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Benzylidene substituted 2,4-pentanedione compounds and use thereof as stabilizers

一种化合物、戊二酮的技术，应用在苯亚甲基取代的2,4-戊二酮化合物和其作为稳定剂的应用领域，能够解决不是、不能减轻氧化应力不稳定性、缺少抗氧化剂活性等问题，达到防止损伤、增强稳定性和功效的效果

Inactive Publication Date: 2013-11-27
SYTHEON LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0032] Lack of antioxidant activity, making it impossible to mitigate oxidative stress-induced instability
even though ST has some antioxidant properties, but it is not as effective as it needs to be, or it is not as effective as one would hope

Method used

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  • Benzylidene substituted 2,4-pentanedione compounds and use thereof as stabilizers
  • Benzylidene substituted 2,4-pentanedione compounds and use thereof as stabilizers
  • Benzylidene substituted 2,4-pentanedione compounds and use thereof as stabilizers

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0091] Example 1: Synthesis of 3-(4-hydroxyl, 3-methoxybenzylidene)-2,4-pentanedione

[0092] In the case of continuous removal of azeotropic water, at reflux temperature, and in the presence of piperidine and cyclohexane as reaction medium, by the reaction of 3-methoxy-4-hydroxybenzaldehyde (citronellal) with acetylacetone Polycondensation, preparation 3-(4-hydroxyl, 3-methoxybenzylidene)-2,4-pentanedione (formula I, wherein R 1 is OCH 3 , and R 2 is H, hereinafter "Synoxyl TM AS"). The reaction takes about eight hours to complete, after which time the reaction product is purified by crystallization from methanol. The usual yield is about 68% and consists of a yellow crystalline powder with a melting point of 135 to 137°C and a lambda max 340nm. The purity of the material was determined to be 99.5% as determined by GC.

Embodiment 2

[0093] Example 2: Synoxyl TM Antioxidative capacity of AS and other antioxidants

[0094] The compound of Comparative Example 1, Synoxyl TM AS and two widely used commercially available antioxidants, natural tocopherol and The antioxidant capacity of ST, ST is a proprietary stabilizer based on diethylhexyl syringylidene malonate (DESM) available from EMD Chemicals, Gibbstown, NJ, USA. Several test methods were utilized. The results are shown in Table 4 along with specific test methods.

[0095] Table 4

[0096]

[0097] *The unit is Trolox equivalent / gm

[0098] 1 Method used: B Ou et al., J Agric Food Chem, 49(10):4619-4626, 2001

[0099] 2 Method used: B Ou et al., J Agric Food Chem, 50(10):2772-2777, 2002

[0100] 3 Method used: L Zhang et al., Free RadicBio Med, 43(suppl.1):S17, 2007

[0101] 4 Method used: Dubost, NJ et al., Food Chem, 105(2):727-735, 2007

[0102] 5 Method used: Zhang, L et al., J Agric Food Chem, 57(7):2861-2867, 2009

[0103] As ...

Embodiment 3

[0104] Example 3: Photostability Study

[0105]A comparative photostability study was performed which compared Synoxyl TM AS with octocrylene and Photostabilizing effect of ST on the stability of avobenzone. The samples for evaluation were prepared as follows:

[0106] Prepare a solution of photosensitive material and photostabilizer in ethanol, usually in a weight ratio of 1:1 to 1:5. A base test solution of 3% avobenzone + 5% octyl salicylate + 10% homosalate in ethanol ("test solution") was prepared. By adding 2%Synoxyl respectively TM AS, 4% octocrylene, 2% ST and 2% dehydrozingerone were added to four aliquots of the test solution, and four additional solutions were prepared.

[0107] Samples of each solution were prepared as ultra-thin films between 2 quartz plates, resulting in a minimum 90% light transmission over the entire spectral range of non-absorbing chromophores. For example, a test formulation absorbs only ingredients in the UV range, resulting in a ...

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Abstract

Substituted benzylidene 2,4-pentanediones are found to provide stabilization to otherwise photosensitive compounds and compositions.

Description

[0001] This application claims the benefit of US Provisional Patent Application No. 61 / 419,962, filed December 6, 2010, which is hereby incorporated by reference in its entirety. technical field [0002] The present invention relates to benzylidene substituted 2,4-pentanedione compounds and their use as antioxidant and / or stabilizer additives for various food, cosmetic, health and beauty supplements, otherwise known as personal care Products, products, and household products and various photosensitive components or ingredients incorporated into these products, such as sunscreen actives, fragrances, fragrances, pigments, antioxidants, vitamins, etc. These compounds protect such products and components from degradation and / or oxidation due to exposure to sunlight, heat and / or air, thereby maintaining or reducing the efficacy, storage stability, viscosity and / or Any loss of color. In addition, the compounds of the present invention have broad antioxidant capacity, thereby allevi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/248C07C39/19C07C39/21G03F7/004
CPCA61K2800/522A61K2800/10A61Q19/00C07C49/255A61Q5/02A61K8/35A61Q17/04C09B67/0085
Inventor 拉坦·K·乔杜里
Owner SYTHEON LTD
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