C2734

5-Carboxytetramethylrhodamine

Name: 5-Carboxytetramethylrhodamine
Brand: SIAL

≥95% purity (HPLC), solid

Synonym(s):

5-TAMRA

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About This Item

Empirical Formula (Hill Notation):

C₂₅H₂₂N₂O₅

CAS Number:

91809-66-4

Molecular Weight:

430.45

UNSPSC Code:

12171500

NACRES:

NA.47

MDL number:

MFCD01073638

Key Documents

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Product Name

5-Carboxytetramethylrhodamine,

SMILES string

N(C)(C)c1cc2[o+]c3c(c(c2cc1)c4c(cc(cc4)C(=O)[O-])C(=O)O)ccc(c3)N(C)C

InChI

1S/C25H22N2O5/c1-26(2)15-6-9-18-21(12-15)32-22-13-16(27(3)4)7-10-19(22)23(18)17-8-5-14(24(28)29)11-20(17)25(30)31/h5-13H,1-4H3,(H-,28,29,30,31)

InChI key

YMZMTOFQCVHHFB-UHFFFAOYSA-N

assay

≥95% (HPLC)

form

solid

solubility

water: slightly soluble

ε (extinction coefficient)

≥85000-97000 at 539-545 nm in methanol

fluorescence

λ_ex ~543 nm; λ_em ~570 nm in methanol

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

room temp

Quality Level

100

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Show Differences

1 of 4

This Item	21953	T5428	8.51026
Sigma-Aldrich C2734 5-Carboxytetramethylrhodamine	Sigma-Aldrich 21953 5(6)-Carboxytetramethylrhodamine	Sigma-Aldrich T5428 Tetramethylrhodamine methyl ester perchlorate	Sigma-Aldrich 8.51026 5-Carboxy-tetramethylrhodamine
fluorescence λ_ex ~543 nm; λ_em ~570 nm in methanol	fluorescence λ_ex 543 nm; λ_em 572 nm in methanol	fluorescence λ_em 573 nm in methanol	fluorescence -
solubility water: slightly soluble	solubility DMF: soluble, DMSO: soluble	solubility methanol: 5 mg/mL, clear	solubility -
application(s) diagnostic assay manufacturing hematology histology	application(s) -	application(s) diagnostic assay manufacturing hematology histology	application(s) peptide synthesis
form solid	form solid	form powder	form powder
assay ≥95% (HPLC)	assay ≥85% (sum of isomers, HPCE)	assay ≥95%	assay ≥96.0% (HPLC), ≥97% (TLC)
Quality Level 100	Quality Level 100	Quality Level 200	Quality Level 200

Application

5-Carboxytetramethylrhodamine has been used in fluorophore characterization.[1]

Biochem/physiol Actions

5-Carboxytetramethylrhodamine can be covalently attached to the DNA and is thereby used in studies involving branched and duplex DNA/RNA structures.[2] It is mainly used for single-molecule studies.[3] 5-Carboxytetramethylrhodamine is also used for the labelling of oligosaccharide for laser-induced fluorescence detection.[4]

General description

An important fluorophore prepared in high purtity with a detection limit of TMR-labeled amino acids by capillary electrophoresis of approx. 600 molecules. Readily excited by the 546 nm spectral line from mercury-arc lamps used in fluorescent microscopes, and is intrinsically more photostable than fluorescein.

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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Dustin J Paul et al.

Nucleic acids research, 37(17), 5894-5907 (2009-09-04)

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The thylakoid membranes of cyanobacteria form a complex intracellular membrane system with a distinctive proteome. The sites of biogenesis of thylakoid proteins remain uncertain, as do the signals that direct thylakoid membrane-integral proteins to the thylakoids rather than to the

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