Ethyl Glucuronide: An Unusual Ethanol Metabolite in Humans. Synthesis, Analytical Data, and Determination in Serum and Urine

Abstract

Ethyl glucuronide (ethyl beta-D-6-glucosiduronic acid), a minor ethanol metabolite in serum or urine, was determined by gas chromatography-mass spectrometry. Prior to this, ethyl glucuronide was synthesized by the reaction of acetobromo-glucosiduronic acid with ethanol. For the determination of ethyl glucuronide, serum samples were precipitated with acetone, and urine specimens were analyzed after evaporation to dryness. The residues were derivatized with acetic anhydride. Capillary gas chromatography was used to find a retention index value of 1920 for the triacetyl derivative. The mass spectrum of the acetylated ethyl glucuronide was recorded. The calibration is linear in the range investigated (0.1-150 mg/L), and the detection limit is 0.1 mg/L. In individual specimens containing between 0.1 and 4 g ethanol per liter serum, ethyl glucuronide could be detected at concentrations between 3 and 14 mg/L and in the corresponding urine specimens at concentrations between 3 and 130 mg/L.

Ethanol Sulfation by the Human Cytosolic Sulfotransferases: A Systematic Analysis

“…1,2) A lesser known and, in fact, minor metabolic fate of ethanol is the conjugation with sulfate or glucuronic acid, forming ethyl sulfate and ethyl glucuronide. 3,4) Upon ethanol ingestion, ethyl sulfate and ethyl glucuronide are excreted for a considerably longer period of time than ethanol, hence allowing urine testing of these minor ethanol metabolites as a sensitive method to screen for alcohol ingestion. 3,[5][6][7] More recently, ethyl sulfate and ethyl glucuronide have also been implicated as biomarkers for in utero exposure to ethanol.…”

Molecular Species of the Alcohol Biomarker Phosphatidylethanol in Human Blood Measured by LC-MS

“…The conjugated minor ethanol metabolites ethyl glucuronide (2 ) and ethyl sulfate (3 ) and fatty acid ethyl esters (4 ) are examples of such tests. Ethyl glucuronide and ethyl sulfate are excreted in urine for a much longer time than ethanol and hence have gained popularity as diagnostically sensitive and specific tests to spot recent alcohol consumption (5)(6)(7).…”

Confirmatory analysis of ethylglucuronide in urine by liquid-chromatography/electrospray ionization/tandem mass spectrometry according to forensic guidelines

“…In urine, it can be detected longer than ethanol. Therefore, EtG meets the need for a sensitive and specific marker to elucidate alcohol use not detected by standard testing [5][6][7][8][9][10][11][12][13]. Furthermore, EtG has been detected in hair samples [14 -16] and post-mortem tissues (liver, brain, fat tissue [17]) of alcohol addicts.…”