7219-89-8

Basic information

• Product Name: 1,3,5[10]-ESTRATRIENE-3,16ALPHA,17BETA-TRIHYDROXY 17-GLUCURONIDE
• Synonyms: ESTRIOL 17BETA-(BETA-D-GLUCURONIDE);3,16ALPHA,17BETA-TRIHYDROXY-1,3,5[10]-ESTRATRIENE 17-GLUCURONIDE;1,3,5[10]-ESTRATRIENE-3,16ALPHA,17BETA-TRIHYDROXY 17-GLUCURONIDE;estriol 17B-(B-D-glucuronide)free acid;estriol 17-glucuronide;oestriol 17beta-(beta-D-glucuronide);1,3,5(10)-Estratriene-3,16α,17β-trihydroxy 17-glucuronide, 3,16α,17β-Trihydroxy-1,3,5(10)-estratriene 17-glucuronide;Estriol 17β-(β-D-glucuronide)
• CAS NO: 7219-89-8
• Molecular Formula: C₂₄H₃₂O₉
• Molecular Weight: 464.51
• Mol File: 7219-89-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 738.3°C at 760 mmHg
• Flash Point: 253.5°C
• Appearance: /
• Vapor Pressure: 6.95E-23mmHg at 25°C
• Storage Temp.: −20°C
• CAS DataBase Reference: 1,3,5[10]-ESTRATRIENE-3,16ALPHA,17BETA-TRIHYDROXY 17-GLUCURONIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5[10]-ESTRATRIENE-3,16ALPHA,17BETA-TRIHYDROXY 17-GLUCURONIDE(7219-89-8)
• EPA Substance Registry System: 1,3,5[10]-ESTRATRIENE-3,16ALPHA,17BETA-TRIHYDROXY 17-GLUCURONIDE(7219-89-8)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-40
• Safety Statements: 22-36
• WGK Germany: 3
• Hazardous Substances Data: 7219-89-8(Hazardous Substances Data)

Usage

Chemical structure

A glucuronide conjugate of estradiol, a steroid hormone.

Formation

Occurs in the liver by the addition of glucuronic acid to the hydroxyl groups at positions 3, 16, and 17 of the estradiol molecule.

Metabolism

Conjugation reaction is a key step in the metabolism and elimination of estradiol from the body.

Solubility

The resulting glucuronide form is more water-soluble compared to the parent compound, estradiol.

Excretion

Can be easily excreted in the urine due to increased water solubility.

Function

Important in the regulation of estrogen levels in the body.

Role

Plays a role in hormone balance and metabolism.

InChI:InChI=1/C24H32O9/c1-24-7-6-13-12-5-3-11(25)8-10(12)2-4-14(13)15(24)9-16(26)21(24)33-23-19(29)17(27)18(28)20(32-23)22(30)31/h3,5,8,13-21,23,25-29H,2,4,6-7,9H2,1H3,(H,30,31)/p-1/t13-,14-,15+,16-,17+,18+,19-,20+,21+,23+,24+/m1/s1

Upstream product

• 50-27-1 Estriol 
• 63700-19-6 uridine-5'-diphospho-α-D-glucuronic acid trisodium salt 
• 63700-19-6 Uridine diphospho-D-glucuronic acid triammonium salt 
• 153003-13-5 methyl 3-acetoxy-16α-(tert-butyldimethylsilyloxy)-1,3,5(10)-estratrien-17β-yl-2,3,4-tri-O-acetyl-β-D-glucopyranosiduronate 
• 153003-11-3 methyl 3-hydroxy-16α-(tert-butyldimethylsilyloxy)-1,3,5(10)-estratrien-17β-yl-2,3,4-tri-O-acetyl-β-D-glucopyranosiduronate 
• 153003-12-4 3-acetoxy-16α-(tert-butyldimethylsilyloxy)-1,3,5(10)-estratrien-17β-ol 
• 104202-84-8 16α-(tert-butyldimethylsilyloxy)-1,3,5(10)-estratrien-3,17β-diol 
• 39130-74-0 methyl 3-acetoxy-16α-hydroxy-1,3,5(10)-estratrien-17β-yl-2,3,4-tri-O-acetyl-β-D-glucopyranosiduronate 
• 18842-02-9 methyl 1-O-<3,16α-dihydroxy-estra-1,3,5(10)-trien-17β-yl>-2,3,4-tri-O-acetyl-β-D-glucopyranosiduronate 

Downstream Products

• 6556-12-3 D-glucuronic acid 
• 50-27-1 Estriol 

Relevant articles and documents

Regiospecificity and stereospecificity of human udpglucuronosyltransferases in the glucuronidation of estriol, 16-epiestriol, 17-epiestriol, and 13-epiestradiols

The glucuronidation of estriol, 16-epiestriol, and 17-epiestriol by the human UDP-glucuronosyltransferases (UGTs) of subfamilies 1A, 2A, and 2B was examined. UGT1A10 is highly active in the conjugation of the 3-OH in all these estriols, whereas UGT2B7 is the most active UGT toward one of the ring D hydroxyls, the 16-OH in estriol and 16-epiestriol, but the 17-OH in 17-epiestriol. Kinetic analyses indicated that the 17-OH configuration plays a major role in the affinity of UGT2B7 for estrogens. The glucuronidation of the different estriols by the human liver and intestine microsomes reflects the activity of UGT1A10 and UGT2B7 in combination with the tissues' difference in UGT1A10 expression. The UGT1A10 mutant 1A10-F93G exhibited much higher Vmax values than UGT1A10 in estriol and 17-epiestriol glucuronidation, but a significantly lower value in 16-epiestriol glucuronidation. To this study on estriol glucuronidation we have added experiments with 13-epiestradiol, a synthetic estradiol in which the spatial arrangement of the methyl on C18 and the hydroxyl on C17 is significantly different than in other estrogens. In comparison with estradiol glucuronidation, the C13 configuration change decreases the turnover of UGTs that conjugate the 3-OH, but increases it in UGTs that primarily conjugate the 17-OH. Unexpectedly, UGT2B17 exhibited similar conjugation rates of both the 17-OH and 3-OH of 13-espiestradiol. The combined results reveal the strong preference of UGT1A10 for the 3-OH of physiologic estrogens and the equivalently strong preference of UGT2B7 and UGT2B17 for the hydroxyls on ring D of such steroid hormones. Copyright

The synthesis of estriol 16- and 17-monoglucuronide from estriol

An efficient and convenient procedure for the synthesis of estriol 16- and 17-monoglucuronides from estriol is described. This is achieved by the selective protection and deprotection of the hydroxy groups in estriol, Koenigs-Knorr reactions with methyl 1-bromo-1-deoxy-2,3,4-tri-O-acetyl-α-D-glucopyranuronate and subsequent hydrolysis. The products have been characterized by proton nuclear magnetic resonance (1H NMR), two-dimensional 1H homonuclear shift-correlated spectra (2D-COSY) and mass spectra. The selective Koenigs-Knorr reaction of the alcoholic hydroxyl group in the presence of a phenolic hydroxyl group is also reported. Keywords: steroids; estriol; estriol 16- and 17-glucuronides; selective protection; Koenigs-Knorr reaction; synthesis.