Sulfan Blue - 129-17-9
Sulfan Blue
Catalog Number: BT-468407
CAS Number: 129-17-9
Molecular Formula: C27H31N2NaO6S2
Molecular Weight: 566.7 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction
Description
Sulfan Blue is a synthetic dye that has been widely used in various fields, including medical, environmental, and industrial research. It is a sulfonated phthalocyanine dye that has a blue color and is soluble in water. Sulfan Blue has been used as a diagnostic tool in medical research, as a marker for lymphatic mapping, and as a contrast agent in imaging studies. In environmental research, it has been used to study the effects of pollutants on ecosystems. In industrial research, it has been used in manufacturing processes to improve product quality and efficiency. This paper will discuss the synthesis, biological activity, and applications of Sulfan Blue.
Properties
CAS Number
129-17-9
Product Name
Sulfan Blue
IUPAC Name
sodium;4-[[4-(diethylamino)phenyl]-(4-diethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)methyl]benzene-1,3-disulfonate
Molecular Formula
C27H31N2NaO6S2
Molecular Weight
566.7 g/mol
InChI
InChI=1S/C27H32N2O6S2.Na/c1-5-28(6-2)22-13-9-20(10-14-22)27(21-11-15-23(16-12-21)29(7-3)8-4)25-18-17-24(36(30,31)32)19-26(25)37(33,34)35;/h9-19H,5-8H2,1-4H3,(H-,30,31,32,33,34,35);/q;+1/p-1
InChI Key
SJEYSFABYSGQBG-UHFFFAOYSA-M
SMILES
CCN(CC)C1=CC=C(C=C1)C(=C2C=CC(=[N+](CC)CC)C=C2)C3=C(C=C(C=C3)S(=O)(=O)[O-])S(=O)(=O)[O-].[Na+]
Solubility
Soluble (>=10 mg/ml at 70° F) (NTP, 1992)
ONE G DISSOLVES IN 20 ML WATER @ 20 °C; PARTLY SOL IN ALCOHOL
30 mg/ml in water; 30 mg/ml in 2-methoxyethanol; 7 mg/ml in ethanol
Synonyms
(4-(alpha-(p-(diethylamino)phenyl)-2,4-disulfobenzylidene)-2,5-cyclohexadien-1-ylidene)diethylammonium hydroxide inner salt sodium salt
acid blue 1
acid blue 3
alphazurine 2G
bleu patent V
blue patent violet
Blue URS
Blue VRS
C.I. acid blue 1
C.I. acid blue 3
disulfine blue
disulphine blue
ethanaminium, n-(4-((4-(diethylamino)phenyl)(2,4-disulfophenyl)methylene)-2,5-cyclohexadien-1-ylidene)-n-ethyl-, hydroxide, inner salt, sodium salt
patent blue V
patent blue violet
sodium 4-((4-(diethylamino)phenyl)(4-(diethyliminio)cyclohexa-2,5-dien-1-ylidene)methyl)benzene-1,3-disulphonate
sulfan blue
sulphan blue
Canonical SMILES
CCN(CC)C1=CC=C(C=C1)C(=C2C=CC(=[N+](CC)CC)C=C2)C3=C(C=C(C=C3)S(=O)(=O)[O-])S(=O)(=O)[O-].[Na+]
Method of Synthesis or Extraction
Sulfan Blue can be synthesized by several methods, including the reaction of phthalic anhydride with urea and sulfuric acid, the reaction of phthalonitrile with sulfuric acid, and the reaction of phthalocyanine with sulfuric acid. The efficiency and yield of each method vary depending on the reaction conditions and the purity of the starting materials. The reaction of phthalic anhydride with urea and sulfuric acid is the most commonly used method, with a yield of up to 80%. However, this method requires high temperatures and long reaction times, and it produces a large amount of waste. The reaction of phthalonitrile with sulfuric acid is a more efficient method, with a yield of up to 95%. This method also produces less waste and requires lower reaction temperatures. The reaction of phthalocyanine with sulfuric acid is the most efficient method, with a yield of up to 99%. However, this method requires high purity starting materials and careful control of the reaction conditions. Environmental and safety considerations should be taken into account when synthesizing Sulfan Blue, as the reaction produces sulfuric acid and other hazardous byproducts.
Chemical Structure and Biological Activity
Sulfan Blue has a complex chemical structure, consisting of a phthalocyanine core with four sulfonate groups attached to the nitrogen atoms. The sulfonate groups make Sulfan Blue highly water-soluble and negatively charged. The mechanism of action of Sulfan Blue is not fully understood, but it is believed to bind to proteins and other biomolecules in cells and tissues. Sulfan Blue has been shown to have a variety of biological activities, including anti-inflammatory, antioxidant, and antimicrobial effects. It has also been used as a photosensitizer in photodynamic therapy for cancer.
Biological Effects
Sulfan Blue has been shown to affect cell function and signal transduction in various cell types. It has been shown to inhibit the production of reactive oxygen species and to modulate the activity of enzymes involved in inflammation and oxidative stress. Sulfan Blue has also been shown to have potential therapeutic effects in various diseases, including cancer, Alzheimer's disease, and diabetes. However, Sulfan Blue can also have toxic effects at high concentrations, and its use should be carefully monitored.
Applications
In medical research, Sulfan Blue has been used as a diagnostic tool for lymphatic mapping and as a contrast agent in imaging studies. It has also been used in drug development, as a photosensitizer in photodynamic therapy for cancer, and as a potential treatment for Alzheimer's disease and diabetes. In environmental research, Sulfan Blue has been used to study the effects of pollutants on ecosystems and to monitor water quality. In industrial research, Sulfan Blue has been used in manufacturing processes to improve product quality and efficiency. However, the use of Sulfan Blue in these applications should be carefully monitored to minimize potential health and environmental risks.
Future Perspectives and Challenges
The use of Sulfan Blue in scientific research is limited by its potential toxicity and environmental impact. Future research should focus on developing safer and more sustainable methods for synthesizing and using Sulfan Blue. Possible solutions include the use of alternative starting materials and reaction conditions, as well as the development of biodegradable forms of Sulfan Blue. Future trends and prospects in the application of Sulfan Blue in scientific research include the development of new diagnostic and therapeutic applications, as well as the use of Sulfan Blue in nanotechnology and materials science.
Conclusion
Sulfan Blue is a synthetic dye that has been widely used in various fields of scientific research. Its complex chemical structure and biological activity make it a valuable tool for studying cell function and signal transduction. However, its potential toxicity and environmental impact should be carefully monitored. Future research should focus on developing safer and more sustainable methods for synthesizing and using Sulfan Blue, as well as exploring new applications in scientific research.
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