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Merck

D1054

Dihydrorhodamine 123

≥95% purity, powder

Synonym(s):

DHR 123; Methyl 2-(3,6-diamino-9H-xanthen-9-yl)benzoate; Benzoic acid, 2-(3,6-diamino-9H-xanthen-9-yl)-, methyl ester

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About This Item

Empirical Formula (Hill Notation):
C21H18N2O3
CAS Number:
109244-58-8
Molecular Weight:
346.38
NACRES:
NA.47
PubChem Substance ID:
24893337
UNSPSC Code:
12171500
MDL number:
MFCD00285712
Beilstein/REAXYS Number:
5989965

Product Name

Dihydrorhodamine 123, ≥95%

InChI

1S/C21H18N2O3/c1-25-21(24)15-5-3-2-4-14(15)20-16-8-6-12(22)10-18(16)26-19-11-13(23)7-9-17(19)20/h2-11,20H,22-23H2,1H3

SMILES string

COC(=O)c1ccccc1C2c3ccc(N)cc3Oc4cc(N)ccc24

InChI key

FNEZBBILNYNQGC-UHFFFAOYSA-N

assay

≥95%

form

powder

technique(s)

titration: suitable

color

pink

solubility

DMSO: >5 mg/mL

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

−20°C

Quality Level

200

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Application

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.

Biochem/physiol Actions

Dihydrorhodamine 123 detects superoxide ions at the single-cell level and is used for probing neutrophils superoxide generation in a respiratory burst event. It is also used for measuring oxidative stress in macrophages and human spermatozoa.
Dihydrorhodamine 123 is used for the detection of ROS (reactive oxygen species). Presence of ROS oxidizes dihydrorhodamine 123 to the fluorescent derivative rhodamine 123. The reaction happens in the presence of a peroxidase or a similar catalyst.

General description

Dihydrorhodamine 123 (DHR123) is an uncharged non-fluorescent dye and a derivative of rhodamine 123 (R123). Dihydrorhodamine 123 (DHR123) is oxidized to fluorescent R123 within cells in the presence of reactive oxygen species and it localizes in mitochondria. It is an analog of 2,7-Dichlorodihydrofluorescein (DCDHF), lipophilic and diffuses through cell membrane.
Peroxidase substrate

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000508876
0000508874
0000508876
0000508874
0000487810

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Chronic granulomatous disease in Morocco: genetic, immunological, and clinical features of 12 patients from 10 kindreds
Baba LA, et al.
Journal of clinical immunology, 34(4), 452-458 (2014)
Xin Chen et al.
Frontiers in molecular neuroscience, 10, 232-232 (2017-08-12)
Alzheimer's disease (AD) is a progressive neurodegeneration. Oligomers of amyloid-β peptides (Aβ) are thought to play a pivotal role in AD pathogenesis, yet the mechanisms involved remain unclear. Two major isoforms of Aβ associated with AD are Aβ40 and Aβ42
Dichlorodihydrofluorescein and dihydrorhodamine 123 are sensitive indicators of peroxynitrite in vitro: implications for intracellular measurement of reactive nitrogen and oxygen species
Crow JP
Nitric Oxide, 1(2), 145-157 (1997)
Characterization of the calcium-mediated response to alkaline stress in Saccharomyces cerevisiae.
Viladevall L, et al.
The Journal of Biological Chemistry, 279, 43614-43624 (2004)
Dihydrorhodamine 123: a fluorescent probe for superoxide generation?
HENDERSON LM and CHAPPELL JB
European Journal of Biochemistry, 217(3), 973-980 (1993)
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