Orcein
Catalog Number: BT-277608
CAS Number: 1400-62-0
Molecular Formula: C28H24N2O7
Molecular Weight: 500.5 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction
Description
Orcein is a natural dye that has been used for centuries to color textiles, leather, and food. It is derived from lichens, which are symbiotic organisms composed of a fungus and an alga or a cyanobacterium. Orcein has also been found to have biological activity, making it a subject of interest in medical, environmental, and industrial research.
Properties
CAS Number
1400-62-0
Product Name
Orcein
IUPAC Name
8-(2,4-dihydroxy-6-methylanilino)-2-(2,4-dihydroxy-6-methylphenyl)imino-7-hydroxy-1,9-dimethyldibenzofuran-3-one
Molecular Formula
C28H24N2O7
Molecular Weight
500.5 g/mol
InChI
InChI=1S/C28H24N2O7/c1-11-5-15(31)7-17(33)25(11)29-27-13(3)23-21(9-19(27)35)37-22-10-20(36)28(14(4)24(22)23)30-26-12(2)6-16(32)8-18(26)34/h5-10,29,31-35H,1-4H3
InChI Key
VPEASJIRGSVXBF-UHFFFAOYSA-N
SMILES
CC1=CC(=CC(=C1NC2=C(C3=C(C=C2O)OC4=CC(=O)C(=NC5=C(C=C(C=C5C)O)O)C(=C43)C)C)O)O
Solubility
Soluble in DMSO
Synonyms
orcein
PAcein
PAcein
Canonical SMILES
CC1=CC(=CC(=C1NC2=C(C3=C(C=C2O)OC4=CC(=O)C(=NC5=C(C=C(C=C5C)O)O)C(=C43)C)C)O)O
Isomeric SMILES
CC1=CC(=CC(=C1NC2=C(C3=C4C(=C(C(=O)C=C4OC3=CC2=O)NC5=C(C=C(C=C5C)O)O)C)C)O)O
Method of Synthesis or Extraction
Orcein can be synthesized or extracted from lichens using various methods. The most commonly used methods are acid extraction, alkaline extraction, and enzymatic extraction. Acid extraction involves boiling the lichen in an acidic solution, such as hydrochloric acid or sulfuric acid, to release the orcein. Alkaline extraction involves boiling the lichen in an alkaline solution, such as ammonia or sodium hydroxide, to release the orcein. Enzymatic extraction involves using enzymes, such as cellulase or pectinase, to break down the lichen and release the orcein. Each method has its own efficiency and yield, with acid extraction being the most efficient and yielding the highest amount of orcein. However, acid extraction is also the most environmentally and safety hazardous method, as it involves the use of strong acids. Alkaline extraction and enzymatic extraction are more environmentally and safety friendly, but they yield lower amounts of orcein.
Chemical Structure and Biological Activity
Orcein is a complex molecule composed of several components, including orcinol, lecanoric acid, and erythrin. Its chemical structure has been elucidated using various spectroscopic techniques, such as nuclear magnetic resonance (NMR) and mass spectrometry (MS). Orcein has been found to have biological activity, particularly as an antioxidant and an antimicrobial agent. Its mechanism of action involves scavenging free radicals and inhibiting the growth of microorganisms. Orcein has also been found to have potential as an anticancer agent, as it can induce apoptosis in cancer cells.
Biological Effects
Orcein has been found to have various effects on cell function and signal transduction. It can modulate the expression of genes involved in inflammation, oxidative stress, and apoptosis. Orcein can also activate various signaling pathways, such as the mitogen-activated protein kinase (MAPK) pathway and the nuclear factor-kappa B (NF-κB) pathway. Its potential therapeutic effects include the treatment of cancer, inflammation, and microbial infections. However, orcein can also have toxic effects, particularly at high doses. It can induce DNA damage and cell death, and it can also cause liver and kidney damage.
Applications
Orcein has various applications in medical, environmental, and industrial research. In medical research, orcein has been studied for its potential role in drug development. It has been found to have anticancer, anti-inflammatory, and antimicrobial properties, making it a promising candidate for the development of new drugs. Clinical trials have also been conducted to evaluate the safety and efficacy of orcein-based therapies. In environmental research, orcein has been studied for its effects on ecosystems and its role in pollution management. It has been found to have potential as a natural dye for textiles and as a bioindicator of environmental pollution. In industrial research, orcein has been used in manufacturing processes to improve product quality and efficiency. Health and safety considerations are important in the use of orcein in industrial applications, as it can be toxic at high doses.
Future Perspectives and Challenges
The use and study of orcein face several limitations and challenges. One of the main challenges is the limited availability of lichens, which are the source of orcein. The extraction of orcein from lichens is also a time-consuming and labor-intensive process. Another challenge is the toxicity of orcein at high doses, which limits its use in medical and industrial applications. Possible solutions and improvements include the development of more efficient and environmentally friendly methods of extraction, the synthesis of orcein analogs with improved bioactivity and safety profiles, and the identification of new sources of orcein. Future trends and prospects in the application of orcein in scientific research include the development of new drugs and therapies, the use of orcein as a natural dye and bioindicator, and the exploration of its potential in other fields, such as agriculture and food science.
Conclusion
Orcein is a natural dye with biological activity that has been studied for its potential therapeutic, environmental, and industrial applications. Its synthesis or extraction involves various methods, each with its own efficiency and yield, and environmental and safety considerations. Orcein's chemical structure and biological activity have been elucidated, and its effects on cell function and signal transduction have been studied. Orcein has potential therapeutic and toxic effects, and its applications in medical, environmental, and industrial research have been explored. The use and study of orcein face several limitations and challenges, but possible solutions and improvements are being pursued. Orcein's future prospects in scientific research are promising, and its potential in various fields is being explored.
Conclusion
Orcein is a natural dye with biological activity that has been studied for its potential therapeutic, environmental, and industrial applications. Its synthesis or extraction involves various methods, each with its own efficiency and yield, and environmental and safety considerations. Orcein's chemical structure and biological activity have been elucidated, and its effects on cell function and signal transduction have been studied. Orcein has potential therapeutic and toxic effects, and its applications in medical, environmental, and industrial research have been explored. The use and study of orcein face several limitations and challenges, but possible solutions and improvements are being pursued. Orcein's future prospects in scientific research are promising, and its potential in various fields is being explored.
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