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Merck

318426

3,3′-Dihexyloxacarbocyanine iodide

98%

Synonym(s):

3-hexyl-2-[3-(3-hexyl-2(3H)benzoxazolylidene)-1-propenyl]benzoxazolium iodide

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About This Item

Empirical Formula (Hill Notation):
C29H37IN2O2
CAS Number:
53213-82-4
Molecular Weight:
572.52
UNSPSC Code:
12171500
NACRES:
NA.47
PubChem Substance ID:
24859130
MDL number:
MFCD00011954
Beilstein/REAXYS Number:
9312562

Key Documents

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Quality Level

100

assay

98%

form

powder or chunks

technique(s)

titration: suitable

mp

219-221 °C (lit.)

solubility

chloroform: 25 mg/mL, clear to slightly hazy, orange

λmax

485 nm

ε (extinction coefficient)

≥120000 at 483-488 nm in methanol at 0.01 g/L

fluorescence

λex 485 nm; λem 501 nm in methanol

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

room temp

SMILES string

[I-].CCCCCCN1\C(Oc2ccccc12)=C\C=C\c3oc4ccccc4[n+]3CCCCCC

InChI

1S/C29H37N2O2.HI/c1-3-5-7-13-22-30-24-16-9-11-18-26(24)32-28(30)20-15-21-29-31(23-14-8-6-4-2)25-17-10-12-19-27(25)33-29;/h9-12,15-21H,3-8,13-14,22-23H2,1-2H3;1H/q+1;/p-1

InChI key

XVLXYDXJEKLXHN-UHFFFAOYSA-M

Related Categories

General description

3,3′-dihexyloxacarbocyanine iodide (DiOC6) is a supravital lipophilic fluorochrome. This cationic dye is employed to stain mitochondria and endoplasmic reticulum in animal and plant cells. In addition, it acts as a very rapid, consistent and highly selective fluorochrome for endophytic ascomycetes in plant roots and liverworts. DiOC6 also facilitates the detection of different mitochondrial changes happening during early apoptosis.

Application

3,3′-Dihexyloxacarbocyanine iodide has been used:
  • to selectively stain endophytic ascomycetes in plant roots and liverworts
  • to visualize thrombus formation and platelet aggregate
  • to visualize forchlorfenuron (FCF)-induced changes in mitochondrial morphology

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Yanyan Zheng et al.
European journal of medicinal chemistry, 125, 902-913 (2016-10-22)
Emodin, a natural anthraquinone derivative isolated from Rheum palmatum L., has been demonstrated to exhibit good anti-cancer effect. In this study, a series of novel quaternary ammonium salts of emodin, anthraquinone and anthrone were synthesized and their anticancer activities were
Xueying Zhuang et al.
Mycological research, 113(Pt 4), 417-431 (2008-12-31)
Growth and organelle morphology in the wood rotting basidiomycete fungus Phanerochaete velutina were examined in Petri dishes, on agar-coated slides, and in submerged cultures, using DIC, fluorescence and four-dimensional (4-D; x,y,z,t) confocal microscopy, with several fluorescent probes. Phanerochaete is ideal
Comparison of DiOC6 (3) uptake and annexin V labeling for quantification of apoptosis in leukemia cells and non-malignant T lymphocytes from children
Ozgen u, et al.
Cytometry, 42(1), 74-78 (2000)
Ashlesha A Kadam et al.
Biochimica et biophysica acta, 1861(1 Pt A), 2942-2955 (2016-10-23)
Apoptosis Inducing Factor (AIF), a phylogenetically conserved mitochondrial inter-membrane space flavoprotein has an important role in caspase independent cell death. Nevertheless, AIF is also essential for cell survival. It is required for mitochondrial organization and energy metabolism. Upon apoptotic stimulation
Microfluidic cell sorting: Towards improved biocompatibility of extracorporeal lung assist devices
Bleilevens C, et al.
Scientific reports, 8(1), 8031-8031 (2018)
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