WO2012080153A1 - Utilisation de dérivés diméthoxy-hydroxy-phénylalkyle substitués comme agents de conservations, procédé de conservation, composés et composition - Google Patents

Utilisation de dérivés diméthoxy-hydroxy-phénylalkyle substitués comme agents de conservations, procédé de conservation, composés et composition Download PDF

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Publication number
WO2012080153A1
WO2012080153A1 PCT/EP2011/072411 EP2011072411W WO2012080153A1 WO 2012080153 A1 WO2012080153 A1 WO 2012080153A1 EP 2011072411 W EP2011072411 W EP 2011072411W WO 2012080153 A1 WO2012080153 A1 WO 2012080153A1
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WO
WIPO (PCT)
Prior art keywords
composition
hair
formula
compound
carbon atoms
Prior art date
Application number
PCT/EP2011/072411
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English (en)
Inventor
Maria Dalko
Laurent Gilbert
Original Assignee
L'oreal
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
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Publication of WO2012080153A1 publication Critical patent/WO2012080153A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
    • 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
    • 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
    • A61K8/34—Alcohols
    • A61K8/347—Phenols
    • 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
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • 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
    • A61Q19/002—Aftershave preparations
    • 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
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q7/00—Preparations for affecting hair growth
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q9/00—Preparations for removing hair or for aiding hair removal
    • A61Q9/04—Depilatories
    • 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

Definitions

  • the present invention relates to the use of substituted derivatives of dimethoxyhydroxyphenylalkyi type, in particular as a preservative in cosmetic or dermatological compositions; the invention also relates to novel compounds that can be used in cosmetology or in dermatology, and also to the compositions comprising these compounds. It is common practice to introduce chemical preservatives into cosmetic or dermatological compositions, these preservatives being intended to combat the growth of microorganisms in these compositions, which would quickly make them unsuitable for use. It is in particular necessary to protect compositions against microorganisms capable of growing inside the composition, for example during production thereof, and also against those which the user might introduce therein while handling it, in particular when taking up products in jars with the fingers.
  • Chemical preservatives commonly used are in particular parabens, organic acids or formol-releasing compounds.
  • these preservatives have the drawback of causing irritation, in particular on sensitive skin, when they are present at relatively high levels.
  • consumers are increasingly searching for environmentally friendly, in particular non-ecotoxic, preserving agents.
  • the effectiveness of the preservatives conventionally used is variable and their formulation can pose problems, in particular of incompatibility, or even of destabilization, of formulas, in particular of emulsions.
  • One object of the present invention is to propose novel preserving agents which in particular have a broad antimicrobial spectrum, at least as broad, or even broader, than that of the already existing compounds, and which do not have the drawbacks of the prior art, in particular which have specific physicochemical properties making it possible to protect cosmetic formulas against microbial contamination while at the same time being well tolerated.
  • a subject of the invention is therefore the use as a preserving agent, in particular in a cosmetic or dermatological composition, of at least one compound of formula
  • R1 represents a hydrogen atom, a methyl or an ethyl
  • R2 represents a C1 -C12, saturated or unsaturated, linear hydrocarbon-based radical.
  • preserving agent is intended to mean a substance which is commonly added to a composition in order to preserve said composition with respect to a contaminating agent.
  • the compounds of formula (I) according to the invention are used as an antimicrobial and/or antibacterial and/or antifungal agent.
  • Another subject of the invention is a method for preserving a cosmetic or dermatological composition, characterized in that it consists in incorporating into said composition at least one compound of formula (I).
  • - X O or -OH
  • R1 represents a hydrogen atom, a methyl or an ethyl
  • R2 represents a C1 -C12, saturated or unsaturated, linear hydrocarbon-based radical.
  • the compounds of formula (I) are such that:
  • - R1 is H and/or
  • R2 represents a C1 -C12, especially C1 -C6, (alkyl) saturated, linear hydrocarbon- based radical, preferably methyl or ethyl.
  • composition does not comprise any preserving agents other than those of formula (I).
  • composition preferably does not contain parabens.
  • Certain compounds of formula (I) are novel and also form a subject of the present invention; they are the compounds of formula ( ⁇ ) hereinafter:
  • - X 0 or -OH
  • R1 represents a hydrogen atom, a methyl or an ethyl
  • R'2 represents a C2-C12, saturated or unsaturated, linear hydrocarbon-based radical.
  • the compounds of formula ( ⁇ ) are such that:
  • - R1 is H and/or
  • R'2 represents a C2-C12, especially C2-C6, (alkyl) saturated, linear hydrocarbon- based radical, preferably ethyl.
  • compositions comprising at least one compound of formula ( ⁇ ) also form a subject of the present invention.
  • the compounds of formula (I) can be readily prepared by those skilled in the art on the basis of their general knowledge. They can thus be prepared from syringaldehyde, in the following manner:
  • the compounds of formula (I), alone or as a mixture, may be used in a proportion of from 0.01 % to 10% by weight, in particular 0.1 % to 5% by weight, or even 0.5% to 2.5% by weight, relative to the weight of the composition, in particular cosmetic or dermatological composition.
  • the cosmetic or dermatological compositions comprise, moreover, a physiologically acceptable, in particular cosmetically or dermatologically acceptable medium, i.e. a medium which is compatible with keratin materials such as facial or body skin, the lips, the hair, the eyelashes, the eyebrows and the nails.
  • a physiologically acceptable, in particular cosmetically or dermatologically acceptable medium i.e. a medium which is compatible with keratin materials such as facial or body skin, the lips, the hair, the eyelashes, the eyebrows and the nails.
  • compositions according to the invention may be in any galenic form conventionally used, in particular for topical application, and in particular in the form of aqueous or aqueous/alcoholic solutions, of oil-in-water (O/W), water-in-oil (W/O) or multiple (triple: W/O/W or O/W/O) emulsions, of aqueous gels or of dispersions of a fatty phase in an aqueous phase using spherules, it being possible for these spherules to be polymeric nanoparticles, such as nanospheres and nanocapsules, or lipid vesicles of ionic and/or nonionic type (liposomes, niosomes or oleosomes), of nanoemulsions, or of thin films.
  • These compositions are prepared according to the usual methods.
  • compositions according to the invention may be more or less fluid and may have the appearance of a white or coloured cream, an ointment, a milk, a lotion, a serum, a paste or a foam. They can optionally be applied to the skin in the form of an aerosol. They can also be in solid form, for example in the form of a stick.
  • composition according to the invention may in particular be in the form of:
  • a body hygiene composition such as a shower gel or a shampoo
  • a pharmaceutical composition
  • a solid composition such as a soap or a cleansing bar
  • an aerosol composition also comprising a pressurized propellent
  • a hair-setting lotion a hair-styling cream or gel, a dyeing composition, a hair- restructuring lotion, a permanent-wave composition, a lotion or a gel for combating hair loss;
  • composition for oro-dental use is provided.
  • the physiologically acceptable medium in which the compounds can be used, and also its constituents, their amount, the galenical form of the composition and the method for preparing said composition may be chosen by those skilled in the art on the basis of their general knowledge as a function of the type of composition desired.
  • the composition may comprise any fatty substance normally used in the field of application envisaged. Mention may in particular be made of silicone fatty substances such as silicone oils, gums and waxes and also nonsilicone fatty substances such as oils, pastes and waxes of plant, mineral, animal and/or synthetic origin.
  • the oils may be volatile or non-volatile.
  • silicone oils mention may be made of volatile or non-volatile polydimethylsiloxanes (PDMSs) with a linear or cyclic silicone chain, which are liquid or pasty at room temperature, in particular cyclopolydimethylsiloxanes such as cyclohexasiloxane; polydimethylsiloxanes comprising alkyl, alkoxy or phenyl groups, which are pendent or at the end of a silicone chain, these groups containing from 2 to 24 carbon atoms; phenylsilicones, for instance phenyl trimethicones, phenyl dimethicones, phenyltrimethylsiloxydiphenylsiloxanes, diphenyl dimethicones, diphenylmethyldiphenyltrisiloxanes or 2-phenylethyl trimethylsiloxy silicates, and polymethylphenylsiloxanes.
  • PDMSs volatile or non-volatile polydimethylsi
  • liquid triglycerides of fatty acids containing from 4 to 10 carbon atoms for instance heptanoic or octanoic acid triglycerides, or alternatively, for example, sunflower oil, maize oil, soybean oil, marrow oil, grapeseed oil, sesame seed oil, hazelnut oil, apricot oil, macadamia oil, arara oil, sunflower oil, castor oil, avocado oil, caprylic/capric acid triglycerides, jojoba oil and shea butter oil.
  • R 1 COOR 2 and R 1 OR 2 in which R 1 represents the residue of a fatty acid containing from 8 to 29 carbon atoms and R 2 represents a branched or unbranched hydrocarbon-based chain containing from 3 to 30 carbon atoms, for instance purcellin oil, isononyl isononanoate, isopropyl myristate, 2-ethylhexyl palmitate, 2-octyldodecyl stearate, 2-octyldodecyl erucate or isostearyl isostearate; hydroxylated esters, for instance isostearyl lactate, octyl hydroxystearate, octyldodecyl hydroxystearate, diisostearyl malate, triisocetyl citrate, fatty alcohol heptanoates, octanoates and decanoates; polyol esters, in particular of formulae R 1 COOR 2 and R 1
  • hydrocarbons of mineral or synthetic origin such as volatile or non-volatile liquid paraffins, and derivatives thereof, petroleum jelly, polydecenes, and hydrogenated polyisobutene such as Parleam oil;
  • - fatty alcohols containing from 8 to 26 carbon atoms for instance cetyl alcohol, stearyl alcohol and a mixture thereof (cetylstearyl alcohol), octyldodecanol, 2- butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol, oleyl alcohol or linoleyl alcohol.
  • the composition may also comprise an aqueous medium that comprises water, an aqueous-alcoholic medium containing a C2-C6 alcohol such as ethanol or isopropanol, or an organic medium comprising standard organic solvents such as C2-C6 alcohols, in particular ethanol and isopropanol, glycols such as propylene glycol, and ketones.
  • a C2-C6 alcohol such as ethanol or isopropanol
  • an organic medium comprising standard organic solvents such as C2-C6 alcohols, in particular ethanol and isopropanol, glycols such as propylene glycol, and ketones.
  • composition according to the invention may also comprise the adjuvants that are customary in the cosmetic and dermatological fields, such as thickeners, emulsifiers, surfactants, gelling agents, active cosmetic agents, fragrances, fillers, colorants, moisturizers, vitamins and polymers.
  • adjuvants that are customary in the cosmetic and dermatological fields, such as thickeners, emulsifiers, surfactants, gelling agents, active cosmetic agents, fragrances, fillers, colorants, moisturizers, vitamins and 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.
  • These adjuvants and the concentrations thereof must be such that they are not detrimental to the advantageous properties of the compounds according to the invention.
  • the pH of the compositions according to the invention when they comprise at least one aqueous phase (for example aqueous solutions, emulsions), 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 Compound tested:
  • the method of determining the antimicrobial activity of the compounds according to the invention involves measuring the minimum inhibitory concentration (MIC) with respect to two gram-negative bacteria (E. coli and P. aeruginosa) and one gram-positive bacterium (S. aureus).
  • MIC minimum inhibitory concentration
  • the bacterial strains used at the outset in the form of calibrated lyophilized discs are rehydrated following the instructions of the supplier (Fisher Scientific S.A.)
  • the strains are inoculated into Trypto-casein-soy medium.
  • the compound to be tested dissolved in water, is placed in contact, in a liquid medium, with the strains in the growth phase.
  • Alamar Blue is added as a metabolic indicator of the viability of various cells and of bacteria.
  • the reduction of the indicator is proportional to the metabolic activity of the bacteria.
  • the metabolic activity of the bacteria is evaluated via an absorbence or a fluorescence reading. In fluorescence, the readings are taken at 544 nm (excitation) and at 590 nm (emission).
  • the minimum inhibitory concentration (MIC) was then determined as being the lowest concentration of the compound tested for which a > 90% inhibition of growth of the bacterium or of the yeast was observed. The following results are obtained: E.coli MIC: 6 mg/ml

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Chemistry (AREA)
  • Dermatology (AREA)
  • Chemical & Material Sciences (AREA)
  • Zoology (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Environmental Sciences (AREA)
  • Emergency Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Pest Control & Pesticides (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne l'utilisation comme agent de conservation, en particulier dans une composition cosmétique ou dermatologique, d'au moins un composé de formule (I) dans laquelle : X représente =O ou -OH ; R1 représente un atome d'hydrogène, un groupe méthyle ou éthyle ; R2 représente un radical à base d'hydrocarbure à structure linéaire en C1 -C12 saturé ou insaturé. L'invention concerne également certains nouveaux composés et les compositions cosmétiques ou dermatologiques les comprenant.
PCT/EP2011/072411 2010-12-13 2011-12-12 Utilisation de dérivés diméthoxy-hydroxy-phénylalkyle substitués comme agents de conservations, procédé de conservation, composés et composition WO2012080153A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR1060402A FR2968657B1 (fr) 2010-12-13 2010-12-13 Utilisation comme conservateur de derives dimethoxy-hydroxyphenyl-alkyl substitues, procede de conservation, compose et composition
FR1060402 2010-12-13
US201061424854P 2010-12-20 2010-12-20
US61/424,854 2010-12-20

Publications (1)

Publication Number Publication Date
WO2012080153A1 true WO2012080153A1 (fr) 2012-06-21

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Country Status (2)

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FR (1) FR2968657B1 (fr)
WO (1) WO2012080153A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013167220A1 (fr) 2012-05-08 2013-11-14 Merck Patent Gmbh Utilisation de dérivés de cyclohexanol-éther à propriétés antimicrobiennes
DE102012023045A1 (de) 2012-11-26 2014-05-28 Airbus Operations Gmbh Flugbegleitersitzanordnung
US9855203B2 (en) 2013-06-27 2018-01-02 The Procter & Gamble Company Preserving personal care compositions

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000047045A1 (fr) * 1999-02-13 2000-08-17 Zylepsis Limited Composes et compositions de conservation
EP1604643A1 (fr) * 2004-06-03 2005-12-14 Cognis France, S.A.S. Utilisation cosmétique de dérivés de l'acide 3-phényl proprionique
WO2008071027A1 (fr) * 2006-12-15 2008-06-19 Givaudan Sa Compositions
WO2009081587A1 (fr) * 2007-12-25 2009-07-02 Kao Corporation Préparation externe pour la peau

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000047045A1 (fr) * 1999-02-13 2000-08-17 Zylepsis Limited Composes et compositions de conservation
EP1604643A1 (fr) * 2004-06-03 2005-12-14 Cognis France, S.A.S. Utilisation cosmétique de dérivés de l'acide 3-phényl proprionique
WO2008071027A1 (fr) * 2006-12-15 2008-06-19 Givaudan Sa Compositions
WO2009081587A1 (fr) * 2007-12-25 2009-07-02 Kao Corporation Préparation externe pour la peau

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
BAKER C.N.; BANERJEE S.N.; TENOVER F.C.: "Evaluation of Alamar colorimetric MIC Method for antimicrobial susceptibility testing of gram-negative bacteria", J. CLIN. MICROBIOL., vol. 32, 1994, pages 1261 - 1267
BAKER C.N.; TENOVER F.C.: "Evaluation of Alamar colorimetric broth microdilution susceptibility testing method for staphylococci and enterococci", J. CLIN. MICROBIOL., vol. 34, 1996, pages 2654 - 2659
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; JOLAD, SHIVANAND D. ET AL: "Commercially processed dry ginger (Zingiber officinale): Composition and effects on LPS-stimulated PGE2 production", XP002654811, retrieved from STN Database accession no. 2005:593011 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; PUEBLA, P. ET AL: "Phenylbutanoid derivatives from Croton schiedeanus", XP002654810, retrieved from STN Database accession no. 2005:511096 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; VAN SMEERDIJK, DIRK G. ET AL: "Characterization of subfossil Sphagnum leaves, rootlets of Ericaceae and their peat by pyrolysis-high-resolution gas chromatography-mass spectrometry", XP002654809, retrieved from STN Database accession no. 1988:440572 *
JOLAD, SHIVANAND D. ET AL: "Commercially processed dry ginger (Zingiber officinale): Composition and effects on LPS-stimulated PGE2 production", PHYTOCHEMISTRY (ELSEVIER) , 66(13), 1614-1635 CODEN: PYTCAS; ISSN: 0031-9422, 2005 *
PUEBLA, P. ET AL: "Phenylbutanoid derivatives from Croton schiedeanus", BIOCHEMICAL SYSTEMATICS AND ECOLOGY , 33(8), 849-854 CODEN: BSECBU; ISSN: 0305-1978, 2005 *
VAN SMEERDIJK, DIRK G. ET AL: "Characterization of subfossil Sphagnum leaves, rootlets of Ericaceae and their peat by pyrolysis-high-resolution gas chromatography-mass spectrometry", JOURNAL OF ANALYTICAL AND APPLIED PYROLYSIS , 11, 377-402 CODEN: JAAPDD; ISSN: 0165-2370, 1987 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013167220A1 (fr) 2012-05-08 2013-11-14 Merck Patent Gmbh Utilisation de dérivés de cyclohexanol-éther à propriétés antimicrobiennes
DE102012023045A1 (de) 2012-11-26 2014-05-28 Airbus Operations Gmbh Flugbegleitersitzanordnung
US9855203B2 (en) 2013-06-27 2018-01-02 The Procter & Gamble Company Preserving personal care compositions

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FR2968657A1 (fr) 2012-06-15
FR2968657B1 (fr) 2013-03-15

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