840529-31-9

Basic information

• Product Name: (3,4-dimethoxy-phenyl)-(5-[1,3]dioxolan-2-yl-benzo[1,3]dioxol-4-yl)-methanol
• Synonyms: (3,4-dimethoxy-phenyl)-(5-[1,3]dioxolan-2-yl-benzo[1,3]dioxol-4-yl)-methanol
• CAS NO: 840529-31-9
• Molecular Weight: 360.364
• Mol File: 840529-31-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (3,4-dimethoxy-phenyl)-(5-[1,3]dioxolan-2-yl-benzo[1,3]dioxol-4-yl)-methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (3,4-dimethoxy-phenyl)-(5-[1,3]dioxolan-2-yl-benzo[1,3]dioxol-4-yl)-methanol(840529-31-9)
• EPA Substance Registry System: (3,4-dimethoxy-phenyl)-(5-[1,3]dioxolan-2-yl-benzo[1,3]dioxol-4-yl)-methanol(840529-31-9)

Safety Data

• Hazardous Substances Data: 840529-31-9(Hazardous Substances Data)

Upstream product

• 120-57-0 piperonal 
• 4405-18-9 5-[1,3]dioxolan-2-yl-benzo[1,3]dioxole 
• 120-14-9 3,4-dimethoxy-benzaldehyde 

Downstream Products

• 1428438-72-5 C₂₅H₂₄O₈ 
• 1428438-71-4 C₂₃H₂₂O₇ 
• 1428438-70-3 C₂₁H₂₀O₆ 
• 1219694-00-4 10-(3,4-dimethoxyphenyl)-furo[3',4':6,7]naphtho[1,2-d][1,3]dioxole-7,9-dione 

Relevant articles and documents

Synthesis and biological evaluation of helioxanthin analogues

Helioxanthin and analogues have been demonstrated to suppress gene expression of human hepatitis B virus. In the continuous attempt to optimize antiviral activity, various structural motifs were grafted on the helioxanthin scaffold. Many such analogues were synthesized and evaluated for their anti-hepatitis B virus activity. Structure-activity relationships of these helioxanthin derivatives are also discussed. Among these new compounds, 15 exhibits the highest activity against HBV (EC50 = 0.06 μM). This compound can suppress viral surface antigen and DNA expression. Furthermore, viral RNA is also diminished while the core promoter is deactivated upon treatment by 15. A plausible working mechanism is postulated. Our results establish helioxanthin lignans as potent anti-HBV agents with unique mode of action. Since their antiviral mechanism is distinct from current nucleoside/nucleotide drugs, helioxanthin lignans constitute a potentially new class of anti-HBV agents for combination therapy.

Synthesis and antiviral activity of helioxanthin analogues

A series of natural product analogues based on helioxanthin (2), with particular attention to modification of the lactone ring and methylenedioxy group, were synthesized and evaluated for their antiviral activities. Among them, lactam derivative 18 and helioxanthin cyclic hydrazide 28 exhibited significant in vitro antiviral activity against hepatitis B virus (EC 50 = 0.08 and 0.03 μM, respectively). Compound 18 showed the most potent antiviral activity against hepatitis C virus (55% inhibition at 1.0 μM). Compound 12, an acid-hydrolyzed product of helioxanthin cyclic imide derivative 9, was found to exhibit broad-spectrum antiviral activity against hepatitis B virus (EC50 = 0.8 μM), herpes simplex virus type 1 (EC50 = 0.15 μM) and type 2 (EC50 50 = 9.0 μM), and cytomegalovirus (EC 50 = 0.45 μM). Helioxanthin lactam derivative 18 also showed marked inhibition of herpes simplex virus type 1 (EC50 = 0.29 μM) and type 2 (EC50 = 0.16 μM). The cyclic hydrazide derivative of helioxanthin 28 and its brominated product 42 exhibited moderately potent activities against human immunodeficiency virus (EC50 = 2.7 and 2.5 μM, respectively). Collectively, these molecules represent a novel set of antiviral compounds with unique structural features.