108260-70-4

Basic information

• Product Name: C₁₁H₁₄O₅
• CAS NO: 108260-70-4
• Molecular Weight: 226.229
• Mol File: 108260-70-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: C₁₁H₁₄O₅(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₁H₁₄O₅(108260-70-4)
• EPA Substance Registry System: C₁₁H₁₄O₅(108260-70-4)

Safety Data

• Hazardous Substances Data: 108260-70-4(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 55-10-7 4-hydroxy-3-methoxy-mandelic acid 

Relevant articles and documents

Structure-activity relationships of the ultrapotent vanilloid resiniferatoxin (RTX): The side chain benzylic methylene

The side chain benzylic methylene is a critical element for the vanilloid activity of resiniferatoxin (2a, RTX), and introduction of branching, oxygen functions, or isosteric substitution at this center proved detrimental, with a decrease of potency of 2-3 orders of magnitude compared to the natural product. Conversely, only a modest erosion of activity was observed upon α-methylation and α-methylenation of the side chain. Surprisingly, introduction of an iodine atom in the guaiacyl moiety of the oxygen isoster 2h led to an unexpected and remarkable (>1000-fold) increase of potency, affording 2i, a compound that outperforms RTX in terms of vanilloid agonism and represents the first one-digit picomolar ligand of a TRP channel discovered to date.