Dihydrorhodamine 123

Base Information

• Chemical Name: Dihydrorhodamine 123
• CAS No.: 109244-58-8
• Molecular Formula: C21H18N2O3
• Molecular Weight: 346.386
• Hs Code.: 2932999099
• European Community (EC) Number: 886-538-4
• DSSTox Substance ID: DTXSID40148859
• Nikkaji Number: J653.521F
• Wikidata: Q72466203
• Mol file: 109244-58-8.mol

Synonyms:dihydrorhodamine 123

Chemical Property of Dihydrorhodamine 123

Chemical Property:

• Vapor Pressure: 3.43E-11mmHg at 25°C
• Melting Point: 163–165℃
• Refractive Index: 1.683
• Boiling Point: 526.877 °C at 760 mmHg
• PKA: 4.70 ± 0.40, most basic, temperature: 25 °C
• Flash Point: 222.398 °C
• PSA: 87.57000
• Density: 1.313g/cm³
• LogP: 5.08590
• Storage Temp.: −20°C
• Solubility.: DMSO: >5mg/mL
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 346.13174244
• Heavy Atom Count: 26
• Complexity: 488

Purity/Quality:

98%Min ^*data from raw suppliers

Dihydrorhodamine 123 ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)C1=CC=CC=C1C2C3=C(C=C(C=C3)N)OC4=C2C=CC(=C4)N
• Description: DHR is a cell-permeable fluorogenic probe that is used as an indicator of intracellular peroxynitrite formation. It is oxidized by peroxynitrite to the highly fluorescent product rhodamine in vitro. Neither nitric oxide, superoxide, nor hydrogen peroxide alone appear to oxidize DHR. Formation of rhodamine can be monitored by fluorescence spectroscopy using excitation and emission wavelengths of 500 and 536 nm, respectively, or by absorbance spectroscopy at 500 nm (ε = 78,800 M?1cm?1). DHR has been used to investigate reactive oxygen intermediates produced by endothelial cells, eosinophils, and reactive microglia.
• Uses: Dihydrorhodamine 123 is the uncharged and nonfluorescent reduction product of the mitochondrion-selective dye rhodamine 123 used for investigation of reacitve oxygen intermediates. Dihydrorhodamine 123 (DHR) has been used for the detection of free intracellular radicals or ROS (reactive oxygen species) in head kidney-derived macrophages. It has also been used in DHR assay in red blood cells and in oxidative burst assay in neutrophils.

Technology Process of Dihydrorhodamine 123

There total 2 articles about Dihydrorhodamine 123 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:

rhodamin 123 (62669-70-9) → Dihydrorhodamine 123 (109244-58-8)

Guidance literature:

With sodium tetrahydroborate; In dichloromethane; water; for 1h;

DOI:10.1021/jm00393a013

Reference yield:

C21H17(2)HN2O3 (1250257-82-9) → Dihydrorhodamine 123 (109244-58-8)

Guidance literature:

With methanol; at 20 ℃; for 4h; pH=7.4; aq. phosphate buffer; Darkness;

DOI:10.1002/anie.201002228

Reference yield: 23.0%

Dihydrorhodamine 123 (109244-58-8) → 4',7'-diiododihydrorhodamine 123 (109244-61-3) + 2',7'-diiododihydrorhodamine 123 (109244-60-2) + 2',4',7'-triiododihydrorhodamine 123 (109244-62-4)

Guidance literature:

With N-chloro-succinimide; ammonium acetate; sodium iodide; In tetrachloromethane; dichloromethane; for 1h; Ambient temperature;

DOI:10.1021/jm00393a013

upstream raw materials:

rhodamin 123

C₂₁H₁₇⁽²⁾HN₂O₃

Downstream raw materials:

4'-iododihydrorhodamine 123

2'-iododihydrorhodamine 123

4',7'-diiododihydrorhodamine 123

2',7'-diiododihydrorhodamine 123

Refernces

• 1、 Kundu, Kousik,Knight, Sarah F.,Lee, Seungjun,Taylor, W. Robert,Murthy, Niren. "A significant improvement of the efficacy of radical oxidant probes by the kinetic isotope effect". supporting information; experimental part. p. 6134 - 6138. Retrieved 2010/12/20.