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3-(2,4-dihydroxy-phenyl)-1,5-di-(2-hydroxy-phenyl)-pentane-1,5-dione and its use
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A dihydroxy, phenyl technology, used in the fields of food, cosmetics and medicine, can solve problems such as low yield, harsh reaction conditions, and increased toxic or harmful reagents
Inactive Publication Date: 2017-01-25
JIANGNAN UNIV
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However, these methods have many drawbacks, such as harsh reaction conditions, toxic reagents and metal catalysts, strong acids and bases, oily products, long reaction times, low yields, low selectivities, and cumbersome post-processing procedures
In addition, in most cases, the synthesis of hydroxychalcone derivatives requires protection and deprotection of hydroxyl groups, which not only increases the number of reaction steps and time, but also increases the chance of using toxic or harmful reagents
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Embodiment 1
[0027] Example 1 Preparation of 3-(2,4-dihydroxy-phenyl)-1,5-bis-(2-hydroxy-phenyl)-pentane-1,5-dione
[0028] Weigh 0.04mol 2,4-dihydroxybenzaldehyde, 0.02mol 2-hydroxyacetophenone, 2.1g boric acid, 0.5g ascorbic acid in a 50mL round bottom flask, add 25mL PEG400 and stir to dissolve, place in 130°C oil bath Stirred and refluxed for 6h, followed the progress of the reaction by TLC. The reaction solution was extracted three times with ethyl acetate, and the organic phase was concentrated to dryness under reduced pressure; the dried sample was applied to a silica gel column (particle size: 200-300 mesh), washed with dichloromethane:methanol=30:1 (v / v) The eluate was collected, and the thin-layer plate was detected. The same fractions were combined, concentrated and dried to obtain a dry sample; by liquid chromatography-mass spectrometry, the fraction with a molecular weight of 392 was determined to be the fraction containing the target substance; the above fractions were dried ...
Embodiment 2
[0040] Example 2 Evaluation method for tyrosinase inhibitory activity
[0041] Dissolve 3-(2,4-dihydroxy-phenyl)-1,5-bis-(2-hydroxy-phenyl)-pentane-1,5-dione in DMSO to make 50, 10, 5, 2.5, 0.5 μg respectively / mL. The positive controlkojic acid was made into solutions with concentrations of 50, 25, 10, 5, and 2.5 μg / mL. Take 300 μL of each of the five concentrations of solutions, use 700 μL of pH6.8 phosphatebuffer solution to make 1 mL, add 0.1 mg / mL tyrosine 1 mL, and then add 1 mL of pH 6.8 phosphatebuffer solution. Tyrosinase (400U / mL), incubate at 37°C for 20min, and measure the absorbance at 492nm.
[0043] A1 is the absorption value without inhibitor at 0 min; A2 is the absorption value without inhibitor after 20 min;
[0044] B1 is the absorption value of inhibitor added at 0 min; B2 is the absorption value of inhibitor added after 20 min.
Embodiment 3
[0045] Example 3 Evaluation of compound tyrosinase inhibitory activity
[0046] 3-(2,4-dihydroxy-phenyl)-1,5-bis-(2-hydroxy-phenyl)-pentane-1,5-dione inhibits IC of tyrosinase 50 The IC of kojic acid was 1.67 μM 50 IC of 50.6 μM, 2,4-dihydroxybenzaldehyde 50 >200 μM, IC of 2-hydroxyacetophenone 50 >400 μM. The tyrosinase inhibitory activity of the compound 3-(2,4-dihydroxy-phenyl)-1,5-bis-(2-hydroxy-phenyl)-pentane-1,5-dione is far greater than that of the positive controlkojic acid, And reaction raw material 2-hydroxyacetophenone and 2,4-dihydroxybenzaldehyde.
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Abstract
The invention discloses a synthesis method and application of 3-(2,4-dihydroxy-phenyl)-1,5-bis-(2-hydroxy-phenyl)-pentane-1,5-dione, and belongs to the fields of foods, cosmetics and medicine. The synthesis method comprises the following steps: carrying out reaction of 2,4-dihydroxy-benzaldehyde in a PEG400 solvent for 6 hours under the catalysis of boric acid and vitamin C, so as to synthesize an efficient tyrosinase inhibitor; then carrying out separation through silica columnchromatography and gel column chromatography, so as to obtain a pure product of the efficient tyrosinase inhibitor. Through massspectrogram and nuclear magnetic analysis, the material is confirmed to be 3-(2,4-dihydroxy-phenyl)-1,5-bis-(2-hydroxy-phenyl)-pentane-1,5-dione. The compound provided by the invention can be effectively used for inhibition of enzymatic browning of fruits and vegetables, whitening cosmetics, and preparation of pharmaceutical preparations used for preventing and curing human body pigmented diseases and melanoma, which are caused by melanism, as well as other pharmaceutical preparations for inhibition of the activity of tyrosinase.
Description
technical field [0001] The invention relates to a synthesis method and application of 3-(2,4-dihydroxy-phenyl)-1,5-bis-(2-hydroxy-phenyl)-pentane-1,5-dione, which belongs to food , cosmetics and pharmaceuticals. Background technique [0002] Browning and spoilage caused by pathogen infection are two important factors causing postharvest losses of fruits and vegetables. During the processing and storage of fruits and vegetables, enzymatic browning caused by tyrosinase (EC 1.14.18.1) not only affects the color and appearance of products, but also destroys the amino acids of essential products, reduces their nutrition and digestion and absorption, and eventually Seriously affect the nutritional value and market value of the product. Many fruits and vegetables have a short shelf life due to factors such as fungal diseases, mechanical damage and aging. Normally, natural flora often exists in fruit and vegetable products, and may also exist in the process of human consumption. ...
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