40555-40-6

Basic information

• Product Name: 3-hydroxy-4-(2,3,4,6-tetraacetyl-β-D-glucopyranos-1-yloxy)benzaldehyde
• Synonyms: 3-hydroxy-4-(2,3,4,6-tetraacetyl-β-D-glucopyranos-1-yloxy)benzaldehyde
• CAS NO: 40555-40-6
• Molecular Weight: 468.414
• Mol File: 40555-40-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 3-hydroxy-4-(2,3,4,6-tetraacetyl-β-D-glucopyranos-1-yloxy)benzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3-hydroxy-4-(2,3,4,6-tetraacetyl-β-D-glucopyranos-1-yloxy)benzaldehyde(40555-40-6)
• EPA Substance Registry System: 3-hydroxy-4-(2,3,4,6-tetraacetyl-β-D-glucopyranos-1-yloxy)benzaldehyde(40555-40-6)

Safety Data

• Hazardous Substances Data: 40555-40-6(Hazardous Substances Data)

Upstream product

• 139-85-5 3,4-dihydroxybenzaldehyde 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 604-69-3 β-D-glucose pentaacetate 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 

Downstream Products

• 26398-99-2 3-β-D-galactopyranosyloxy-4-β-D-glucopyranosyloxy-benzaldehyde 
• 1159278-15-5 1,7-bis[3-hydroxy-4-(2,3,4,6-tetraacetyl-β-D-glucopyranos-1-yloxy)phenyl]hepta-1,6-diene-3,5-dione 
• 1186032-12-1 5-[3-hydroxy-4-((2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyloxy)benzylidene]-barbituric acid 
• 1186032-17-6 5-[3-hydroxy-4-((2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyloxy)benzylidene]-2-thiobarbituric acid 
• 26398-99-2 3,4-bis-β-D-glucopyranosyloxy-benzaldehyde 
• 499-21-8 methyl 4-O-β-glucopyranosyl-(E)-caffeate 
• 485388-48-5 3,4-bis-(tetra-O-acetyl-β-D-glucopyranosyloxy)-benzaldehyde 
• 40555-38-2 3-hydroxy-4-O-β-D-glucopyranosylbenzaldehyde 
• 121358-45-0 (4-formyl-2-ethoxyphenyl) 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 119014-23-2 3-hydroxy-4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-trans-cinnamic acid ethyl ester 
• 51482-43-0 4-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)vanillin 

Relevant articles and documents

Synthesis, cytotoxic and combined cDDP activity of new stable curcumin derivatives

New curcumin derivatives are synthesized in order to improve chemical properties of curcumin. The aromatic ring glycosylation of curcumin provides more water-soluble compounds with a greater kinetic stability which is a fundamental feature for drug bioavailability. The glycosylation reaction is quite simple, low cost, with high yield and minimum waste. NMR data show that the ability of curcumin to coordinate metal ion, in particular Ga(III), is maintained in the synthesized products. Although the binding of glucose to curcumin reduces the cytotoxicity of the derivatives towards cisplatin (cDDP)-sensitive and -resistant human ovarian carcinoma cell lines, the compounds display a good selectivity since they are much less toxic against non-tumourigenic Vero cells. The combination of cDDP with the most active glycosyl-curcuminoid drug against both cDDP-sensitive and -resistant as well as against Vero cell lines is tested. The results show an improvement of cDDP efficacy with higher selectivity towards cancer cells than non-cancer cells. These studies indicate the need for developing new valid components of drug treatment protocols to cDDP-resistant cells as well.

Synthesis, chemical and biological studies on new Fe3+-glycosilated β-diketo complexes for the treatment of iron deficiency

A simple synthetic pathway to obtain glycosilated β-diketo derivatives is proposed. These compounds show a good iron(III) affinity therefore we may suggest the use of their Fe3+-complexes as oral iron supplements in the treatment of anaemia. The glycosilated compounds (6-GlcH, 6-GlcOH and 6-GlcOCH3) are characterized by means of spectroscopic (UV, 1H and 13C NMR) and potentiometric techniques; they have a good water solubility, are kinetically stable in physiological condition (t1/2 > 100 h) and show a low cytotoxicity also in high concentrations (IC50 > 400 μM). They are able to bind Fe3+ ion in acid condition (pH ～ 2) forming complex species thermodynamically more stable than those of other ligands commonly used in the treatment of iron deficiency. The iron complexes show also a good kinetic stability both in acidic and physiological pH and have a good lypophilicity (log P > -0.7) that suggests an efficient gastrointestinal absorption in view of their possible use in oral therapy. In addition they demonstrate a poor affinity for competitive biological metal ion such as Ca2+, and in particular 6-GlcOCH3 is able to inhibit lipid peroxidation.