the present disclosure, the formulation comprises one or more actives different from Punica granatum extract. In one embodiment, the formulation comprises ascorbic acid as an additional active different from Punica granatum extract. In one another embodiment, the formulation comprises Tinogard Q as an additional active different from Punica granatum extract. In an additional embodiment, the formulation comprises ascorbic acid and Tinogard Q as additional actives different from Punica granatum extract. pH adjusters

[0103] The formulation, according to embodiments herein, includes at least one pH adjuster.

[0104] The term “pH adjuster” as used herein refers to those substances that establish and maintain the pH of the formulations in a desired range.

[0105] The pH adjusters can be an “acidifying agent”, which can be inorganic acids, such as hydrochloric acid, orthophosphoric acid, or sulfuric acid; or organic acids, preferably carboxylic acids, such as acetic acid, tartaric acid, citric acid or lactic acid, or sulfonic acids, and their mixtures.

[0106] The pH adjusters can be a “basifying agent”, which can be organic, such as arginine, lysine, amines as mono-, di- and triethanolamines, or inorganic, such as aqueous ammonia, alkali metal carbonates, sodium hydroxide, potassium hydroxide or their mixtures.

[0107] In an embodiment of the present disclosure, the pH adjuster is one or more basifying agents selected from arginine, triethanolamine, sodium hydroxide, or mixtures thereof.

[0108] The amount of pH adjusters present in the formulation may vary and is determined based on the desired pH that is to be maintained for the formulation.Surfactants

[0109] The formulation, according to embodiments herein, includes one or more surfactants, selected from amphoteric surfactants, anionic surfactants, cationic surfactants, non-ionic surfactants, or mixtures thereof.

[0110] According to preferred embodiments, the surfactant is anionic surfactant selected from polyglyceryl-2-laurate, sodium cocoyl sarcosinate, isopropyl lauroyl sarcosinate, or mixtures thereof.

[0111] The amount of surfactant present in the formulation, according to embodiments herein, may vary. The surfactants, according to embodiments herein, may be present in the formulation in a weight range of 0.1% to 20%, preferably ina weight range of 0.5% to 15%, more preferably in a weight range of 1% to 10% relative to the total weight of the formulation.Thickening agent

[0112] The formulation, according to the embodiments herein, includes one or more thickening agents, which provides the desired viscosity to the formulation.

[0113] Examples of thickening agents include but are not limited to carboxy polymers, acrylates / C10-C30 alkyl acrylate crosspolymer, polyacrylamides and derivatives, polysaccharides, water-soluble or water-dispersible silicone derivatives, or mixtures thereof.

[0114] Examples of carboxy vinyl polymers that may be suitably used in the present disclosure are the Carbopols® (Carbomers) and the Pemulens, such as Pemulen TRI® and Pemulen TR2® (Acrylates / C10-C30 Alkyl Acrylate Crosspolymer).

[0115] Examples of polyacrylamides and derivatives that may be suitably used in the present disclosure are the crosslinked copolymers sold under the names Sepigel 305® (CTFA name: polyacrylamide / C13-14 isoparaffin / laureth-7) or Simulgel 600 (CTFAname:acrylamide / sodiumacryloyldimethyltauratecopolymer / isohexadecane / polysorbate 80) by SEPPIC; 2-acrylamido-2-methylpropanesulfonic acid polymers and copolymers which are optionally crosslinked and / or neutralized, such as the poly(2-acrylamido-2-methylpropanesulfonic acid) sold by Hoechst under the trade name Hostacerin AMPS® (CTFA name: ammonium polyacryloyldimethyl taurate) or Simulgel 800® sold by SEPPIC (CTFA name: sodium polyacryloyldimethyl taurate / polysorbate 80 / sorbitan oleate); copolymers of 2-acrylamido-2- methylpropanesulfonic acid and of hydroxyethyl acrylate, such as Simulgel NS® and Sepinov EMT 10® sold by SEPPIC.

[0116] Examples of polysaccharides that may be suitably used in the present disclosure are gums, such as xanthan gum, chitosan; linear polysaccharides, such as chitosan and beta glucan; and cellulose derivatives, such ashydroxyethylcellulose; water-soluble or water-dispersible silicone derivatives, such as acrylic silicones, poly ether silicones and cationic silicones, and their mixtures.

[0117] In an embodiment of the present disclosure, the thickening agent is preferably selected from polysaccharides, more preferably selected from cellulose derivatives, gums, linear polysaccharides, or mixtures thereof.

[0118] The amount of thickening agent present in the formulation, according to the embodiments herein, may vary. The thickening agent, according to embodiments herein, may be present in the formulation in a weight range of 0.1% to 10%, preferably in a weight range of 0.2% to 8%, more preferably in a weight range of 0.5% to 5% relative to the total weight of the formulation.Other additives

[0119] The formulation may further comprise other additives that are conventionally used in cosmetics, and / or dermatology field, such as fragrances, preservatives, fillers, oils, and colouring agents. It is understood that a person skilled in the art will take care to select the optional additives and / or the amount thereof such that the advantageous properties of the formulation used according to the disclosure are not, or are not substantially, adversely affected by the envisaged addition. All such embodiments including the optional additives are understood to be included within the scope of the present disclosure.

[0120] In an embodiment of the present disclosure, the formulation comprises of no trisodium ethylene diamine disuccinate or less than 0.2% thereof. In another embodiment of the present disclosure, the formulation comprises less than 0.2%, less than 0.1%, less than 0.05% by weight of trisodium ethylene diamine disuccinate thereof, relative to the total weight of the formulation.Preparation of the formulations according to the disclosure

[0121] The formulations according to the disclosure may be prepared using known methods, generally used in the cosmetics or dermatology field. Typically, themethod includes mixing of water, a pH adjuster, at least one surfactant and at least one stabilizer to obtain a first mixture. Mixing Punica granatum and at least one organic solvent to obtain a clear transparent solution, which is added along with one or more additives to the first mixture and mixed to obtain a homogenous transparent or translucent formulation (cosmetic formulation).Applications

[0122] A formulation, according to embodiments herein, may more particularly be a formulation for treating keratin material, such as skin. Preferably, the formulation, according to embodiments herein, is a formulation for treating the skin. Accordingly, the formulation, in various embodiments herein, may be in the form of a serum.

[0123] In an embodiment of the present disclosure, the pH of the formulation is in a range of 2 to 8, preferably in a range of 3 to 7.

[0124] In an embodiment of the present disclosure, the formulation has a punicalagin marker stability of more than 91% when stored at room temperature for at least 2 months. In another embodiment of the present disclosure, the formulation has a punicalagin marker stability of more than 91% when stored at room temperature for 4 months, for 6 months, for 8 months, for 10 months or for 12 months.

[0125] In an embodiment of the present disclosure, the formulation has a punicalagin marker stability of more than 91% when stored at room temperature for 2 weeks, 1 month or 2 months, such as 2 weeks.

[0126] In one embodiment of the present disclosure, the formulation when comprising N-acetyl cysteine as an additional stabilizer has a punicalagin marker stability of more than 91% when stored at accelerated conditions for 2 weeks, 1 month or 2 months, such as 2 weeks.

[0127] The formulation, according to embodiments herein, can be applied optionally with an applicator on the skin, followed by working the formulation on the skin.

[0128] Although the present disclosure has been described in considerable detail with reference to certain embodiments and implementations thereof, other embodiments are possible to cover the modifications and variations of the present disclosure.Examples

[0129] The disclosure will now be illustrated with working examples, which is intended to illustrate the working of disclosure and not intended to take restrictively to imply any limitations on the scope of the present disclosure. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood to one of ordinary skill in the art to which this disclosure belongs. Although methods and materials similar or equivalent to those described herein can be used in the practice of the disclosed methods and compositions, the exemplary methods, devices, and materials are described herein. It is to be understood that this disclosure is not limited to particular methods, and experimental conditions described, as such methods and conditions may apply.

[0130] Ingredient amounts are indicated in the following examples in active material weight percentages.Example 1Preparation of Punica granatum extract

[0131] Dried pericarp of Punica granatum (1kg) was extracted at 42 °C with 5 litres of ethanol (purity 99.5%) with stirring at 800 rpm for a brief period of 4h. The ethanolic extract obtained was filtered through a Buchner funnel containing cotton cloth (mesh size: 20 micron). The filtered extract was evaporated under vacuum at 38 °C, to afford a brown amorphous powder. The extraction was repeated successively for two consecutive times under the conditions explained above. The combined dried extract consists of the major phenolic compounds ie: ellagic acid and punicalagins.

[0132] The specifications of the extract are as follows in Table la and Table lb:Table laTable lbExample 2 :Preparation of formulations

[0133] The formulations listed in Table 2a and Table 2b were prepared as described below.

[0134] Phase A ingredients (a pH adjuster, at least one surfactant and at least one stabilizer) were weighed and added with water to a first vessel and mixed at 400 rpm. Phase B ingredients (Extract of Punica granatum according to Example 1 and at least one organic solvent) were weighed and added to a second vessel and mixed in a magnetic stirrer at 300 rpm at 45 to 50° C to obtain a clear transparent solution, which was then added to the first vessel under mixing at 400 rpm. Phase C 1ingredients (at least one thickening agent) were added to the first vessel and dispersed by stirring at 600 rpm for 10 minutes. Phase D ingredients (additional surfactants) and Phase E ingredients (an additional organic solvent) were added to the first vessel and mixed for 10 minutes to obtain a homogenous transparent or translucent gel.Table 2aTable 2bExample 3Evaluation of stability of the formulations

[0135] The formulations PK01 to PK07 (Table 2a) and the formulations PPI to PP4 (Table 2b) as prepared in the above Example 2 were evaluated for their stability at room temperature and accelerated conditions.

[0136] The formulations were stored for 2 weeks or 2 months at room temperature and analyzed for the marker Punicalagin content (using Ultra Performance Liquid Chromatography (UPLC) method) at initial time point (TO), and after 2 weeks (T2W) or 2 months (T2M) at room temperature. Some of the formulations were analyzed for the marker Punicalagin content (using Ultra Performance Liquid Chromatography (UPLC) method) at initial time point (TO), and at accelerated condition i.e. after 2 weeks at 55°C (T2W 55°C).

[0137] Punicalagin (mix of punicalagin A and punicalagin B) standard preparation: In a 10 mL volumetric flask, Punicalagin standard (5 mg, > 93.4 % purity, CASNO. : 65995-63-3, Chromadex) was dissolved in methanol (10 mL) and sonicated (10 min). For the calibration curve preparation, serial dilutions were prepared from the standard stock solution (minimum 6 calibration points) with methanol as diluent.

[0138] Separation was achieved by reversed phase Liquid Chromatography (LC)and performed on a Nexera Ultra Performance LC system equipped with a photodiode array detector (Shimadzu). The details of the method are mentioned below.(i) Column Agilent Zorbax Eclipse XDB-C18, 5pm, 4.6 X 150mm(ii) Mobile phase A: 0.1% Ortho-phosphoric acid in Water(iii) Mobile phase B: 0.1% Ortho-phosphoric acid in Acetonitrile(iv) Gradient:(v) Flow Rate: 1 mL / min(vi) Run Time: 25 minutes(vii) Column Temperature: 30°C(viii) Detector: PDA(ix) Detection Wavelength: Punicalagin - 258 nm(x) Injection Volume: 10 pL(xi) Retention Time: Punicalagin A - 3.5 min; Punicalagin B - 4.8 min

[0139] The percentage decrease in punicalagin content was calculated using the formula as below:Percentage decrease in Punicalagin content = Punicalagin content at 2Weeks (RT or 55°C) time point T(2W) Punicalagin content at initial time point TO x 100

[0140] The percentage decrease of less than 9% in the marker Punicalagin content Vs initial content was acceptable.ResultsTable 3a

[0141] From Table 3a, it is evident that the formulations (PK03 and PK07) devoid of sodium thiosulphate as a stabilizer exhibited poor marker stability of less than 91% after being stored for 2 weeks at room temperature conditions.

[0142] A similar observation was noted in the formulations PPI and PP2 that do not comprise sodium thiosulphate as depicted in Table 3b.

[0143] Further, it was observed that the use of N-acetyl cysteine as an additional stabilizer improved the punicalagin marker stability to over 91% at accelerated conditions, as shown in Table 3c for samples PK01 and PP4, respectively.Table 3bTable 3cExample 4Effect of water and organic solvent (polyol) content on the stability of the formulations

[0144] The stability of the formulations containing varying high amounts of organic solvent were tested. The different amounts tested are mentioned in Table 4a. The formulations P4 to P5 as tested comprised water, various polyols as organic solvents along with 0.5% by weight of extract described in example 1, 0.2% by weight of sodium thiosulphate and 0.1% by weight of N-acetyl cysteine (Table 4b). Phase Aingredients (at least one stabilizer) were weighed and added with water to a first vessel and mixed at 400 rpm. Phase B ingredients (Extract of Punica granatum according to Example 1 and at least one organic solvent) were weighed and added to a second vessel and mixed in a magnetic stirrer at 300 rpm at 45 to 50° C to obtain a clear transparent solution, which was then added to the first vessel under mixing at 400 rpm to obtain the formulations Pl and P2. It was observed that the presence of an organic solvent of more than 30% with respect to the total weight of the formulation improved the dispersion (or solubility) of the extract in the formulation and thereby improved the stability of the extract in the formulation (refer to the result as depicted for Formulations Pl and P2 in Table 4c).Table 4aTable 4bTable 4cExample 5

[0145] Furthermore, use of any other stabilizer other than sodium thiosulphate did not yield similar level of punicalagin marker stability (Table 5a) after storing at room temperature for 1 month. PR1, PR2, PR3 formulations comprising sodium thiosulphate, or sodium metabisulphite or sodium sulphite were prepared using the method as described in Example 2. For example, the use of sodium metabisulphite and sodium sulphite yielded less than 91% marker stability when compared to formulation comprising sodium thiosulphate (PR1) (Table 5b).Table 5aTable 5bAdvantages of the present disclosure

[0146] The present disclosure provides a formulation in a cosmetically acceptable medium comprising a) an extract of Punica granatum; b) at least one stabilizer comprising sodium thiosulphate; c) water; and d) at least one organic solvent. The use of sodium thiosulphate as a stabilizer provides more than 91% of stability for punicalagin, a marker for the Punica granatum extract in the formulation. Further, the use of N-acetyl cysteine amino acid as an additional stabilizer provides better stability of the formulation at accelerated conditions.

Claims

I / We Claim:

1. A formulation in a cosmetically acceptable medium, comprising: a) an extract of Punica granatum; b) at least one stabilizer comprising sodium thiosulphate; c) water; and d) at least one organic solvent.

2. The formulation as claimed in claim 1 wherein the extract of Punica granatum comprises: i. at least 10% by weight of the total weight of the dry extract, of punicalagins; and ii. at least 10% by weight of the total weight of the dry extract, of ellagic acid; and wherein the weight ratio [ellagic acid / punicalagins] is in a range from 0.5 to 2.

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

4. The formulation as claimed in one of the preceding claims comprising: i. at least 0.001% by weight of the total weight of the formulation, of punicalagins preferably in a weight range of 0.001% to 1% relative to the total weight of the formulation; and ii. at least 0.001% by weight of the total weight of the formulation, of ellagic acid preferably in a weight range of 0.001% to 1% relative to the total weight of the formulation; and wherein the weight ratio [ellagic acid / punicalagins] is ranging from 0.5 to 2.

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

6. The formulation as claimed in one of the preceding claims, wherein the stabilizer further comprises N-acetyl cysteine.

7. The formulation as claimed in claim 6, wherein N-acetyl cysteine is in a weight range of 0.01% to 2%, preferably in a weight range of 0.03% to 1% relative to the total weight of the formulation.

8. The formulation as claimed in one of the preceding claims, wherein the formulation comprises at least one organic solvent selected from C1-C4 monoalcohols (ethanol or isopropanol or 2-ethoxyethanol), or polyols such as C2- C8 polyols, (triol, such as glycerol; hexols, such as sorbitol; diols, such as caprylyl glycol, 1,2-pentanediol, propanediol, butanediol, ethylene glycol, propylene glycol, butylene glycol, dipropylene glycol, diethylene glycol, 1,2-propylene glycol, 1,3 -butylene glycol, pentylene glycol, hexylene glycol, diethylene glycol monomethyl ether, or triethylene glycol monomethyl ether), or mixtures thereof.

9. The formulation as claimed in claim 8, wherein the at least one organic solvent is more than 30% and less than 90% by weight relative to the total weight of the formulation.

10. The formulation as claimed in one of the preceding claims, wherein water is more than 10% and less than 70% by weight relative to the total weight of the formulation.

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

12. The formulation as claimed in one of the preceding claims, further comprising additives selected from pH adjusters, surfactants, thickening agent, or mixtures thereof.

13. The formulation as claimed in claim 12, wherein the pH adjuster is selected from acidifying agent, (hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids, acetic acid, tartaric acid, citric acid or lactic acid, sulfonic acids), a basifying agent (arginine, lysine, aqueous ammonia, alkali metal carbonates, mono-, di- and triethanolamines and their derivatives, sodium hydroxide, potassium hydroxide) or mixtures thereof, preferably is one or more basifying agents, more preferably is selected from arginine, triethanolamine, sodium hydroxide, or mixtures thereof.

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

15. The formulation as claimed in claim 12, wherein the surfactant is selected from amphoteric surfactants, anionic surfactants, cationic surfactants, non-ionic surfactants, or mixtures thereof.

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

17. The formulation as claimed in claim 12, wherein the thickening agent is selected from carboxy polymers, acrylates / C10-C30 alkyl acrylate crosspolymer, polyacrylamides and derivatives, polysaccharides (cellulose derivatives, gums), water-soluble or water-dispersible silicone derivatives, or mixtures thereof.

18. The formulation as claimed in claim 17, wherein the thickening agent is in a weight range of 0.1% to 10%, preferably in a weight range of 0.2% to 8% relative to the total weight of the formulation.

19. The formulation as claimed in one of the preceding claims, wherein the formulation comprises no trisodium ethylene diamine disuccinate or less than 0.2% thereof.

20. The formulation as claimed in one of the preceding claims, wherein the formulation is provided in the form of a serum.

21. The formulation as claimed in one of the preceding claims, wherein the formulation has a punic alagin marker stability of more than 91% when stored at room temperature for at least 2 months.

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

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

24. Use of the formulation as claimed in any one of the claims 1 to 21 for the treatment of skin.

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