62669-70-9

Basic information

• Product Name: Rhodamine 123
• Synonyms: Rhodamine methyl ester hydrochloride;Rhodamin 123 Chloride, laser grade;2-(6-Amino-3-imino-3H-xanthen-9-yl)benzoic acid methyl ester monohydrochloride;Benzoic acid, 2-(6-amino-3-imino-3H-xanthen-9-yl)-, methyl ester, monohydrochloride;Xanthylium, 3,6-diamino-9-(2-(methoxycarbonyl)phenyl)-, chloride;Rhodamine 123 ,98%;RHODAMINE 123, 99+%, PURE;Rhodamine 123, pure
• CAS NO: 62669-70-9
• Molecular Formula: C₂₁H₁₇N₂O₃*Cl
• Molecular Weight: 380.82
• EINECS: 263-687-8
• Product Categories: Fluorescent Labels & Indicators;Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Xanthene
• Mol File: 62669-70-9.mol

Chemical Properties

• Melting Point: 235 °C
• Appearance: Red-brown to brown or dark green/Powder
• Density: 1.2224 (rough estimate)
• Refractive Index: 1.6500 (estimate)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: ethanol: 20 mg/mL, clear, red
• Water Solubility: Partially soluble
• Stability: Hygroscopic
• BRN: 6030951
• CAS DataBase Reference: Rhodamine 123(CAS DataBase Reference)
• NIST Chemistry Reference: Rhodamine 123(62669-70-9)
• EPA Substance Registry System: Rhodamine 123(62669-70-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: ZE0883000
• Hazardous Substances Data: 62669-70-9(Hazardous Substances Data)

Usage

Uses

Used in Biomedical Research:
Rhodamine 123 is used as a fluorescent dye for detecting side population stem cells and studying the function of P-glycoprotein (P-gp) in efflux activity.
Used in Flow Cytometry:
Rhodamine 123 is used as a functional reporter for P-gp in flow cytometry, allowing for the quantification of P-gp functional efflux activity in vivo.
Used in Drug Delivery and Development:
Rhodamine 123 is used as a fluorescent dye-labeled compound for studying drug delivery systems and the development of novel therapeutic agents.
Used in Cell Biology:
Rhodamine 123 is used as a mitochondrial-specific fluorescent dye to study mitochondrial function and oxidative phosphorylation.
Used in Multiparameter Analysis:
Rhodamine 123 can be used in combination with common protein labeling dyes such as PE-Cy5 and AMCA (7-amino-4-methylcoumarin-3-acetic acid) for multiparameter analyses without fluorescence interference.
Used in Laser Applications:
Rhodamine 123 is used as a laser dye and has selective cell growth effects, making it useful in various laser applications.

in vitro

rhodamine 123, which was identified as a member of the rhodamine family of flurone dyes, was used to examine membrane transport by the abcb1 gene product, mdr1. previous study determined the λmax for excitation and emission for rhodamine 123 in commonly used solvents and extraction buffers, indicating that the fluorescence of rhodamine 123 was highly dependent on the chemical environment. the optimal parameters are 1% methanol in hbss. in addition, the uptake of rhodamine 123 into cells was via both passive and active processes, and this occurred mainly by oatp1a2-mediated transport. furthermore, this previous study quantified the intracellular sequestration and metabolism of rhodamine 123, showing that these were both cell line-dependent factors that might influence the interpretation of transport assays [1].

references

[1] samantha forster et al. characterization of rhodamine-123 as a tracer dye for use in in vitro drug transport assays. plos one. 2012; 7(3): e33253.

InChI:InChI=1/C21H17N2O3.ClH/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;/h2-11H,22-23H2,1H3;1H/q+1;/p-1

Synthetic route

methanol (67-56-1) + rhodamine 110 chloride (13558-31-1) → rhodamin 123 (62669-70-9)

Conditions	Yield
With hydrogenchloride 1.) reflux, 6 h, 2.) RT, overnight;
With sulfuric acid at 50℃; Esterification;
With acetyl chloride at 50℃; Fischer esterification;

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

Conditions	Yield
In acetone Electrochemical reaction;

rhodamin 123 (62669-70-9) → 2'-(6-amino-4,5-dibromo-3-imino-3H-xanthen-9-yl)benzoic acid methyl ester hydrochloride

Conditions	Yield
With bromine In ethanol for 73.5h; Ambient temperature;	100%

potassium tetrachloroplatinate(II) (10025-99-7) + rhodamin 123 (62669-70-9) → bis(rhodamine 123)tetrachloroplatinate(II) tetrahydrate (104114-29-6)

Conditions	Yield
In water stirring (30 min, pptn.); filtration, washing (H2O, 1N HCl, EtOH, ether), drying (vac.); elem. anal.;	78%

rhodamin 123 (62669-70-9) → 2-(6-Amino-3-imino-2,7-diiodo-3H-xanthen-9-yl)-benzoic acid methyl ester; hydrochloride

Conditions	Yield
With Iodine monochloride In tetrahydrofuran for 5h; Ambient temperature;	76%

rhodamin 123 (62669-70-9) → 2-(6-Amino-2,7-dibromo-3-imino-3H-xanthen-9-yl)-benzoic acid methyl ester; hydrochloride

Conditions	Yield
With bromine In ethanol at -40℃; for 2h;	76%

rhodamin 123 (62669-70-9) → 2-(6-Amino-2-bromo-3-imino-3H-xanthen-9-yl)-benzoic acid methyl ester; hydrochloride

Conditions	Yield
With bromine In ethanol for 1h;	62%

rhodamin 123 (62669-70-9) → 2-(6-Amino-2,4,5,7-tetrabromo-3-imino-3H-xanthen-9-yl)-benzoic acid methyl ester; hydrochloride

Conditions	Yield
With bromine In ethanol for 2h; Ambient temperature;	56.45%

rhodamin 123 (62669-70-9) → 2-(6-Amino-3-imino-2-iodo-3H-xanthen-9-yl)-benzoic acid methyl ester; hydrochloride

Conditions	Yield
With Iodine monochloride In tetrahydrofuran for 5h; Ambient temperature;	34%

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

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

rhodamin 123 (62669-70-9) → [125]I-methyl o-(2-iodo-6-amino-3-imino-3H-xanthen-9-yl)benzoate monochloride

Conditions	Yield
With peracetic acid; sodium (¹²⁵I)iodide; [131I]-sodium iodide; acetate buffer; sodium acetate for 1h; Ambient temperature; Yield given;

rhodamin 123 (62669-70-9) → 2-(6-Amino-3-imino-3H-xanthen-9-yl)-benzoic acid methyl ester; compound with perchloric acid

Conditions	Yield
With sodium perchlorate In water cation exchange;

p-Aminophenethylamine (13472-00-9) + rhodamin 123 (62669-70-9) → 2-(6-amino-3-imino-3H-xanthen-9-yl)-N-[2-(4-amino-phenyl)-ethyl]-benzamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 12h; amidation;

4-Aminobutanol (13325-10-5) + rhodamin 123 (62669-70-9) → 2-(6-amino-3-imino-3H-xanthen-9-yl)-N-(4-hydroxy-butyl)-benzamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 12h; amidation;

rhodamin 123 (62669-70-9) + 17-(2-amino-ethylamino)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-ol → 2-(6-amino-3-imino-3H-xanthen-9-yl)-N-[2-(3-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ylamino)-ethyl]-benzamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 96h; amidation;

rhodamin 123 (62669-70-9) → 2-{6-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-[(Z)-9H-fluoren-9-ylmethoxycarbonylimino]-2-iodo-3H-xanthen-9-yl}-benzoic acid methyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: 34 percent / ICl / tetrahydrofuran / 5 h / Ambient temperature 2: 70 percent / diisopropylethylamine / CH2Cl2 / 4 h View Scheme

rhodamin 123 (62669-70-9) → 2-[6-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-imino-2-iodo-3H-xanthen-9-yl]-benzoic acid methyl ester; hydrochloride

Conditions	Yield
Multi-step reaction with 2 steps 1: 34 percent / ICl / tetrahydrofuran / 5 h / Ambient temperature 2: diisopropylethylamine / CH2Cl2 / 4 h View Scheme

rhodamin 123 (62669-70-9) → 4'-iododihydrorhodamine 123 (109282-63-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaBH4 / CH2Cl2; H2O / 1 h 2: 11 percent / NaI, N-chlorosuccinimide (NClS), 0.2 M NH4OAc / methanol; CH2Cl2; CCl4 / 1 h / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: NaBH4 / CH2Cl2; H2O / 1 h 2: 5 percent / NaI, N-chlorosuccinimide (NClS), 0.2 M NH4OAc / methanol; CH2Cl2; CCl4 / 1 h / Ambient temperature View Scheme

rhodamin 123 (62669-70-9) → 2'-iododihydrorhodamine 123 (109244-59-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaBH4 / CH2Cl2; H2O / 1 h 2: 21 percent / NaI, N-chlorosuccinimide (NClS), 0.2 M NH4OAc / methanol; CH2Cl2; CCl4 / 1 h / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: NaBH4 / CH2Cl2; H2O / 1 h 2: 44 percent / NaI, N-chlorosuccinimide (NClS), 0.2 M NH4OAc / methanol; CH2Cl2; CCl4 / 1 h / Ambient temperature View Scheme

rhodamin 123 (62669-70-9) → 4',7'-diiododihydrorhodamine 123 (109244-61-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaBH4 / CH2Cl2; H2O / 1 h 2: 12 percent / NaI, N-chlorosuccinimide (NClS), 0.2 M NH4OAc / methanol; CH2Cl2; CCl4 / 1 h / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: NaBH4 / CH2Cl2; H2O / 1 h 2: 23 percent / NaI, N-chlorosuccinimide (NClS), 0.2 M NH4OAc / CH2Cl2; CCl4 / 1 h / Ambient temperature View Scheme

rhodamin 123 (62669-70-9) → 2',7'-diiododihydrorhodamine 123 (109244-60-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaBH4 / CH2Cl2; H2O / 1 h 2: 17 percent / NaI, N-chlorosuccinimide (NClS), 0.2 M NH4OAc / methanol; CH2Cl2; CCl4 / 1 h / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: NaBH4 / CH2Cl2; H2O / 1 h 2: 9 percent / NaI, N-chlorosuccinimide (NClS), 0.2 M NH4OAc / methanol; CH2Cl2; CCl4 / 1 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: NaBH4 / CH2Cl2; H2O / 1 h 2: 25 percent / NaI, N-chlorosuccinimide (NClS), 0.2 M NH4OAc / CH2Cl2; CCl4 / 1 h / Ambient temperature View Scheme

rhodamin 123 (62669-70-9) → 2',4',7'-triiododihydrorhodamine 123 (109244-62-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaBH4 / CH2Cl2; H2O / 1 h 2: 7 percent / NaI, N-chlorosuccinimide (NClS), 0.2 M NH4OAc / CH2Cl2; CCl4 / 1 h / Ambient temperature View Scheme

rhodamin 123 (62669-70-9) + Cycloheximide (66-81-9) → C36H39N3O6

Conditions	Yield
With sodium cyanoborohydride; acetic acid In methanol; water at 37℃; for 16h;

rhodamin 123 (62669-70-9) + β‐cyclodextrin (7585-39-9) → C42H70O35*C21H16N2O3*ClH

Conditions	Yield
In water at 14.84℃; Thermodynamic data; Temperature;

heptakis(2,6-di-O-methyl)cyclomaltoheptaose (51166-71-3) + rhodamin 123 (62669-70-9) → C56H98O35*C21H16N2O3*ClH

Conditions	Yield
In water at 14.84℃; Thermodynamic data; Temperature;

rhodamin 123 (62669-70-9) + lithium bis((pentafluoroethyl)sulfonyl)amide → C21H16N2O3*C4F10NO4S2(1-)*H(1+)

Conditions	Yield
In dichloromethane; water at 20℃; for 48h;

sodium tetraphenyl borate (143-66-8) + rhodamin 123 (62669-70-9) → C21H16N2O3*C24H20B(1-)*H(1+)

Conditions	Yield
In dichloromethane; water at 20℃; for 48h;

Upstream product

• 67-56-1 methanol 
• 13558-31-1 rhodamine 110 chloride 
• 109244-58-8 Dihydrorhodamine 123 

Downstream Products

• 109244-58-8 Dihydrorhodamine 123 
• 109282-63-5 4'-iododihydrorhodamine 123 
• 109244-59-9 2'-iododihydrorhodamine 123 
• 109244-61-3 4',7'-diiododihydrorhodamine 123 
• 109244-60-2 2',7'-diiododihydrorhodamine 123 
• 109244-62-4 2',4',7'-triiododihydrorhodamine 123 
• 104114-29-6 bis(rhodamine 123)tetrachloroplatinate(II) tetrahydrate 

Relevant articles and documents

Phototoxicity of some bromine-substituted rhodamine dyes: synthesis, photophysical properties and application as photosensitizers.

The synthesis of some bromine-substituted rhodamine derivatives viz., 4,5-dibromorhodamine methyl ester (dye 2) and 4,5-dibromorhodamine n-butyl ester (dye 3) are reported. These dyes were synthesized to promote a more efficient cancer cell photosensitizer for potential use in in vitro bone marrow purging in preparation for autologous bone marrow transplantation. Spectroscopic and photophysical characterization of these dyes together with rhodamine 123 (dye 1) are reported in water, methanol, ethanol and also in a microheterogeneous system, sodium dodecyl sulfate. The possible mechanism of photosensitization is characterized in terms of singlet oxygen efficiency of these dyes. Singlet oxygen quantum yields for bromine-substituted dyes are in the range of 0.3-0.5 depending on the solvent. For dye 1 no singlet oxygen production is found. The photodynamic actions of these dyes in different cell lines are tested. It was found that dye 2 and dye 3 are efficient photosensitizers and mediate eradication of K562, EM2, myeloid cell lines (CML) and the SMF-AI rhabdomyosarcoma line.

Facile synthesis of rhodamine esters using acetyl chloride in alcohol solution

The rhodamines are a highly fluorescent class of compound used in many different fields of research, from the lasing medium in dye lasers to biological stains and markers for cellular drug resistance. In this study, esters (2-7) of rhodamine 110 (1) were conveniently prepared via the addition of acetyl chloride to a solution of the free acid (1) in the appropriate alcohol. This method conferred several advantages over previous preparations, namely that for low boiling alcohols, simple evaporation of the solution afforded the ester in quantitative yield with no need for purification. For higher boiling point alcohols, a method has been developed which allows the separation of longer chain esters from the alcohol solvent. Copyright Taylor & Francis Group, LLC.

Does Perthionitrite (SSNO-) Account for Sustained Bioactivity of NO? A (Bio)chemical Characterization

Hydrogen sulfide (H2S) and nitric oxide (NO) are important signaling molecules that regulate several physiological functions. Understanding the chemistry behind their interplay is important for explaining these functions. The reaction of H2S with S-nitrosothiols to form the smallest S-nitrosothiol, thionitrous acid (HSNO), is one example of physiologically relevant cross-talk between H2S and nitrogen species. Perthionitrite (SSNO-) has recently been considered as an important biological source of NO that is far more stable and longer living than HSNO. In order to experimentally address this issue here, we prepared SSNO- by two different approaches, which lead to two distinct species: SSNO- and dithionitric acid [HON(S)S/HSN(O)S]. (H)S2NO species and their reactivity were studied by 15N NMR, IR, electron paramagnetic resonance and high-resolution electrospray ionization time-of-flight mass spectrometry, as well as by X-ray structure analysis and cyclic voltammetry. The obtained results pointed toward the inherent instability of SSNO- in water solutions. SSNO- decomposed readily in the presence of light, water, or acid, with concomitant formation of elemental sulfur and HNO. Furthermore, SSNO- reacted with H2S to generate HSNO. Computational studies on (H)SSNO provided additional explanations for its instability. Thus, on the basis of our data, it seems to be less probable that SSNO- can serve as a signaling molecule and biological source of NO. SSNO- salts could, however, be used as fast generators of HNO in water solutions.

1H and 13C NMR spectra of commercial rhodamine ester derivatives

Ethyl and methyl esters of commercial rhodamines B, 19, 101 and 110 and propyl and butyl esters of commercial rhodamine B were synthesized and isolated with different counterions (yields 70-98%). The 1H and 13C NMR spectral data for these compounds were fully assigned by a combination of one-and two-dimensional experiments. The Fourier transform IR and UV-visible spectra were also recorded and the main bands were identified. Copyright