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DE10201223A1 - Esters, useful as antioxidants in cosmetics or pharmaceuticals, prepared by catalytic reaction of natural vitamins (e.g. A, E or C) with phenols - Google Patents

Esters, useful as antioxidants in cosmetics or pharmaceuticals, prepared by catalytic reaction of natural vitamins (e.g. A, E or C) with phenols

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Publication number
DE10201223A1
DE10201223A1 DE10201223A DE10201223A DE10201223A1 DE 10201223 A1 DE10201223 A1 DE 10201223A1 DE 10201223 A DE10201223 A DE 10201223A DE 10201223 A DE10201223 A DE 10201223A DE 10201223 A1 DE10201223 A1 DE 10201223A1
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esters
antioxidants
vitamins
cosmetics
phenols
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German (de)
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Knut Oppenlaender
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • A61K8/67—Vitamins
    • A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
    • 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
    • A61K8/67—Vitamins
    • A61K8/676—Ascorbic acid, i.e. vitamin C
    • 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
    • A61K8/67—Vitamins
    • A61K8/678—Tocopherol, i.e. vitamin E
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/06—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms
    • C07C403/12—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms by esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/62—Three oxygen atoms, e.g. ascorbic acid
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
    • C09K15/08—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen containing a phenol or quinone moiety
    • 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
    • A61K2800/522—Antioxidants; Radical scavengers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Cosmetics (AREA)

Abstract

Esters of natural vitamins, poly-phenols and monophenols are new. An Independent claim is also included for the preparation of the esters by a 3-stage process.

Description

Antioxidantien haben im Humanbereich zunehmend an Bedeutung gewonnen, seit der Mechanismus der Lipidperoxidation mit Sauerstoff Ozon oder Stickoxiden über freie Radikale aufgeklärt wurde. Dies gilt vor allem für den Nahrungsmittelsektor mit dem verstärkten Einsatz ungesättigter Fette und den Kosmetikbereich mit der Verwendung leicht oxidierbarer Öle sowie für die unterstützende Therapie und Prävention arteriosklerotischer Gefäßerkrankungen. Hierbei sind besonders antioxidativ wirksame Vitamine wie A, E und C sowie Polyphenole zu nennen. Sie können dazu beitragen, thrombotische Prozesse und entzündliche Reaktionen im Körper zu verhindern und die LDL-Oxidation zu schädlichen Plaques zu verlangsamen, d. h. sie wirken cardioprotektiv (vgl. auch Fett/Lipid 101, 1999, Nr. 12, S. 450-455: Food antioxidants and phytochemicals. Present and future perspectives; sowie Fett/ Lipid 101, 1999, Nr. 9, S. 343-346: Antioxidative cosmetic additives for the proteetion of human skin surface lipids against enviromental stress). Antioxidants have become increasingly important in humans since the mechanism lipid peroxidation with oxygen, ozone or nitrogen oxides has been elucidated about free radicals. This is especially true for the food sector with the increased use of unsaturated fats and the cosmetics sector with the use of easily oxidizable oils and for supportive therapy and prevention of arteriosclerotic vascular diseases. Here are particularly antioxidant Vitamins such as A, E and C and polyphenols to name a few. They can help thrombotic Prevent processes and inflammatory reactions in the body and increase LDL oxidation slow down harmful plaques, d. H. they have a cardioprotective effect (see also Fett / Lipid 101, 1999, No. 12, pp. 450-455: Food antioxidants and phytochemicals. Present and future perspectives; such as Fett / Lipid 101, 1999, No. 9, pp. 343-346: Antioxidative cosmetic additives for the proteetion of human skin surface lipids against environmental stress).

Polyphenole sind in derivatisierter oder freier Form Bestandteil vieler Pflanzen u. a. Produkte der Chromanreihe wie Flavone bzw. Flavonoide (Quercetin, Pelargonidin, Delphinidin) oder Anthocyane bzw. Anthocyanidine in Blütenfarbstoffen, grünem Tee (Gallocatechingallate), ferner Catechine und Tannine, Gallussäurester, Rosmarin und Beerenextrakte. Polyphenols are in derivatized or free form part of many plants. a. Products of Chromium series such as flavones or flavonoids (quercetin, pelargonidine, delphinidine) or anthocyanins or anthocyanidins in flower pigments, green tea (gallocatechin gallates), also catechins and Tannins, gallic acid esters, rosemary and berry extracts.

Auf dem Vitaminsektor wird Vitamin E (Tocopherol) speziell zur Oxidationsinhibierung von ungesättigten Fettsäuren eingesetzt. Es kann die Peroxidwirkung verhindern, die u. a. zur Inaktivierung von Enzymen und Hormonen führen kann. In the vitamin sector, vitamin E (tocopherol) is used specifically to inhibit the oxidation of unsaturated fatty acids used. It can prevent the peroxide effect which u. a. for inactivation of enzymes and hormones.

Allgemein nachteilig bei den obigen Vitaminen ist, bedingt durch ihre chemische Konstitution, ihre Empfindlichkeit gegen Oxidanden wie Luft bzw. Sauerstoff und Peroxide bzw. entsprechende Radikale, z. B. die leichte Oxidierbarkeit von Vitamin A und die leichte Zersetzung durch Lichteinwirkung. Zur Stabilisierung der genannten Vitamine werden mehrfach Mischung mit Polyphenolen oder anderen Vitaminen beschrieb. Besonders in der Kosmetik werde zur Erhöhung der Haltbarkeit und Lagerstabilität solche Kombinationen eingesetzt. In der DE 198 45 319 werden Flavone zum Schutz dermatologischer und kosmetischer Zubereitungen beschrieben. Ebenso in DE 198 24 727 und 198 07 774 Catechine und Extrakte von grünem Tee. EP 964047 beschreibt Gemische von Polyphenolen und Tocopherol- bzw. Ascorbinsäureestern als Antioxidantien für kosmetische Formulierungen. In FR 2777183 wird 3,4',5- Trishydroxystilben in dermatologischen Formulierungen gegen die oxidative Hautalterung eingesetzt. Schließlich beschreibt EP 911016 die Stabilisierung von Vitamin A in kosmetischen Formulierungen durch Zugabe von Ascorbyl-2'-monophosphat. A general disadvantage of the above vitamins is, due to their chemical constitution, their sensitivity to oxidants such as air or oxygen and peroxides or corresponding Radicals, e.g. B. the easy oxidizability of vitamin A and the easy decomposition by Light. To stabilize the vitamins mentioned, mix several times with polyphenols or other vitamins. Especially in cosmetics, the increase in Durability and storage stability used such combinations. In DE 198 45 319 flavones are used Protection of dermatological and cosmetic preparations described. Likewise in DE 198 24 727 and 198 07 774 Catechins and green tea extracts. EP 964047 describes mixtures of polyphenols and tocopherol or ascorbic acid esters as antioxidants for cosmetic formulations. FR 2777183 describes 3,4 ', 5-trishydroxystilbene in dermatological formulations against oxidative skin aging used. Finally, EP 911016 describes the stabilization of vitamin A. in cosmetic formulations by adding ascorbyl 2'-monophosphate.

Nachteilig ist hierbei die häufig unterschiedliche Löslichkeit der Mischungskomponenten, sodaß die Zugabe entsprechender Lösungsvermittler und Solubilisatoren notwendig ist. The disadvantage here is the often different solubility of the mixture components, so that the Addition of appropriate solubilizers and solubilizers is necessary.

Für den Pharmabereich ist der unterschiedliche Metabolismus und Stoffwechsel im Organismus problematisch. Diese Nachteile lassen sich in überraschend einfacher Weise umgehen, wenn die Poly phenolkomponenten mit den natürlichen antioxidativen Vitaminen chemisch verknüpft werden. Ein längerfristiger "gemeinsamer" Metabolismus wird gewährleiste, zusätzlich ist die erwünschte Löslichkeit durch die Polyphenolkomponente beeinflußbar bzw. einstellbar. Der Oxidationsschutz für das jeweilige Vitamin ist damit im Molekül eingebaut und kann gleichzeitig die Antioxidationswirkung des Vitamins verstärken. Von besonderer Bedeutung ist daher der Erhalt der antioxidativen Funktionalitäten bzw. eine erhebliche Verstärkung derselben, nach oder durch die Derivatisierung, die zur Kombination zweier Redoxsysteme in einem Molekül führt. Besonders vorteilhaft sind daher Polyphenole mit > 2 phenolischen OH-Gruppen einsetzbar, die unter Oxidationsbedingungen ein o- oder p-chinoides System ausbilden können, z. B. das trans-3,4',5-Trishydroxystilben oder Resveratrol, ein Inhaltsstoff der roten Trauben.

The different metabolism and metabolism in the organism is problematic for the pharmaceutical sector. These disadvantages can be circumvented in a surprisingly simple manner if the polyphenol components are chemically linked to the natural antioxidative vitamins. A longer-term "common" metabolism is guaranteed, in addition, the desired solubility can be influenced or set by the polyphenol component. The oxidation protection for the respective vitamin is thus built into the molecule and can at the same time increase the antioxidant effect of the vitamin. It is therefore of particular importance to maintain the antioxidative functionalities or to considerably increase them, after or through the derivatization, which leads to the combination of two redox systems in one molecule. It is therefore particularly advantageous to use polyphenols with> 2 phenolic OH groups, which can form an o- or p-quinoid system under oxidation conditions, e.g. B. the trans-3,4 ', 5-trishydroxystilben or resveratrol, an ingredient of the red grapes.

Die chemische Verknüpfung erfolgt in 3 Stufen:

  • - Überführung des Polyphenols in das entsprechende Mono-Na-phenolat mit NaOH.
  • - Umsetzung des Na-Phenolats mit Chloressigsäure unter NaCL-Bildung zur entsprechenden Phenoxycarbonsäure.
  • - Verknüpfung der Phenoxicarbonsäure mit der Vitaminkomponente durch konventionelle, sauer katalysierte Veresterung mit einer alkoholischen oder phenolischen OH-Funktion des Vitamins.
The chemical linkage takes place in 3 stages:
  • - Conversion of the polyphenol into the corresponding mono-Na phenolate with NaOH.
  • - Reaction of the Na phenolate with chloroacetic acid with formation of NaCL to the corresponding phenoxycarboxylic acid.
  • - Linking the phenoxy carboxylic acid with the vitamin component by conventional, acid-catalyzed esterification with an alcoholic or phenolic OH function of the vitamin.

Ein Beispiel ist nachstehend für Vitamin C (L(+)-Ascorbinsäure) dargestellt. Die Veresterung erfolgt unter den üblichen Bedingungen (H+-Katalyse) an der CH OH-Gruppierung in 6-Stellung der Ascorbinsäure.

An example is shown below for vitamin C (L (+) - ascorbic acid). The esterification takes place under the usual conditions (H + catalysis) on the CH OH group in the 6-position of the ascorbic acid.

Die für das Redoxsystem wichtige En-Diol bzw. Redukton-Gruppierung der Ascorbinsäure bleibt erhalten. The en-diol or reductone grouping of ascorbic acid, which is important for the redox system, remains receive.

In analoger Weise läßt sich aus Vitamin A-Alkohol ein entsprechendes "Vitamin A-Phenoxiacetat" herstellen. Vitamin A-Phenoxiacetat (Retinyl-Phenoxiacetat)

In a similar way, a corresponding "vitamin A phenoxyacetate" can be produced from vitamin A alcohol. Vitamin A phenoxyacetate (retinyl phenoxyacetate)

In einem speziellen Fall kann auch Vitamin E bzw. α-Tocopherol als Monophenol eingesetzt werden, das nach Überführung in die entsprechende Phenoxiessigsäure mit L(+) Ascorbinsäure oder auch Vitamin A verestert wird. Hierbei wird ebenfalls eine gegenseitige Schutzwirkung der beiden Reaktionskomponenten erreicht bzw. gleichzeitig die Kombination zweier wichtiger Vitamine bewirkt; z. B.


In a special case, vitamin E or α-tocopherol can also be used as monophenol, which is esterified with L (+) ascorbic acid or vitamin A after conversion into the corresponding phenoxy acetic acid. A mutual protective effect of the two reaction components is also achieved, or the combination of two important vitamins is effected at the same time; z. B.


Als weiteres Monophenol eignet sich auch 2,6-Di-tert. butyl-p-Kresol (s. u.), das aufgrund seiner chemischen Struktur durch die sterisch gehinderte phenolische OH-Gruppe gute anioxidative Eigenschaften aufweist.

2,6-Di-tert is also suitable as a further monophenol. butyl-p-cresol (see below), which has good anioxidative properties due to its chemical structure due to the sterically hindered phenolic OH group.

Die neuen Antioxidantien können in den für die erwähnten Anwendungsbereiche Pharma und Kosmetik, üblichen Konzentrationen eingesetzt werden. The new antioxidants can be used in the pharmaceutical and Cosmetics, usual concentrations are used.

Claims (7)

1. Ester aus natürlichen Vitaminen und Polyphenolen. 1. Esters from natural vitamins and polyphenols. 2. Produkte gemäß 1. dadurch gekennzeichnet, daß als Vitamin-Komponenten A, E und C oder deren Gemische eingesetzt werden. 2. Products according to 1. characterized in that as vitamin components A, E and C or whose mixtures are used. 3. Als Polyphenole können alle Phenole mit > 2 phenolischen OH-Gruppen, die ein o- oder p-chinoides System ausbilden, vorzugsweise Produkte der Chromanreihe wie Flavone und Flavonoide, u. a. Catechine, Quercetin etc., ferner Anthocyane bzw. Anthocyanidine und natürliche Tannine eingesetzt werden. 3. All phenols with> 2 phenolic OH groups which are an o- or Form p-quinoid system, preferably products from the Chroman range such as Flavone and Flavonoids, u. a. Catechins, quercetin etc., also anthocyanins or anthocyanidins and natural ones Tannins can be used. 4. Als Monophenole sind α-Tocopherol sowie 2,6-Di-tert. butyl - p-Kresol vorzugsweise einzusetzen. 4. The monophenols are α-tocopherol and 2,6-di-tert. butyl - p-cresol should preferably be used. 5. Als speziell bevorzugtes Polyphenol ist trans- 3,4',5-Trishydroxystilben, das sogenannte Reservatrol, ein Inhaltsstoff der roten Trauben, zu nennen. 5. A particularly preferred polyphenol is trans-3,4 ', 5-trishydroxystilbene, the so-called Reservatrol, an ingredient in red grapes. 6. Verfahren zur Herstellung der Ester nach 1. dadurch gekennzeichnet, daß zunächst die Polyphenole nach gängiger Methode vorzugsweise in die entsprechenden Mono-Na-Phenolate überführt und anschließend mit Chloressigsäure zu den entsprechenden Monophenoxiessigsäuren umgesetzt werden. In einem weiteren Schritt erfolgt die sauer katalysierte Veresterung mit den OH-Gruppen der Vitamine. 6. Process for the preparation of the esters according to 1, characterized in that the Polyphenols according to the usual method, preferably in the corresponding mono-Na phenolates transferred and then with chloroacetic acid to the corresponding Monophenoxyacetic acids are implemented. The acid-catalyzed esterification takes place in a further step with the OH groups of the vitamins. 7. Einsatz der Produkte gemäß 1. als Antioxidantien für Kosmetik- und Pharmasektor mit den für dieses Einsatzgebiet üblichen Dosierungen. 7. Use of the products according to 1. as antioxidants for cosmetics and pharmaceuticals with usual dosages for this application.
DE10201223A 2002-01-15 2002-01-15 Esters, useful as antioxidants in cosmetics or pharmaceuticals, prepared by catalytic reaction of natural vitamins (e.g. A, E or C) with phenols Withdrawn DE10201223A1 (en)

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20130090409A (en) * 2010-07-29 2013-08-13 이스트만 케미칼 컴파니 Esters of o-substituted hydroxy carboxylic acids and preparations thereof
US9701625B2 (en) 2014-03-07 2017-07-11 Dow Global Technologies Llc Nitrone compounds and their use in personal care
US9730874B2 (en) 2014-05-12 2017-08-15 Dow Global Technologies Llc Nitrone compounds and their use in personal care
US10130574B2 (en) 2015-03-20 2018-11-20 Dow Global Technologies Llc Nitrone inhibition of oxidation of unsaturated fats
US10137071B2 (en) 2015-03-20 2018-11-27 Dow Global Technologies Llc Nitrone inhibition of oxidation of unsaturated fats
CN115677677A (en) * 2022-10-14 2023-02-03 常州大学 Amphiphilic vitamin E vitamin C ester and preparation method thereof

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20130090409A (en) * 2010-07-29 2013-08-13 이스트만 케미칼 컴파니 Esters of o-substituted hydroxy carboxylic acids and preparations thereof
JP2013539457A (en) * 2010-07-29 2013-10-24 イーストマン ケミカル カンパニー O-substituted hydroxycarboxylic acid esters and their preparation
US9532938B2 (en) 2010-07-29 2017-01-03 Eastman Chemical Company Esters of O-substituted hydroxy carboxylic acids and preparations thereof
KR101899606B1 (en) * 2010-07-29 2018-09-17 이스트만 케미칼 컴파니 Esters of o-substituted hydroxy carboxylic acids and preparations thereof
EP2598471B1 (en) * 2010-07-29 2020-11-25 Eastman Chemical Company Esters of o-substituted hydroxy carboxylic acids and preparations thereof
US9701625B2 (en) 2014-03-07 2017-07-11 Dow Global Technologies Llc Nitrone compounds and their use in personal care
US9828335B2 (en) 2014-03-07 2017-11-28 Dow Global Technologies Llc Nitrone compounds and their use in personal care
US9730874B2 (en) 2014-05-12 2017-08-15 Dow Global Technologies Llc Nitrone compounds and their use in personal care
US9796667B2 (en) 2014-05-12 2017-10-24 Dow Global Technologies Llc Nitrone compounds and their use in personal care
US10130574B2 (en) 2015-03-20 2018-11-20 Dow Global Technologies Llc Nitrone inhibition of oxidation of unsaturated fats
US10137071B2 (en) 2015-03-20 2018-11-27 Dow Global Technologies Llc Nitrone inhibition of oxidation of unsaturated fats
CN115677677A (en) * 2022-10-14 2023-02-03 常州大学 Amphiphilic vitamin E vitamin C ester and preparation method thereof

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