WO1997047289A1 - Stabilized hinokitiol and compositions containing same - Google Patents

Stabilized hinokitiol and compositions containing same Download PDF

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Publication number
WO1997047289A1
WO1997047289A1 PCT/US1997/009835 US9709835W WO9747289A1 WO 1997047289 A1 WO1997047289 A1 WO 1997047289A1 US 9709835 W US9709835 W US 9709835W WO 9747289 A1 WO9747289 A1 WO 9747289A1
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WO
WIPO (PCT)
Prior art keywords
composition
hinokitiol
microcapsules
cosmetic
preservative
Prior art date
Application number
PCT/US1997/009835
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English (en)
French (fr)
Inventor
Althea Knight
Julius Zecchino
Steven Schnittger
Original Assignee
E-L Management Corporation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by E-L Management Corporation filed Critical E-L Management Corporation
Priority to EP97929825A priority Critical patent/EP0952852A1/en
Priority to AU33794/97A priority patent/AU3379497A/en
Priority to JP10501709A priority patent/JP2000512294A/ja
Publication of WO1997047289A1 publication Critical patent/WO1997047289A1/en

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/005—Antimicrobial preparations
    • 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
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/11—Encapsulated compositions
    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/29—Titanium; Compounds thereof
    • 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
    • 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
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • A61K8/65—Collagen; Gelatin; Keratin; Derivatives or degradation products thereof
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/735—Mucopolysaccharides, e.g. hyaluronic acid; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • 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
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns
    • 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
    • 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
    • A61K2800/74—Biological properties of particular ingredients
    • A61K2800/75—Anti-irritant
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1629—Organic macromolecular compounds
    • A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1629—Organic macromolecular compounds
    • A61K9/1658—Proteins, e.g. albumin, gelatin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5005—Wall or coating material
    • A61K9/5021—Organic macromolecular compounds
    • A61K9/5036—Polysaccharides, e.g. gums, alginate; Cyclodextrin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5005—Wall or coating material
    • A61K9/5021—Organic macromolecular compounds
    • A61K9/5052—Proteins, e.g. albumin

Definitions

  • the present invention relates to preservatives useful m pharmaceutical and cosmetic compositions.
  • the invention relates to a stabilized, anti-irritant preservative, hinokitiol.
  • Hinokitiol is a wood extract obtainable from pine, cedar, etc. Methods for its production are described, for example, in JP 0586396 and JP 05105898. This material is known to have potent antimicrobial effects, and,as such, has been previously used for a variety of purposes.
  • hinokitiol has been used in food preservation and prevention of discoloration (JP 78035145; JP 6277019; JP 6153788; JP 6090661; JP 5344861; JP 59085279); in combination with zinc, or with ethyl alcohol and propylene glycol for antisepsis and/or the treatment of infection(WO 9317559; JP 3133334); in detergent compositions (WO 9205240); and as a wood preservative(JP 1038203).
  • Hinokitiol has also been used in various types of cosmetic and pharmaceutical compositions.
  • DE 4202964 discloses a water-phase hair and body treatment comprising hinokitiol and heliotropin or a cosmetic alcohol, wherein the heliotropin and alcohol is said to synergistically enhance the antimicrobial activity of hinokitiol.
  • JP 2243607 describes the use in cosinetic compositions of a preservative containing hinokitiol in combination with phenoxyethanol and phthalate ester.
  • hinokitiol also possesses a heretofore unappreciated anti-irritancy effect.
  • hinokitiol has been shown to be an effective preservative under a wide variety of conditions, it is not itself completely stable under all conditions in which its use might be desired. For example, its use in compositions in polyethylene plastic containers can result in a discolored and/or unpleasant-smelling product. It also may not be stable after direct contact with light or air. These are limitations which under ordinary circumstances would not be acceptable, and which would recommend against its use in a cosmetic composition, where appearance and fragrance can be critical.
  • hinokitiol can itself be stabilized in the desired composition, and yet retain its useful biological properties, such as antimicrobial and anti-irritant activity.
  • the present invention provides the means by which hinokitiol can be effectively used in cosmetic compositions.
  • the present invention provides cosmetic and pharmaceutical compositions containing hinokitiol-containing microcapsules, the microcapsules comprising a matrix containing collagen and a glycosaminoglycan.
  • the microcapsule provides adequate stability to the hinokitiol, preventing it from discoloration and unpleasant odor in the composition containing same, while nonetheless permitting the hinokitiol to exert its preservative and anti-irritant effect on the composition containing it.
  • the invention also provides a method for preserving a cosmetic or pharmaceutical composition, comprising adding to the composition a preservative-effective amount of the hinokitiol containing microcapsules, as well as a method for reducing irritation on the skin by application of a cosmetic composition containing an effective amount of hmokitiol-contaming microspheres.
  • microcapsules used m the present invention are prepared according to the methodology disclosed in US Patent No. 5,395,620, the contents of which are incorporated herein by reference. Briefly, the microcapsules are prepared by combining a solution containing atelocollagen and a solution containing a polyholoside, preferably a glycosaminoglycan, m the presence of the hinokitiol and a crosslmkmg agent.
  • Atelocollagen is a type of collagen from which the telopeptides which crosslink typical collagen have been removed.
  • glycosammoglyeans are well known in the art, and for the present purposes may be selected, for example, from chondroitm 4-sulfate, chondroitm 6-sulfate, dermatan sulfate, heparan sulfate, keratan sulfate, heparm and derivatives thereof; preferably the cosmetically or pharmaceutically acceptable salts, such as calcium or sodium salts, are employed.
  • the amount of glycosaminoglycan present in the microcapsules will typically be about 15-50% by weight of the atelocollagen used in the formulation.
  • the amount of atelocollagen m the starting solution is approximately 0.5-2% by weight, and the glycosaminoglycan solution contains about 0.5-4%, preferably 0.5-2% by weight of glycosammoglycans.
  • both the atelocollagen and the glycosammoglycans are of marine origin.
  • Cross-linking reagents useful in preparing the microcapsules include, but are not limited to, an acid dichloride, an acid anhydride, or a dibasic or polybasic carboxylic acid. With respect to the hinokitiol, this material is present in an amount of between 0.01-10% by weight, preferably 0.5-4% by weight, of the starting solution.
  • the microcapsules containing hinokitiol provide an unexpectedly high level of preservative efficacy, while itself remaining stable in the compositions m which it is included.
  • the retention of antimicrobial activity, at the levels seen herein, is particularly surprising m view of the fact that the hinokitiol itself is not expected to be m direct contact with the medium is intended to preserve.
  • the microcapsules m which the hinokitiol is contained are essentially impermeable, i.e., there is apparently substantially no leakage of the hinokitiol into the medium in which the microcapsules are contained, as evidenced by the absence of unpleasant odor or color m the products containing them. Since the hinokitiol is used in quantities essentially the same as used m its unencapsulated form, the substantially complete retention of antimicrobial activity by the "protected" hinokitiol is quite unexpected.
  • the encapsulated hinokitiol can be used in a wide variety of cosmetic and/or pharmaceutical compositions, as well as a preservative in food compositions.
  • the hinokitiol can be used in virtually any form in which such compositions may be formulated, e.g., solutions, colloidal dispersions, emulsions, suspensions, creams, lotions, gels, foams, mousses and the like.
  • Methods and components for preparing such compositions are well known in the art, and can be found for example, in CTFA International Cosmetics Ingredients Dictionary, The Cosmetic, Toiletry, and Fragrance Association, Washington, DC, 1991.
  • the amount of the hmokitiol-containmg microspheres will vary depending on the nature of the composition and the amount of hinokitiol contained in the microspheres, but a preservative-effective amount of hinokitiol per se will generally be in the range of from about 0.1-1% by weight of the composition as a whole, given the amount of hinokitiol in the microspheres is as stated above. It is well within the skill of the art to determine the desired microsphere concentration in the formulation, given these parameters.
  • compositions of the present invention will also comprise a pharmaceutically or cosmetically acceptable carrier, in an amount appropriate to accomodate the other components of the formulation.
  • pharmaceutically or cosmetically acceptable carrier refers to a vehicle, for either pharmaceutical or cosmetic use, which vehicle delivers the active components to the intended target and which will not cause harm to humans or other recipient organisms.
  • pharmaceutical or “cosmetic” will be understood to encompass both human and animal pharmaceuticals or cosmetics.
  • the carrier may be in any form appropriate to the mode of delivery, for example, solutions, colloidal dispersions, emulsions, suspensions, creams, lotions, gels, foams, mousses and the like.
  • the carrier is a suspension, dispersion or emulsion.
  • the emulsion may be an oil-in-water emulsion, or a water-in-oil emulsion. These emulsions contain one or more oil components, an aqueous component, and a specific emulsifier component chosen depending on the nature of the desired emulsion.
  • the oil component may be any pharmaceutically or cosmetically acceptable material which is substantially insoluble in water. These materials can be found for example in the CTFA International Dictionary of Cosmetic Ingredients as well as the U.S. Pharmacopoeia or equivalent sources.
  • Suitable oil components include, but are not limited to, natural oils, such as coconut oil; hydrocarbons, such as mineral oil and hydrogenated polyisobutene; fatty alcohols, such as octyldodecanol; esters, such as C12-15 alkyl benzoate; diesters, such as propylene glycol dipelargonate; triesters, such as glyceryl trioctanoate; sterol derivatives, such as lanolin; animal waxes, such as beeswax; plant waxes, such as carnauba; mineral waxes, such as ozokerite; petroleum waxes, such as paraffin wax; synthetic waxes, such as polyethylene; and mixtures thereof.
  • Suitable oil components may also be silicones including, but not limited to, volatile silicones such as cyclomethicone; polymeric silicones such as dimethicone; alkylated derivatives of polymeric silicones, such as cetyl dimethicone and lauryl trimethicone; hydroxylated derivatives of polymeric silicones, such as dir ⁇ ethiconol; and mixtures thereof.
  • volatile silicones such as cyclomethicone
  • polymeric silicones such as dimethicone
  • alkylated derivatives of polymeric silicones such as cetyl dimethicone and lauryl trimethicone
  • hydroxylated derivatives of polymeric silicones such as dir ⁇ ethiconol
  • mixtures thereof such as dir ⁇ ethiconol
  • the aqueous component refers to any pharmaceutically or cosmetically acceptable material consisting essentially or predominantly of water.
  • the oil-in- water emulsifier will be an emulsifier having a hydrophilic- lipoph ' ilic balance (HLB) of at least 6, or a mixture of such emulsifiers with one or more water-in-oil emulsifiers (i.e. , emulsifiers having an HLB of from about 2 to about 6) , in which case the type and amount of each emulsifier present in the mixture is selected such that the effective HLB of the resultant oil-in-water emulsifier component is at least about 6.
  • HLB hydrophilic- lipoph ' ilic balance
  • Suitable oil-in-water emulsifiers include, but are not limited to, sorbitol derivatives, such as sorbitan monolaurate and polysorbate 20; ethoxylated alcohols such as laureth-23, ethoxylated fatty acids such as PEG-1000 stearate; amidoamine derivatives such as stearamidoethyl diethylamine; sulfate esters such as sodium lauryl sulfate; phosphate esters such as DEA cetyl phosphate; fatty acid amine salts such as TEA stearate; and mixtures thereof.
  • sorbitol derivatives such as sorbitan monolaurate and polysorbate 20
  • ethoxylated alcohols such as laureth-23, ethoxylated fatty acids such as PEG-1000 stearate
  • amidoamine derivatives such as stearamidoethyl diethylamine
  • sulfate esters such
  • the emulsion may also be a water-in-oil emulsion.
  • a water-in-oil emulsifier is employed. This refers to any cosmetically acceptable emulsifier having an HLB of no greater than 6, preferably from about 2 to about 4.
  • Suitable water-in-oil emulsifiers include, but are not limited to, sorbitan derivatives such as sorbitan laurate and sorbitan palmitate; alkoxylated alcohols such as laureth-4; hydroxylated derivatives of polymeric silicones, such as dimethicone copolyol; alkylated derivatives of hydroxylated polymeric silicones, such as cetyl dimethicone copolyol; glyceryl esters such as polyglyceryl-4 isostearate; beeswax derivatives such as sodium isostearoyl-2 lactylate; lecithin; and mixtures thereof.
  • sorbitan derivatives such as sorbitan laurate and sorbitan palmitate
  • alkoxylated alcohols such as laureth-4
  • hydroxylated derivatives of polymeric silicones such as dimethicone copolyol
  • alkylated derivatives of hydroxylated polymeric silicones such as cety
  • the active component of the pharmaceutical or cosmetic compositions will depend on the intended purpose of the compositions.
  • active agents which may form part of the composition include, but are not limited to, those that improve or eradicate age spots, keratoses and wrinkles, analgesics, anesthetics, anti-acne agents, antibacterials, antiyeast agents, antifungal agents, antiviral agents, antidandruff agents, antidermatitis agents, antipruritic agents, antiemetics, antimotion sickness agents, anti- inflammatory agents, antihyperkeratolytic agents, anti-dry skin agents, antiperspirants, antipsoriatic agents, antiseborrheic agents, hair conditioners and hair treatment agents, antiaging agents, antiwrinkle agents, antiasthmatic agents and bronchodilators, sunscreen agents, antihistamine agents, skin lightening agents, depigmenting agents, vitamins, corticosteroids, tanning agents, hormones, retinoids, topical cardiovascular agents, clotrimazole, ketocon
  • the composition is a sunscreen-containing composition.
  • sunscreen refers to any material which is capable of protecting human skin from ultraviolet radiation having a wavelength of from about 280 to about 400nm, by effectively absorbing such radiation, and/or reflecting or scattering such radiation away from the surface of human skin.
  • Suitable sunscreens for purposes of this invention include but not limited to, titanium derivatives such as titanium dioxide, especially titanium dioxide having an average particle size of from 10 to 100 nanometers, most especially titanium dioxide having an average particle size of from 10 to 100 nanometers and comprising a hydrophobic coating agent to minimize agglomeration; zinc derivatives such as zinc oxide, especially zinc oxide having an average particle size of from 10 to 100 nanometers; melanin and melanin derivatives; dioxybenzone; 2-ethylhexyl 2-cyano-3,3- diphenylacrylate; 2-ethylhexyl p-methoxycinnamate; 2-ethylhexyl salicyLate; homosalate; menthyl anthranilate; oxybenzone; octyl dimethyl PABA; red petrolatum; ferulic acid ester; and mixtures thereof .
  • titanium derivatives such as titanium dioxide, especially titanium dioxide having an average particle size of from 10 to 100 nanometers, most especially titanium dioxide having
  • compositions may also comprise additional preservatives, fragrances, emollients, antiseptics, antunflammatories, antibacterials, stabilizers, antioxidants, vitamins, pigments, dyes, humectants, and propellants, as well as other classes of materials the presence of which in the compositions may be cosmetically, medicinally, or otherwise desired.
  • additional preservatives fragrances, emollients, antiseptics, antunflammatories, antibacterials, stabilizers, antioxidants, vitamins, pigments, dyes, humectants, and propellants, as well as other classes of materials the presence of which in the compositions may be cosmetically, medicinally, or otherwise desired.
  • Thalaspheres® (30 ⁇ m) containing hinokitiol are provided by Bioetica, Inc., Portland, Maine) .
  • the composition of the Thalaspheres®, in grams per lOOg, is as follows:
  • Xanthan gum 0.5 0.71% atelocollagen 0.441 1, .47% chondroitm 0.165 0. .55%
  • the encapsulated hinokitiol as described in Example 1, is incorporated by art-recognized procedures into a sunscreen- containing dispersion, a moisturizing cream emulsion, and a skin desensitizing lotion emulsion.
  • the components are as follows :
  • the formulations so prepared exhibit no deterioration, no discoloration and no unpleasant odor even after prolonged storage, showing the encapsulated hinokitiol retains its preservative effect while at the same time being stabilized by the encapsulation.
  • Hinokitiol alone is tested for its ability to prevent irritation.
  • Hinokitiol (unencapsulated, 0.5% by weight) is applied to the ventral forearms of panelists. The material is allowed to absorb for twenty minutes and then Balsam of Peru, an irritant, is applied to the test sites. Skin irritation is measured in terms of increase in skin redness. Cola n ⁇ t ⁇ da(10% hydro-alcohol 1:1) is used as a positive control.
  • the degree of redness is measured with the Minolta chromameter and compared with the positive and negative controls.
  • the positive control is the color of skin treated with Balsam of Peru alone and the negative control is the skin treated with cola material challenged as with the hinokitiol.
  • Hinokitiol exhibits a 71% activity, as compared with an average of 67% for cola.
  • the encapsulated hinokitiol is then tested for its retained anti-irritant activity.
  • Encapsulated hinokitiol, prepared as described above, is prepared in 4.2% and 2.8% aqueous solution. These solutions are tested against empty microcapsules, as well as against cola n ⁇ t ⁇ da(10% hydro-alcohol 1:1), using the same protocol as described in the previous example.
  • results show that the activity of the encapsulated hinokitiol at 4.2% is approximately equivalent to that of 10% cola (61% vs 64%, respectively) m reducing the onset of irritation due to Balsam of Peru.
  • the lower concentration of hinokitiol capsules shows 53% activity, while empty microcapsules show 28% activity.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Chemical & Material Sciences (AREA)
  • Dermatology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Inorganic Chemistry (AREA)
  • Emergency Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Cosmetics (AREA)
  • Medicinal Preparation (AREA)
  • Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
PCT/US1997/009835 1996-06-12 1997-06-09 Stabilized hinokitiol and compositions containing same WO1997047289A1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP97929825A EP0952852A1 (en) 1996-06-12 1997-06-09 Stabilized hinokitiol and compositions containing same
AU33794/97A AU3379497A (en) 1996-06-12 1997-06-09 Stabilized hinokitiol and compositions containing same
JP10501709A JP2000512294A (ja) 1996-06-12 1997-06-09 安定化されたヒノキチオールおよびこれを含有する組成物

Applications Claiming Priority (2)

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US08/662,870 US5811114A (en) 1996-06-12 1996-06-12 Stabilized hinokitiol and compositions containing same
US08/662,870 1996-06-12

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JP (1) JP2000512294A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
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EP1214926A1 (en) * 2000-12-12 2002-06-19 Kabushiki Kaisha Kishohin Kagaku Kaiho Kenkyujo Topical composition
EP0989846B1 (en) * 1997-09-30 2004-11-24 E-L Management Corp. Non-irritating cosmetic and pharmaceutical compositions
WO2005018322A1 (en) * 2003-08-22 2005-03-03 Danisco A/S Encapsulated antimicrobial material
EP1441685A4 (en) * 2001-10-05 2007-10-31 Color Access Inc ANTI-IRRITATING TREATMENT OF ROSACEA ACNE
US8337923B2 (en) 2003-08-22 2012-12-25 Dupont Nutrition Biosciences Aps Encapsulated antimicrobial material
WO2017021014A1 (en) * 2015-08-06 2017-02-09 Laboratori Derivati Organici Spa Compositions comprising dermatan sulfate and chondroitin sulfate and use thereof in cosmetological compositions
FR3064179A1 (fr) * 2017-03-24 2018-09-28 Greenpharma Agent conservateur contenant de l'hinokitiol avec au moins un acide et compositions preservees par ledit agent
US10271557B2 (en) 2003-08-22 2019-04-30 Dupont Nutrition Biosciences Aps Composition comprising a bacteriocin and an extract from a plant of the Labiatae family

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JP4087938B2 (ja) * 1998-02-04 2008-05-21 高砂香料工業株式会社 ヒノキチオ−ル類の分岐サイクロデキストリン包接化合物からなる抗菌剤およびそれを含有する組成物
JP3134068B2 (ja) * 1999-02-03 2001-02-13 株式会社トピックス ヒノキチオール含有芳香抗菌剤の製造方法
US6217913B1 (en) * 1999-07-15 2001-04-17 Fatemeh Mohammadi Cosmetic compositions with gorgonian extract
US20040120915A1 (en) * 2002-12-19 2004-06-24 Kaiyuan Yang Multifunctional compositions for surface applications
US7211249B2 (en) * 2003-03-17 2007-05-01 Color Access, Inc. Heat-generating composition for topical application to skin
US20070027152A1 (en) * 2005-07-27 2007-02-01 Clark Kathleen L Topical anti-pruritic compositions and methods of action of same
US20090029856A1 (en) * 2007-07-24 2009-01-29 Marrone Organic Innovations, Inc. Hinokitiol As A Plant Pesticide
US9717818B2 (en) * 2009-05-08 2017-08-01 Medline Industries, Inc. Absorbent articles having antimicrobial properties and methods of manufacturing the same
US9180112B2 (en) * 2010-03-23 2015-11-10 Ermis Labs, LLC Dermal compositions containing gorgonian extract
JP5642002B2 (ja) * 2011-03-28 2014-12-17 株式会社コーセー ベシクル含有組成物、それを含有する化粧料又は皮膚外用剤
JP2024517077A (ja) * 2021-04-07 2024-04-19 ユニリーバー・アイピー・ホールディングス・ベスローテン・ヴェンノーツハップ ヒノキチオールを含む化粧品組成物

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0989846B1 (en) * 1997-09-30 2004-11-24 E-L Management Corp. Non-irritating cosmetic and pharmaceutical compositions
EP1214926A1 (en) * 2000-12-12 2002-06-19 Kabushiki Kaisha Kishohin Kagaku Kaiho Kenkyujo Topical composition
EP1441685A4 (en) * 2001-10-05 2007-10-31 Color Access Inc ANTI-IRRITATING TREATMENT OF ROSACEA ACNE
WO2005018322A1 (en) * 2003-08-22 2005-03-03 Danisco A/S Encapsulated antimicrobial material
US8337923B2 (en) 2003-08-22 2012-12-25 Dupont Nutrition Biosciences Aps Encapsulated antimicrobial material
US10271557B2 (en) 2003-08-22 2019-04-30 Dupont Nutrition Biosciences Aps Composition comprising a bacteriocin and an extract from a plant of the Labiatae family
WO2017021014A1 (en) * 2015-08-06 2017-02-09 Laboratori Derivati Organici Spa Compositions comprising dermatan sulfate and chondroitin sulfate and use thereof in cosmetological compositions
AU2016304201B2 (en) * 2015-08-06 2022-03-31 Opocrin S.P.A. Compositions comprising dermatan sulfate and chondroitin sulfate and use thereof in cosmetological compositions
FR3064179A1 (fr) * 2017-03-24 2018-09-28 Greenpharma Agent conservateur contenant de l'hinokitiol avec au moins un acide et compositions preservees par ledit agent

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EP0952852A4 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1999-11-03
JP2000512294A (ja) 2000-09-19
EP0952852A1 (en) 1999-11-03
CA2257850A1 (en) 1997-12-18
AU3379497A (en) 1998-01-07
US5811114A (en) 1998-09-22
ZA975204B (en) 1997-12-31

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