34994-50-8

Basic information

• Product Name: RESORUFIN SODIUM SALT
• Synonyms: RESORUFIN;RESORUFIN SODIUM SALT;7-HYDROXY-3H-PHENOXAZIN-3-ONE SODIUM SALT;resorufin sodium;RESORUFIN SODIUM SALT (DYE CONTENT 75%);RESORUFIN, FOR MICROSCOPY;3H-Phenoxazin-3-one, 7-hydroxy-, sodium salt;RESORUFIN, SODIUM SALT *FLUORESCENCE REFERENCE STANDARD*
• CAS NO: 34994-50-8
• Molecular Formula: C₁₂H₆NO₃*Na
• Molecular Weight: 235.17
• EINECS: 252-310-2
• Product Categories: Aromatics;Heterocycles
• Mol File: 34994-50-8.mol

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 2.08E-07mmHg at 25°C
• Storage Temp.: −20°C
• Solubility: Methanol (Slightly), Water (Slightly)
• BRN: 174850
• CAS DataBase Reference: RESORUFIN SODIUM SALT(CAS DataBase Reference)
• NIST Chemistry Reference: RESORUFIN SODIUM SALT(34994-50-8)
• EPA Substance Registry System: RESORUFIN SODIUM SALT(34994-50-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37-36
• WGK Germany: 3
• RTECS: SP7698000
• Hazardous Substances Data: 34994-50-8(Hazardous Substances Data)

Usage

Uses

Used in Cytochrome P450 Activity Analysis:
Resorufin Sodium Salt is used as a fluorescent indicator for determining the cytochrome P450 (CYP) 2A5 coumarin 7-hydroxylase (COH) activity changes over a broad range of lipopolysaccharide (LPS) doses. It helps in monitoring the activity of this enzyme, which is crucial for understanding various biological processes.
Used in Ethoxyresorufin-O-Deethylase (EROD) Analysis:
Resorufin Sodium Salt is utilized as an internal standard for EROD analysis. This application aids in the accurate measurement of enzyme activity, which is essential for research and diagnostic purposes.
Used in Fluorescence Detection:
Resorufin Sodium Salt is used as a fluorescent indicator in various fluorescence detection methods. Its ability to fluoresce upon exposure to UV light makes it a valuable tool in the field of molecular biology and biochemistry for detecting and quantifying specific molecules or reactions.

Purification Methods

The free acid is purified by dissolving it in conc H2SO4 which on dilution precipitates resorufin and is filtered off, washed well with hot H2O and dried. [Eichler J Prakt Chem 139 113 1934.] Detailed UV and IR studies were reported by Musso & Mattheis Chem Ber 90 1814 1957]. [pKa: Musso & Rathjen Chem Ber 92 751 1959, Beilstein 27 1V 2263.] The monoacetate [1152-14-3] M 252.2, m 2 2 3o is a fluorogenic substrate used for hydrolytic enzymes, and its fluorescence has Emax 593nm (Eex 500nm, in 0.1M phosphate pH 8.0 with lipase) [Kitson & Kitson Biochem J 322 701 1997]. [Beilstein 27 IV 2263.] The O7-methylresorufin (7-methoxy-3H-phenoxazin-3-one) [5735-89-3] M 227.2, m > 2 2 0o has fluorescence at Emax 585nm (Eexcit 571 nm in deacylase solution) and is used to differentiate isoenzymes of cytochrome P-450. It is insoluble in H2O and dilute alkali but is soluble in EtOH and CHCl3 to give an orange yellow colour. [Kehrmann Justus Liebigs Ann Chem 372 352 1910, Beilstein 27 II 108.]

InChI:InChI=1/C12H7NO3.Na/c14-7-1-3-9-11(5-7)16-12-6-8(15)2-4-10(12)13-9;/h1-6,14H;/q;+1/p-1

Upstream product

• 698-31-7 4-nitroso-1,3-benzenediol 
• 108-46-3 recorcinol 
• 62758-13-8 resazurin sodium salt 
• 7647-01-0 hydrogenchloride 
• 550-82-3 resazurin 
• 7664-93-9 sulfuric acid 
• 123-30-8 4-amino-phenol 
• 1152-14-3 7-acetoxy-3H-phenoxazin-3-one 
• 637-62-7 p-benzoquinone oxime 
• 637-61-6 benzoquinone N-chloroimine 
• 98-95-3 nitrobenzene 
• 1258210-06-8 resorufin levulinate 
• 102-71-6 triethanolamine 

Downstream Products

• 1152-14-3 7-acetoxy-3H-phenoxazin-3-one 
• 550-82-3 resazurin 
• 1166-21-8 7-hydroxyresorufinyl 2-benzoate 
• 635-78-9 resorufin 
• 852671-32-0 (5S,6R,7R)-5,8-Dioxo-3-[(Z)-3-(7-oxo-7H-phenoxazin-3-yloxy)-propenyl]-7-(2-thiophen-2-yl-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 438226-89-2 4,5-bis(1,3,2-dithioarsolan-2-yl) resorufin 
• 101490-85-1 resorufin β-D-glucopyranoside 
• 1363277-75-1 C₂₅H₂₄BNO₅ 
• 79-37-8 oxalyl dichloride 
• 1431540-44-1 resorufin nosylate 
• 1431540-45-2 resorufin tosylate 

Relevant articles and documents

A highly sensitive and selective fluorescence off-on probe for the detection of intracellular endogenous tyrosinase activity

A resorufin-based highly sensitive and selective fluorescence off-on probe with a new recognition moiety for tyrosinase is developed, and applied to detect and image endogenous tyrosinase activity in different living cells.

Organized media effect on the photochemical deoxygenation of resazurin in the presence of triethanolamine

The photodeoxygenation of the synthetic dye resazurin in the presence of triethanolamine was investigated in water, CTAC and SDS direct micelles, AOT and BHDC reverse micelles, and soybean lecithin microemulsions (LEC). In all cases the only product observed was the deoxygenated dye resorufin. Triplet and reaction quantum yields were determined in all media. The photoreaction proceeds more efficiently in the microheterogenous systems with positive interface, CTAC and BHDC, while the lower yield is observed in AOT, SDS and LEC. The initial step in the mechanism is the interaction of the triplet state of the dye with the amine, and the effect of the interface is interpreted by a decrease of the recombination rate of the radicals formed in the initial electron transfer step. Negative and zwitterionic interfaces have no effect on the quantum yield.

Colorimetric and fluorescence analysis of percarbonate and oxygen bleach by perhydrolysis of resorufin ester

Percarbonate is an important oxidant that is widely used in industrial applications and daily life. In this study, a simple colorimetric and fluorescence method for percarbonate determination using resorufin-based probe 1, carrying a pivaloyl protection group as a signaling switch, was developed. Probe 1 exhibited selective and sensitive signaling behavior for percarbonate via perhydrolysis of the pivaloyl group by hydrogen peroxide that was produced from percarbonate, in the presence of commonly encountered metal ions and anions. Among the esters tested as signaling switches, pivalate was optimal owing to its resistance to spontaneous hydrolysis and high signaling speed under the employed conditions. The detection limit for percarbonate was estimated to be 0.45 μM. The probe was applied to the analysis of percarbonate in domestic bleach using a scanner as a field-oriented signal-capturing device.

Chromogenic and fluorogenic signaling of sulfite by selective deprotection of resorufin levulinate

A new sulfite-selective probe system based on resorufin was investigated. Levulinate of resorufin exhibited a prominent chromogenic and turn-on type fluorogenic signaling toward sulfite ions in aqueous media based on the selective deprotection of the levulinate group. The sulfite-selective signaling was possible in the presence of commonly encountered anions.

The catalysed NADH reduction of resazurin to resorufin

Details are reported on the mechanism whereby NADH can be used for the reduction of resazurin 1 to give the fluorescent product resorufin 2, a process requiring the use of a catalyst, such as N-methylphenazinium methosulfate 3.

Reduction of Resazurin by Glutathione activated by Sulfanes and Selenite

Reduction of resazurin by glutathione is efficiently promoted by sulfanes (RSSSR and tetrathionate) or by traces of selenite: the effect can be explained by formation and redox cycling of persulfide (GSSH) and selenopersulfide (GSSeH), which appear to be significantly better reductants (antioxidants) than GSH.