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320684

Sigma-Aldrich

3,3′-Diethyloxacarbocyanine iodide

98%

Synonym(s):

3-Ethyl-2-[3-(3-ethyl-2(3H)-benzoxazolylidene)-1-propenyl]benzoxazolium iodide, DOC Iodide, DiOC2(3)

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About This Item

Empirical Formula (Hill Notation):
C21H21IN2O2
CAS Number:
905-96-4
Molecular Weight:
460.31
EC Number:
212-996-6
MDL number:
MFCD00011952
UNSPSC Code:
12352103
PubChem Substance ID:
57648658
NACRES:
NA.23

Assay

98%

form

solid

mp

278 °C (dec.) (lit.)

λmax

483 nm

SMILES string

[I-].CCN1\C(Oc2ccccc12)=C\C=C\c3oc4ccccc4[n+]3CC

InChI

1S/C21H21N2O2.HI/c1-3-22-16-10-5-7-12-18(16)24-20(22)14-9-15-21-23(4-2)17-11-6-8-13-19(17)25-21;/h5-15H,3-4H2,1-2H3;1H/q+1;/p-1

InChI key

FIZZUEJIOKEFFZ-UHFFFAOYSA-M

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General description

3,3′-Diethyloxacarbocyanine iodide(DiOC) is a cyanine based dye which is used in the photosensitization of mitochondria and endoplastic recticulum in animals and plant cells.

Application

DiOC may be used as a conjugate for labelling cells for cytofluorometry studies . It may also be used in the imaging of carbon nanotubes(CNTs) using fluorescence microscopy. Staining of spermatozoa can potentially be done by DiOC which can be used in flow cytometric measurement and viability assay.

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’.

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Picosecond flash photolysis and spectroscopy: 3,3?-diethyloxadicarbocyanine iodide (DODCI)
Magde D and Windsor MW
Chemical Physics Letters, 27(1), 31-36 (1974)
Visualization of individual carbon nanotubes with fluorescence microscopy using conventional fluorophores.
Prakash R, et al.
Applied Physics Letters, 83(6), 1219-1221 (2003)
The functionality of mitochondria differentiates human spermatozoa with high and low fertilizing capability.
Gallon F, et al.
Fertility and Sterility, 86(5), 1526-1530 (2006)
Photosensitization by 3, 3?-dihexyloxacarbocyanine iodide: specific disruption of microtubules and inactivation of organelle motility.
Lee C, et al.
Cancer Research, 55(10), 2063-2069 (1995)
Sheng-Chieh Wang et al.
International journal of molecular sciences, 21(17) (2020-09-10)
The sensitizing effect of chromone-derived compounds on UVC-induced proliferation inhibition has not been comprehensively investigated so far. The subject of this study was to examine the proliferation change of oral cancer cells while using the combined treatment of UVC (254
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