50611-86-4

Basic information

• Product Name: Benzeneacetamide,4-hydroxy-N-[5-(4-hydroxyphenyl)- 3-(phenylmethyl)pyrazinyl]-
• Synonyms: COELENTERAMIDE;CEI;Oxidized Oplophorus luciferin;2psj;N-[2-benzyl-6-(4-oxocyclohexa-2,5-dien-1-ylidene)-1H-pyrazin-3-yl]-2-(4-hydroxyphenyl)acetamide
• CAS NO: 50611-86-4
• Molecular Formula: C25H21N3O3
• Molecular Weight: 411.46
• Mol File: 50611-86-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Benzeneacetamide,4-hydroxy-N-[5-(4-hydroxyphenyl)- 3-(phenylmethyl)pyrazinyl]- (CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneacetamide,4-hydroxy-N-[5-(4-hydroxyphenyl)- 3-(phenylmethyl)pyrazinyl]- (50611-86-4)
• EPA Substance Registry System: Benzeneacetamide,4-hydroxy-N-[5-(4-hydroxyphenyl)- 3-(phenylmethyl)pyrazinyl]- (50611-86-4)

Safety Data

• Hazardous Substances Data: 50611-86-4(Hazardous Substances Data)

Upstream product

• 1161931-09-4 coelenterazine hydroperoxide 
• 1186119-92-5 coelenteramide dimethyl ether 
• 55779-48-1 coelenterazine 

Downstream Products

• 1238832-10-4 5-(4-acetoxyphenyl)-2-(4-acetoxyphenyl)acetylamino-3-benzylpyrazine 

Relevant articles and documents

Formation of Coelenteramine from 2-Peroxycoelenterazine in the Ca2+-Binding Photoprotein Aequorin

Aequorin consists of apoprotein (apoAequorin) and (S)-2-peroxycoelenterazine (CTZ-OOH) and is considered to be a transient-state complex of an enzyme (apoAequorin) and a substrate (coelenterazine and molecular oxygen) in the enzymatic reaction. The degradation process of CTZ-OOH in aequorin was characterized under various conditions of protein denaturation. By acid treatment, the major product from CTZ-OOH was coelenteramine (CTM), but not coelenteramide (CTMD), and no significant luminescence was observed. The counterparts of CTM from CTZ-OOH were identified as 4-hydroxyphenylpyruvic acid (4HPPA) and 4-hydroxyphenylacetic acid (4HPAA) by liquid chromatography/electrospray ionization–time-of-flight mass spectrometry (LC/ESI-TOF-MS). In the luminescence reaction of aequorin with Ca2+, similar amounts of 4HPPA and 4HPAA were detected, indicating that CTM is formed by two pathways from CTZ-OOH through dioxetanone anion and not by hydrolysis from CTMD.

Synthesis, structural characterization and antioxidative properties of aminopyrazine and imidazolopyrazine derivatives

The reaction of 2-aminopyrazine 1 with the glyoxal derivatives 2a-c gave the bicyclic imidazolopyrazinones 3a,b and the monocyclic N-substituted aminopyrazines 4b and 5c. Compounds 3 feature unique crystallographic characteristics. Their reactivity towards superoxide anion is about five times the reactivity of Trolox , while the monocyclic pyrazines are inactive.