Coelenteramine

Base Information

• Chemical Name: Coelenteramine
• CAS No.: 55779-48-1
• Molecular Formula: C26H21 N3 O3
• Molecular Weight: 423.471
• Hs Code.: 29339900
• Mol file: 55779-48-1.mol

Synonyms:Coelenterazin;Coelenterazine; Coelenterazine ntv; Luciferin; Luciferin (Oplophorus);NanoFuel; Native coelenterazine; Preluciferin; Preluciferin (Watasenia);Watasenia preluciferin

Chemical Property of Coelenteramine

Chemical Property:

• Appearance/Colour: Yellow Solid
• Vapor Pressure: 4.77E-17mmHg at 25°C
• Melting Point: 176–181 ℃ (decompose)
• Boiling Point: 641.4°Cat760mmHg
• PKA: 9.91±0.15(Predicted)
• Flash Point: 341.7°C
• PSA: 90.62000
• Density: 1.32g/cm³
• LogP: 4.28240
• Storage Temp.: −20°C
• Sensitive.: Moisture & Light Sensitive
• Solubility.: methanol and ethanol: soluble

Purity/Quality:

99% ^*data from raw suppliers

Coelenterazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: Coelenterazine, native was used:-For Aequorin assaysFor measuring the intracellular calcium concentration in response to ionomycin or PMA using aequorin in COS-7 cellsIn Bioluminescence imaging for analysing the presence of virus-dependent luciferase activity Coelenterazine is a luminophore of the aequorin complex which is oxidized by oxygen to illuminate at 465nm when Ca2+ binds to the complex. Used to measure Ca2+ concentration in cells with high sensitivity an dlarge dynamic range.

Technology Process of Coelenteramine

There total 54 articles about Coelenteramine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.5%

8-Benzyl-6-(4-hydroxy-phenyl)-2-[1-(4-hydroxy-phenyl)-meth-(Z)-ylidene]-2H-imidazo[1,2-a]pyrazin-3-one → coelenterazine (55779-48-1)

Guidance literature:

With sodium tetrahydroborate; In 1,4-dioxane; methanol; for 0.166667h;

DOI:10.3987/COM-98-8207

Reference yield: 65.0%

1,1-diethoxy-3-(4-hydroxyphenyl)-2-propan-2-one (625848-58-0) + 3-benzyl-5-(4-[tert-butyl(dimethyl)silyloxy]phenyl)-3-phenyl-2-pyrazinamine (353497-17-3) → coelenterazine (55779-48-1)

Guidance literature:

With hydrogenchloride; In ethanol; water; for 8h; Inert atmosphere; Reflux;

DOI:10.1055/s-0033-1340556

Reference yield: 64.0%

C12H12O4 + 4-(5-amino-6-benzyl-pyrazin-2-yl)-phenol (37156-84-6) → coelenterazine (55779-48-1)

Guidance literature:

With hydrogenchloride; In ethanol; water; at 80 ℃; for 4.5h; Inert atmosphere;

DOI:10.1021/ol901275n

upstream raw materials:

watasenia preluciferyl β-D-glucopyranosiduronic acid

4-hydroxyphenylpiruvic acid

4-(5-amino-6-benzyl-pyrazin-2-yl)-phenol

3-(p-hydroxyphenyl)-2-oxopropanal

Downstream raw materials:

coelenterazine hydroperoxide

imidazo[1,2-a]pyrazin-3-ol,6-[4-(acetyloxy)phenyl]-2-[[4-(acetyloxy)phenyl]methyl]-8-(phenylmethyl)-3-acetate

coelenteramide

4-(5-amino-6-benzyl-pyrazin-2-yl)-phenol

Refernces

• 1、 Inouye, Satoshi,Nakamura, Mitsuhiro,Hosoya, Takamitsu. "Enzymatic conversion of dehydrocoelenterazine to coelenterazine using FMN-bound flavin reductase of NAD(P)H:FMN oxidoreductase". . p. 24 - 28. Retrieved 2021/12/04.
• 2、 -. "ATP-INDEPENDENT BIOLUMINESCENT REPORTER VARIANTS TO IMPROVE IN VIVO IMAGING". Page/Page column 38; 45-46. . Retrieved 2020/09/12.