1852-43-3

Basic information

• Product Name: ANDROSTERONE GLUCURONIDE CRYSTALLINE
• Synonyms: ANDROSTERONE GLUCURONIDE CRYSTALLINE;(2S,3S,4S,5R,6R)-6-[[(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-3,4,5-trihydroxy-oxane-2-carboxylic acid;3α-Hydroxy-5α-androstan-17-one 3-glucuronide, 5α-Androstan-3α-ol-17-one glucosiduronate;Nsc113101;Androsterone β-D-Glucuronide;3α-Hydroxy-5α-androstan-17-one 3-glucuronide;5α-Androstan-3α-ol-17-one glucosiduronate;androsterone 3-glucosiduronic acid
• CAS NO: 1852-43-3
• Molecular Formula: C₂₅H₃₈O₈
• Molecular Weight: 466.56442
• Product Categories: Glucuronides;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Steroids
• Mol File: 1852-43-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 656.1°Cat760mmHg
• Flash Point: 219.5°C
• Appearance: /
• Density: 1.34g/cm³
• Vapor Pressure: 5.37E-20mmHg at 25°C
• Refractive Index: 1.591
• Storage Temp.: −20°C
• CAS DataBase Reference: ANDROSTERONE GLUCURONIDE CRYSTALLINE(CAS DataBase Reference)
• NIST Chemistry Reference: ANDROSTERONE GLUCURONIDE CRYSTALLINE(1852-43-3)
• EPA Substance Registry System: ANDROSTERONE GLUCURONIDE CRYSTALLINE(1852-43-3)

Safety Data

• Hazardous Substances Data: 1852-43-3(Hazardous Substances Data)

Usage

Definition

ChEBI: A steroid glucosiduronic acid having androsterone as the steroid component.

InChI:InChI=1/C25H38O8/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/h12-16,18-21,23,27-29H,3-11H2,1-2H3,(H,30,31)

Upstream product

• 53-41-8 cis-androsterone 
• 2616-64-0 uridine diphosphoglucuronic acid 
• 777038-38-7 α-D-glucuronyl fluoride 
• 57820-69-6 (3R,4S,5S,6S)-2-bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 313948-92-4 methyl 1-deoxy-1-iodo-2,3,4-tri-O-pivaloyl-α-D-glucopyranuronate 
• 86448-91-1 methyl O¹,O²,O³,O⁴-tetra(2,2-dimethyl-1-oxopropyl)-β-D-glucuronate 
• 21085-73-4 (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-((3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-17-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 

Downstream Products

• 65535-18-4 5α-androstane-3α,17β-diol-3-O-glucuronide 
• 6556-12-3 D-glucuronic acid 
• 53-41-8 cis-androsterone 

Relevant articles and documents

The Escherichia coli glucuronylsynthase promoted synthesis of steroid glucuronides: Improved practicality and broader scope

A library of steroid glucuronides was prepared using the glucuronylsynthase derived from Escherichia coli β-glucuronidase, followed by purification using solid-phase extraction. A representative range of steroid substrates were screened for synthesis on t

Mass spectrometry of steroid glucuronide conjugates. I. Electron impact fragmentation of 5α-/5β-androstan-3α-ol-17-one glucuronides, 5α-estran-3α-ol-17-one glucuronide and deuterium-labelled analogues

Owing to the developments of analytical instruments and interfaces (e.g. coupling high-performance liquid chromatography to mass spectrometry), there has been increased interest in new reference materials, for example in doping analysis with steroid glucuronide conjugates. The synthesized reference material has to pass several characterization steps including the use of gas chromatography/mass spectrometry (GC/MS) for its structure confirmation. In the present study, the fragmentation and mass spectrometric behaviour of several steroid glucuronide conjugates of endogenous and anabolic steroids after derivatization to pertrimethylsilylated products and to methyl ester pertrimethylsilylated products were investigated using GC/MS ion trap and GC/MS quadrupole instruments. The mass spectra of the derivatives of androsterone glucuronide, d5-androsterone glucuronide, epiandrosterone glucuronide, etiocholanolone glucuronide, 11β-hydroxy etiocholanolone glucuronide, 19-norandrosterone glucuronide, d4-19-norandrosterone glucuronide and 1α-methyl-5α-androstan-3α-ol-17-one glucuronide are presented and the origin of typical fragment ions of the glycosidic and steroidal moieties is proposed, based on different derivatization techniques including derivatization with d18-bistrimethylsilylacetamide, methyl ester and trimethylsilyl ester derivatization and selected reaction monitoring. Typical fragmentation patterns which are related to the steroid structure are discussed. Copyright