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42364

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:
8251870
MDL number:
MFCD00142354
UNSPSC Code:
12171500
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 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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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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