65535-18-4

Usage

Steroid metabolite

17-hydroxyandrostane-3-glucuronide is a steroid metabolite, which means it is a product of the breakdown of a steroid hormone.

Produced in the liver

This metabolite is produced in the liver through the conjugation of the steroid hormone 17-hydroxyandrostane with glucuronic acid.

Commonly found in urine

17-hydroxyandrostane-3-glucuronide is commonly found in urine due to its increased water solubility, which facilitates its excretion from the body.

Marker for androgen levels

This chemical serves as a marker for androgen levels and is often measured to assess adrenal androgens.

Monitors production of androgen hormones

17-hydroxyandrostane-3-glucuronide is used to monitor the production of androgen hormones by the adrenal glands.

Implicated as a potential biomarker

This metabolite has been implicated as a potential biomarker for certain diseases and conditions, such as polycystic ovary syndrome and androgen-secreting tumors.

Crucial role in hormone regulation

17-hydroxyandrostane-3-glucuronide plays a crucial role in the body's hormone regulation.

Valuable tool for medical diagnosis and research

This metabolite serves as a valuable tool for medical diagnosis and research.

InChI:InChI=1/C25H40O8/c1-24-9-7-13(32-23-20(29)18(27)19(28)21(33-23)22(30)31)11-12(24)3-4-14-15-5-6-17(26)25(15,2)10-8-16(14)24/h12-21,23,26-29H,3-11H2,1-2H3,(H,30,31)/t12?,13?,14?,15?,16?,17-,18-,19+,20-,21-,23-,24+,25+/m1/s1

Upstream product

• 1852-43-3 Androsterone glucuronide 

Relevant academic research and scientific papers

Mass spectrometry of steroid glucuronide conjugates. II - Electron impact fragmentation of 3-keto-4-en- and 3-keto-5α-steroid-17-O-β glucuronides and 5α-steroid-3α,17β-diol 3- and 17-glucuronides

The steroid glucuronide conjugates of 16,16,17-d3-testosterone, epitestosterone, nandrolone (19-nortestosterone), 16,16,17-d3-nortestosterone, methyltestosterone, metenolone, mesterolone, 5α-androstane-3α, 17β-diol, 2,2,3,4,4-d5-5α-androstane-3α,17β-diol, 19-nor-5α-androstane-3α,17β-diol, 2,2,4,4-d4-19-nor-5α-androstane-3α,17β-diol and 1α-methyl-5α-androstane-3α/β,17β-diol were synthesized by means of the Koenigs-Knorr reaction. Selective 3- or 17-O-conjugation of bis-hydroxylated steroids was performed either by glucuronidation of the corresponding steroid ketole and subsequent reduction of the keto group or via a four-step synthesis starting from a mono-hydroxylated steroid including (a) protection of the hydroxy group, (b) reduction of the keto group, (c) conjugation reaction and (d) removal of protecting groups. The mass spectra and fragmentation patterns of all glucuronide conjugates were compared with those of the commercially available testosterone glucuronide and their characterization was performed by gas chromatography/mass spectrometry and nuclear magnetic resonance spectroscopy. For mass spectrometry the substances were derivatized to methyl esters followed by trimethylsilylation of hydroxy groups and to pertrimethylsilylated products using labelled and unlabelled trimethylsilylating agents. The resulting electron ionization mass spectra obtained by GC/MS quadrupole and ion trap instruments, full scan and selected reaction monitoring experiments are discussed, common and individual fragment ions are described and their origins are proposed. Copyright