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318426

Sigma-Aldrich

3,3′-Dihexyloxacarbocyanine iodide

98%

Synonym(s):

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

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250 MG
$80.65
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$243.20

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250 MG
$80.65
1 G
$243.20

About This Item

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

$80.65

List Price$84.90Save 5%
Web-Only Promotion

Available to ship onMay 13, 2025Details

Request a Bulk Order

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

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General description

3,3′-dihexyloxacarbocyanine iodide (DiOC6) is a supravital lipophilic fluorochrome.[1][2] This cationic dye is employed to stain mitochondria[3] and endoplasmic reticulum in animal and plant cells.[1][2] In addition, it acts as a very rapid, consistent and highly selective fluorochrome for endophytic ascomycetes in plant roots and liverworts.[2] DiOC6 also facilitates the detection of different mitochondrial changes happening during early apoptosis.[3]

Application

3,3′-Dihexyloxacarbocyanine iodide has been used:
  • to selectively stain endophytic ascomycetes in plant roots and liverworts[2]
  • to visualize thrombus formation and platelet aggregate[3]
  • to visualize forchlorfenuron (FCF)-induced changes in mitochondrial morphology[4]

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKBL7987V
MKBG8334V
MKBG8160V
11826MD
08024HD

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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
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
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
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)
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Questions

  1. 本製品をクロロホルムで溶解するときの推奨プロトコルはございますでしょうか。クロロホルムは原液でしょうか。 他社の DiOC6 の説明では溶媒として DMSO も挙げられるようですが、本製品の DMSO への溶解性はいかがでしょうか。

    1 answer

    1. No formal protocol exists for dissolving this product in chloroform. The Specification Sheet and the Certificate of Analysis indicate that solubility is tested at 25 mg/mL in chloroform during quality control testing. It is suggested to dissolve up to 25 mg/mL in chloroform and mix well until the solid is dissolved.
      The chemical may be soluble in other solvents. No attempt is made during quality control to test in a range of solvents. It is certainly possible that other companies may test in DMSO or other solvents. If other companies claim DIOC6 is soluble in a particular solvent, product 318426 should also be soluble. Since the only solvent used for solubility testing is chloroform, there is no guarantee product 318426 will meet the solubility claims from other companies.

      Conn's Biological Stains, 10th Edition advises that 3,3?-Dihexyloxacarbocyanine iodide is also soluble in DMSO and methanol. No exact values are provided for the solubility of DiOC6 in either DMSO or methanol. No solubility data is available from PubChem, The Merck Index or Martindale The Extra Pharmacopeia.

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