Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
  • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
  • C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
  • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
  • C07C49/24—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
  • C07C49/245—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups containing six-membered aromatic rings
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
  • A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
  • A01N31/16—Oxygen or sulfur directly attached to an aromatic ring system with two or more oxygen or sulfur atoms directly attached to the same aromatic ring system
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
  • A01N35/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aliphatically bound aldehyde or keto groups, or thio analogues thereof; Derivatives thereof, e.g. acetals
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
  • A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
  • A01P3/00—Fungicides
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
  • A23B2/00—Preservation of foods or foodstuffs, in general
  • A23B2/70—Preservation of foods or foodstuffs, in general by treatment with chemicals
  • A23B2/725—Preservation of foods or foodstuffs, in general by treatment with chemicals in the form of liquids or solids
  • A23B2/729—Organic compounds; Microorganisms; Enzymes
  • A23B2/742—Organic compounds containing oxygen
  • A23B2/75—Organic compounds containing oxygen with doubly-bound oxygen
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
  • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
  • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
  • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/35—Ketones, e.g. benzophenone
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P17/00—Drugs for dermatological disorders
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
  • C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
  • A61K2800/52—Stabilizers
  • A61K2800/524—Preservatives
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
  • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
  • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
  • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Definitions

• vanillin derivatives as a preservative, preservation process, compounds and composition
• the present invention relates to the use of vanillin derivatives in particular as a preservative in cosmetic, dermatological or pharmaceutical compositions, or even nutraceuticals or oral cosmetics; the invention also relates to novel compounds which can be used in cosmetics, dermatology or pharmacy, or even nutraceutical or oral cosmetic, in particular as a preservative, as well as compositions comprising these compounds.
• the object of the present invention is to propose novel preserving agents having in particular a broad antimicrobial spectrum, at least as large as or even greater than that of the already existing compounds, and not having the drawbacks of the prior art, in particular having specific physicochemical properties to protect cosmetic formulations from microbial contamination while being well tolerated.
• An object of the invention is therefore the use as preservative agent, in particular in a cosmetic, dermatological, pharmaceutical, nutraceutical or oral cosmetic composition, of at least one compound of formula (I):
• R2 represents a hydrogen atom
• R2 represents a methyl or ethyl radical
• R3 represents a C1-C12 linear (saturated) alkyl radical, optionally substituted with a hydroxyl group; or a C 2 -C 12 linear (unsaturated C 1 -C 4) alkenyl radical, optionally substituted by a hydroxyl group.
• preservative is meant a substance that is commonly added to a composition to ensure its preservation vis-à-vis a contaminant.
• the compounds of formula (I) according to the invention are used as antimicrobial and / or antibacterial and / or antifungal agent.
• Another subject of the invention is a method for preserving a cosmetic, dermatological, pharmaceutical, nutraceutical or oral cosmetic composition, characterized in that it consists in incorporating into said composition at least one compound of formula (I).
• the compounds correspond to formula (I), in which:
• the composition does not comprise other preservatives than those of formula (I).
• the composition does not contain parabens.
• R2 represents a hydrogen atom
• R3 represents a linear (saturated) C2-C6 alkyl radical, optionally substituted with a hydroxyl group
• R3 represents a linear (saturated) C2-C6 alkyl radical, optionally substituted with a hydroxyl group
• C2-C6 linear (unsaturated C C) alkenyl radical, or a C2-C12 linear alkenyl radical substituted by a hydroxyl group
• R2 represents a methyl or ethyl radical
• R3 represents a C1-C12 linear (saturated) alkyl radical optionally substituted by a hydroxyl group
• C 2 -C 12 linear (unsaturated C C) alkenyl radical, optionally substituted with a hydroxyl group.
• Cosmetic, dermatological or pharmaceutical compositions comprising at least one compound of formula (I), or of formula ( ⁇ ), also form an object of the present invention.
• the compounds of formula (I) can be prepared easily by those skilled in the art on the basis of his general knowledge.
• the following bibliographic references may notably be cited: J. Asian Natural Products Research, 2006, 8 (8), 683-688; Helv. Chimica Acta, 2006, 89 (3), 483-495; Chem. Pharm. Bull., 2006, 54 (3), 377-379; and Bioorg. Med. Chem. Lett., 2004, 14 (5), 1287-1289.
• the compounds of formula (I), alone or as a mixture, can be employed in a proportion of 0.01 to 5% by weight, especially 0.1 to 2.5% by weight, relative to the weight of the composition, in the cosmetic, dermatological or pharmaceutical compositions.
• the cosmetic, dermatological or pharmaceutical compositions also comprise a medium that is cosmetically, dermatologically or pharmaceutically acceptable, that is to say compatible with keratin materials such as the skin of the face or of the body, the lips, the hair , eyelashes, eyebrows and nails.
• compositions according to the invention can be in any form classically used galenics, especially for topical application, and especially in the form of aqueous solutions, hydroalcoholic, oil-in-water (O / W) or water-in-oil (W / O) or multiple (triple: E) emulsions / H / E or H / E / H), aqueous gels, or dispersions of a fatty phase in an aqueous phase using spherules, these spherules may be polymeric nanoparticles such as nanospheres and nanocapsules, or lipid vesicles of ionic and / or nonionic type (liposomes, niosomes, oleosomes), nanoemulsions, or thin films.
• These compositions are prepared according to the usual methods.
• compositions according to the invention can be more or less fluid and have the appearance of a white or colored cream, an ointment, a milk, a lotion, a serum, a paste, of a foam. They may optionally be applied to the skin in the form of an aerosol. They may also be in solid form, for example in the form of a stick.
• composition according to the invention may especially be in the form:
• a personal hygiene composition such as a shower gel or a shampoo
• a solid composition such as a soap or a cleaning roll
• an aerosol composition also comprising a propellant under pressure
• a styling lotion a cream or a styling gel, a dyeing composition, a restructuring lotion for hair, a permanent composition, a lotion or an anti-fall gel;
• composition for oral use a composition for oral use.
• the physiologically acceptable medium in which the compounds may be employed, as well as its constituents, their quantity, the galenic form of the composition and its method of preparation, may be chosen by those skilled in the art on the basis of their general knowledge in function the type of composition sought.
• the composition may comprise any fatty substance usually used in the intended field of application. Mention may in particular be made of silicone fatty substances such as oils, gums and silicone waxes, as well as non-silicone fatty substances such as oils, pastes and waxes of vegetable, mineral, animal and / or synthetic origin. .
• the oils may optionally be volatile or non-volatile.
• silicone oils there may be mentioned polydimethylsiloxanes (PDMS) volati- with or without a linear or cyclic silicone chain, liquid or pasty at room temperature, in particular cyclopolydimethylsiloxanes such as cyclohexasiloxane; polydimethylsiloxanes comprising alkyl, alkoxy or phenyl groups, during or at the end of the silicone chain, groups having from 2 to 24 carbon atoms; phenyl silicones such as phenyltrimethicones, phenyldimethicones, phenyltrimethylsiloxydiphenylsiloxanes, diphenyl-dimethicones, diphenylmethyldiphenyltrisiloxanes, 2-phenylethyltrimethylsiloxysilicates, and polymethylphenylsiloxanes;
• PDMS polydimethylsiloxanes
• liquid triglycerides of fatty acids containing from 4 to 10 carbon atoms such as the triglycerides of heptanoic or octanoic acids, or else, for example, sunflower, corn or soybean oils.
• triglycerides of heptanoic or octanoic acids or else, for example, sunflower, corn or soybean oils.
• esters and synthetic ethers in particular of formula R 1 COOR 2 and R 1 OR 2 in which R 1 represents the residue of a fatty acid comprising from 8 to 29 carbon atoms, and R 2 represents a hydrocarbon-based chain, branched or unbranched, containing from 3 to 30 carbon atoms, for example purcellin oil, isononyl iso-nonanoate, isopropyl myristate, 2-ethylhexyl palmitate, stearate of octyl-2-dodecyl, octyl-2-dodecyl erucate, isostearyl isostearate; hydroxylated esters such as isostearyl lactate, octylhydroxy stearate, octyldodecyl hydroxystearate, diisostearyl malate, triisocyanet citrate, heptanoates, octanoates, decanoates of fatty
• linear or branched hydrocarbons of mineral or synthetic origin such as paraffin oils, volatile or not, and their derivatives, petroleum jelly, polyenedenes, hydrogenated polyisobutene such as sesam oil;
• fatty alcohols having from 8 to 26 carbon atoms such as cetyl alcohol, stearyl alcohol and their mixture (cetylstearyl alcohol), octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol, oleic alcohol or linoleic alcohol.
• the composition may also comprise an aqueous medium which comprises water, a hydroalcoholic medium containing a C2-C6 alcohol such as ethanol or isopropanol, or an organic medium comprising usual organic solvents such as C2 alcohols. -C6, especially ethanol and isopropanol, glycols such as propylene glycol, ketones.
• the composition according to the invention may also comprise the usual adjuvants in the cosmetic and dermatological fields, such as thickeners, emulsifiers, surfactants, gelling agents, cosmetic active ingredients, perfumes, fillers, dyestuffs, moisturizers, vitamins, polymers.
• the amounts of these various adjuvants are those conventionally used in the fields under consideration, for example from 0.001 to 20% of the total weight of the composition.
• the pH of the compositions according to the invention when they comprise at least one aqueous phase (aqueous solutions, emulsions for example), is preferably between 4 and 9, preferably between 4 and 7, advantageously between 5 and 6.
• Example 1 Determination of the antimicrobial activity of a compound according to the invention
• the antimicrobial efficacy of a compound of formula (I) was evaluated by the Challenge Test method or artificial contamination.
• the challenge-test method consists of an artificial contamination of the sample by microbial strains of collection (bacteria, yeasts and molds) and an evaluation of the number of revivable microorganisms seven days after inoculation.
• Gram bacteria Esscherichia coli and Pseudomonas aeruginosa
• Gram + bacterium Enterococcus faecalis
• yeast Candida albicans
• mold Aspergillus niger
• a suspension in Tryptone salt diluent is prepared for the bacteria and the yeast, respectively, so as to obtain on the spectrophotometer a suspension of optical density of between 35% and 45% of light transmitted at 544 nm;
• the spores are removed by washing the agar with 6 to 7 ml of harvest solution and the suspension is recovered in a sterile flask or tube.
• the level of microorganisms present in the product corresponds after homogenous at a concentration of 10 6 germs per gram of product or inoculation at 1% of an inoculum at 10 8 germs per ml.
• An emulsion comprising (% by weight) is prepared:
• cetylstearyl glucoside cetyl alcohol, stearyl alcohol mixture
• a lotion comprising (% by weight) is prepared:

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• Life Sciences & Earth Sciences (AREA)
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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• General Health & Medical Sciences (AREA)
• Engineering & Computer Science (AREA)
• Animal Behavior & Ethology (AREA)
• Public Health (AREA)
• Veterinary Medicine (AREA)
• Wood Science & Technology (AREA)
• Epidemiology (AREA)
• General Chemical & Material Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Plant Pathology (AREA)
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• Emergency Medicine (AREA)
• Medicinal Chemistry (AREA)
• Pharmacology & Pharmacy (AREA)
• Birds (AREA)
• Dermatology (AREA)
• Pest Control & Pesticides (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Agronomy & Crop Science (AREA)
• Dentistry (AREA)
• Polymers & Plastics (AREA)
• Bioinformatics & Cheminformatics (AREA)
• Food Science & Technology (AREA)
• Materials Engineering (AREA)
• Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
• Microbiology (AREA)
• Mycology (AREA)
• Cosmetics (AREA)
• Medicinal Preparation (AREA)
• Coloring Foods And Improving Nutritive Qualities (AREA)
• Food Preservation Except Freezing, Refrigeration, And Drying (AREA)

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Cited By (54)

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• 2009
  • 2009-10-01 FR FR0956843A patent/FR2950884B1/fr active Active
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• 2010
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