WO2004012697A1 - Utilisation cosmetique de lignanes - Google Patents

Utilisation cosmetique de lignanes Download PDF

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Publication number
WO2004012697A1
WO2004012697A1 PCT/EP2003/007882 EP0307882W WO2004012697A1 WO 2004012697 A1 WO2004012697 A1 WO 2004012697A1 EP 0307882 W EP0307882 W EP 0307882W WO 2004012697 A1 WO2004012697 A1 WO 2004012697A1
Authority
WO
WIPO (PCT)
Prior art keywords
skin
use according
lignan
composition
flax seeds
Prior art date
Application number
PCT/EP2003/007882
Other languages
English (en)
Inventor
Béatrice Renault
Philippe Catroux
Original Assignee
L'oréal
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
Priority claimed from FR0209450A external-priority patent/FR2842732B1/fr
Application filed by L'oréal filed Critical L'oréal
Priority to AU2003250999A priority Critical patent/AU2003250999A1/en
Priority to EP03766235A priority patent/EP1526832A1/fr
Publication of WO2004012697A1 publication Critical patent/WO2004012697A1/fr

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Classifications

    • 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
    • A61Q19/007—Preparations for dry skin
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • 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

Definitions

  • the invention relates to the cosmetic use of at least one lignan of given formula, derived in particular from flax seeds, in a composition suitable for topical application to the skin and containing a cosmetically acceptable medium, for preventing or treating dryness of the skin, rough skin and/or a dull complexion.
  • Human skin consists of two compartments, namely a surface compartment, the epidermis, and a deep compartment, the dermis .
  • Natural human epidermis is composed mainly of three types of cells: keratinocytes, which form the vast majority, melanocytes and Langerhans cells. Each of these cell types contributes, by virtue of its intrinsic functions, towards the essential role played in the body by the skin.
  • keratinocytes undergo a process of continuous oriented maturation which, for the keratinocytes located in the basal layer of the epidermis, results in the formation of corneocytes, which are totally keratinized dead cells consisting of keratinocytes in the final stage of their differentiation.
  • This differentiation process makes it possible to result in the formation of epidermal lipids organized as a bilayer in the stratum corneum, which is thus responsible for the barrier function of the epidermis .
  • NMF Natural Moisturizing Factor
  • the stratum corneum thus plays a fundamental role in the barrier function and moisturization.
  • the importance of ensuring good differentiation of the keratinocytes to maintain the integrity of the skin barrier and thus to prevent dryness of the skin may therefore be appreciated on reading the text hereinabove.
  • an impairment in the differentiation of the keratinocytes will have the effect of accumulating squamae at the surface of the skin, which will modify the interaction between the surface of the skin and the light and will be responsible for a dull, coarse appearance of the skin.
  • the discomfort caused by the phenomenon of dry skin will thus often be accompanied by unaesthetic sensations that it is also sought to combat.
  • the Applicant has now discovered, surprisingly and unexpectedly, that certain lignans, extracted in particular from flax seeds, increase the differentiation of keratinocytes and are thus useful in particular for combating dryness of the skin.
  • Lignans constitute a vast group of natural products characterized by the coupling of two propylbenzene units via a ⁇ - ⁇ ' bond. In other words, they thus have a 2,3-dibenzylbutane structure. These compounds are present especially in a number of cereals, fruit and vegetables and in particular in plants such as flax (especially secoisolariciresinol and isolariciresinol) , chaparral (nordihydroguaiaretic acid) or sesame (sesaminol, sesamolinol and pinoresinol) , in the form of glycosides. These are the main sources of lignans. However, lignans are also found in schisandra, arborvitae, birthwort, orina, nutmeg, magnolia, forsythia and nettle.
  • the lignan that is most commonly known is nordihydroguaiaretic acid, which is an antioxidant used especially in retinol-based anti-ageing compositions, to prevent oxidation of the latter (EP-0 440 398) .
  • Glycosylated lignans derived from sesame have moreover been described as being useful for firming the skin and preventing the formation of wrinkles and slackening of the skin by scavenging OH° radicals (JP-09 095 417) . They are also well known as antioxidants and may be used in moisturizing and protective creams (US-5 993 795) ..
  • glycosylated lignans derived from flax seeds are known to inhibit the production of melanin and thus bleach the skin (JP2001-261 570) , as agents for increasing the activity of catalase and fibroblasts and the synthesis of hyaluronic acid, for preventing or treating UV-induced wrinkles and for reinforcing the elasticity of the skin (JP2001-114 636 and JP2001-122 733) .
  • Lignans for example those derived from flax, have moreover been described as being useful in preventing osteoporosis and certain cancers, but also as anti -viral agents and fungicides. It has thus been proposed to use them to treat the symptoms of the menopause (EP-0 906 761) .
  • certain lignans in aglycone form derived in particular from flax seeds, can be useful in compositions applied topically to the skin in particular for combating dryness of the skin.
  • one subject of the invention is the cosmetic use of at least one lignan corresponding to formula (I) :
  • Ri and R each represent a -CH 2 -OH group or, taken together, form a furanone ring
  • R 3 and R 4 independently represent a hydroxyl group or an
  • R 5 , R 6 and R 7 independently represent a hydroxyl group or an -0-CH 3 group or a hydrogen atom, it being understood that at least one of the groups R 3 and R 4 and at least one of the groups R 5 , R 6 and R 7 represents an -0-CH 3 group,
  • R 8 and R 9 each represent a hydrogen atom or together form a bond, or of a plant extract containing it, in a composition suitable for topical application to the skin and containing a cosmetically acceptable medium, for preventing or treating dryness of the skin, rough skin and/or a dull complexion, and/or for moisturizing or softening the skin.
  • a subject of the invention is also a cosmetic process for treating dry skin, comprising the topical application to the said skin of a composition containing, in a cosmetically acceptable medium, at least one lignan such as defined above.
  • the term "cosmetically acceptable” means an inert medium that is compatible with the skin, its integuments and/or mucous membranes, which does not result in itching, stinging, tautness or redness liable to put the user off using the composition, and which has a pleasant appearance, odour and feel.
  • the lignans corresponding to formula (I) above are advantageously chosen from: secoisolariciresinol, isolariciresinol and matairesinol .
  • Secoisolariciresinol is available, for example, from the company Apin Chemicals in powder form.
  • the plant , extract used according to the invention may be obtained from any plant material cultivated in vivo or in vitro.
  • the expression "in vivo cultivation” means any cultivation of conventional type, i.e. in the soil in the open air or in a greenhouse, or alternatively out of the soil.
  • the expression “in vitro cultivation” means all the techniques known to those skilled in the art for artificially obtaining a plant or part of a plant .
  • the selection pressure imposed by the physicochemical conditions during the growth of plant cells in vitro makes it possible to obtain standardized plant material available throughout the year, in contrast with plants cultivated in vivo.
  • the lignans may especially be extracted from flax seeds, in particular from the species Linum usitatissinum, which thus constitutes the preferred source for supplying lignans of formula (I) or a plant extract according to the invention.
  • the extraction process used for extracting the lignans according to the invention in aglycone form usually comprises the following steps: a) the enzymatic hydrolysis of flax seeds in aqueous medium, or the extraction of flax seeds with an aqueous, alcoholic or aqueous-alcoholic solvent, and b) the acidic hydrolysis of the extract obtained.
  • the acidic hydrolysis step allows the lignans to be isolated in aglycone form.
  • the solvent used in step (a) is generally chosen from water, ethanol and methanol, and mixtures thereof .
  • the above process also comprises a preliminary step of defatting the flax seeds using an organic solvent such as n-hexane.
  • an organic solvent such as n-hexane.
  • the lignans according to the invention may be obtained by acidic hydrolysis of glycosylated lignans obtained according to the process described in US-5 705 618.
  • This process comprises the extraction of a commercially available defatted flax seed meal, using an aqueous-alcoholic mixture, followed by the removal of the residual solids and the removal of the lignan-rich alcoholic solvent, to obtain a concentrate that is subjected to a basic hydrolysis intended to decomplex the lignans.
  • This hydrolysed concentrate is then subjected to a liquid/liquid fractionation, for example using an ethyl acetate/water mixture, or is passed through an ion-exchange resin to concentrate the lignans, which are then separated out by chromatography.
  • the amount of lignan (s) that may be used according to the invention obviously depends on the desired effect and may thus vary within a wide range. To give an order of magnitude, an amount of lignan (s) representing from 0.001% to 10% of the total weight of the composition and preferably from 0.01% to 2% of the total weight of the composition may be used.
  • composition according to the invention may be in any presentation form normally used in cosmetics and dermatology, and it may especially be in the form of an optionally gelled solution, a dispersion of the lotion type, optionally a two-phase lotion, an emulsion obtained by dispersing a fatty phase in an aqueous phase (O/W emulsion) or conversely ( /O emulsion) , or a triple emulsion ( /O/ or 0/ /O emulsion) or a vesicular dispersion of ionic and/or nonionic type.
  • These compositions are prepared according to the usual methods .
  • compositions of 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 mousse. It may optionally be applied in the form of an aerosol. It may also be in solid form, in particular in the form of a stick or a patch. It may be used as a care product and/or as a makeup product for the skin.
  • the composition of the invention may also contain adjuvants that are common in cosmetics, such as hydrophilic or lipophilic gelling agents, hydrophilic or lipophilic active agents, preserving agents, antioxidants, solvents, fragrances, fillers, screening agents, pigments, odour absorbers and dyestuffs.
  • these various adjuvants are those conventionally used in the field under consideration, for example from 0.01% to 20% relative to the total weight of the composition. Depending on their nature, these adjuvants may be introduced into the fatty phase, into the aqueous phase, or into lipid vesicles. In any case, these adjuvants, and also the proportions thereof, will be chosen so as not to harm the desired properties of the lignans according to the invention.
  • the proportion of the fatty phase may range from 5% to 80% by weight and preferably from 5% to 50% by weight relative to the total weight of the composition.
  • the oils, emulsifiers and co-emulsifiers used in the composition in emulsion form are chosen from those conventionally used in the field under consideration.
  • the emulsifier and co-emulsifier are present in the composition in a proportion ranging from 0.3% to 30% by weight and preferably from 0.5% to 20% by weight relative to the total weight of the composition.
  • mineral oils liquid petroleum jelly
  • oils of plant origin oils of plant origin
  • oils of animal origin lanolin
  • synthetic oils perhydrosqualene
  • silicone oils cyclomethicone
  • fluoro oils perfluoropolyethers
  • Fatty alcohols cetyl alcohol
  • fatty acids and waxes may also be used as fatty substances.
  • emulsifiers and co-emulsifiers examples include fatty acid esters of polyethylene glycol such as
  • PEG-20 stearate and fatty acid esters of glycerol such as glyceryl stearate.
  • Hydrophilic gelling agents that may be mentioned in particular include carboxyvinyl polymers (carbomer) , acrylic copolymers such as acrylate/alkylacrylate copolymers, polyacrylamides, polysaccharides, natural gums and clays, and lipophilic gelling agents that may be mentioned include modified clays, for instance bentones, metal salts of fatty acids, hydrophobic silica and polyethylenes .
  • the composition also contains at least one compound chosen from desquamating agents.
  • the term "desquamating agent” means any compound capable of acting: either directly on desquamation by promoting exfoliation, such as ⁇ -hydroxy acids, in particular salicylic acid and its derivatives (including 5-n- octanoylsalicylic acid) ; ⁇ -hydroxy acids, such as glycolic acid, citric acid, lactic acid, tartaric acid, malic acid or mandelic acid; urea; gentisic acid; oligofucoses; cinnamic acid; extract of Saphora japonica; resveratrol; or on the enzymes involved in the desquamation or degradation of corneodesmosomes, glycosidases, stratum corneum chymotryptic enzyme (SCCE) , or even other proteases (trypsin, chymotrypsin-like) .
  • ⁇ -hydroxy acids such as glycolic acid, citric acid, lactic acid, tartaric acid, malic acid or mandelic acid
  • agents for chelating mineral salts include EDTA; N-acyl-N,N' ,N' -ethylenediaminetriacetic acid; amino- sulphonic compounds and in particular (N-2-hydroxy- ethylpiperazine-N-2-ethane) sulphonic acid (HEPES) ; 2-oxothiazolidine-4-carb ⁇ xylic acid (procysteine) ; ⁇ -amino acid derivatives of the type such as glycine (as described in EP-0 852 949, and sodium methyl glycine diacetate sold by BASF under the trade name Trilon M) ; honey; sugar derivatives such as 0-octanoyl- 6-D-maltose and N-acetylglucosamine.
  • glycine as described in EP-0 852 949, and sodium methyl glycine diacetate sold by BASF under the trade name Trilon M
  • honey sugar derivatives such as 0-octan
  • concentration of these optional additional agents in the composition according to the invention may range from 0.0001% to 20% by weight and is preferably between 0.001% and 5% by weight relative to the total weight of the composition.
  • the composition according to the invention may also contain UVA and/or UVB screening agents, in the form of organic or mineral compounds, the latter optionally being coated to make them hydrophobic.
  • the organic screening agents may be chosen especially from: anthranilates, in particular menthyl anthranilate; benzophenones, in particular benzophenone-1, benzophenone-3 , benzophenone-5, benzophenone-6, benzophenone-8 , benzophenone-9, benzophenone-12 and, preferably, benzophenone-2 (oxybenzone) or benzophenone-4 (Uvinul MS40 available from BASF) ; benzylidenecamphors , in particular 3-benzylidenecamphor, benzylidenecamphorsulphonic acid, camphor benzalkonium methosulphate, polyacrylamido- methylbenzylidenecamphor, terephthalylidenedicamphor- sulphonic acid and, preferably, 4-methylbenzylidenecamphor (Eu
  • the mineral screening agents preferably consist of zinc oxide and/or titanium dioxide, preferably of nanometric size, optionally coated with alumina and/or stearic acid.
  • the study consists in evaluating the effect of secoisolariciresinol (Apin Chemical) on keratinocyte differentiation, by measuring the transglutaminase (TGk) activity of cultured human epidermal keratinocytes.
  • TGk is a marker of terminal differentiation of the keratinocyte and of the formation of the cornified envelope (corneocyte) .
  • Human epidermal keratinocytes used at the 3rd passage are inoculated into 96-well plates at a density of 10 000 cells per well and cultured in complete SFM medium (Gibco 170005034, EGF and pituitary extract). After preincubation for 24 hours, the cells are placed in contact with the product (tested at 30 ⁇ M) for 48 hours . The cells are subsequently washed and then sonicated on ice in pH 8 Tris/EDTA buffer. The membrane-bound enzyme is extracted in the presence of Triton X100. The TGk activity is assayed by measuring the covalent addition of tritiated putrescine at 2 ⁇ Ci/ml final to casein.
  • the casein is precipitated with 20% trichloroacetic acid containing 1 mM of putrescine.
  • the precipitates are collected on Skatron filters and collector.
  • the precipitates are washed in 5% TCA medium containing 0.1 mM of putrescine and ethanol.
  • the dry filters are counted by liquid scintillation.
  • the proteins are assayed on each sample using a Dc Protein Assay kit (BioRad) .
  • the TGk activities are given in ⁇ g of protein.
  • Retinol (10 -6 M) and a calcium-poor medium were used as references of an anti-differentiating effect .
  • UVA-screening agent 1.9 %
  • This composition may be prepared in the following manner: phases A and B are heated separately to 65°C and are then cooled to room temperature (25°C) . Phase B is then introduced into phase A to obtain an O/W emulsion, which is then subjected to high-pressure homogenization (500b, 1 to 3 times) .
  • This fluid is useful, when applied daily to the face and neck, for improving the radiance of the complexion and making the skin soft .
  • phase A is heated with stirring until homogeneous. After cooling, phase A' is added and phase B is then heated with stirring, followed by adding phase A, with continued stirring. After cooling to 50°C, phase C is incorporated into the emulsion. A cream that is effective in restoring the skin barrier and thus keeping the skin moisturized is obtained.

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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)
  • Dermatology (AREA)
  • Mycology (AREA)
  • Microbiology (AREA)
  • Botany (AREA)
  • Biotechnology (AREA)
  • Engineering & Computer Science (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention concerne l'utilisation cosmétique d'au moins un lignane représenté par une formule donnée ou d'un extrait végétal le contenant (tel qu'un extrait de graines de lin), dans une composition qui convient pour une application topique sur la peau et contenant un milieu répondant aux normes cosmétiques, cette composition étant destinée à prévenir ou à traiter une sécheresse de la peau, une rugosité cutanée et/ou un teint terne et/ou à hydrater ou adoucir la peau. Cette invention concerne aussi un processus cosmétique de traitement de la sécheresse cutanée qui consiste en une application topique sur la peau d'une composition contenant au moins un lignane ou un extrait végétal le contenant, dans un milieu répondant aux normes cosmétiques.
PCT/EP2003/007882 2002-07-25 2003-07-18 Utilisation cosmetique de lignanes WO2004012697A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU2003250999A AU2003250999A1 (en) 2002-07-25 2003-07-18 Cosmetic use of lignans
EP03766235A EP1526832A1 (fr) 2002-07-25 2003-07-18 Utilisation cosmetique de lignanes

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR02/09450 2002-07-25
FR0209450A FR2842732B1 (fr) 2002-07-25 2002-07-25 Utilisation cosmetique de lignanes
US39944602P 2002-07-31 2002-07-31
US60/399,446 2002-07-31

Publications (1)

Publication Number Publication Date
WO2004012697A1 true WO2004012697A1 (fr) 2004-02-12

Family

ID=31497205

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2003/007882 WO2004012697A1 (fr) 2002-07-25 2003-07-18 Utilisation cosmetique de lignanes

Country Status (3)

Country Link
EP (1) EP1526832A1 (fr)
AU (1) AU2003250999A1 (fr)
WO (1) WO2004012697A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004105715A1 (fr) * 2003-05-30 2004-12-09 Isomers Laboratories Inc. Cosmetique comportant comme support un extrait de graine de lin
US7048960B2 (en) 2002-03-22 2006-05-23 Glenn Roy Pizzey High lignan flaxseed product and product by process
WO2007096092A1 (fr) * 2006-02-22 2007-08-30 Beiersdorf Ag Hydroxymatairésinol utilisé contre la sécheresse cutanée
US7595078B2 (en) 2005-03-15 2009-09-29 Glanbia Nutritionals Ireland Limited Methods of increasing flaxseed hull recovery and resultant flax products
EP2762128A1 (fr) * 2011-09-30 2014-08-06 Shiseido Company, Ltd. Produit cosmétique sous forme d'émulsion de type huile-dans-l'eau

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR967164A (fr) * 1948-05-03 1950-10-27 Produit hygiénique pour l'entretien des mains et des pieds
JPH10279464A (ja) * 1997-04-01 1998-10-20 Nisshin Oil Mills Ltd:The 皮膚外用剤
EP0906761A2 (fr) * 1997-10-02 1999-04-07 Archer-Daniels-Midland Company Procédé de préparation et d'utilisation de produits phytochimiques
JPH11255639A (ja) * 1998-03-13 1999-09-21 Kansai Kouso Kk チロシナーゼ活性阻害剤及び化粧料
US5993795A (en) * 1995-11-09 1999-11-30 Takemoto Yushi Kabushiki Kaisha Protein composition derived from sesame seed and use thereof
JP2001122733A (ja) * 1999-10-26 2001-05-08 Noevir Co Ltd カタラーゼ産生促進剤、及びこれを含有する皮膚外用剤
US20010014343A1 (en) * 1999-02-11 2001-08-16 Marie Harbeck Skin care composition
DE10218476A1 (de) * 2002-04-25 2003-11-06 Beiersdorf Ag Zubereitungen mit Lignanen

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10223486A1 (de) * 2002-05-27 2003-12-11 Beiersdorf Ag Kosmetische und/oder dermatologische Zubereitung mit 2,3-Dibenzylbutyrolactonen

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR967164A (fr) * 1948-05-03 1950-10-27 Produit hygiénique pour l'entretien des mains et des pieds
US5993795A (en) * 1995-11-09 1999-11-30 Takemoto Yushi Kabushiki Kaisha Protein composition derived from sesame seed and use thereof
JPH10279464A (ja) * 1997-04-01 1998-10-20 Nisshin Oil Mills Ltd:The 皮膚外用剤
EP0906761A2 (fr) * 1997-10-02 1999-04-07 Archer-Daniels-Midland Company Procédé de préparation et d'utilisation de produits phytochimiques
JPH11255639A (ja) * 1998-03-13 1999-09-21 Kansai Kouso Kk チロシナーゼ活性阻害剤及び化粧料
US20010014343A1 (en) * 1999-02-11 2001-08-16 Marie Harbeck Skin care composition
JP2001122733A (ja) * 1999-10-26 2001-05-08 Noevir Co Ltd カタラーゼ産生促進剤、及びこれを含有する皮膚外用剤
DE10218476A1 (de) * 2002-04-25 2003-11-06 Beiersdorf Ag Zubereitungen mit Lignanen

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 1999, no. 01 29 January 1999 (1999-01-29) *
PATENT ABSTRACTS OF JAPAN vol. 1999, no. 14 22 December 1999 (1999-12-22) *
PATENT ABSTRACTS OF JAPAN vol. 2000, no. 22 9 March 2001 (2001-03-09) *
QIU S-X ET AL: "ISOLATION AND CHARACTERIZATION OF FLAXSEED (LINUM USITATISSIMUM) CONSTITUENTS", PHARMACEUTICAL BIOLOGY, SWETS AND ZEITLINGER, LISSE,, NL, vol. 37, no. 1, 1999, pages 1 - 7, XP008015490, ISSN: 1388-0209 *
See also references of EP1526832A1 *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7048960B2 (en) 2002-03-22 2006-05-23 Glenn Roy Pizzey High lignan flaxseed product and product by process
WO2004105715A1 (fr) * 2003-05-30 2004-12-09 Isomers Laboratories Inc. Cosmetique comportant comme support un extrait de graine de lin
US7595078B2 (en) 2005-03-15 2009-09-29 Glanbia Nutritionals Ireland Limited Methods of increasing flaxseed hull recovery and resultant flax products
WO2007096092A1 (fr) * 2006-02-22 2007-08-30 Beiersdorf Ag Hydroxymatairésinol utilisé contre la sécheresse cutanée
EP2762128A1 (fr) * 2011-09-30 2014-08-06 Shiseido Company, Ltd. Produit cosmétique sous forme d'émulsion de type huile-dans-l'eau
EP2762128A4 (fr) * 2011-09-30 2015-04-29 Shiseido Co Ltd Produit cosmétique sous forme d'émulsion de type huile-dans-l'eau
US9956148B2 (en) 2011-09-30 2018-05-01 Shiseido Company, Ltd. Oil-in-water-type emulsion cosmetic

Also Published As

Publication number Publication date
AU2003250999A1 (en) 2004-02-23
EP1526832A1 (fr) 2005-05-04

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