Synthesis method of stable isotope 18O labeled nipagin ester

A paraben ester and synthesis method technology, applied in the direction of isotope introduction of organic compounds, acyclic/carbocyclic compound isotope introduction, organic chemical methods, etc., can solve neonatal genital deformities, paraben residues, increase female uterus Cancer risk and other issues, to achieve the effect of small dilution, high utilization rate, and good application prospects

Active Publication Date: 2018-04-20
SHANGHAI RES INST OF CHEM IND
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are also research reports that paraben will accumulate in the human body, increasing the risk of breast cancer and uterine cancer in women, and a large number of paraben residues are found in the pathological sections of a large number of breast cancer patients
What's more serious is that pregnant women who use excessive paraben ester preservatives can cause genital deformities in newborns

Method used

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  • Synthesis method of stable isotope 18O labeled nipagin ester
  • Synthesis method of stable isotope 18O labeled nipagin ester

Examples

Experimental program
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Effect test

Embodiment 1

[0023] a stable isotope 18 The synthetic method of the methylparaben of O mark adopts the following steps:

[0024] (1) In a 100ml glass three-neck flask, add 18.45g (0.075mol) of benzoic acid-4-diazosulfate and 50mL of anhydrous tetrahydrofuran, control the reaction temperature at 0°C, and add slowly under stirring 18 O labeled water 0.9g (0.05mol), reacted at low temperature for 4h, then heated the oil bath to 60°C for 2h, then stirred at room temperature for 4h, directly evaporated the solvent under reduced pressure, and separated by silica gel column chromatography to obtain 6.3g of intermediate product nipol Auric acid- 18 O.

[0025] (2) In a 100ml glass three-necked bottle, add the above-mentioned Nipaginic acid- 18 O and 25mL of methanol, in the process of stirring, slowly add 4.4g of concentrated sulfuric acid as a catalyst, then the oil bath is heated to reflux, after 8 hours of reaction, it is lowered to room temperature, the solvent is evaporated under reduced p...

Embodiment 2

[0027] a stable isotope 18 The synthetic method of the propylparaben of O mark adopts the following steps:

[0028] (1) In a 100ml glass three-necked flask, add 24.6g (0.1mol) of benzoic acid-4-diazosulfate and 50mL of anhydrous 2-methyltetrahydrofuran, control the reaction temperature at 5°C, and add slowly under stirring 18 O marked water 0.9g (0.05mol), reacted at low temperature for 6h, then heated the oil bath to 80°C for 4h, then stirred at room temperature for 8h, directly evaporated the solvent under reduced pressure, and then separated by silica gel column chromatography to obtain 6.1g of intermediate product Ni Parkinic acid- 18 O.

[0029] (2) In a 100ml glass three-necked bottle, add the above-mentioned Nipaginic acid- 18 O and 25mL propanol, in the process of stirring, slowly add 7.5g p-toluenesulfonic acid as a catalyst, then the oil bath is heated to reflux, after 6 hours of reaction, it is lowered to room temperature, the solvent is evaporated to dryness und...

Embodiment 3

[0031] a stable isotope 18 The synthetic method of the O-marked octylparaben adopts the following steps:

[0032] (1) In a 100ml glass three-necked flask, add 36.9g (0.15mol) of benzoic acid-4-diazosulfate and 50mL of anhydrous 1,4-dioxane, control the reaction temperature at 5°C, and add dropwise under stirring slow 18 O labeled water 0.9g (0.05mol), reacted at low temperature for 8h, then heated the oil bath to 80°C for 6h, then stirred at room temperature for 6h, directly evaporated the solvent under reduced pressure, and then separated by silica gel column chromatography to obtain 6.0g intermediate product Ni Parkinic acid- 18 O.

[0033] (2) In a 100ml glass three-necked bottle, add the above-mentioned Nipaginic acid- 18 O, add octanol 24.7g (0.21mol) and 25mL toluene again, in stirring process, slowly add the concentrated sulfuric acid of 4.1g as catalyst, then oil bath is warmed up to reflux, and utilizes water divider to divide water, after reaction 12h, drop to A...

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Abstract

The invention relates to a synthesis method of stable isotope 18O labeled nipagin ester. The synthesis method comprises the following steps: taking stable isotope 18O-water as a raw material to reactwith benzoic acid-4-diazosulfate by utilizing different feeding amounts of the 18O-water; carrying out column chromatography silica gel separation to obtain an intermediate product p-hydroxy benzoic acid-18O or p-hydroxy benzoic acid-18O2 respectively; then enabling the intermediate product to be subjected to condensation reaction with a hydroxyl compound under the condition of a catalyst and an organic solvent; finally, separating and purifying to obtain a target product nipagin ester-18O or nipagin ester-18O2. According to the synthesis method provided by the invention, the prepared 18O labeled nipagin ester series product has the advantages that the chemical purity is higher than 98 percent and the abundance of stable isotopes is higher than 95 percent atom 18O; the product can sufficiently meet a mass spectrum detection internal standard substance for detecting content of nipagin ester type preservatives in foods and cosmetics.

Description

technical field [0001] The invention belongs to the technical field of stable isotope-labeled compound synthesis, in particular to a stable isotope 18 Synthetic method of O-labeled parabens. Background technique [0002] In 1932, paraben ester was officially approved as an antifungal agent and fungicide for use in food, and later it was used in cosmetics, medicine and other fields. Among them, in the food industry, paraben esters, as internationally recognized broad-spectrum and high-efficiency food preservatives, have been approved for use in food by the United States, Europe, Japan, Canada, China, Russia and other countries. Currently, they are mainly used in Condiments such as soy sauce and vinegar, pickled products, baked food, sauce products, beverages, rice wine, and fruit and vegetable preservation. China Food Additives Use Hygienic Standard (GB2760-2007) also stipulates that ethylparaben, propylparaben and sodium methylparaben, sodium ethylparaben and sodium propyl...

Claims

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Application Information

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IPC IPC(8): C07C67/08C07C69/88C07C51/367C07C65/03C07B59/00G01N27/62
CPCC07B59/001C07C51/367C07C67/08G01N27/62C07C69/88C07C65/03
Inventor 邱俊王帅肖斌李虎林姜永悦
Owner SHANGHAI RES INST OF CHEM IND
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