Solvent Green 7

Solvent Green 7 Property

Melting point:

62-63.5 °C(lit.)

Boiling point:

171-178 °C10 mm Hg(lit.)

Density 

2.15

vapor pressure 

0Pa at 25℃

Flash point:

250 °C

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

methanol: 0.1 g/mL, clear

Colour Index 

59040

form 

Powder

pka

7.3, (at 22℃)

color 

yellow

Water Solubility 

300 g/L (25 ºC)

λmax

403 nm (Buffer pH 4.0); 454 nm (Buffer pH 9.0)

Merck 

7954

BRN 

4107272

Major Application

Adhesives; 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 Applications

Antiperspirants; 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

LogP

-3.97 at 25℃

CAS DataBase Reference

6358-69-6(CAS DataBase Reference)

EPA Substance Registry System

C.I. Solvent Green 7 (6358-69-6)

Safety

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38

Safety Statements 

36/37-37/39-26-36

WGK Germany 

3

RTECS 

UR2700000

TSCA 

Yes

HS Code 

29089990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

Solvent Green 7 Chemical Properties,Usage,Production

Chemical Properties

yellow to green-yellow powder

Uses

Pyranine 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.

Definition

ChEBI: 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.

Preparation

commonly 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?).

Flammability and Explosibility

Not classified

Biological Activity

Pyranine (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

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 vitro

Pyranine 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 Applications

yellow 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.

Purification Methods

Purify 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