1-Bromo-2,3,4-tri-O-acetyl-a-D-glucuronide methyl ester 1% CaCO3

1-Bromo-2,3,4-tri-O-acetyl-α-D-glucuronide methyl ester (1% CaCO3) is a chemically synthesized glucuronic acid derivative where the glucopyranuronic acid core is fully acetylated at the 2, 3, and 4 positions, methylated at the carboxyl group, and brominated at the anomeric position in the α-configuration. Supplied often as a 1% calcium carbonate dispersion to stabilize the compound, it appears as a white crystalline solid with high purity and is utilized as a reactive intermediate in synthetic carbohydrate chemistry and glycobiology. Its molecular formula is C13H17BrO9 with a molecular weight of approximately 397.17 g/mol. The compound serves as a key building block for synthesizing glucuronide prodrugs, enzyme substrates, and glycomimetic analogs. It exhibits selective sugar specificity as an α-D-glucuronide derivative. Manufactured via acetylation, methylation, and bromination of glucuronic acid derivatives, it achieves purity levels ≥98% and minimizes microbial contamination through rigorous synthesis and handling protocols. Analytical validation includes NMR, MS, and chromatographic techniques accompanied by Certificates of Analysis. Recommended storage is in sealed containers at 2–8 °C, protected from moisture and light, ensuring a shelf life of 1–2 years. Applications include synthesis of prodrug conjugates (e.g., JAK inhibitors), enzymatic study tools, and biochemical intermediates relevant for drug delivery and anti-inflammatory therapies.​

IUPAC Name

• Methyl 1-bromo-2,3,4-tri-O-acetyl-α-D-glucopyranuronate

Appearance

• White crystalline solid (often supplied as 1% CaCO3 dispersion)

Source

• Chemical synthesis via controlled acetylation, methylation, and bromination of glucuronic acid derivatives

Molecular Weight and Structure

• Molecular Formula: C13H17BrO9
• Molecular Weight: 397.17 g/mol
• Structure: α-D-glucopyranuronic acid methyl ester with acetyl protections at positions 2, 3, and 4, bromine substituent at anomeric carbon
• Features include esterified carboxyl group and brominated anomeric site enhancing reactivity

Sugar Specificity

• α-D-glucopyranuronic acid derivative with selective acetylation and methylation
• Recognized for enzyme-related synthetic applications and prodrug conjugation

Biological Activity

• Functions as a chemical intermediate, enabling prodrug synthesis and enzyme substrate design
• Acts indirectly in biological activity by controlled release of conjugated therapeutics
• Supports anti-inflammatory drug targeting and biochemical research

Purity and Microbial Contamination

• Purity ≥98%, validated by NMR, MS, and HPLC
• Manufactured using sterile chemical synthesis workflows minimizing microbial contamination

Identity and Quality Control

• Confirmed identities through 1H-NMR, 13C-NMR, mass spectrometry, and chromatographic methods
• Certificates of Analysis and Safety Data Sheets included
• Melting point and other physicochemical properties recorded for quality assurance

Shelf Life and Storage

• Store in tightly sealed containers at 2–8 °C
• Protect from moisture, light, and elevated temperatures
• Stable for approximately 1–2 years under recommended conditions

Application

• Precursor for synthesis of glucuronide prodrugs such as JAK inhibitors
• Used in enzyme substrate assays evaluating β-glucuronidase activity
• Employed in pharmaceutical chemistry for site-specific drug delivery systems
• Facilitates biochemical and medicinal research into glucuronidation pathways

Key Characteristics

• α-D-glucuronide methyl ester, brominated and acetylated for synthetic reactivity
• CAS Number: 21085-72-3
• Molecular Weight: 397.17 g/mol
• White crystalline solid with controlled composition and purity
• Acetylation and bromination enable precise chemical transformations
• Supplied with robust analytic and quality assurance data
• Incorporated in diverse glycochemistry and pharmaceutical syntheses
• Provided as a stabilized compound with CaCO3 for research use

Citations

• Cymit Química product details​
• PubChem molecular information​
• ChemicalBook chemical data​
• Watson Bio profile​
• TCI Chemicals catalog​
• Sigma-Aldrich product specification​
• DiscofineChem research applications​
• Clearsynth chemical profile​
• Pharmaffiliates supplier data​
• PMC glucuronide synthesis article