156334-29-1

Upstream product

• 64302-83-6 1-(prop-2'-enyloxy)anthraquinone 
• 887496-40-4 C₂₆H₃₀O₄ 
• 1086461-09-7 1-benzyloxy-2-propyl-9,10-anthraquinone 
• 67-56-1 methanol 
• 791615-15-1 1-(4-hydroxy-2-nonenyloxy)-2-propyl-9,10-anthraquinone 
• 791808-24-7 2-(3-hydroxy-oct-1-enyl)-11b-methoxy-4-propyl-11bH-1,3-dioxa-benzo[de]anthracen-7-one 

Downstream Products

• 1086461-09-7 1-benzyloxy-2-propyl-9,10-anthraquinone 

Relevant academic research and scientific papers

Observation of heavy atom effects in the development of water soluble caged 4-hydroxy-trans-2-nonenal

During the course of our study on the photochemistry of 1-alkoxy-9,10-anthraquinones, we have developed a second generation of a caged 4-hydroxy-trans-2-nonenal (4-HNE). As we optimized the anthraquinonyl chromophore to achieve water solubility, we studied the photochemistry of various substituents to understand their effect on the photochemistry. We observed a significant heavy atom effect that severely reduced the rate of oxidative cleavage of the alkoxy group. Based on the results of our substituent study, we designed a new caged 4-HNE that is soluble under physiological conditions, and that releases 4-HNE photochemically in high yield.

Caged trans-4-hydroxy-2-nonenal

(Chemical Equation Presented) A caged 4-hydroxy-2-nonenal (4-HNE) has been prepared and its photochemistry investigated. Upon photolysis, 1 releases 4-HNE in up to 100% yield. From these photolyses, 4-HNE could be isolated in up to 91% yield. 4-HNE is produced under either aerobic or anaerobic conditions. The caging strategy does not require prior preparation of 4-HNE and, therefore, represents a three-step synthetic route to the bioactive enal in 48% overall yield.