Skip to Content
Merck
All Photos(3)

Key Documents

View All Documentation

318426

Sigma-Aldrich

3,3′-Dihexyloxacarbocyanine iodide

98%

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

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

Quality Level

100

Assay

98%

form

powder or chunks

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

Looking for similar products? Visit Product Comparison Guide

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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
Examination of living and fixed gametes and early embryos stained with supravital fluorochromes (Hoechst 33342 and 3, 3?-dihexyloxacarbocyanine iodide)
Luttmer SJ and Longo FJ
Gamete Research, 15(3), 267-283 (1986)
View All Related Papers

Articles

Sensor Dyes

Nitric oxide (NO) as a signal transporter in neurons, endothelial cells and in the immune system.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service