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Key Documents

D4292

Sigma-Aldrich

3,3′-Dioctadecyloxacarbocyanine perchlorate

≥98% purity (TLC), powder

Synonym(s):

DiOC18(3), ‘DiO’

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About This Item

Empirical Formula (Hill Notation):
C53H85ClN2O6
CAS Number:
Molecular Weight:
881.70
Beilstein:
4122771
MDL number:
UNSPSC Code:
12171500
PubChem Substance ID:
NACRES:
NA.47

product name

3,3′-Dioctadecyloxacarbocyanine perchlorate,

Assay

≥98% (TLC)

form

powder

color

orange

solubility

chloroform: 50 mg/mL

fluorescence

λex 484 nm; λem 501 nm in methanol

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

2-8°C

SMILES string

[O-]Cl(=O)(=O)=O.CCCCCCCCCCCCCCCCCCN1C(\Oc2ccccc12)=C/C=C/c3oc4ccccc4[n+]3CCCCCCCCCCCCCCCCCC

InChI

1S/C53H85N2O2.ClHO4/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-37-46-54-48-40-33-35-42-50(48)56-52(54)44-39-45-53-55(49-41-34-36-43-51(49)57-53)47-38-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2;2-1(3,4)5/h33-36,39-45H,3-32,37-38,46-47H2,1-2H3;(H,2,3,4,5)/q+1;/p-1

InChI key

GFZPJHFJZGRWMQ-UHFFFAOYSA-M

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Application

3,3′-Dioctadecyloxacarbocyanine perchlorate has been used for lipid bilayer labeling in antigen-presenting cells. It has also been used as a lipophilic dye for labeling in zebrafish embryos.

Biochem/physiol Actions

3,3′-Dioctadecyloxacarbocyanine perchlorate is a fluorescent probe of lipid bilayer model membranes. It is a fluorescent marker for living cells in culture.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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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A simple trogocytosis-based method to detect, quantify, characterize and purify antigen-specific live lymphocytes by flow cytometry, via their capture of membrane fragments from antigen-presenting cells.
Daubeuf S, et al.
Nature Protocols, 1, 2536-2536 (2006)
Maria B C de Matos et al.
Frontiers in pharmacology, 10, 1463-1463 (2019-12-24)
Mistletoe lectin-1 (ML1) is a nature-derived macromolecular cytotoxin that potently induces apoptosis in target cells. Non-specific cytotoxicity to normal cells is one of the major risks in its clinical application, and we therefore propose to encapsulate ML1 in a nanocarrier
Dynamic behavior of fluorescent probes in lipid bilayer model membranes.
R A Badley et al.
Biochemistry, 12(2), 268-275 (1973-01-16)
Jayesh A Kulkarni et al.
Nanoscale, 11(18), 9023-9031 (2019-04-26)
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