649551-69-9

Basic information

• Product Name: (E)-1-(2-hydroxy-4-iodo-phenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• CAS NO: 649551-69-9
• Molecular Formula: C₁₈H₁₇IO₅
• Molecular Weight: 440.229
• Mol File: 649551-69-9.mol

Chemical Properties

• Boiling Point: 555.6°C at 760 mmHg
• Flash Point: 289.8°C
• Density: 1.559g/cm³
• Vapor Pressure: 5.93E-13mmHg at 25°C
• Refractive Index: 1.641
• CAS DataBase Reference: (E)-1-(2-hydroxy-4-iodo-phenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-1-(2-hydroxy-4-iodo-phenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one(649551-69-9)
• EPA Substance Registry System: (E)-1-(2-hydroxy-4-iodo-phenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one(649551-69-9)

Safety Data

• Hazardous Substances Data: 649551-69-9(Hazardous Substances Data)

Upstream product

• 42861-71-2 3-iodophenylacetate 
• 626-02-8 3-Iodophenol 
• 39730-66-0 1-(2-hydroxy-4-iodophenyl)ethan-1-one 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 

Relevant articles and documents

Potential therapeutic antioxidants that combine the radical scavenging ability of myricetin and the lipophilic chain of vitamin E to effectively inhibit microsomal lipid peroxidation

The flavonol myricetin, reacts with oxygen-centred galvinoxyl radicals 28 times faster than d-α-tocopherol (vitamin E), the main lipid-soluble antioxidant in biological membranes. Moreover, each myricetin molecule reduces twice as many such radicals as vitamin E. However, myricetin fails to protect vitamin E-deficient microsomes from lipid peroxidation as assessed by the formation of thiobarbituric acid reactive substances (TBARS). Novel and potentially therapeutic antioxidants have been prepared that combine the radical-scavenging ability of a myricetin-like head group with a lipophilic chain similar to that of vitamin E. C6-C12 alkyl chains are attached to the A-ring of either a 3,3′,4 ′,5′-tetrahydroxyflavone or a 3,2 ′,4′,5′-tetrahydroxyflavone head group to give lipophilic flavonoids (ClogP=4 to 10) that markedly inhibit iron-ADP catalysed oxidation of microsomal preparations. Orientation of the head group as well as total lipophilicity are important determinants of antioxidant efficacy. MM2 models indicate that our best straight chain 7-alkylflavonoids embed to the same depth in the membrane as vitamin E. The flavonoid head groups are prepared by aldol condensation followed by Algar-Flynn-Oyamada (AFO) oxidation or by Baker-Venkataraman rearrangement. The alkyl tails are introduced by Suzuki or Negishi palladium-catalysed cross-coupling or by cross-metathesis catalysed by first generation Grubbs catalyst, which tolerate phenolic hydroxyl and ketone groups.

FLAVONOID COMPOUNDS AS THERAPEUTIC ANTIOXIDANTS

Novel flavonoid compounds having anti-oxidant activity are described. The compounds have been shown to exhibit anti-oxidative properties in biological systems and their utility in a sunscreen or skincare composition or to treat conditions involving oxidative damage, especially curative or prophylactic treatment of Alzheimer's disease or ischaemia-reperfusion injury, is described.