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CN-122003227-A - 3-Hydroxypropyl esters as antioxidants and tocopherol accelerators

CN122003227ACN 122003227 ACN122003227 ACN 122003227ACN-122003227-A

Abstract

The present invention relates generally to compounds of formula (I) and their use as antioxidants and/or antioxidant accelerators.

Inventors

  • Zabine Langer
  • Ricarda Krelling
  • Sebastian Blanc
  • Nongzio Simone Ippolito

Assignees

  • 西姆莱斯有限公司

Dates

Publication Date
20260508
Application Date
20230710

Claims (15)

  1. 1. Use of at least one compound of formula (I) as antioxidant and/or antioxidant promoter , Wherein the method comprises the steps of X is a straight chain C 5 -C 14 , preferably C 6 -C 14 , more preferably C 7 -C 13 , still more preferably C 8 -C 12 , most preferably C 9 -C 11 , alkyl or alkenyl; Or (b) X is selected from the group consisting of: Or (b) Wherein R 3 is-OCH 3 、-OCH 2 CH 3 or-O (CH 2 ) 2 CH 3 , And wherein R 1 is selected from the group consisting of-H and-OH, and R 2 is selected from the group consisting of-H, -CH 2 (OH)、-CH(OH)-CH 2 (OH) and-CH (OH) -CH (OH) -CH 2 (OH); Or (b) R 1 is-OH and R 2 is taken together with the-OH group shown in formula (I) to form a compound of formula (I-a): , Or (b) R 1 and R 2 are combined together to form a compound of formula (I-b): 。
  2. 2. the use according to claim 1, wherein X is selected from the group consisting of: 、 、 、 And 。
  3. 3. The use according to claim 1 or 2, wherein R 1 and R 2 are both-H.
  4. 4. Use according to any one of the preceding claims, wherein the use as antioxidant and/or antioxidant promoter relates to protecting unsaturated fatty acids from oxidation, wherein the fatty acids are preferably part of a vegetable oil.
  5. 5. The use according to any one of the preceding claims, wherein the formulation is selected from the group consisting of personal care formulations, household formulations, pharmaceutical formulations and food formulations.
  6. 6. A formulation selected from the group consisting of personal care formulations, household formulations, pharmaceutical formulations, and food formulations, comprising: (i) At least one compound of formula (I) as defined in any one of claims 1 to 3; (ii) Unsaturated fatty acids, preferably derived from, or contained in, oils, preferably vegetable oils, and/or (Iii) At least one further antioxidant different from the compounds of formula (I) as defined in any one of claims 1 to 3.
  7. 7. The formulation of claim 6, wherein the vegetable oil is selected from the group consisting of caprylic/capric triglyceride, sunflower (sunflower) seed oil, jojoba (jojoba) seed oil, olive (olive) fruit oil, moromill nut oil (argan kernel oil), sweet almond (sweet almond) oil, avocado (avocado) oil, shea (shea butter), cocoa (coconut) seed oil, cocoa butter, and mixtures of two or more of the foregoing vegetable oils.
  8. 8. The formulation of claim 6 or 7, wherein the at least one additional antioxidant is selected from the group consisting of dimethylmethoxychromanol, hydroxyacetophenone, ascorbic acid and salts thereof, hydroxymethylphenyl decanone, β -aspartyl arginine, uric acid, urea, hydroxyppinacol retinoic acid ester, vitamin a and vitamin a derivatives, butylhydroxytoluene (BHT), butylhydroxyanisole (BHA), hydroxyphenylpropionylaminobenzoic acid, ascorbyl palmitate, ascorbyl phosphate and salts thereof, carnosine, rutin, tocopherol, tocopheryl acetate, ubiquinone-10, dilauryl thiodipropionate, pentaerythritol tetrakis (bis-t-butylhydroxyhydrocinnamate), triethyl citrate, diethylhexyl butylidenyl malonate, lactobacillus fermentate, lactobacillus filtrate, lactobacillus lysate, hydroxyphenylpropionamide benzoic acid, green tea extract, ginger root extract, tropolone, allantoin, o-cymene-5-ol, and mixtures of two or more of the antioxidants.
  9. 9. The formulation according to claim 8, wherein the at least one other antioxidant is selected from the group consisting of tocopherols, preferably wherein the at least one other antioxidant comprises or consists of alpha-tocopherol.
  10. 10. Formulation according to any one of claims 6 to 9, comprising 0.0001 wt to 10,0 wt. -%, preferably 0.0005 wt to 8.0 wt. -%, more preferably 0.001 wt to 5.0 wt. -% of the at least one other antioxidant, preferably tocopherol, based on the total weight of the formulation.
  11. 11. The formulation according to any one of claims 6 to 10, comprising 0.01 wt to 10 wt%, preferably 0.05 wt to 2.5 wt%, more preferably 0.1 wt to 1.0 wt% by weight of the one or more compounds of formula (I), based on the total weight of the formulation.
  12. 12. The formulation according to any one of claims 6 to 11, wherein the formulation is in a form selected from the group consisting of: Dispersions, anhydrous oily formulations, liquid surfactant formulations, solid surfactant formulations and aqueous solutions, Wherein, preferably The dispersion is preferably an emulsion, in particular an oil-in-water emulsion, a water-in-oil emulsion, a complex emulsion, a water-dispersed gel, a balsam, a water-in-oil (water-in-oil-in-water) or an oil-in-water (oil-in-water-in-oil) complex emulsion, a PIT emulsion, a Pickering emulsion, a microemulsion, a liquid, a lotion, a suspension, an emulsion, an ointment, a slurry, a gel, an oil-based cream or a liposome-based formulation, and/or The aqueous-based solutions include aqueous solutions, aqueous alcoholic solutions, and aqueous glycollic acid solutions.
  13. 13. A method of preventing oxidation of an object comprising or consisting of the steps of: (a) Providing at least one compound of formula (I) as defined in any one of claims 1 to 3 or a formulation as defined in any one of claims 6 to 12; (b) Providing an object to be protected against oxidation, and (C) Applying the compound or the formulation in step (a) to the object in step (b) in an amount sufficient to provide an antioxidant effect.
  14. 14. The method according to claim 13, wherein the object to be protected against oxidation is a formulation comprising unsaturated fatty acids, wherein the unsaturated fatty acids preferably originate from oils, preferably vegetable oils, and wherein the formulation is preferably selected from the group consisting of personal care formulations, household formulations, pharmaceutical formulations and food formulations.
  15. 15. Use according to any one of claims 1 to 5, wherein the formulation is as defined in any one of claims 8 to 14.

Description

3-Hydroxypropyl esters as antioxidants and tocopherol accelerators Technical Field The present invention relates generally to compounds of formula (I) and their use as antioxidants and/or antioxidant accelerators. The present invention relates to one of a series of inventions of 3-hydroxypropyl esters and structurally related compounds co-filed by the same applicant on the same date as PCT patent application entitled "3-hydroxypropyl esters as antioxidants and tocopherol accelerators", "3-hydroxypropyl esters as solubility enhancers of lipophilic ingredients", "3-hydroxypropyl esters as foam and viscosity modifiers in surfactant-containing formulations", "3-hydroxypropyl esters as emulsifiers" and "3-hydroxypropyl esters as antimicrobial agents", the contents of which are incorporated herein by reference. Background Oxidation of lipids (mainly unsaturated fatty acids) in personal care products, household products, pharmaceuticals or foods is a key element to control and prevent because it affects the life of the product, consumer's perception of the product, the nutritional value of the product and consumer's health. The oxidation of unsaturated fatty acids under atmospheric oxygen begins with free radical chain reactions, producing highly reactive peroxides and hydroperoxides. These peroxides and hydroperoxides, in turn, react with the substrate present in the matrix, producing carboxylic acids, aldehydes, ketones, etc., which alter the organoleptic properties of the product and may harm the health of the consumer. Therefore, antioxidants are widely used in the industry to prevent or retard the occurrence of oxidative decomposition. Various natural or synthetic substances have been shown to have antioxidant efficacy. In addition to vitamin C (ascorbic acid), the most well known antioxidants include various carotene derivatives (e.g. beta-carotene, lycopene, lutein), in particular vitamin E and its derivatives (tocopherols, tocopheryl acetate and tocopheryl palmitate). Another important group of antioxidants includes polyphenols, particularly anthocyanins and isoflavones, which are found, for example, in various red fruits. Known antioxidants are of a wide variety. However, it goes without saying that no antioxidant can meet all requirements. In addition, it is generally desirable to replace existing materials with "green" alternatives. Thus, there is a need to continuously improve the efficacy potential and range of such antioxidants, achieving higher performance at the same level, or conversely, achieving the same performance at lower levels. In addition, in finding antioxidants, it must be considered that the substances allowed to be used by the regulatory authorities must be toxicologically acceptable, well tolerated by the user (for example the skin of the user) and remain stable in the matrix forming the product. Furthermore, preferred antioxidants are odorless or at least pleasant to smell, inexpensive and readily available. However, there is no clear correlation between the chemical structure of a substance and its oxidation resistance, which also makes it difficult to find a suitable substance. Furthermore, the relationship between antioxidant properties, toxicological acceptability, tolerability and stability of the material is unpredictable. Disclosure of Invention It is therefore an object of the present invention to provide a formulation, such as a personal care formulation, a household formulation, a pharmaceutical formulation or a food formulation, comprising an antioxidant, such that the formulation exhibits enhanced antioxidant properties. The antioxidant properties advantageously provide antioxidant stability to a formulation, such as a personal care formulation, a household formulation, a pharmaceutical formulation or a food formulation, or adapt a formulation, such as a personal care formulation or a pharmaceutical formulation, to protect the human body from oxidative damage, such as when the formulation is applied to the skin. It is a further object of the present invention to provide a substance which enhances the antioxidant effect of antioxidants and/or enhances the antioxidant effect of the formulation when applied. Furthermore, it is an object of the present invention to provide a substance by means of which the amount of antioxidants in a formulation, such as a personal care formulation, a household formulation, a pharmaceutical formulation or a food formulation, can be reduced. The above objects are achieved by various aspects of the invention as described herein. The first aspect of the present invention relates to the use of at least one compound of formula (I) as an antioxidant and/or antioxidant accelerator. The compounds of formula (I) as described herein are defined as follows: , Wherein the method comprises the steps of X is: Straight chain C 5-C14, preferably C 6-C14, more preferably C 7-C13, still more preferably C 8-C12, most preferably C 9-C11, alkyl or alkenyl; Or (b)