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Preparation method of ethyl glucuronide and ethyl sulfate of ethyl alcohol non-oxidative metabolite

A technology of glucuronide and ethyl sulfate, which is applied in the field of compound preparation, can solve the problems of lack of purification methods, low yield and purity, etc., and achieve the effects of easy implementation, simple operation, and low environmental requirements

Pending Publication Date: 2020-05-22
SHANXI MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The yield and the purity of the two substances synthesized by this method are low, and the purity and the yield of ethyl sulfate have been improved through method optimization, but the purification method of the two substances is lacking

Method used

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  • Preparation method of ethyl glucuronide and ethyl sulfate of ethyl alcohol non-oxidative metabolite
  • Preparation method of ethyl glucuronide and ethyl sulfate of ethyl alcohol non-oxidative metabolite
  • Preparation method of ethyl glucuronide and ethyl sulfate of ethyl alcohol non-oxidative metabolite

Examples

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Effect test

Embodiment 1

[0038] Synthetic ethanol non-oxidative metabolite ethyl glucuronide, its preparation method is as follows:

[0039](1) Raw materials for the synthesis of triacetylbromoglucuronide methyl ester (BGAME): mix 16.7g glucuronolactone with 200ml methanol (containing 0.3g sodium methoxide), sonicate until completely dissolved, let stand for 30min, 40 ℃ water bath to dry; then add 68ml of acetic anhydride to completely dissolve, then add 10ml of acetic anhydride (containing 0.3ml of perchloric acid) drop by drop, control the temperature during the dropwise addition not to exceed 40°C, overnight at room temperature; add 0.1ml of perchloric acid After mixing evenly, precipitate crystals overnight in a refrigerator at -20°C. After filtration, take the solid part, rinse it with ether until it is milky white, dry it, and put it in a beaker. Use hot ethanol to recrystallize to obtain triacetylbromoglucose Raw material of methyl alkydate (BGAME).

[0040] (2) Synthesis of methyl triacetylbr...

Embodiment 2

[0045] Synthetic ethanol non-oxidative metabolite ethyl glucuronide, its preparation method is as follows:

[0046] (1) Raw materials for the synthesis of triacetylbromoglucuronide methyl ester (BGAME): mix 15.0g glucuronolactone with 250ml methanol (containing 0.2g sodium methoxide), sonicate until completely dissolved, let stand, 40°C Evaporate to dryness in a water bath; add acetic anhydride to dissolve it, add 12ml of acetic anhydride solution dropwise (wherein the acetic anhydride solution contains 3% perchloric acid by volume), overnight at room temperature; then add 0.1ml of perchloric acid After mixing evenly, put it in the refrigerator at -20°C overnight until the crystals are precipitated; after filtering, take the solid part, rinse it with ether to milky white, and dry it to obtain the raw material of triacetyl bromoglucuronide methyl ester (BGAME).

[0047] (2) Synthesis of methyl triacetylbromoglucuronate (BGAME): After mixing 5 g of the BGAME raw material prepare...

Embodiment 3

[0050] Synthetic ethanol non-oxidative metabolite ethyl glucuronide, its preparation method is as follows:

[0051] (1) Raw materials for the synthesis of triacetylbromoglucuronide methyl ester (BGAME): mix 18.0g glucuronolactone with 150ml methanol (containing 0.5g sodium methoxide), sonicate until completely dissolved, let it stand at 40°C Add acetic anhydride to make it dissolve again, dropwise add 12ml of acetic anhydride solution containing perchloric acid (wherein the volume percentage of perchloric acid is 3%), ensure that the temperature of the reaction system in the dropping process is not higher than 40°C overnight at room temperature; then add 0.1ml of perchloric acid, mix well and place in a refrigerator at -20°C overnight until crystals are precipitated; after filtering, take the solid part, wash it with ether until milky white, and dry it to get Raw material of triacetylbromoglucuronide methyl ester (BGAME).

[0052] (2) Synthesis of methyl triacetylbromoglucuro...

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Abstract

The invention relates to a preparation method of ethyl glucuronide and ethyl sulfate of ethyl alcohol non-oxidative metabolite, and belongs to the field of compound preparation. According to the preparation method, glucuronolactone is used as a basic reaction raw material, the ethyl glucuronide of the ethyl alcohol non-oxidative metabolite can be obtained by reacting under ultrasonic, water bath heating and other conditions through a triacetyl bromide glucuronic acid methyl ester intermediate, and the preparation method has the advantages of low environmental factors, simple operation and easyrealization; and in addition, absolute ethyl alcohol and sulfuric acid are used as raw materials, and the ethyl sulfate of the ethyl alcohol non-oxidative metabolite is obtained through heating, filtration, precipitation, water bath evaporating and other operations, and the preparation method has the advantages of wide source of raw materials, low requirements for environmental factors, simple operation and easy realization.

Description

technical field [0001] The invention belongs to the field of compound preparation, and in particular relates to a preparation method of ethyl glucuronide and ethyl sulfate, non-oxidative metabolites of ethanol. Background technique [0002] Ethanol, commonly known as alcohol, is a major substance of abuse worldwide. In forensic practice, in traffic accidents, suspected poisoning suicides, homicide cases, especially in cases involving death, it is necessary to analyze and explain the blood alcohol concentration (BloodAlcohol Concentration, BAC), and the test results are often used to judge Key evidence of party liability. Studies have shown that after ethanol enters the body, four types of non-oxidative metabolites will be generated, including ethyl glucuronate (EtG), ethyl sulfate (EtS), fatty acid ethyl ester (FAEE) and phosphatidylethanol (PEth), They are highly specific and specific and considered to be important biomarkers of ethanol intake. By detecting these non-oxi...

Claims

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Application Information

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IPC IPC(8): C07H15/04C07H1/00C07C303/24C07C303/44C07C305/06
CPCC07H15/04C07H1/00C07C303/24C07C303/44C07C305/06
Inventor 贠克明路玉平尉志文张潮马红娟王颖黄博王乐乐王锐利
Owner SHANXI MEDICAL UNIV
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