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Sigma-Aldrich

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
Beilstein/REAXYS Number:
8251870
MDL number:
MFCD00142354
UNSPSC Code:
12352200
PubChem Substance ID:
57650110
NACRES:
NA.32

product line

BioReagent

Quality Level

100

assay

≥98.0% (TLC)

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

SMILES string

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

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

InChI key

JVXZRNYCRFIEGV-UHFFFAOYSA-M

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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).

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.

Other Notes

Lipophilic fluorescent probe for studying membranes

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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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
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
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
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)
Yiwen Li et al.
Nature protocols, 3(11), 1703-1708 (2008-10-11)
We describe a protocol to rapidly and reliably visualize blood vessels in experimental animals. Blood vessels are directly labeled by cardiac perfusion using a specially formulated aqueous solution containing 1,1'-dioctadecyl-3,3,3',3'-tetramethylindocarbocyanine perchlorate (DiI), a lipophilic carbocyanine dye, which incorporates into endothelial
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