1237825-85-2

Upstream product

• 108-73-6 3,5-dihydroxyphenol 
• 80522-42-5 triisopropylsilyl trifluoromethanesulfonate 
• 1622988-32-2 1,3,5-tris(triisopropylsilyloxy)benzene 

Downstream Products

• 1622988-35-5 3,5-dihydroxyphenyl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate 
• 1622988-46-8 4-[3,5-bis(triisopropylsilyloxy)phenoxy]-4-oxobutanoic acid 
• 1622988-47-9 5-[3,5-bis(triisopropylsilyloxy)phenoxy]-5-oxopentanoic acid 
• 1622988-33-3 3,5-bis(triisopropylsilyloxy)phenyl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate 

Relevant academic research and scientific papers

NEW LIPOPHENOL COMPOUNDS AND USES THEREOF

The present invention relates to a compound of formula (I) wherein: - i is 0 or 1; j is 0 or 1; k is 0 or 1; - R1 and R2 are in particular H, (C1-C12)alkyl, or a group of formula C(O)R; - R is a, linear or branched, alkyl radical, comprising at least 19 carbon atoms; - R3 is H and k=0 when j=1; or, when j=0, R3 is -C(O)R or -L-C(O)R; - L, U and L" are linkers; wherein, when j=0, at least one of the groups R1; R2 and R3 comprises a radical R.

Synthesis and evaluation of polyunsaturated fatty acid-phenol conjugates as anti-carbonyl-stress lipophenols

Carbonyl and oxidative stress play a substantial role in various neurodegenerative diseases such as Alzheimer's Disease, Parkinsonism, and Age-related Macular Degeneration (AMD). In retinal pathologies, both mechanisms are involved in the transformation of all-trans-retinal (AtR, reactive aldehyde) into bis-retinoid A2E. Since an accumulation of AtR and A2E contributes to photoreceptor apoptosis, we designed and synthesized a series of O-alkylated resorcinol derivatives featuring enhanced anti-carbonyl-stress properties. Additionally, these phenolic structures are linked to a polyunsaturated fatty acid such as docosahexaenoic acid (C22:6 n-3; DHA) or to a lysophosphatidylcholine-DHA conjugate, in order to specifically increase their bioavailability, and thus, to target the retina. Selective syntheses of phloroglucinol-DHA, resveratrol-DHA, and phloroglucinol-DHA-PC (PC = phosphatidylcholine) conjugates using silyl protecting group strategies are presented, along with results of testing that demonstrate their ability to lower AtR toxicity in ARPE-19 cell lines. In order to use resorcinol derivatives to fight against the carbonyl-stress mechanism observed in retina pathologies, new lipophenol conjugates were synthesized with the aim of increasing bioavailability and reaching retina tissue. Strategies to link polyunsaturated fatty acids to polyphenol backbones are presented, along with the results of testing against retinal pigment epithelial cell lines. Copyright

Synthetic access to bent polycycles by cation-π cyclization

(Equation Presented). The presence of an ether oxygen within a chain undergoing cation-polyene cyclization has a profound influence on the stereochemistry of this important construction, apparently due to nucleophilic participation of oxygen in the cyclization process and formation of an oxonium intermediate, leading to bent fused ring systems.