625848-58-0

Usage

Class

Ketones

Use

Active ingredient in sunscreens

Function

Absorbs ultraviolet radiation (UVB rays)

Additional uses

Cosmetic and personal care products (lotions, moisturizers, lip balms)

Skin irritation

Low potential

Health concerns

Disrupts the endocrine system, may affect hormone function

Regulation

Closely monitored and regulated by health authorities

Upstream product

• 165330-28-9 3-(4-((tert-butyldimethylsilyl)oxy)phenyl)-1,1-diethoxypropan-2-one 
• 123-08-0 4-hydroxy-benzaldehyde 
• 138585-08-7 (4-((tert-butyldimethylsilyl)oxy)phenyl)methanol 
• 138585-09-8 4-(tert-butyldimethylsilyloxy)benzyl chloride 
• 836-42-0 4-benzyloxybenzyl chloride 
• 836-43-1 4-benzyloxybenzyl alcohol 
• 623-05-2 (4-hydroxyphenyl)methanol 

Downstream Products

• 55779-48-1 coelenterazine 
• 123437-48-9 8-benzyl-6-(4-fluorophenyl)-2-(4-hydroxyphenylmethyl)-3,7-dihydroimidazo[1,2-a]pyrazin-3-one 
• 124469-80-3 8-benzyl-6-(N,N-dimethyl-4-aminophenyl)-2-(4-hydroxyphenylmethyl)-3,7-dihydroimidazo[1,2-a]pyrazin-3-one 
• 625848-43-3 ethyl 4-[4-(3,3-diethoxy-2-oxopropyl)phenoxy]butanoate 

Relevant academic research and scientific papers

Coelenterazine analog and preparing method and application thereof

The invention discloses a coelenterazine analog and a preparing method and application thereof. The coelenterazine analog has the general structure formula (I) shown in the description, wherein R1, R2 and R3 in the formula are different substituents. According to application of the compound as a bioluminescence substrate, the existence and quantity (including the enzyme level, the cell level and the animal level) of coelenterazine luciferase can be detected with bioluminescence, and the in vitro, cell and in vivo distribution imaging of luciferase can be detected; the compound can serve as a report signal to detect the pharmacologic action and the toxic effect of medicine on the enzyme level, the cell level and the animal level under the existence of luciferase.

Strategies for large-scale synthesis of coelenterazine for in vivo applications

A new application of two Negishi-type coupling reactions for the synthesis of coelenterazine is reported. The synthesis of coelenterazine in high purity on a gram scale will enable numerous approaches to bioluminescence imaging and possibly photodynamic therapy of deep-seated tumors. Coelenterazine is the substrate for several luciferases, among them Gaussia luciferase (gLuc). This synthesis starts with pyrazin-2-amine and uses inexpensive starting materials and catalysts. Georg Thieme Verlag Stuttgart New York.

Synthesis of 3,7-dihydroimidazo[1,2a]pyrazine-3-ones and their chemiluminescent properties

A series of 3,7-dihydroimidazo[1,2a]pyrazine-3-ones were prepared from 2-amino-3,5-dibromopyrazine. The concise synthesis of coelenterazine (5j), in three steps, 48% overall yield and >99% purity exemplifies the strategy. Further, the synthetic approach facilitated the regiospecific incorporation of carboxyalkyl linkers on the 3,7-dihydroimidazo[1,2a]pyrazine-3-one nucleus that are required for bioconjugation. Peroxymonocarbonate, an electrophilic oxidant, was used to initiate 'pseudo-flash' chemiluminescence from this class of molecules.