DE19928495A1 - Use of flavonoids for photostabilizing sorbate-containing compositions - Google Patents
Use of flavonoids for photostabilizing sorbate-containing compositionsInfo
- Publication number
- DE19928495A1 DE19928495A1 DE1999128495 DE19928495A DE19928495A1 DE 19928495 A1 DE19928495 A1 DE 19928495A1 DE 1999128495 DE1999128495 DE 1999128495 DE 19928495 A DE19928495 A DE 19928495A DE 19928495 A1 DE19928495 A1 DE 19928495A1
- Authority
- DE
- Germany
- Prior art keywords
- sorbate
- flavonoid
- composition according
- cosmetic
- sorbic acid
- Prior art date
- Legal status (The legal status 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 status listed.)
- Withdrawn
Links
- WSWCOQWTEOXDQX-MQQKCMAXSA-M (E,E)-sorbate Chemical compound C\C=C\C=C\C([O-])=O WSWCOQWTEOXDQX-MQQKCMAXSA-M 0.000 title claims abstract description 24
- 229940075554 sorbate Drugs 0.000 title claims abstract description 24
- 229930003935 flavonoid Natural products 0.000 title claims abstract description 20
- 150000002215 flavonoids Chemical class 0.000 title claims abstract description 20
- 235000017173 flavonoids Nutrition 0.000 title claims abstract description 20
- 239000000203 mixture Substances 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 4
- 239000002537 cosmetic Substances 0.000 claims description 30
- 235000010199 sorbic acid Nutrition 0.000 claims description 21
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 claims description 20
- 239000004334 sorbic acid Substances 0.000 claims description 20
- 229940075582 sorbic acid Drugs 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 230000006641 stabilisation Effects 0.000 claims description 8
- 238000011105 stabilization Methods 0.000 claims description 8
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- HVQAJTFOCKOKIN-UHFFFAOYSA-N flavonol Natural products O1C2=CC=CC=C2C(=O)C(O)=C1C1=CC=CC=C1 HVQAJTFOCKOKIN-UHFFFAOYSA-N 0.000 claims description 6
- 235000011957 flavonols Nutrition 0.000 claims description 6
- 229930003944 flavone Natural products 0.000 claims description 5
- 235000011949 flavones Nutrition 0.000 claims description 5
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 claims description 5
- XHEFDIBZLJXQHF-UHFFFAOYSA-N fisetin Chemical compound C=1C(O)=CC=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 XHEFDIBZLJXQHF-UHFFFAOYSA-N 0.000 claims description 4
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 claims description 3
- HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 claims description 3
- 150000002213 flavones Chemical class 0.000 claims description 3
- 150000002216 flavonol derivatives Chemical class 0.000 claims description 3
- 239000004302 potassium sorbate Substances 0.000 claims description 3
- 235000010241 potassium sorbate Nutrition 0.000 claims description 3
- 235000005875 quercetin Nutrition 0.000 claims description 3
- 229960001285 quercetin Drugs 0.000 claims description 3
- SCZVLDHREVKTSH-UHFFFAOYSA-N 4',5,7-trihydroxy-3'-methoxyflavone Chemical compound C1=C(O)C(OC)=CC(C=2OC3=CC(O)=CC(O)=C3C(=O)C=2)=C1 SCZVLDHREVKTSH-UHFFFAOYSA-N 0.000 claims description 2
- QAGGICSUEVNSGH-UHFFFAOYSA-N Diosmetin Natural products C1=C(O)C(OC)=CC=C1C1=CC(=O)C2=CC=C(O)C=C2O1 QAGGICSUEVNSGH-UHFFFAOYSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- YXOLAZRVSSWPPT-UHFFFAOYSA-N Morin Chemical compound OC1=CC(O)=CC=C1C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1 YXOLAZRVSSWPPT-UHFFFAOYSA-N 0.000 claims description 2
- IKMDFBPHZNJCSN-UHFFFAOYSA-N Myricetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC(O)=C(O)C(O)=C1 IKMDFBPHZNJCSN-UHFFFAOYSA-N 0.000 claims description 2
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- KZNIFHPLKGYRTM-UHFFFAOYSA-N apigenin Chemical compound C1=CC(O)=CC=C1C1=CC(=O)C2=C(O)C=C(O)C=C2O1 KZNIFHPLKGYRTM-UHFFFAOYSA-N 0.000 claims description 2
- 229940117893 apigenin Drugs 0.000 claims description 2
- MCFVRESNTICQSJ-RJNTXXOISA-L calcium sorbate Chemical compound [Ca+2].C\C=C\C=C\C([O-])=O.C\C=C\C=C\C([O-])=O MCFVRESNTICQSJ-RJNTXXOISA-L 0.000 claims description 2
- 235000010244 calcium sorbate Nutrition 0.000 claims description 2
- 239000004303 calcium sorbate Substances 0.000 claims description 2
- UOSZQIQUCYTISS-UHFFFAOYSA-N chrysoeriol Natural products C1=C(O)C(C)=CC(C=2OC3=CC(O)=CC(O)=C3C(=O)C=2)=C1 UOSZQIQUCYTISS-UHFFFAOYSA-N 0.000 claims description 2
- 235000015428 diosmetin Nutrition 0.000 claims description 2
- MBNGWHIJMBWFHU-UHFFFAOYSA-N diosmetin Chemical compound C1=C(O)C(OC)=CC=C1C1=CC(=O)C2=C(O)C=C(O)C=C2O1 MBNGWHIJMBWFHU-UHFFFAOYSA-N 0.000 claims description 2
- 229960001876 diosmetin Drugs 0.000 claims description 2
- 235000011990 fisetin Nutrition 0.000 claims description 2
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- 235000009498 luteolin Nutrition 0.000 claims description 2
- IQPNAANSBPBGFQ-UHFFFAOYSA-N luteolin Chemical compound C=1C(O)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(O)C(O)=C1 IQPNAANSBPBGFQ-UHFFFAOYSA-N 0.000 claims description 2
- UXOUKMQIEVGVLY-UHFFFAOYSA-N morin Natural products OC1=CC(O)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 UXOUKMQIEVGVLY-UHFFFAOYSA-N 0.000 claims description 2
- 235000007708 morin Nutrition 0.000 claims description 2
- PCOBUQBNVYZTBU-UHFFFAOYSA-N myricetin Natural products OC1=C(O)C(O)=CC(C=2OC3=CC(O)=C(O)C(O)=C3C(=O)C=2)=C1 PCOBUQBNVYZTBU-UHFFFAOYSA-N 0.000 claims description 2
- 235000007743 myricetin Nutrition 0.000 claims description 2
- 229940116852 myricetin Drugs 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 150000002214 flavonoid derivatives Chemical class 0.000 claims 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 239000004283 Sodium sorbate Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 235000019250 sodium sorbate Nutrition 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 239000000047 product Substances 0.000 description 26
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
- 238000002845 discoloration Methods 0.000 description 15
- 235000013305 food Nutrition 0.000 description 13
- 230000000694 effects Effects 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 8
- POJWUDADGALRAB-UHFFFAOYSA-N allantoin Chemical compound NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 description 8
- 239000003963 antioxidant agent Substances 0.000 description 8
- 235000006708 antioxidants Nutrition 0.000 description 8
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- 239000004615 ingredient Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- DOUMFZQKYFQNTF-WUTVXBCWSA-N (R)-rosmarinic acid Chemical compound C([C@H](C(=O)O)OC(=O)\C=C\C=1C=C(O)C(O)=CC=1)C1=CC=C(O)C(O)=C1 DOUMFZQKYFQNTF-WUTVXBCWSA-N 0.000 description 5
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
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- IVTMALDHFAHOGL-UHFFFAOYSA-N eriodictyol 7-O-rutinoside Natural products OC1C(O)C(O)C(C)OC1OCC1C(O)C(O)C(O)C(OC=2C=C3C(C(C(O)=C(O3)C=3C=C(O)C(O)=CC=3)=O)=C(O)C=2)O1 IVTMALDHFAHOGL-UHFFFAOYSA-N 0.000 description 4
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- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
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Classifications
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/351—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom not condensed with another ring
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- 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
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
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- 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
- A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
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- 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
- A61K8/60—Sugars; Derivatives thereof
- A61K8/602—Glycosides, e.g. rutin
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- 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
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- 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
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- 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
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- 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
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Landscapes
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- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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- Birds (AREA)
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- Pharmacology & Pharmacy (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
Abstract
Description
Die Erfindung betrifft sorbatkonservierte Mittel, Verfahren zu ihrer Herstellung sowie ihre Verwendung, insbesondere als farbstabilisierte kosmetische und pharmazeutische Mittel.The invention relates to sorbate-preserved agents, processes for their preparation and their use, in particular as color-stabilized cosmetic and pharmaceutical Medium.
Kosmetische Mittel sind Stoffe oder Zubereitungen aus Stoffen, die dazu bestimmt sind, äußerlich am Menschen oder in Körperhöhlen (z. B. in der Mundhöhle) zur Reinigung, Pflege oder zur Beeinflussung des Aussehens oder des Körpereigenge ruchs oder zur Vermittlung von Geruchseindrücken angewendet zu werden. Pharma zeutische Mittel sind Stoffe oder Zubereitungen aus Stoffen, die vornehmlich dazu bestimmt sind, Krankheiten, Leiden, Körperschäden oder krankhafte Beschwerden zu lindern oder zu beseitigen.Cosmetic products are substances or preparations of substances intended for this purpose are externally on humans or in body cavities (eg in the oral cavity) Cleaning, care or to influence the appearance or the body's property odor or to impart odor impressions. Pharma Ecological agents are substances or preparations of substances primarily intended for this purpose are determined, illnesses, suffering, body damage or pathological complaints too alleviate or eliminate.
Kosmetische Mittel sind beispielsweise Haar- und Körperreinigungsprodukte wie Shampoos, Duschgele oder Waschlotionen, Cremes, Lotionen und Gele zur Haut pflege und zum Schutz gegen Sonnenbestrahlung, Mund- und Zahnpflegeprodukte, dekorative Kosmetik, Mittel zur Selbstbräunung, wasser-, alkohol- oder tensidhaltige Tücher zur Reinigung oder Erfrischung und weitere Produkte im Sinne der oben genannten Definition.Cosmetic agents include, for example, hair and body cleansing products Shampoos, shower gels or washing lotions, creams, lotions and gels for the skin care and protection against sun exposure, oral and dental care products, decorative cosmetics, self-tanning preparations, water-, alcohol- or surfactant-containing Towels for cleaning or refreshment and other products in the sense of the above mentioned definition.
Pharmazeutische Mittel im Sinne dieser Erfindung sind wässrige oder alkoholhaltige Lösungen, Gele oder Emulsionen aus einer Wasser- und einer Lipidphase, die phar mazeutisch wirksame Stoffe enthalten. Beispiele sind oral applizierbare Arzneimittel, Salben, Cremes, Augen- oder Nasentropfen, Sprays, Tinkturen, Injektionslösungen und weitere mehr.Pharmaceutical agents in the context of this invention are aqueous or alcoholic Solutions, gels or emulsions from a water and a lipid phase, the phar containing pharmaceutically active substances. Examples are orally administered drugs, Ointments, creams, eye or nose drops, sprays, tinctures, injectable solutions and more more.
Typische Inhaltsstoffe kosmetischer und pharmazeutischer Mittel sind Wasser, Tensi de und Co-Tenside, Öle, Fette, Wachse, Emulgatoren, Solubilisatoren, Filmbilder, Polymere, Konditioniermittel, Konsistenzgeber, Verdicker, Gelbildner, Farbstoffe, Pigmente, Perlglanzmittel, Duftstoffe, Lichtschutzfilter, Deowirkstoffe, Feuchthalte mittel, Naturstoffextrakte wie Kräuter, Pflanzenextrakte oder ätherische Öle, Lösungs mittel, Abrasiva und weitere mehr. Des weiteren finden verschiedenste Wirkstoffe in solchen Produkten Verwendung, beispielsweise hautglättende, entzündungshemmen de, schmerzstillende, antibakterielle, antifungale und antivirale Stoffe.Typical ingredients of cosmetic and pharmaceutical agents are water, tensi de and co-surfactants, oils, fats, waxes, emulsifiers, solubilizers, film images, Polymers, conditioners, bodying agents, thickeners, gel formers, dyes, Pigments, pearlescers, fragrances, sunscreens, deodorants, moisturizers medium, natural extracts such as herbs, plant extracts or essential oils, solutions medium, abrasives and more. Furthermore, find a variety of active ingredients in use of such products, for example skin-smoothing, anti-inflammatory agents analgesic, antibacterial, antifungal and antiviral agents.
Kosmetische und pharmazeutische Mittel, insbesondere wasserhaltige, oder solche die durch den Zutritt von Wasser oder Luftfeuchtigkeit Wasser aufnehmen können, enthalten in der Regel einen oder mehrere Konservierungsstoffe, die das Mittel wäh rend der Lagerung und während des Gebrauchs gegen Befall mit verderbniserregen den oder krankheitserregenden Mikroorganismen schützen.Cosmetic and pharmaceutical compositions, in particular hydrous, or such which can absorb water through the ingress of water or humidity, usually contain one or more preservatives that the agent currency during storage and during use against infestation with spoiling protect or pathogenic microorganisms.
Sorbinsäure (2,4-Hexadiensäure) und ihre Salze, im besonderen das gut wasserlösli che Kaliumsalz, werden seit vielen Jahren zur Konservierung von Lebensmitteln, sowie kosmetischen und pharmazeutischen Mitteln weltweit verwendet. Bei Sorbinsäure handelt es sich um eine ungesättigte Fettsäure, die sich durch besondere physiologi sche Verträglichkeit auszeichnet. Sorbinsäure wird im menschlichen Körper analog zu seiner Fettsäure verstoffwechselt, akkumuliert nicht und wird von den wissenschaftli chen Beratungsgremien der Weltgesundheitsorganisation und der Europäischen Union als sicher eingestuft. Der von beiden Gremien für Sorbinsäure festgelegte ADI-Wert, der als Maß für die physiologische Unbedenklichkeit von Lebensmittelzusatzstoffen gewertet werden kann, beträgt 0 bis 25 mg/kg Körpergewicht und Tag und ist damit der mit Abstand höchste ADI-Wert aller Konservierungsstoffe. Sorbinsäure und Sorba te gelten als nicht allergen und werden daher auch in keiner der bekannten Allergie datenbanken (z. B. Leatherhead Food Tolerance Databanks Project) erwähnt. Be züglich der Verwendung in kosmetischen Mitteln stuft das CIR-Expert Panel der CTFA basierend auf den zu Sorbinsäure und Sorbaten bekannten toxikologischen und allergologischen Daten diese Konservierungsstoffe als "sicher" ein. Sorbinsäure und Sorbate sind weltweit in der überwiegenden Zahl der Länder zur Konservierung von kosmetischen Mitteln zugelassen. Sorbic acid (2,4-hexadienoic acid) and its salts, in particular the good water-soluble potassium salt, have been used for many years for the preservation of food, as well cosmetic and pharmaceutical agents used worldwide. For sorbic acid it is an unsaturated fatty acid, which is characterized by special physiologi tolerability. Sorbic acid becomes analogous in the human body its fatty acid metabolizes, does not accumulate and is used by the scientific Advisory Councils of the World Health Organization and the European Union classified as safe. The ADI value established by both bodies of sorbic acid, as a measure of the physiological safety of food additives is 0 to 25 mg / kg body weight and day and is with it By far the highest ADI value of all preservatives. Sorbic acid and sorba te are considered non-allergenic and therefore are not in any of the known allergy databases (eg Leatherhead Food Tolerance Databanks Project). Be excluding use in cosmetic products, the CTI CIR Expert Panel rates based on the known toxicological and sorbate sorbates allergological data consider these preservatives to be "safe". Sorbic acid and Sorbates are present in the vast majority of countries worldwide for the preservation of approved cosmetic products.
Die Wirksamkeit der Sorbinsäure richtet sich vor allem gegen Hefen und Schimmelpil ze, sowie gegen zahlreiche Bakterien. Die Wirksamkeit der Sorbinsäure hängt vom undisoziierten Anteil und damit vom pH-Wert des zu konservierenden Gutes ab. Aufgrund des hohen pK-Wertes von 4,76 ist Sorbinsäure im Gegensatz zu anderen Konservierungsstoffen auf Basis organischer Säuren auch zur Konservierung von schwach sauren Gütern (bis pH 6,5) geeignet.The effectiveness of sorbic acid is mainly directed against yeasts and mold ze, as well as against numerous bacteria. The effectiveness of sorbic acid depends on undisoziierten share and thus the pH of the good to be preserved. Due to the high pK value of 4.76, sorbic acid is unlike others Preservatives based on organic acids also for the preservation of weakly acidic goods (up to pH 6.5).
In fester Form sind Sorbinsäure und die meisten Sorbate, insbesondere Kaliumsorbat und Calciumsorbat, stabil. In wässriger Lösung, in Lebensmitteln und in kosmetischen Mitteln unterliegt Sorbinsäure jedoch oxidativen Einflüssen. Besonders durch oxidative Spaltung der Doppelbindungen können Aldehyde und Ketone entstehen, die die Ursache für Off-flavours sein können. Polymerisationsprodukte dieser Aldehyde können ebenso für farbliche Veränderungen, im besonderen Bräunungsreaktionen, verantwortlich sein, wie die Reaktionsprodukte dieser Aldehyde mit Aminosäuren bzw. anderen primären oder sekundären Aminogruppen. Derartige Produkte werden als Maillard-Produkte bezeichnet und sind vielfach für Farbveränderungen in kosmeti schen Mitteln und Lebensmitteln verantwortlich.In solid form are sorbic acid and most sorbates, especially potassium sorbate and calcium sorbate, stable. In aqueous solution, in food and in cosmetic However, sorbic acid is subject to oxidative influences. Especially by oxidative Cleavage of the double bonds can give rise to aldehydes and ketones, which cause the Cause of off-flavors. Polymerization products of these aldehydes can also be used for color changes, in particular browning reactions, be responsible for how the reaction products of these aldehydes with amino acids or other primary or secondary amino groups. Such products are called Maillard products are and are often for color changes in kosmeti responsible for food and foodstuffs.
Gerade in kosmetischen Mitteln, für die deutlich längere Lagerzeiten angenommen werden müssen als für die meisten Lebensmittel und die oxidativen Einflüssen ausge setzt sind, ist eine sorbatinduzierte Braunverfärbung beschrieben (Domsch, A. (1994): Die kosmetischen Präparate, Band 2, wässrige und tensidhaltige Formulierungen, 4. Auflage, S. 329, Augsburg, Verlag für chemische Industrie).Especially in cosmetic products, for which significantly longer storage times assumed Must be considered as for most foods and oxidative influences a sorbate-induced brown discoloration is described (Domsch, A. (1994): The cosmetic preparations, Volume 2, aqueous and surfactant-containing formulations, 4. Edition, p. 329, Augsburg, publishing house for chemical industry).
Der Mechanismus der Oxidation von Sorbinsäure und entsprechende Stabilisierungs maßnahmen sind vielfach Gegenstand wissenschaftlicher Untersuchungen gewesen (Arya, S. (1980): Stability of sorbic acid in aqueous solutions, Journal Agric. Food Chem. 28, 1246-1249; Arya, S., Thakur, B. (1988): Degradation products of sorbic acid in aqueous solutions, Food Chem. 29, 41-49; Ledward, D. (1990): Stability of sorbic acid in intermediate moisture systems, Food Add. Contam. 7, 677-683; Merciades, M., Mohammed, K., Maniere, F. (1992): Stabilized sorbic acid or salt thereof, EP-A 0 595 576; Thakur, B., Singh, R., Arya, S. (1994): Chemistry of sorbates - a basic perspective. Food Rev. Intern. 10, 71-91).The mechanism of oxidation of sorbic acid and corresponding stabilization Measures have often been the subject of scientific research (Arya, S. (1980): Stability of sorbic acid in aqueous solutions, Journal Agric. Food Chem. 28, 1246-1249; Arya, S., Thakur, B. (1988): Degradation products of sorbic acid in aqueous solutions, Food Chem. 29, 41-49; Ledward, D. (1990): Stability of sorbic acid in intermediate moisture system, Food Add. Contam. 7, 677-683; Merciades, M., Mohammed, K., Maniere, F. (1992): Stabilized sorbic acid or salt thereof, EP-A 0 595 576; Thakur, B., Singh, R., Arya, S. (1994): Chemistry of sorbates - a basic perspective. Food Rev. Intern. 10, 71-91).
Da zumindest der erste Schritt der Reaktionskette, die im weiteren Verlauf zur Bildung gefärbter Verbindungen führt, wahrscheinlich einen oxidativen Angriff auf eine der im Sorbinsäuremolekül enthaltenen Doppelbindungen darstellt, erscheint die Mitverwen dung eines antioxidativ wirkenden Bestandteils nötig. Es ist allerdings bekannt, daß gängige Antioxidantien wie z. B. Propylgallat oder BHA (t-Buthylmethoxyphenol), die aufgrund ihrer hohen antioxidativen Kapazität in zahlreichen kosmetischen Produkten und auch in manchen Lebensmitteln gebräuchlich sind, auf sorbathaltige kosmetische oder pharmazeutische Formulierungen nicht farbstabilisierend wirken.Since at least the first step of the reaction chain, which in the further course to the education colored compounds, probably an oxidative attack on one of the Sorbinsäuremolekül contained double bonds, the Mitverwen appears tion of an antioxidant ingredient needed. However, it is known that common antioxidants such. B. propyl gallate or BHA (t-butylmethoxyphenol), the due to their high antioxidant capacity in numerous cosmetic products and are also used in some foods, on sorbate-containing cosmetic or pharmaceutical formulations do not have a color-stabilizing effect.
Im Rahmen der o. g. Untersuchungen wurde teilweise versucht, die beschriebenen sorbatinduzierten Verfärbungen und geruchlichen Veränderungen von Lebensmitteln durch den Zusatz von Metallionen (insbesondere Mangan) im Konzentrationsbereich von 0,1 bis 5 ppm zu vermindern. Metallionen sind jedoch nur in einem äußerst engen Dosierungsbereich antioxidativ wirksam. US-A 5,354,902 beschreibt die Farbstabilisie rung sorbathaltiger wässriger Systeme unter Verwendung von Mangan-Ionen. Ins gesamt scheint der Zusatz von Schwermetall-Ionen zur Lösung des Verfärbungs problems aber wenig geeignet, da von den Schwermetallen sowohl toxische, wie auch ökologische ungünstige Wirkungen ausgehen. Hinzu kommt, daß die genannten Schwermetalle je nach gewählter Konzentration auch prooxidativ wirken können.In the context of o. G. Investigations were partially attempted, the described sorbate-induced discoloration and odor changes in food by the addition of metal ions (in particular manganese) in the concentration range from 0.1 to 5 ppm. However, metal ions are only in a very narrow Dosage range antioxidant effective. US Pat. No. 5,354,902 describes color stabilization sorbate-containing aqueous systems using manganese ions. in the Overall, the addition of heavy metal ions seems to solve the discoloration problems but not very suitable because of the heavy metals both toxic, as well ecologically unfavorable effects. In addition, the mentioned Heavy metals can also act prooxidatively depending on the selected concentration.
US-A 2,866,817 beschreibt die Stabilisierung wässriger Lösungen von Sorbinsäure und ihren Salzen, insbesondere Na-Sorbat, mit 0,0005 bis 0,5% Glucono-delta-lacton. In Kombination mit typischen Bestandteilen kosmetischer Mittel wie z. B. Protein hydrolysaten, Ethanolamiden oder Amidopropylbetainen, die eine Verfärbung zusätz lich begünstigen, führt diese Methode jedoch nicht zum Erfolg. Na-Sorbat hat zudem aufgrund seiner begrenzten Stabilität bereits in fester Form als Konservierungsstoff für Lebensmittel, sowie kosmetische und pharmazeutische Mittel keine Bedeutung. US-A 2,866,817 describes the stabilization of aqueous solutions of sorbic acid and their salts, especially Na sorbate, with 0.0005 to 0.5% glucono-delta-lactone. In combination with typical ingredients of cosmetic products such. For example protein hydrolyzates, ethanolamides or Amidopropylbetainen, which discoloration additional However, this method does not lead to success. Na sorbate also has already in solid form as a preservative due to its limited stability Food, as well as cosmetic and pharmaceutical agents are of no importance.
Die bisher am häufigsten durchgeführte protektive Maßnahme zur Verminderung sorbatinduzierter Verfärbungen ist die Mitverwendung komplexierender Agenzien (z. B. EDTA (Ethylendiamintetraacetat) und Citronensäure oder deren Salze), die durch Komplexierung prooxidativ wirkender Metallionen sorbatinduzierte Verfärbungen verlangsamen.The hitherto most frequently performed protective measure for the reduction sorbate-induced discoloration is the concomitant use of complexing agents (eg EDTA (ethylenediamine tetraacetate) and citric acid or its salts) obtained by Complexation of pro-oxidative metal ions sorbate-induced discoloration slow it down.
Diese Maßnahme ist besonders dann von Vorteil, wenn eine Verunreinigung durch Spuren prooxidativ wirksamer Metallionen im kosmetischen Produkt gegeben ist. Unter ungünstigen Bedingungen (z. B. erhöhte Temperaturen oder intensive Tageslicht bestrahlung des sorbathaltigen Produktes) treten Verfärbungen jedoch auch in Abwe senheit von solchen prooxidativen Faktoren ein, so daß Komplexbildner allein keinen ausreichenden Schutz bieten können.This measure is particularly advantageous if contamination by Traces of pro-oxidatively active metal ions in the cosmetic product is given. Under unfavorable conditions (eg elevated temperatures or intense daylight irradiation of the sorbate-containing product), however, discolorations also occur in Abwe senility of such pro-oxidative factors, so that complexing alone alone can provide adequate protection.
DE-A 195 04 999 beschreibt die Verwendung von Allantoin mit oder ohne Citronensäu re oder eines deren Salze zur Verminderung sorbatinduzierter Verfärbungen in Kos metika und Lebensmitteln. Diese Lösung besitzt jedoch den Nachteil, daß die farb stabilisierende Wirkung in Verbindung mit einigen häufig verwendeten Inhaltsstoffen kosmetischer Produkte nicht ausreichend ist. Hier sind insbesondere solche Inhalts stoffe von Bedeutung, die aufgrund ihrer Herstellung Restgehalte an freien Aminen enthalten oder selbst Moleküle mit primären oder sekundären Amimogruppen dar stellen. Beispiele für in dieser Weise nachteilig wirkende Inhaltsstoffe sind Amido propylbetaine, Proteinhydrolysate oder Ethanolamide, sowie deren Fettsäure-Ester.DE-A 195 04 999 describes the use of allantoin with or without citric acid or one of their salts to reduce sorbate-induced discolouration in Kos metika and food. However, this solution has the disadvantage that the color Stabilizing effect in combination with some commonly used ingredients cosmetic products is insufficient. Here are in particular such contents substances of importance because of their production residual amounts of free amines contain or even molecules with primary or secondary amino groups put. Examples of ingredients that are detrimental in this way are amido propylbetaine, protein hydrolysates or ethanolamides, and their fatty acid esters.
Insbesondere unter intensiver Bestrahlung durch Tageslicht werden an das farb stabilisierende Prinzip einer sorbathaltigen kosmetischen oder pharmazeutischen Formulierung besondere Anforderungen gestellt, die alleine durch den Einsatz von Allantoin in Verbindung mit Citronensäure und Citraten nur teilweise erfüllt werden können. Die Verfärbung entsprechender Produkte wird durch den Zusatz von Allantoin in Verbindung mit Citronensäure und Citraten zwar vermindert, bleibt jedoch optisch wahrnehmbar. In particular, under intensive irradiation by daylight to the color stabilizing principle of a sorbate-containing cosmetic or pharmaceutical Formulation made special demands that alone through the use of Allantoin in conjunction with citric acid and citrates are only partially met can. The discoloration of corresponding products is due to the addition of allantoin Although reduced in connection with citric acid and citrates, it remains optically imperceptible.
Daher besteht auch weiterhin ein Bedarf für farbstabilisierende Additive, die in der Lage sind, sorbatinduzierte Verfärbungen in kosmetischen oder pharmazeutischen Mitteln zu unterbinden oder diese selbst unter ungünstigen Bedingungen wie erhöhter Licht- und Wärmebelastung merklich zu verringern.Therefore, there is still a need for color stabilizing additives that are known in the art Are capable of sorbate-induced discoloration in cosmetic or pharmaceutical Prevent them or even under unfavorable conditions such as increased Noticeably reduce light and heat load.
Eine effektive Farbstabilisierung gelingt überraschenderweise dadurch, daß man den sorbathaltigen Mitteln ein Flavonoid zusetzt, insbesondere ein Flavon oder Flavonol, bevorzugt ein wasserlösliches 3- oder 7-Glycosid eines Flavonols, besonder bevorzugt Rutin, das Rutinosid des Quercetin. Die erfindungsgemäßen Flavonoide sind in der Regel pflanzlicher Herkunft.An effective color stabilization succeeds surprisingly in that the adding a flavonoid to sorbate-containing agents, in particular a flavone or flavonol, preferably a water-soluble 3- or 7-glycoside of a flavonol, particularly preferred Rutin, the Rutinoside of Quercetin. The flavonoids of the invention are in the Usually of vegetable origin.
Flavonoide sind selbst schwach gelbliche Produkte, die z. B. in der Naturfärberei Verwendung finden. Auf dem pharmazeutischen Feld wird einigen Flavonoiden bzw. ihren Glycosiden protektive Wirkung gegen Erkrankungen der Venen (Biflavonoide wie Hesperidin und Rutin) und des Leberparenchyms (Silybin) zugeschrieben, außerdem eine Verbesserung der coronaren Durchblutung (Weißdorn-Extrakt) und diuretische (Birkenblätter-) oder spasmolytische (Kamillen-Drogen) Wirkungen. (Römpp Lexikon Chemie, 10. Auflage, Thieme Verlag, Stuttgart, New York).Flavonoids are themselves pale yellowish products, the z. B. in natural dyeing Find use. In the pharmaceutical field, some flavonoids or their glycosides protective action against diseases of the veins (biflavonoids such Hesperidin and rutin) and liver parenchyma (silybin), as well an improvement in coronary blood flow (hawthorn extract) and diuretic (Birch leaves) or spasmolytic (camomile) effects. (Römpp Lexicon Chemie, 10th Edition, Thieme Verlag, Stuttgart, New York).
Glycoside im Sinne dieser Erfindung sind Verbindungen der Flavonoide mit Mono-
oder Oligosacchariden, bestehend aus den monomeren Bausteinen Glucose, Rham
nose, Arabinose, Galactose, Xylose oder anderen Monosacchariden, am C-Atom 3
oder 7 des Flavonoids, wie sie in heimischen Obstarten und Südfrüchten häufig
vorkommen:
Glycosides for the purposes of this invention are compounds of the flavonoids with mono- or oligosaccharides, consisting of the monomeric building blocks glucose, Rham nose, arabinose, galactose, xylose or other monosaccharides, at the C atom 3 or 7 of the flavonoid, as in domestic fruits and Tropical fruits are common:
Formel (I) zeigt den Grundkörper eines Flavons (3 = H) bzw. Flavonols (3 = OH, 4' = OH).
Beispiele für erfindungsgemäß wirksame Flavonoide sind die Flavone
Apigenin (5 = OH, 7 = OH)
Luteolin (5 = OH, 7 = OH, 3' = OH)
Diosmetin (4' = OCH3, 3' = OH)
Chrysoeriol (3' = OCH3, 4' = OH)
sowie die Flavonole
Kämpferol (5 = OH, 7 = OH)
Quercetin (5 = OH, 7 = OH, 3' = OH)
Morin (5 = OH, 7 = OH, 2' = OH)
Robinetin (7 = OH, 3' = OH, 5' = OH)
Gossypetin (5 = OH, 7 = OH, 3' = OH, 8 = OH)
Myricetin (5 = OH, 7 = OH, 3' = OH, 5' = OH)
Fisetin (7 = OH,3' = OH)
Isohamnetin (3' = OCH3)
sowie deren 3- und 7-Glycoside.Formula (I) shows the basic body of a flavone (3 = H) or flavonol (3 = OH, 4 '= OH). Examples of flavonoids which are effective according to the invention are the flavones
Apigenin (5 = OH, 7 = OH)
Luteolin (5 = OH, 7 = OH, 3 '= OH)
Diosmetin (4 '= OCH 3 , 3' = OH)
Chrysoeriol (3 '= OCH 3 , 4' = OH)
as well as the flavonols
Kämpferol (5 = OH, 7 = OH)
Quercetin (5 = OH, 7 = OH, 3 '= OH)
Morin (5 = OH, 7 = OH, 2 '= OH)
Robinetine (7 = OH, 3 '= OH, 5' = OH)
Gossypetine (5 = OH, 7 = OH, 3 '= OH, 8 = OH)
Myricetin (5 = OH, 7 = OH, 3 '= OH, 5' = OH)
Fisetin (7 = OH, 3 '= OH)
Isohamnetin (3 '= OCH 3 )
and their 3- and 7-glycosides.
Alle diese Verbindungen besitzen aufgrund ihrer natürlichen Herkunft eine hohe Akzeptanz als Inhaltsstoffe kosmetischer und pharmazeutischer Mittel und kommen in der Natur in zahlreichen Beerenobstarten, Citrusfrüchten sowie anderen Obst- und Gemüsesorten und in einigen Kräuterpflanzen vor.All of these compounds are high in their natural origin Acceptance as ingredients of cosmetic and pharmaceutical agents and come in nature in numerous berry fruits, citrus fruits and other fruit and Vegetables and in some herb plants.
Die farbstabilisierende Wirkung dieser Substanzen ist vor allem deshalb überraschend, da andere Vertreter der Stoffgruppe der pflanzlichen Polyphenole entweder nicht farbstabilisierend auf sorbatkonservierte kosmetische oder pharmazeutische Mittel wirken, oder unter ungünstigen Bedingungen, wie z. B. intensiver Tageslichtbestrah lung, sogar zu einer Beschleunigung unerwünschter Verfärbungsreaktionen führen. Beispiele für Verbindungen, die auf sorbathaltige kosmetische Mittel nicht farbstabili sierend wirken sind die großen Gruppen der Hydroxyzimtsäuren, Hydroxycumarsäuren und Hydroxybenzoesäuren sowie deren natürlich vorkommende Ester mit Chinasäure, Shikimisäure, Äpfelsäure, Weinsäure und myo-Inosit. Einige dieser Verbindungen wirken sogar verstärkend auf unerwünschte Verfärbungen.The color-stabilizing effect of these substances is therefore surprising, above all because other representatives of the substance group of vegetable polyphenols either not color-stabilizing on sorbate-preserved cosmetic or pharmaceutical agents act, or under unfavorable conditions, such. B. intense daylightbestrah even accelerate unwanted discoloration reactions. Examples of compounds which are not color stable on sorbate-containing cosmetic agents The large groups of hydroxycinnamic acids, hydroxycumaric acids, have a reducing effect and hydroxybenzoic acids and their naturally occurring esters with quinic acid, Shikimic acid, malic acid, tartaric acid and myo-inositol. Some of these connections even exaggerate unwanted discoloration.
Als Beispiele seien hier Ferualsäure sowie Rosmarinsäure genannt, welche häufig aufgrund einer ihnen zugeschriebenen antioxidativen Wirkung in kosmetischen Mitteln verwendet werden, bezüglich der Farbstabilisierung sorbathaltiger Produkte jedoch keine positive Wirkung zeigen.As examples here are called Ferualsäure and rosmarinic acid, which often due to their attributed antioxidant effect in cosmetic products however, with respect to the color stabilization of sorbate-containing products show no positive effect.
Auch synthetische Antioxidantien wie Propylgallat oder BHA wirken auf sorbathaltige kosmetische oder pharmazeutische Formulierungen nicht farbstabilisierend.Also, synthetic antioxidants such as propyl gallate or BHA act on sorbate-containing Cosmetic or pharmaceutical formulations not color-stabilizing.
Um so bemerkenswerter ist das dazu unterschiedliche Verhalten flavonoider Verbin dungen sowie insbesondere deren 3-Glycoside und 7-Glycoside.All the more remarkable is the different behavior of flavonoid verb and in particular their 3-glycosides and 7-glycosides.
Während nicht zum Ausdruck gebracht werden soll, daß die Erfindung auf den nach folgend beschriebenen Wirkmechanismus beschränkt ist, so kann dennoch folgende Erklärung vermutet werden: Die farbstabilisierende Wirkung könnte zum einen in den günstigeren Löslichkeitseigenschaften (bessere Wasserlöslichkeit durch den größeren Anteil hydrophiler Strukturen im Molekül), aber ebenso in einer sterischen Hinderung von Oxidations- bzw. Polymerisationsaktionen an den phenolischen Gruppen des Moleküls begründet sein. Beides sind Eigenschaften, die antioxidativ wirkende Verbin dungen nicht notwendigerweise besitzen und deren Fehlen mithin ihrer Wirksamkeit in anderen Systemen keineswegs abträglich ist, denen jedoch überraschenderweise für die vorliegende Problemstellung eine besondere Bedeutung zuzukommen scheint.While not to express that the invention in the after The following mechanism of action is limited as follows Explanation can be assumed: The color-stabilizing effect could be on the one hand in the more favorable solubility properties (better water solubility by the larger Proportion of hydrophilic structures in the molecule), but also in steric hindrance of oxidation or polymerization actions on the phenolic groups of the Molecule be justified. Both are properties, the antioxidant Verbin not necessarily have their own and their absence therefore their effectiveness in other systems by no means detrimental, but surprisingly for the present problem seems to be of particular importance.
Das Flavonoid und/oder sein 3- bzw. 7-Glycosid werden dem Mittel - insbesondere dem kosmetischen bzw. pharmazeutischen Mittel - vorteilhaft in einer Konzentration von 0,005 bis 10 Gewichtsprozent zugesetzt, insbesondere 0,01 bis 2 Gewichts prozent, bevorzugt 0,01 bis 1 Gewichtsprozent, besonders bevorzugt 0,015 bis 0,2 Gewichtsprozent bezogen auf die Gesamtmasse des Produkts. Bei den bevorzugten Einsatzkonzentrationen sind Flavonoide selbst nur sehr schwach farbgebend.The flavonoid and / or its 3- or 7-glycoside are the means - in particular the cosmetic or pharmaceutical agent - advantageously in one concentration from 0.005 to 10 weight percent added, especially 0.01 to 2 weight percent, preferably 0.01 to 1 weight percent, more preferably 0.015 to 0.2% by weight based on the total mass of the product. In the preferred Use concentrations are flavonoids themselves very weakly coloring.
Die sorbatkonservierten Mittel, insbesondere die kosmetischen und pharmazeutischen Mittel enthalten zwischen 0,005 und 5 Gewichtsprozent Sorbinsäure oder eines derer Salze, insbesondere zwischen 0,05 und 2 Gewichtsprozent, bevorzugt zwischen 0,1 und 0,8 Gewichtsprozent, besonders bevorzugt zwischen 0,15 und 0,4 Gewichts prozent.The sorbate-preserved products, in particular the cosmetic and pharmaceutical Agents contain between 0.005 and 5 percent by weight of sorbic acid or one of these Salts, in particular between 0.05 and 2 weight percent, preferably between 0.1 and 0.8 weight percent, more preferably between 0.15 and 0.4 weight percent.
Im folgenden wird die Erfindung anhand von Beispielen näher erläutert:In the following the invention is explained in more detail by means of examples:
Eine sorbatkonservierte kosmetische Modellformulierung (Haarshampoo) ohne Verdic
kungszusatz wurde nach folgender Grundrezeptur hergestellt:
A sorbate-preserved cosmetic model formulation (hair shampoo) without thickening additive was prepared according to the following basic recipe:
Das so hergestellte Produkt wurde mit verschiedenen Zusätzen vermischt, um deren farbstabilisierende Wirkung zu untersuchen. Zur Quantifizierung der Schutzwirkung dieser Zusätze gegenüber unerwünschten Produktverfärbungen kam folgende Ver suchsanordnung zum Einsatz.The product thus prepared was mixed with various additives to their to investigate color-stabilizing effect. To quantify the protective effect these additives to unwanted product discoloration came following Ver Suchsanordnung used.
Das zu untersuchende Produkt wurde in ein oben offenes Behältnis gefüllt und für 20- 30 Tage unter einer starken Lichtquelle (366 nm) gelagert. Die Temperatur des Pro dukts während der Lagerung betrug dabei ca. 30°C. Während dieser Lagerzeit wurden die jeweiligen Produkte mehrfach mittels eines Farbmeßgerätes (Minolta Chromameter) auf die eingetretene Verfärbung vermessen. Aus den Meßwerten, ausgedrückt in ΔE, wurde mittels einer Regressionsanalyse die mittlere tägliche Zu nahme des Farbwertes berechnet und als Differenz zu den entsprechenden täglichen Zunahmen des Farbwertes einer Kontrollprobe (ohne Zusätze) angegeben. Damit drücken positive Werte eine beschleunigte, negative Werte eine verminderte Verfär bung des Modellproduktes an.The product to be tested was placed in an open-topped container and stored for 20-30 days under a strong light source (366 nm). The temperature of the product during storage was about 30 ° C. During this storage period, the respective products were measured several times by means of a colorimeter (Minolta Chromameter) on the discoloration occurred. From the measured values, expressed in Δ E, a regression analysis was used to calculate the average daily increase of the color value and to give the difference to the corresponding daily increases in the color value of a control sample (without additives). Thus positive values indicate an accelerated, negative values a reduced discoloration of the model product.
Im einzelnen ergaben sich damit für die getesteten Zusätze folgende Ergebnisse:
In particular, the following results were obtained for the additives tested:
Aus diesen Ergebnissen ist ersichtlich, daß Rutin, als Vertreter der Substanzklasse der glycosylierten Flavonoide bereits in einer Dosierung von 0,025 Gewichtsprozent eine deutliche Schutzwirkung gegenüber der sorbatabhängigen, licht- und wärmeinduzier ten Verfärbung kosmetischer Mittel aufweist. Diese Wirkung übertrifft die farbstabilisie rende Wirkung von Allantoin sowie die von EDTA deutlich. Andere phenolische Pflan zeninhaltsstoffe wie Ferulasäure oder Rosmarinsäure zeigen praktisch keine oder sogar eine verfärbungsfördernde Wirkung. Häufig gebrauchte synthetische Antioxidan tien wie BHA und Propylgallat verstärken ebenfalls die Verfärbungsneigung des sorbatkonservierten Systems, statt sie, wie aufgrund ihres antioxidativen Potentials vermutet werden könnte, zu vermindern.From these results it can be seen that rutin, as a representative of the substance class of glycosylated flavonoids already in a dosage of 0.025 weight percent one clear protection against the sorbate-dependent, light and heat induced discoloration of cosmetic agents. This effect surpasses the color stabilization effect of allantoin and that of EDTA. Other phenolic Pflan zeninhaltsstoffe such as ferulic acid or rosmarinic acid show virtually no or even a discoloration-promoting effect. Frequently used synthetic antioxidant such as BHA and propyl gallate also increase the tendency for discoloration of sorbate-preserved system, instead of them, as due to their antioxidant potential could be supposed to lessen.
Claims (10)
mit 3 = H(Flavone) oder 3 = OH, 4' = OH(Flavonole).3. Composition according to claim 1 or 2, characterized in that the flavonoid or flavonoid derivative is a compound of formula (I)
with 3 = H (flavones) or 3 = OH, 4 '= OH (flavonols).
Flavone:
Apigenin (5 = OH, 7 = OH)
Luteolin (5 = OH, 7 = OH, 3' = OH)
Diosmetin (4' = OCH3, 3' = OH)
Chrysoeriol (3' = OCH3, 4' = OH)
Flavonole:
Kämpferol (5 = OH, 7 = OH)
Quercetin (5 = OH, 7 = OH, 3' = OH)
Morin (5 = OH, 7 = OH, 2' = OH)
Robinetin (7 = OH, 3' = OH, 5' = OH)
Gossypetin (5 = OH, 7 = OH, 3' = OH, 8 = OH)
Myricetin (5 = OH, 7 = OH, 3' = OH, 5' = OH)
Fisetin (7 = OH,3' = OH)
Isohamnetin (3' = OCH3)
sowie deren 3- und 7-Glycoside.4. Composition according to claim 3, characterized in that the flavonoid or Flavonoidderivat a compound of formula (I) is th with the following substituents:
flavones:
Apigenin (5 = OH, 7 = OH)
Luteolin (5 = OH, 7 = OH, 3 '= OH)
Diosmetin (4 '= OCH 3 , 3' = OH)
Chrysoeriol (3 '= OCH 3 , 4' = OH)
flavonols:
Kämpferol (5 = OH, 7 = OH)
Quercetin (5 = OH, 7 = OH, 3 '= OH)
Morin (5 = OH, 7 = OH, 2 '= OH)
Robinetine (7 = OH, 3 '= OH, 5' = OH)
Gossypetine (5 = OH, 7 = OH, 3 '= OH, 8 = OH)
Myricetin (5 = OH, 7 = OH, 3 '= OH, 5' = OH)
Fisetin (7 = OH, 3 '= OH)
Isohamnetin (3 '= OCH 3 )
and their 3- and 7-glycosides.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1999128495 DE19928495A1 (en) | 1999-06-22 | 1999-06-22 | Use of flavonoids for photostabilizing sorbate-containing compositions |
| EP00110882A EP1055408A1 (en) | 1999-05-26 | 2000-05-23 | Sorbate preserved compositions, process for their manufacture and their use |
| AU36397/00A AU3639700A (en) | 1999-05-26 | 2000-05-24 | Sorbate-preserved compositions, method for the preparation thereof and their use |
| JP2000155122A JP2000336062A (en) | 1999-05-26 | 2000-05-25 | Formulated substance preserved with sorbate, its production and its use |
| US09/577,948 US6495718B1 (en) | 1999-05-26 | 2000-05-25 | Method for suppressing sorbate- and/or sorbic acid-induced discoloration |
| KR1020000028296A KR20010029741A (en) | 1999-05-26 | 2000-05-25 | Sorbate-preserved compositions, method for the preparation thereof and their use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1999128495 DE19928495A1 (en) | 1999-06-22 | 1999-06-22 | Use of flavonoids for photostabilizing sorbate-containing compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19928495A1 true DE19928495A1 (en) | 2000-12-28 |
Family
ID=7912101
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1999128495 Withdrawn DE19928495A1 (en) | 1999-05-26 | 1999-06-22 | Use of flavonoids for photostabilizing sorbate-containing compositions |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE19928495A1 (en) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10034102A1 (en) * | 2000-07-13 | 2002-01-24 | Beiersdorf Ag | Cosmetic or dermatological gels including iminodisuccinic acid to inhibit skin irritation, especially stinging |
| DE10034101A1 (en) * | 2000-07-13 | 2002-01-24 | Beiersdorf Ag | Cosmetic or dermatological emulsions including iminodisuccinic acid to inhibit skin irritation, especially stinging |
| WO2002055050A1 (en) * | 2001-01-10 | 2002-07-18 | Beiersdorf Ag | Cosmetic and dermatological washing preparations containing an effective quantity of iminodisuccinic acid and/or the salts thereof |
| EP1284129A1 (en) * | 2001-08-17 | 2003-02-19 | Beiersdorf AG | Cosmetic and dermatological sunscreen compositions comprising water-soluble UV filters and iminodisuccinic acid and/or salts thereof |
| EP1284130A2 (en) * | 2001-08-17 | 2003-02-19 | Beiersdorf AG | Cosmetic and dermatological sunscreen formulations |
| EP1284131A1 (en) * | 2001-08-17 | 2003-02-19 | Beiersdorf Aktiengesellschaft | Cosmetic and dermatological sunscreen compositions comprising benzotriazoles and iminodisuccinic acid and/or the salts thereof |
| EP1284132A1 (en) * | 2001-08-17 | 2003-02-19 | Beiersdorf Aktiengesellschaft | Cosmetic and dermatological sunscreen compositions comprising triazines and iminodisuccinic acid and/or the salts thereof |
| DE10142927A1 (en) * | 2001-09-01 | 2003-03-20 | Beiersdorf Ag | Increasing the stability of cosmetic preparations by adding iminodisuccinic acid |
| DE10142932A1 (en) * | 2001-09-01 | 2003-03-27 | Beiersdorf Ag | Cosmetic or dermatological compositions useful as aftersun or skin care products, especially against acne, comprises lecithin- and/or chitosan and iminodisuccinic acid |
| DE10142931A1 (en) * | 2001-09-01 | 2003-03-27 | Beiersdorf Ag | Increasing the skin moisturizing properties of polyols |
| EP1310236A1 (en) * | 2001-11-09 | 2003-05-14 | Beiersdorf AG | Cosmetic and dermatological sunscreen compositions comprising hydroxybenzophenones and iminodisuccinic acid and/or the salts thereof |
| EP1486200A2 (en) * | 2003-06-14 | 2004-12-15 | Beiersdorf AG | Cosmetic compositions comprising stabilized preservatives |
| EP1683512A1 (en) * | 2004-12-23 | 2006-07-26 | KPSS-Kao Professional Salon Services GmbH | Hair conditioning composition containing flavone derivatives |
-
1999
- 1999-06-22 DE DE1999128495 patent/DE19928495A1/en not_active Withdrawn
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10034102A1 (en) * | 2000-07-13 | 2002-01-24 | Beiersdorf Ag | Cosmetic or dermatological gels including iminodisuccinic acid to inhibit skin irritation, especially stinging |
| DE10034101A1 (en) * | 2000-07-13 | 2002-01-24 | Beiersdorf Ag | Cosmetic or dermatological emulsions including iminodisuccinic acid to inhibit skin irritation, especially stinging |
| WO2002055050A1 (en) * | 2001-01-10 | 2002-07-18 | Beiersdorf Ag | Cosmetic and dermatological washing preparations containing an effective quantity of iminodisuccinic acid and/or the salts thereof |
| EP1284129A1 (en) * | 2001-08-17 | 2003-02-19 | Beiersdorf AG | Cosmetic and dermatological sunscreen compositions comprising water-soluble UV filters and iminodisuccinic acid and/or salts thereof |
| EP1284130A2 (en) * | 2001-08-17 | 2003-02-19 | Beiersdorf AG | Cosmetic and dermatological sunscreen formulations |
| EP1284131A1 (en) * | 2001-08-17 | 2003-02-19 | Beiersdorf Aktiengesellschaft | Cosmetic and dermatological sunscreen compositions comprising benzotriazoles and iminodisuccinic acid and/or the salts thereof |
| EP1284132A1 (en) * | 2001-08-17 | 2003-02-19 | Beiersdorf Aktiengesellschaft | Cosmetic and dermatological sunscreen compositions comprising triazines and iminodisuccinic acid and/or the salts thereof |
| EP1284130A3 (en) * | 2001-08-17 | 2003-02-26 | Beiersdorf AG | Cosmetic and dermatological sunscreen formulations |
| DE10142927A1 (en) * | 2001-09-01 | 2003-03-20 | Beiersdorf Ag | Increasing the stability of cosmetic preparations by adding iminodisuccinic acid |
| DE10142932A1 (en) * | 2001-09-01 | 2003-03-27 | Beiersdorf Ag | Cosmetic or dermatological compositions useful as aftersun or skin care products, especially against acne, comprises lecithin- and/or chitosan and iminodisuccinic acid |
| DE10142931A1 (en) * | 2001-09-01 | 2003-03-27 | Beiersdorf Ag | Increasing the skin moisturizing properties of polyols |
| EP1310236A1 (en) * | 2001-11-09 | 2003-05-14 | Beiersdorf AG | Cosmetic and dermatological sunscreen compositions comprising hydroxybenzophenones and iminodisuccinic acid and/or the salts thereof |
| EP1486200A2 (en) * | 2003-06-14 | 2004-12-15 | Beiersdorf AG | Cosmetic compositions comprising stabilized preservatives |
| EP1486200A3 (en) * | 2003-06-14 | 2005-05-25 | Beiersdorf AG | Cosmetic compositions comprising stabilized preservatives |
| EP1683512A1 (en) * | 2004-12-23 | 2006-07-26 | KPSS-Kao Professional Salon Services GmbH | Hair conditioning composition containing flavone derivatives |
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