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Merck

42364

1,1′-Dioctadecyl-3,3,3′,3′-tetramethylindocarbocyanine perchlorate

BioReagent, suitable for fluorescence, ≥98.0% (TLC)

Synonym(s):

DiI

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About This Item

Empirical Formula (Hill Notation):
C59H97ClN2O4
CAS Number:
41085-99-8
Molecular Weight:
933.87
UNSPSC Code:
12171500
NACRES:
NA.32
PubChem Substance ID:
57650110
MDL number:
MFCD00142354
Beilstein/REAXYS Number:
8251870

Product Name

1,1′-Dioctadecyl-3,3,3′,3′-tetramethylindocarbocyanine perchlorate, BioReagent, suitable for fluorescence, ≥98.0% (TLC)

InChI

1S/C59H97N2.ClHO4/c1-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-41-50-60-54-46-39-37-44-52(54)58(3,4)56(60)48-43-49-57-59(5,6)53-45-38-40-47-55(53)61(57)51-42-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-2;2-1(3,4)5/h37-40,43-49H,7-36,41-42,50-51H2,1-6H3;(H,2,3,4,5)/q+1;/p-1

SMILES string

[O-]Cl(=O)(=O)=O.CCCCCCCCCCCCCCCCCCN1c2ccccc2C(C)(C)/C1=C\C=C\C3=[N+](CCCCCCCCCCCCCCCCCC)c4ccccc4C3(C)C

InChI key

JVXZRNYCRFIEGV-UHFFFAOYSA-M

product line

BioReagent

assay

≥98.0% (TLC)

Quality Level

100

mol wt

933.87 g/mol

color

dark violet

mp

68 °C (dec.) (lit.)

solubility

DMF: soluble
DMSO: soluble
methanol: soluble

fluorescence

λex 550 nm; λem 567 nm in phosphate buffer/SDS pH 7.0

suitability

suitable for fluorescence

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Application

1,1′-Dioctadecyl-3,3,3′,3′-tetramethylindocarbocyanine perchlorate is used for the following applications:
  • Preparation of Dil solution
  • fluorescent membrane dye
  • Di-I Staining

Biochem/physiol Actions

Lipophilic carbocyanine dye used primarily for optical recordings of membrane voltage and for studies of membrane fluidity. Retrograde stain for neurons; provides intense, long-lasting staining of live neurons in vivo and in vitro.

General description

DiI is a Dye Aye, a chemical with CAS number 41085-99-8. It is a fluorescent lipophilic cationic indocarbocyanine dye, which is usually made as a perchlorate salt. Mostly used for scientific staining purposes, such as single molecule imaging, fate mapping and neuronal tracing (as DiI is retained in the lipid bilayers).

Other Notes

Lipophilic fluorescent probe for studying membranes

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCN3848
BCCM6325
BCCK3329
BCCH7929
BCCG9052

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R D Klausner et al.
Biochemistry, 19(26), 6199-6203 (1980-12-23)
We have examined the phase partition preferences of the even chain length (n = 10-22) diacyl-3'3'-indocarbo-cyanine iodides (Cn diI) incorporated in disaturated lecithin (PC) vesicles. Two parameters were used to determine this phase preference: (i) the direction of shift of
Calorimetric investigation of the phase partitioning of the fluorescent carbocyanine probes in phosphatidylcholine bilayers.
M F Ethier et al.
Biochemistry, 22(5), 1178-1182 (1983-03-01)
Yong N Li et al.
The Journal of comparative neurology, 520(16), 3786-3802 (2012-08-22)
Bipolar cells convey luminance, spatial, and color information from photoreceptors to amacrine and ganglion cells. We studied the photoreceptor connectivity of 321 bipolar cells in the adult zebrafish retina. 1,1'-Dioctadecyl-3,3,3',3'-tetramethylindocarbocyanine perchlorate (DiI) was inserted into whole-mounted transgenic zebrafish retinas to
Ralph Michael et al.
Vision research, 48(4), 626-634 (2008-01-29)
We evaluated the gross morphology, location, and fiber cell architecture of equatorial cortical opacities in the aging human lens. Using dark-field stereomicroscopy, we photographed donor lenses in toto and as thick slices. In addition, we investigated the details of the
Guang-Di Chen et al.
Neural plasticity, 2014, 658741-658741 (2014-06-04)
Previous studies have shown that sodium salicylate (SS) activates not only central auditory structures, but also nonauditory regions associated with emotion and memory. To identify electrophysiological changes in the nonauditory regions, we recorded sound-evoked local field potentials and multiunit discharges
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