21085-72-3

Basic information

• Product Name: ACETOBROMO-ALPHA-D-GLUCURONIC ACID METHYL ESTER
• Synonyms: ACETOBROMO-A-D-GLUCURONIC ACID, METHYL ESTER;methyl tri-O-acetyl-1-bromo-1-deoxy-alpha-D-glucopyranuronate;1-BROMO-2,3,4-TRI-O-ACETYL-ALPHA-D-GLUCURONIC ACID METHYL ESTER; Methyl a-Acetobromoglucuronate;Bromo-2,3,4-tri-O-acetyl-a-d-glucopyranuronic Acid Methyl Ester;(2,3,4-tri-o-acetyl-α-d-glucopyranosyl bromide)uronic acid methyl ester;acetobromo-α-d-glucuronic acid methyl ester;1-Bromo-2,3,4-tri-O-acetyl-a-D-glucuronidemethylester
• CAS NO: 21085-72-3
• Molecular Formula: C₁₃H₁₇BrO₉
• Molecular Weight: 397.17
• EINECS: 244-203-4
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals;carbohydrate
• Mol File: 21085-72-3.mol

Chemical Properties

• Melting Point: 80-110 °C(lit.)
• Boiling Point: 388.6 °C at 760 mmHg
• Flash Point: 188.8 °C
• Appearance: White to gray/Crystalline Powder or Solid
• Density: 1.52
• Vapor Pressure: 3.02E-06mmHg at 25°C
• Refractive Index: 1.504
• Storage Temp.: −20°C
• Solubility: Acetonitrile (Slightly), Chloroform (Slightly, Heated, Sonicated), Dichlorometha
• Stability: Moisture and Temperature Sensitive
• BRN: 96281
• CAS DataBase Reference: ACETOBROMO-ALPHA-D-GLUCURONIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: ACETOBROMO-ALPHA-D-GLUCURONIC ACID METHYL ESTER(21085-72-3)
• EPA Substance Registry System: ACETOBROMO-ALPHA-D-GLUCURONIC ACID METHYL ESTER(21085-72-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 3-8-10-21
• Hazardous Substances Data: 21085-72-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
ACETOBROMO-ALPHA-D-GLUCURONIC ACID METHYL ESTER is used as a synthetic intermediate for the development of HMR1098-S-glucuronide methyl ester, a novel K-ATP-blocking agent. ACETOBROMO-ALPHA-D-GLUCURONIC ACID METHYL ESTER is being researched for its potential in preventing sudden cardiac death.
Used in Cancer Treatment:
ACETOBROMO-ALPHA-D-GLUCURONIC ACID METHYL ESTER is utilized in the synthesis of water-soluble glucuronide derivatives of Camptothecin. These derivatives are employed in cancer prodrug monotherapy and antibody-directed enzyme prodrug therapy (ADEPT), enhancing the targeted delivery and efficacy of Camptothecin in cancer treatment.
Used in Inflammatory Disease Treatment:
ACETOBROMO-ALPHA-D-GLUCURONIC ACID METHYL ESTER is also used in the synthesis of glucuronide prodrug compounds of the Janus kinase (JAK) inhibitor tofacitinib. These prodrugs can be cleaved by β-glucuronidase enzymes, such as those produced by the microbiome in the gastrointestinal tract. This targeted release increases the levels of tofacitinib at the site of gastrointestinal inflammation while limiting systemic exposure, making it a more effective treatment for localized inflammatory diseases.

InChI:InChI=1/C13H17BrO9/c1-5(15)20-8-9(21-6(2)16)11(13(18)19-4)23-12(14)10(8)22-7(3)17/h8-12H,1-4H3

Upstream product

• 40269-24-7 methyl (1,2,3,4-tetra-O-acetyl-α,β-D-galactopyranosid) uronate 
• 18486-47-0 methyl D-galactopyranuronate 
• 67-56-1 methanol 
• 124-41-4 sodium methylate 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 32449-92-6 D-glucurono-6,3-lactone 
• 62133-77-1 1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronic acid 
• 474426-72-7 acetic 1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronic anhydride 
• 489-91-8 D-glucuronic acid 
• 18281-92-0 β-D-glucurono-6,3-lactone 
• 65615-69-2 methyl (5R)-1,2,3,4-tetra-O-acetyl-5-C-bromo-β-D-glucopyranuronate 
• 57690-62-7 methyl 3,4-di-O-acetyl-1,2-dideoxy-D-arabino-hex-1-enopyranuronate 
• 82228-14-6 methyl D-glucopyranuronate 

Downstream Products

• 7355-18-2 (2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 162552-89-8 Methyl O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1->4)-O-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(tert-butyl 2,3-di-O-benzyl-β-D-glucopyranoside)uronate 
• 176718-61-9 (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-(3-cyano-4-nitro-phenoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 176718-56-2 (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-(3-cyano-2-nitro-phenoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 148580-09-0 (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-(4-chloro-2-formyl-phenoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 191352-29-1 (2S,3R,4S,5S,6S)-2-(2-((tert-butoxycarbonyl)(methyl)amino)-4-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 202577-46-6 Methyl 2,3,4-tri-O-acetyl-1-O-2,4-dinitrobenzyl-β-D-glucopyranuronate 
• 202577-47-7 Methyl 2,3,4-tri-O-acetyl-1-O-2,6-dinitrobenzyl-β-D-glucopyranuronate 
• 148579-56-0 (2S,3R,4S,5S,6S)-2-(4-formylphenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 676606-03-4 methyl 2,3,4-tri-O-acetyl-(2'-(4''-methylphenyl)-3'-oxo-1'-(E)-propenyloxy)-β-D-glucopyranosiduronate 
• 221287-88-3 methyl 1-<2-(benzyloxycarbonyl)phenyl>-2,3,4-tri-O-acetyl-β-D-glucopyranuronate 
• 676606-01-2 methyl 2,3,4-tri-O-acetyl-(2'-(4''-nitrophenyl)-3'-oxo-1'-(E)-propenyloxy)-β-D-glucopyranosiduronate 
• 676606-02-3 methyl 2,3,4-tri-O-acetyl-(2'-(4''-fluorophenyl)-3'-oxo-1'-(E)-propenyloxy)-β-D-glucopyranosiduronate 
• 20290-09-9 Morphine 3-b-D-glucuronide 

Relevant articles and documents

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