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3,6-Diamino-9-(2-(methoxycarbonyl)phenyl)xanthylium chloride

HCID 65217
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
62669-70-9
Standard SMILES
COC(=O)c1ccccc1-c1c2ccc(=[NH2+])cc-2oc2cc(N)ccc12.[Cl-]
InChIKey
MYFATKRONKHHQL-UHFFFAOYSA-N
Molecular formula
C21H17ClN2O3
Average molar mass
380.8 g/mol
Monoisotopic mass
380.0927701

Overview

Rhodamine 123 is an organic chloride salt and a xanthene dye. It has a role as a fluorochrome. It contains a rhodamine 123(1+).

Names & identifiers

Preferred name
3,6-Diamino-9-(2-(methoxycarbonyl)phenyl)xanthylium chloride
IUPAC
[6-amino-9-(2-methoxycarbonylphenyl)xanthen-3-ylidene]azanium chloride
English name
Rhodamine 123
Molecular formula
C21H17ClN2O3
Molecular weight
380.83

Names & synonyms

3,6-Diamino-9-(2-(methoxycarbonyl)phenyl)xanthylium chloride3,6-Diamino-9-[2-(methoxycarbonyl)phenyl]xanthylium ChlorideRhodamine 123 (chloride)MFCD00012664Rhodamine 123?SCHEMBL37743Rhodamine 123? (chloride)Xanthylium, 3,6-diamino-9-orb1219754DTXSID00886503TUFFYSFVSYUHPA-UHFFFAOYSA-MHY-D0816
Show more names
rh123R 302R 22420RHODAMINE 123-Cellstain-Rh123Rhodamine 123 ,98%Rhodamine 123, 99+%Rhodamine 123, pureRhodamine 123 (RH-123Rhodamine 123 (Green)
6-amino-9-[2-(methoxycarbonyl)phenyl]-3H-xanthen-3-iminium chlorideAKOS015917525AKOS015958728CS-7693BP-42026SY076555NS00055379T16743

Database identifiers

CAS
62669-70-9

Properties

Computed structural properties

Topological polar surface area
87.1 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
5
Rotatable bonds
3
Heavy atoms
27
Formal charge
0
Complexity
670

Physicochemical properties

Melting point
235 °C · 235 °C
Density
1.2224 · 1.2224 (rough estimate)
refractive index
1.65 · 1.6500 (estimate)
storage temp.
-20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
solubility
20 mg/mL, · ethanol: 20 mg/mL, clear, red
form
Powder
color
Red-brown to brown or dark green
Appearance
brown crystals
Water Solubility
Partially soluble
λmax
501 nm, · 501 nm, 507 nm
ex/em
512 · λex 512, 332 nm; λem 531 nm in EtOH
BRN
6030951 · 6030951
Stability
Hygroscopic
Major Application
Colored bubbles; color filters; liquid crystal displays; light-emitting diodes; luminescent materials;nanophotonic composites; paints; semiconductor electrodes;solar cells
Biological Applications
Measuring membrane potential; detecting cancer cells,spores,prostate cancer,stress biomarkers; treating disc degenerative disease,epilepsy,erectile dysfunction; apoptosis assays; tumor cell multidrug resistance assay; implantable

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
tsca
TSCA listed
rtecs
ZE0883000
hs_code
32049010
risk_code
22
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xn
safety_code
22-24/25
Storage Class
11 - Combustible Solids
Hazard statements
H302
Precautionary statements
P264-P270-P301+P312+P330-P501

Chemistry & industry

Applications · 6 items

DescriptionRhodamine 123 is a membrane-permeable cationic dye that is readily accumulated within living cells. It is a substrate for the efflux pump P-glycoprotein (P-gp; also known as multidrug resistance protein 1 and ABCB1) and is rapidly exported from cells with functional P-gp. As P-gp is expressed on a population of stem cells known as the side population, rhodamine 123 is used to detect this group of stem cells. Rhodamine 123 also accumulates within mitochondria due to its positive charge and can inhibit oxidative phosphorylation. Rhodamine 123 has excitation/emission maxima of 507/529 nm.

UsesRhodamine derivative, a fluoresent dye-labeled compound.

UsesFluorescent dye most commonly used as functional reporter in flow cytometry.

UsesUseful as a laser dye and to have selective cell growth effects. Mitochondrial specific fluorescent dye and substrate for P-glycoprotein.

UsesRhodamine-123 is a fluorescent dye most commonly used in flow cytometry as functional reporter for Pgp. Rhodamine 123 (R123), as a typical of P-glycoprotein substrate, was widely used to quantify P-glycoprotein (P-gp) functional efflux activity in vivo. Rhodamine-123 can be used in multiparameter analyses without fluorescence interference in combination with common protein labeling dyes such as PE-Cy5 and AMCA (7-amino-4-methylcoumarin-3-acetic acid).

UsesRhodamine-123 lycoprotein (P-gp) functional efflux activity in vivo. Rhodamine-123 PE-Cy5 and AMCA (7-amino-4-methylcoumarin-3-acetic acid).

Upstream & downstream products

Upstream raw materials

Fuming sulfuric acidSodium chlorideAcetyl chlorideTrimellitic AnhydrideEthyl acetatePhthalic anhydride

Related reactions

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New reaction record

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
PubChem CID
65217
DTXSID
DTXSID00886503
ChEBI
CHEBI:8828
Nikkaji
J3.766.031K
InChI
1S/C21H16N2O3.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;/h2-11,22H,23H2,1H3;1H
InChIKey
MYFATKRONKHHQL-UHFFFAOYSA-N
SMILES
Cl[H].COC(=O)c1ccccc1C2=C3C=CC(=N)C=C3Oc4cc(N)ccc24
CAS DataBase Reference
62669 · 62669-70-9(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
1 N3CZ14C5O · 1N3CZ14C5O
EPA Substance Registry System
3 · Xanthylium, 3,6-diamino-9-[2-(methoxycarbonyl)phenyl]-, chloride (62669-70-9)
UNSPSC Code
12352116 · 12352116
NACRES
47 · NA.47
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302
Precautionary statements
264 · P264-P270-P301+P312+P330-P501
PPE
95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes
Xn
Risk Statements
22 · 22
Safety Statements
22 · 22-24/25
WGK Germany
3 · 3
RTECS
883000 · ZE0883000
TSCA
TSCA listed
HS Code
32049010 · 32049010
Storage Class
11 · 11 - Combustible Solids
Hydrochloric acid
Dichloromethane
Methanol
3-Aminophenol
Sulfuric acid
Ammonia

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京广文精细化工研究所010-69293631 13522011782 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海康朗生物科技有限公司021-61998208 18217752821 · [email protected]
武汉欣扬瑞和化学科技有限公司13720274133 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
上海遐瑞医药科技有限公司+86-021-61551413 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
上海仲因实业有限公司2537653158 16621191650 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
北京欧凯纳斯生化科技有限公司010-62651721 18610486005 · [email protected]
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武汉易泰科技有限公司上海分公司18930552037 · [email protected]
上海晶抗生物工程有限公司021-54721350 13524668266 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
安耐吉化学&3A(安徽泽升科技有限公司)021-58432009 400-005-6266 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
南京圣亿来化工有限公司19951936396 · [email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
上海景颜化工科技有限公司13817811078 · [email protected]
维赛诺化学技术(北京)有限公司13811761079 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
长沙瀚辰生物科技有限公司18175992585 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
湖南汇百侍生物科技有限公司0731-85526065 13308475853 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
赛默飞世尔科技(中国)有限公司800-810-5118 · [email protected]
上海倍卓生物科技有限公司021-61119791,13386096464 · [email protected]
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上海将来实业股份有限公司021-61552785 · [email protected]
Labnetwork lnc.+86-27-50766799 +86-18062016861 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
陕西缔都医药化工有限公司+86-29-87569262 +86-15003564040 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
Alfa Chemistry1-516-6625404 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
九鼎化学(上海)科技有限公司4009209199 · [email protected]
BOC Sciences16314854226; +8616314854226 · [email protected]
北京禾兴源科技有限公司18511709189 · [email protected]
Henan Alfa Chemical Co., Ltd+8618339805032 · [email protected]
西安美川生物科技有限公司029-89275612 +8618991951683 · [email protected]
上海珈得尔化学技术有限公司13564435016 13564435016 · [email protected]
浙江珲达生物科技有限公司0571-89903022 18679456698 · [email protected]
箴德化工科技(上海)有限公司15601952568 · [email protected]
武汉多普乐生物医药有限公司+86-02787215551 19945035818 · [email protected]
天津康利欣科技有限公司18622939839 · [email protected]
南京熙朗化工产品有限公司18936048580 · [email protected]