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Solvent Green 7

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  • Pyranine
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Solvent Green 7 Basic information
Product Name:Solvent Green 7
Synonyms:1,3,6-Pyrenetrisulfonicacid,8-hydroxy-,trisodiumsalt;11389green;3,6-pyrenetrisulfonicacid,8-hydroxy-trisodiumsalt;8-hydroxypyrene-1,3,6-trisulfonicacidsodiumsalt;c.i.solventgreen7;c.i.solventgreen9;SOLVENT GREEN 7;PYRANINE
CAS:6358-69-6
MF:C16H7Na3O10S3
MW:524.39
EINECS:228-783-6
Product Categories:Aromatic Nitriles;Dyes and Pigments;Pyrenes;Fluorescent Indicators and Probes;Fluorescent Probes;Labels;Luminescent Compounds/Detection;Particles and Stains;pH Sensitive Probes and Indicators;Sulfonic/Sulfinic Acids;Wavelength Index;Alphabetical;Biochemicals and Reagents;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfur Compounds
Mol File:6358-69-6.mol
Solvent Green 7 Structure
Solvent Green 7 Chemical Properties
Melting point 62-63.5 °C(lit.)
Boiling point 171-178 °C10 mm Hg(lit.)
density 2.15
vapor pressure 0Pa at 25℃
Fp 250 °C
storage temp. Keep in dark place,Inert atmosphere,Room temperature
solubility methanol: 0.1 g/mL, clear
Colour Index 59040
form Powder
pka7.3, (at 22℃)
color yellow
Water Solubility 300 g/L (25 ºC)
λmax403 nm (Buffer pH 4.0); 454 nm (Buffer pH 9.0)
Merck 7954
BRN 4107272
Major ApplicationAdhesives; agrochemicals; ammonia sensor; carbon dioxide sensor; oxygen sensor; anionic surfactants sensor; measuring the size of the organoclay aggregates; detecting cracks/flaws in metallic surfaces, refrigerant leaking; detergents; correction fluid; highlighters; inks; markers; paints; pencils; toners; chemically amplified resist; color filters; chemiluminescent materials; electrophoretic display (EPD) film materials; electroluminescent displays/materials; fuel cell; lasers; liquid crystal displays; luminescent materials; nanoparticles; papers; photoresist processes; photonic ionic liquids; soils; solar cell; sol–gel materials/processes/thin films; sonophotoluminescence; water tracers; evaluating liquid water flow in wood during drying
Biological ApplicationsAntiperspirants; bath preparations; cleansing products; cosmetics; contact lens; hair dyes; hygiene products/soaps; food products; controlled-release system for proteins; drug delivery; in ophthalmology/retinal surgery; sugar sensors (glucose, fructose, lactose, sucrose); as a substrate for measuring acetylcholinesterase (AChE) activity, carbonic anhydrase activity, esterases activity, β-glucuronidase activity, lipase activity, acidic/alkaline phosphatases activity, pyrophosphatase activity, sucrose phosphorylase (SPO) activity, phosphoglucomutase (PGM) activity; treating cancer, infection, immune/autoimmune disease, mastitis, tonsillitis, tuberculosis
Cosmetics Ingredients FunctionsCOLORANT
HAIR DYEING
LogP-3.97 at 25℃
CAS DataBase Reference6358-69-6(CAS DataBase Reference)
EPA Substance Registry SystemC.I. Solvent Green 7 (6358-69-6)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 36/37/38
Safety Statements 36/37-37/39-26-36
WGK Germany 3
RTECS UR2700000
TSCA TSCA listed
HS Code 29089990
MSDS Information
ProviderLanguage
Solvent Green 7 English
ACROS English
SigmaAldrich English
ALFA English
Solvent Green 7 Usage And Synthesis
Chemical Propertiesyellow to green-yellow powder
UsesPyranine is used as a fluorescent pH indicator with emission change in the physiological pH range. It acts as a dye in optical sensor applications. It finds application as a coloring agent and biological stain. It is also used in the measurement of pH of intracellular fluid in the cells.
Preparationcommonly known as Pyranine. Pyrene-1,3,6,8-tetrasulfonic acid?and 15 ~ 20% sodium hydroxide reflux, also can use ammonia water on hydrolysis reaction, this condition the product contains APTS(8-Aminopyrene-1,3,6-trisulfonic acid?).
DefinitionChEBI: Pyranine is an organic sodium salt. It has a role as a fluorochrome. It contains a pyranine(3-). It derives from a hydride of a pyrene.
Flammability and ExplosibilityNot classified
Biological ActivityPyranine (HPTS; Solvent Green 7) is a pH-sensitive fluorescent indicator. Pyranine is a class of fluorescent chemosensors for Cu+ ions (λex=450 nm, λem=510 nm).
Synthesis
1,3,6,8-PYRENETETRASULFONIC ACID TETRASODIUM SALT

59572-10-0

Solvent Green 7

6358-69-6

The general procedure for the synthesis of solvent green 7 from 1,3,6,8-pyrene tetrasulfonic acid tetrasodium salt is as follows: 1,200 g of concentrated sulfuric acid is added to a 2,000 ml three-necked flask with stirring, 120 g of 1,3,6,8-pyrene tetrasulfonic acid tetrasodium salt is added, and the temperature is slowly raised to 90°C and maintained for 1 hour after being slightly heated to promote complete dissolution. Upon completion of the reaction, the reaction mixture was cooled to below 40°C using a water bath, and 480 g of liquid sulfur black was slowly added dropwise, with the dropwise addition process being controlled to be completed within 3 hours. Subsequently, the reaction temperature was maintained at about 100°C to continue the reaction for 5 hours. At the end of the reaction, it was cooled to room temperature, and the reaction mixture was poured into 720 g of ice water to obtain a viscous material, and the filter cake was dried after filtration to obtain pyrene tetrasulfonic acid tetrasodium salt. Next, the tetrasodium salt of pyrene tetrasulfonate was dissolved in 1000 ml of water, transferred to a 2000 ml three-necked flask, adjusted to neutrality with sodium hydroxide solution, and 300 g of flaked sodium hydroxide was added. It was slowly heated to a slight boil and kept for 5 hours. After the reaction was completed, it was cooled, and the pH was adjusted to about 7 with hydrochloric acid, then 100 g of sodium chloride was added and stirred until it was completely dissolved, and a light yellow solid was slowly precipitated. After filtering and drying, about 245 g of 8-hydroxy-1,3,6-pyrene trisodium sulfonate was finally obtained.

in vitroPyranine is capable of discriminating ranges of cations from the Cu + ion, even in competing environment. Pyranine displays a rapid fluorescence response (t 1/2 =1.66 min) towards the Cu + ion, and the micromolar detection limit enables the detection of the ion in environmental samples. The observed stoichiometry of complexation between Pyranine and Cu + is 2:1.The pH-sensitive fluorescent indicator Pyranine is studied to determine its usefulness as probes for the living cornea and anterior chamber. Adequate concentrations are reached in the cornea and anterior chamber after topical administration; measurements can be made by fluorophotometry for many hours. The pH is calculated by measuring the ratio of fluorescent intensity at two excitation wavelengths, I463/I404, a measurement which is dependent on pH but independent of the concentration of the fluorophore and other variables which can alter the intensity. In the rabbit eye, Pyranine in the cornea and anterior chamber is observed to undergo easily measurable changes in fluorescent ratios associated with lid closure and contact lens wear, indicating its sensitivity to mild changes in pH.
Properties and Applicationsyellow green. Slightly soluble in glacial acetic acid, 30% hydrochloric acid, insoluble in acetic acid and 10% hydrochloric acid. Mainly used in medicine and cosmetics coloring.
Standard Light Fastness Heat-resistant(℃) water Sodium Carbonate(5%) Hydrochloric acid(5%)
Melting point Stable
ISO Dissole
Purification MethodsPurify the salt by chromatography with an alumina column, and elute with n-propanol/water (3:1, v/v). Recrystallise it from aqueous acetone (5:95, v/v) using decolorising charcoal. [Beilstein 1 III 565.] IRRITANT.
References[1] Patent: CN105272886, 2016, A. Location in patent: Paragraph 0013; 0026; 0027
Solvent Green 7 Preparation Products And Raw materials
Raw materials1,3,6,8-Pyrenetetrasulphonic acid-->1,3,6,8-PYRENETETRASULFONIC ACID TETRASODIUM SALT-->Sodium hydroxide-->Water
Tag:Solvent Green 7(6358-69-6) Related Product Information
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