Description

Carbocyanine (Pinacyanol Iodide) is a highly versatile cyanine dye with the molecular formula C₂₅H₂₅IN₂ and CAS number 15185-48-5. This organic compound, also known by its IUPAC name (2E)-1-ethyl-2-[(E)-3-(1-ethylquinolin-1-ium-2-yl)prop-2-enylidene]quinoline;iodide, is widely utilized in fluorescence labeling, bioimaging, and photodynamic therapy due to its strong absorption and emission properties in the visible spectrum. Its cationic structure and iodine counterion enhance solubility in polar solvents, making it ideal for aqueous and organic phase applications. Researchers value Carbocyanine for its photostability, high molar extinction coefficient, and ability to form J-aggregates, which are critical for advanced spectroscopic studies. Supplied as a dark green crystalline powder, it is packaged under inert conditions to ensure long-term stability and performance consistency.

Properties

• CAS Number: 15185-48-5
• Complexity: 527
• IUPAC Name: (2E)-1-ethyl-2-[(E)-3-(1-ethylquinolin-1-ium-2-yl)prop-2-enylidene]quinoline;iodide
• InChI: InChI=1S/C25H25N2.HI/c1-3-26-22(18-16-20-10-5-7-14-24(20)26)12-9-13-23-19-17-21-11-6-8-15-25(21)27(23)4-2;/h5-19H,3-4H2,1-2H3;1H/q+1;/p-1
• InChI Key: QWYZFXLSWMXLDM-UHFFFAOYSA-M
• Exact Mass: 480.10625
• Molecular Formula: C25H25IN2
• Molecular Weight: 480.4
• SMILES: CCN1/C(=C/C=C/C2=[N+](C3=CC=CC=C3C=C2)CC)/C=CC4=CC=CC=C41.[I-]
• Topological: 7.1
• Monoisotopic Mass: 480.10625
• Synonyms: Pinacyanol iodide, 605-91-4, Carbocyanine, Pinacyanole, Pinacyanol, Sensitol Red, Eastman kodak 622, DTXCID7026576, DTXSID9046576, CHEBI:52218, NSC-403532, EINECS 210-099-4, NSC 403532, G 1700, 1-ethyl-2-[3-(1-ethylquinolin-2(1H)-ylidene)prop-1-en-1-yl]quinolinium iodide, 1-Ethyl-2-(3-(1-ethyl-2(1H)-quinolylidene)propenyl)quinolinium iodide, 1-ethyl-2-[3-(1-ethyl-2(1H)-quinolylidene)prop-1-enyl]quinolinium iodide, G-1700, 1-ethyl-2-(3-(1-ethylquinolin-2(1H)-ylidene)prop-1-en-1-yl)quinolinium iodide, 1-Ethyl-2-(3-(1-ethyl-2(1H)-quinolylidene)prop-1-enyl)quinolinium iodide, Quinolinium, 1-ethyl-2-(3-(1-ethyl-2(1H)-quinolylidene)propenyl)-, iodide, Quinolinium, 1-ethyl-2-[3-(1-ethyl-2(1H)-quinolinylidene)-1-propen-1-yl]-, iodide (1:1), QUINOLINIUM, 1-ETHYL-2-(3-(1-ETHYL-2(1H)-QUINOLINYLIDENE)-1-PROPEN-1-YL)-, IODIDE (1:1), 94623a1122, 1,1′-Diethyl-2,2′-carbocyanine iodide, 1,1-DIETHYL-2,2-CARBOCYANINE IODIDE, Pinacyanol (iodide), MFCD00011975, 15185-48-5, (2E)-1-ethyl-2-[(E)-3-(1-ethylquinolin-1-ium-2-yl)prop-2-enylidene]quinoline;iodide, (2Z)-1-ethyl-2-[(E)-3-(1-ethylquinolin-1-ium-2-yl)prop-2-enylidene]quinoline;iodide, 1-ethyl-2-[(1E)-3-[(2E)-1-ethyl-1,2-dihydroquinolin-2-ylidene]prop-1-en-1-yl]quinolin-1-ium iodide, CAS-605-91-4, Quinaldine Blue, Iodide, 1-ethyl-2-((E)-3-((E)-1-ethylquinolin-2(1H)-ylidene)prop-1-en-1-yl)quinolin-1-ium iodide, NCGC00166247-01, 1,1′-DIETHYL-2,2′-CARBOCYANINEIODIDE, Tox21_112373, NSC403532, AKOS000805665, Tox21_112373_1, HY-W216621, Quinolinium, 1-ethyl-2-[3-(1-ethyl-2(1H)-quinolinylidene)-1-propenyl]-, iodide, NCGC00166247-02, DA-48982, CS-0279185, P0436, EN300-240239, T72688, 1,1′-Diethyl-2,2′-carbocyanine iodide, 97%, EN300-24494647, 1-ethyl-2-[3-(1-ethyl-1,2-dihydroquinolin-2-ylidene)prop-1-en-1-yl]quinolin-1-ium iodide, 1-ethyl-2-[3-(1-ethylquinolin-1-ium-2-yl)prop-2-enylidene]quinoline;iodide

Application

Carbocyanine is extensively used as a fluorescent probe in biological staining and microscopy, particularly for visualizing cellular membranes and nucleic acids. Its sharp absorption bands make it valuable in sensitizing photographic emulsions and as a spectral sensitizer in optoelectronic devices. Additionally, it serves as a key component in nonlinear optical materials and laser dye applications due to its exceptional light-harvesting properties.

Safety and Hazards

GHS Hazard Statements

• H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
• H311 (100%): Toxic in contact with skin [Danger Acute toxicity, dermal]
• H331 (90.9%): Toxic if inhaled [Danger Acute toxicity, inhalation]

Precautionary Statements

• P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 3 (100%)
• Acute Tox. 3 (100%)
• Acute Tox. 3 (90.9%)

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