Preparation method and application of sesamol intermediate heliotropin

A technology for piperonal and sesamol is applied in the field of preparation of piperonal, an intermediate product of sesamol, and can solve the problems of large-scale use of high-concentration hydrochloric acid, increase in product impurities, deepening of color, etc., and achieves low raw material cost, simple reaction process, The effect of high decarboxylation efficiency

Active Publication Date: 2014-04-16
JINAN UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Using hydrochloric acid as a decarboxylation agent, the effect is not good when the concentration is low, and the effect is acceptable when the concentration is high, but the volatility of high concentration hydrochloric acid brings inconvenience to large-scale use
The decarboxylation effect of high-concentration sulfuric acid is better, but it is easy to produce carbonization, which will increase the impurities and deepen the color of the product

Method used

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  • Preparation method and application of sesamol intermediate heliotropin
  • Preparation method and application of sesamol intermediate heliotropin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] (1) Add 0.98g of concentrated sulfuric acid with a mass fraction of 98% and 2.96g of glyoxylic acid into a self-made reaction vessel equipped with an electric stirrer, and drop into 0.2mL of water, keep the temperature at 0°C, and then Add 4.9g of peppercycline at the speed of drops, mix and stir for 2.5h; the solution at the beginning of the reaction is a colorless and transparent solution, after dropping peppercyclene, it gradually becomes a milky white viscous liquid, and layers, and finally becomes a milky white opaque viscous liquid;

[0027] (2) The above reaction product was diluted with 10mL of water under stirring, then washed by suction filtration, and dried in the air to obtain a white solid powder which was 3,4-methylenedioxymandelic acid;

[0028] (3) Add 19.60 g of 3,4-methylenedioxymandelic acid obtained in step (2) and 5.25 g of nitric acid solution with a mass fraction of 3.1% in a three-neck flask equipped with a stirring and reflux condensing device. ...

Embodiment 2

[0031] (1) Add 0.88g of concentrated sulfuric acid with a mass fraction of 98% and 2.66g of glyoxylic acid into a self-made reaction vessel equipped with an electric stirrer, and drop into 0.2mL of water, keep the temperature at 4°C, and then Add 4.05g of peppercycline at the speed of drops, mix and stir for 3 hours; the solution is a colorless transparent solution at the beginning of the reaction, after dropping peppercyclene, it gradually becomes a milky white viscous liquid, and layers, and finally becomes a milky white opaque viscous liquid;

[0032] (2) The above reaction product was diluted with 10mL of water under stirring, then washed by suction filtration, and dried in the air to obtain a white solid powder which was 3,4-methylenedioxymandelic acid;

[0033] (3) Add 17.64g of 3,4-methylenedioxymandelic acid obtained in step (2) and 5.25g of nitric acid solution with a mass fraction of 3.1% in a three-neck flask equipped with a stirring and reflux condensing device. He...

Embodiment 3

[0036] (1) Add 1.07g of concentrated sulfuric acid with a mass fraction of 98% and 3.25g of glyoxylic acid into a self-made reaction vessel equipped with an electric stirrer, and drop into 0.2mL of water, keep the temperature at 5°C, and then Add 4.95g of peppercycline at the speed of drops, mix and stir for 3.5h; the solution at the beginning of the reaction is a colorless and transparent solution, after dropping peppercyclene, it gradually becomes a milky white viscous liquid, and layers, and finally becomes a milky white opaque viscous liquid;

[0037] (2) The above reaction product was diluted with 10mL of water under stirring, then washed by suction filtration, and dried in the air to obtain a white solid powder which was 3,4-methylenedioxymandelic acid;

[0038] (3) Add 21.56g of 3,4-methylenedioxymandelic acid obtained in step (2) and 5.25g of nitric acid solution with a mass fraction of 3.1% in a three-neck flask equipped with a stirring and reflux condensing device. H...

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Abstract

The invention belongs to the field of food additives and provides a preparation method of a sesamol intermediate heliotropin. The preparation method is convenient to use by taking nitric acid as a decarboxylating agent; the product, namely the sesamol intermediate heliotropin is good in purity; especially the decarboxylation efficiency is high, so that the decarboxylation reaction can be efficiently carried out to directly influence the synthesis yield of the overall preparation route; compared with other synthesis routes, the heliotropin synthesis route disclosed by the invention has considerable advantage on the cost, and the product competitiveness is relatively strong. The synthesis method disclosed by the invention has the advantages of cheap raw materials, simple reaction process and high yield and can be applied to large-scale synthesis of sesamol.

Description

technical field [0001] The invention belongs to the field of food additives, in particular to a preparation method and application of a sesamol intermediate product, piperonal. Background technique [0002] Sesamol, chemical name 3,4-methylenedioxyphenol (3,4-methylenedioxyphenol, MDP), molecular formula C 7 h 6 o 3 , the structural formula is as follows: [0003] [0004] Sesamol is a natural product present in sesame oil. Sesame oil is more stable than other vegetable oils, mainly due to the role of sesamol, which shows that sesamol has better antioxidant activity. Humans have been eating sesame oil for a long time without any obvious safety problems, which shows that sesamol has relatively good safety. It is an important direction of food additive research to develop safe and efficient food additives guided by naturally occurring active substances. The oxidative decarboxylation of 3,4-methylenedioxymandelic acid to obtain piperonal is an air oxidation reaction un...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/54C07D317/64
CPCC07D317/54C07D317/64
Inventor 晏日安李江平罗忠明
Owner JINAN UNIVERSITY
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