1421589-35-6

Basic information

• Product Name: (6-{3,5-dihydroxy-2-[3-(4-hydroxyphenyl)propanoyl]phenoxy}-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl (4Z,7Z,10Z,13Z,16Z,19Z)-4,7,10,13,16,19-docosahexaenoate
• Synonyms: (6-{3,5-dihydroxy-2-[3-(4-hydroxyphenyl)propanoyl]phenoxy}-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl (4Z,7Z,10Z,13Z,16Z,19Z)-4,7,10,13,16,19-docosahexaenoate
• CAS NO: 1421589-35-6
• Molecular Weight: 746.895
• Mol File: 1421589-35-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (6-{3,5-dihydroxy-2-[3-(4-hydroxyphenyl)propanoyl]phenoxy}-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl (4Z,7Z,10Z,13Z,16Z,19Z)-4,7,10,13,16,19-docosahexaenoate(CAS DataBase Reference)
• NIST Chemistry Reference: (6-{3,5-dihydroxy-2-[3-(4-hydroxyphenyl)propanoyl]phenoxy}-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl (4Z,7Z,10Z,13Z,16Z,19Z)-4,7,10,13,16,19-docosahexaenoate(1421589-35-6)
• EPA Substance Registry System: (6-{3,5-dihydroxy-2-[3-(4-hydroxyphenyl)propanoyl]phenoxy}-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl (4Z,7Z,10Z,13Z,16Z,19Z)-4,7,10,13,16,19-docosahexaenoate(1421589-35-6)

Safety Data

• Hazardous Substances Data: 1421589-35-6(Hazardous Substances Data)

Upstream product

• 10417-94-4 all cis-5,8,11,14,17-eicosapentaenoic acid 
• 60-81-1 phloridizin 
• 6217-54-5 docosahexaenoic acid 

Relevant articles and documents

Docosahexaenoic acid ester of phloridzin inhibit lipopolysaccharide-induced inflammation in THP-1 differentiated macrophages

Phloridzin or phlorizin (PZ) is a predominant phenolic compound found in apple and also used in various natural health products. Phloridzin shows poor absorption and cellular uptake due to its hydrophilic nature. The aim was to investigate and compare the effect of docosahexaenoic acid (DHA) ester of PZ (PZ-DHA) and its parent compounds (phloridzin and DHA), phloretin (the aglycone of PZ) and cyclooxygenase inhibitory drugs (diclofenac and nimesulide) on production of pro-inflammatory biomarkers in inflammation-induced macrophages by lipopolysaccharide (LPS)-stimulation. Human THP-1 monocytes were seeded in 24-well plates (5 × 105/well) and treated with phorbol 12-myristate 13-acetate (PMA, 0.1 μg/mL) for 48 h to induce macrophage differentiation. After 48 h, the differentiated macrophages were washed with Hank's buffer and treated with various concentrations of test compounds for 4 h, followed by the LPS-stimulation (18 h). Pre-exposure of PZ-DHA ester was more effective in reducing tumor necrosis factor-alpha (TNF-α), interleukin-6 (IL-6) and cyclooxygenase-2 (COX-2) protein levels compared to DHA and nimesulide. However, diclofenac was the most effective in reducing prostaglandin (PGE2) level by depicting a dose-dependent response. However, PZ-DHA ester and DHA were the most effective in inhibiting the activation of nuclear factor-kappa B (NF-κB) among other test compounds. Our results suggest that PZ-DHA ester might possess potential therapeutic activity to treat inflammation related disorders such as type 2 diabetes, asthma, atherosclerosis and inflammatory bowel disease.

Biocatalytic synthesis, structural elucidation, antioxidant capacity and tyrosinase inhibition activity of long chain fatty acid acylated derivatives of phloridzin and isoquercitrin

Our present investigation describes the regioselective enzymatic acylation of two series of acylated derivatives of phloridzin and isoquercitrin with six different long chain saturated, mono- and poly-unsaturated fatty acids. The biocatalytic synthesis wa