24751-40-4

Basic information

• Product Name: 5-N-acetyl-2-O-(3-methoxyphenyl)-alpha-D-neuraminic acid
• Synonyms: 5-N-acetyl-2-O-(3-methoxyphenyl)-alpha-D-neuraminic acid
• CAS NO: 24751-40-4
• Molecular Formula: C₁₈H₂₅NO₁₀
• Molecular Weight: 415.3918
• Mol File: 24751-40-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 803.3 °C at 760 mmHg
• Flash Point: 439.6 °C
• Appearance: /
• Density: 1.49 g/cm³
• Vapor Pressure: 3.08E-27mmHg at 25°C
• Refractive Index: 1.615
• CAS DataBase Reference: 5-N-acetyl-2-O-(3-methoxyphenyl)-alpha-D-neuraminic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-N-acetyl-2-O-(3-methoxyphenyl)-alpha-D-neuraminic acid(24751-40-4)
• EPA Substance Registry System: 5-N-acetyl-2-O-(3-methoxyphenyl)-alpha-D-neuraminic acid(24751-40-4)

Safety Data

• Hazardous Substances Data: 24751-40-4(Hazardous Substances Data)

Usage

General Description

5-N-acetyl-2-O-(3-methoxyphenyl)-alpha-D-neuraminic acid, also known as 3-methoxy-4-hydroxybenzyl ester of N-acetylneuraminic acid, is a synthetic compound that is used in biochemical research and drug development. It is a derivative of sialic acid, which is a key component of many glycoproteins and glycolipids. This chemical has potential therapeutic applications in the treatment of various diseases, including cancer and viral infections. It is also used as a tool in the study of sialic acid metabolism and its role in cellular processes. The unique structural features of 5-N-acetyl-2-O-(3-methoxyphenyl)-alpha-D-neuraminic acid make it a valuable tool for understanding the biological functions of sialic acids and developing new drugs targeting sialic acid-related pathways.

InChI:InChI=1/C18H25NO10/c1-9(21)19-14-12(22)7-18(17(25)26,29-16(14)15(24)13(23)8-20)28-11-5-3-4-10(6-11)27-2/h3-6,12-16,20,22-24H,7-8H2,1-2H3,(H,19,21)(H,25,26)/t12-,13+,14+,15+,16+,18+/m0/s1

Upstream product

• 6770-41-8 Methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosyl chloride)onate 
• 150-19-6 O-methylresorcine 
• 128678-37-5 Methyl (3-methoxyphenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate 

Relevant articles and documents

PHASE-TRANSFER-CATALYZED SYNTHESIS OF ARYL α-KETOSIDES OF N-ACETYLNEURAMINIC ACID. A 2-METHYLFLUORAN-6-YL GLYCOSIDE OF N-ACETYLNEURAMINIC ACID, 2-METHYL-6-(5-ACETAMIDO-3,5-DIDEOXY-α-D-glycero-D-galacto-NONULOPYRANOSYLONIC ACID)XANTHENE-9-SPIRO-1'-ISOBENZOFURAN-3'-ONE, A NEW SUBSTRATE..

Glycosidation of N-acetylneuraminic acid by phase-transfer catalysis in chloroform-aqueous alkali gave several known and some new aryl α-ketosides in a short reaction time and in good yields.The 4-methylumbelliferyl α-ketoside, the standard substrate for neuraminidase, was prepared in a yield of up to 70percent.New Neu5Ac ketosides were prepared with fluorescein and the fluorescein analog, 2-methyl-6-hydroxyfluoran (2-methyl-6-hydroxyxanthene-9-spiro-1'-isobenzofuran-3'-one) as aglycons, the latter being synthesized from 2-(2-hydroxy-5-methylbenzoyl) benzoic acid and 3-fluorophenol.The α configuration was ascertained by 400-MHz 1H-NMR spectroscopy and by cleavage of the ketosides with neuraminidases from Vibrio cholerae and Clostridium perfringens.The enzymic hydrolysis of the 2-methylfluoran-6-yl ketoside gave Km values of 82 μM (V. cholerae) and 96 μM (C. perfringens).