1852-50-2

Basic information

• Product Name: Estriol-16beta-D-glucopyranosiduronic acid
• Synonyms: ESTRIOL 16-GLUCURONIDE;ESTRIOL 16ALPHA-(BETA-D-GLUCURONIDE);1,3,5(10)-ESTRATRIEN-3,16-ALPHA, 17-BETA-TRIOL 16-GLUCOSIDURONATE;1,3,5[10]-ESTRATRIENE-3,16ALPHA,17BETA-TRIOL 16-GLUCURONIDE;3,16ALPHA,17BETA-TRIHYDROXY-1,3,5[10]-ESTRATRIENE 16-GLUCURONIDE;estriol 16A-(B-D-glucuronide);1,3,5(10)-estratriene-3,16α,17β-triol 16-glucuronide;oestriol 16alpha-(beta-D-glucuronide)
• CAS NO: 1852-50-2
• Molecular Formula: C₂₄H₃₂O₉
• Molecular Weight: 464.51
• Mol File: 1852-50-2.mol

Chemical Properties

• Boiling Point: 738.3°Cat760mmHg
• Flash Point: 253.5°C
• Appearance: /
• Density: 1.51g/cm³
• Vapor Pressure: 6.95E-23mmHg at 25°C
• Refractive Index: 1.667
• Storage Temp.: −20°C
• PKA: 2.82±0.70(Predicted)
• BRN: 67674
• CAS DataBase Reference: Estriol-16beta-D-glucopyranosiduronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Estriol-16beta-D-glucopyranosiduronic acid(1852-50-2)
• EPA Substance Registry System: Estriol-16beta-D-glucopyranosiduronic acid(1852-50-2)

Safety Data

• Hazard Codes: Xn
• Statements: 40
• Safety Statements: 36/37
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 1852-50-2(Hazardous Substances Data)

Usage

Uses

Used in Hormone Replacement Therapy:
Estriol-16beta-D-glucopyranosiduronic acid is used as a hormone replacement agent for addressing symptoms associated with menopause and other conditions where estrogen levels are low. Its increased water solubility and ease of excretion make it a potentially safer and more effective option for hormone replacement therapy.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Estriol-16beta-D-glucopyranosiduronic acid is used as a precursor for the synthesis of various estrogen-based drugs. Its enhanced properties allow for better control over drug formulation and delivery, potentially improving the efficacy and safety of estrogen-based medications.
Used in Research and Development:
Estriol-16beta-D-glucopyranosiduronic acid is utilized in research settings to study the effects of estrogen on various biological processes and to develop new therapeutic agents targeting estrogen receptors. Its unique properties provide valuable insights into the role of estrogen in health and disease, contributing to the advancement of medical knowledge and treatment options.

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(21(24)29)32-23-19(28)17(26)18(27)20(33-23)22(30)31/h3,5,8,13-21,23,25-29H,2,4,6-7,9H2,1H3,(H,30,31)

Upstream product

• 153003-10-2 methyl 3,17β-diacetoxy-1,3,5(10)-estratrien-16α-yl-2,3,4-tri-O-acetyl-β-D-glucopyranosiduronate 
• 50-27-1 Estriol 
• 104202-84-8 16α-(tert-butyldimethylsilyloxy)-1,3,5(10)-estratrien-3,17β-diol 
• 104202-86-0 3,17β-diacetoxy-1,3,5(10)-estratrien-16α-ol 
• 104202-85-9 3,17β-diacetoxy-16α-(tert-butyldimethylsilyloxy)-1,3,5(10)-estratrien 
• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 
• 63700-19-6 Uridine diphospho-D-glucuronic acid triammonium salt 

Downstream Products

• 75088-44-7 N-(6-benzyloxycarbonylaminohexyl)-(3,17β-dihydroxy-1,3,5(10)-estratrien-16α-yl-β-D-glucopyranosid)uronamide 
• 76648-58-3 estriol-16α-glucuronide aminobutyl ethyl isoluminol conjugate 
• 6556-12-3 D-glucuronic acid 
• 50-27-1 Estriol 

Relevant articles and documents

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.

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