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1,8-Naphthalenediol, also known as 1,8-dihydroxynaphthalene, is an organic compound that typically appears as a gray white solid powder. It has a certain solubility in water and is easily soluble in alkaline aqueous solutions and common organic solvents. It belongs to the class of phenolic derivatives, with significant acidity and strong nucleophilicity. Under alkaline conditions, corresponding hydrogen peroxide negative ions can be generated, which have certain coordination ability and can form corresponding complexes with transition metals. This substance has high chemical reactivity and can be used to synthesize cyclic compounds derived from 1,8-naphthol through its nucleophilicity. It can also react with common alkyl electrophilic reagents to obtain corresponding ether or ester organic compounds. It is an important intermediate in organic synthesis, which can be used to synthesize various organic compounds, such as bactericidal active molecules and cyclic compounds derived from 1,8-naphthol. In the field of medicinal chemistry, it also has certain application value and can be used to synthesize certain drugs or drug intermediates.
Additional information of chemical compound:
|
Chemical Formula |
C10H8O2 |
|
Exact Mass |
160.05 |
|
Molecular Weight |
160.17 |
|
m/z |
160.05 (100.0%), 161.06 (10.8%) |
|
Elemental Analysis |
C, 74.99; H, 5.03; O, 19.98 |
|
Melting point |
137-143℃ |
|
Boiling point |
140℃(Press: 10 Torr) |
|
Density |
1.33 |
|
Storage conditions |
2-8℃ |
|
|
|
1,8-Naphthalenediol, also known as 1,8-dihydroxynaphthalene, is an organic compound with a unique chemical structure and a wide range of applications. The following will elaborate on its applications in multiple fields and analyze its development prospects:
1,8-dihydroxynaphthalene contains two phenolic hydroxyl groups, which enhances its intermolecular hydrogen bonding and improves its chemical reactivity. With its nucleophilicity, 1,8-dihydroxynaphthalene can be used to synthesize various cyclic compounds derived from 1,8-naphthol. For example, 1,8-dihydroxynaphthalene can react with phosphine trichloride to form corresponding oxygen complexed chlorophosphine compounds. These compounds have important application value in organic synthesis and can be further used to synthesize other complex organic molecules. 1,8-dihydroxynaphthalene can also react with common alkyl electrophilic reagents to obtain corresponding ether or ester organic compounds. These compounds serve as important intermediates in organic synthesis and can be used for further synthesis of drugs, dyes, fragrances, and more. For example, through etherification reaction, 1,8-dihydroxynaphthalene can be converted into ether compounds with specific functions; Through esterification reaction, ester compounds with different ester structures can be obtained. It can also undergo condensation, addition and other reactions with other organic compounds to generate organic molecules with specific structures and functions. These molecules have important application value in organic synthesis and can be used to synthesize new materials, drugs, etc.
Pharmaceutical chemical intermediates
1,8-dihydroxynaphthalene has important application value in medicinal chemistry and can be used as a synthetic intermediate for various drugs. Its unique chemical structure and reactivity enable it to participate in the construction process of various drug molecules. For example, some drug molecules with biological activities such as antibacterial, anti-inflammatory, and antioxidant contain structural units of 1,8-dihydroxynaphthalene. By synthesizing these drug molecules containing 1,8-dihydroxynaphthalene, new drug options can be provided for the treatment of related diseases. 1,8-dihydroxynaphthalene also plays an important role in drug development. Researchers can utilize its unique chemical properties to design and synthesize novel drug molecules with specific biological activities. By screening and optimizing these new drug molecules, drug candidates with better efficacy and lower side effects can be discovered, providing new ideas and methods for drug development.
1,8-dihydroxynaphthalene can be used as an additive for functional materials to improve their performance. For example, adding 1,8-dihydroxynaphthalene to polymer materials can improve their thermal stability, mechanical properties, and chemical corrosion resistance. In addition, 1,8-dihydroxynaphthalene can also combine with other functional groups to form polymer materials with specific functions. These materials have broad application prospects in fields such as electronics, optoelectronics, and sensing. 1,8-dihydroxynaphthalene can be used to synthesize various dyes and pigments. Its unique chemical structure allows it to bind with various chromophores, forming dye molecules with bright colors and good dyeing properties. These dyes and pigments have a wide range of applications in industries such as textiles, leather, plastics, etc. By adjusting the binding mode and proportion of 1,8-dihydroxynaphthalene with other chromophores, dyes and pigments with different colors and properties can be synthesized.
1,8-Naphthalenediol also plays a crucial defensive role in plants
1,8-Naphthalenediol is a phenolic organic compound with the molecular formula C10H8O2, formed by two hydroxyl groups (- OH) replacing the carbon atoms at positions 1 and 8 of the naphthalene ring. Its chemical properties include:
Acidity and nucleophilicity
The presence of hydroxyl groups gives it significant acidity, which can generate negative ions (O ⁻) under alkaline conditions, enhance nucleophilicity, and participate in various chemical reactions.
Coordination ability
Hydrogen peroxide negative ions can form stable complexes with transition metals such as nickel, copper, and zinc, which may participate in metal ion transport or enzyme activity regulation in vivo.
Reactivity
As an intermediate, 1,8-dihydroxynaphthalene can be used to synthesize bioactive molecules such as spironone A benzoanalogues, naphthopyran derivatives, and palmitoyl CP17 analogues, suggesting that it may act as a precursor in plant metabolism to participate in the synthesis of defense substances.
The role of secondary metabolites in plant defense mechanisms
Plants resist pathogens and herbivorous insects through secondary metabolites such as phenols, terpenes, and alkaloids. These metabolites are divided into two categories:
Constituent defense metabolites
pre synthesized and stored in plants, directly inhibiting pathogens or insects.
Induced defense metabolites
specifically synthesized after invasion, with more economical energy consumption, are the core of plant chemical defense.
1,8-dihydroxynaphthalene may be a precursor or intermediate of inducible defense metabolites, and its defense function needs to be analyzed in conjunction with specific metabolic pathways.
Potential role of 1,8-dihydroxynaphthalene in plant defense
As a precursor for melanin synthesis, it enhances the physical barrier
Fungal melanin production: 1,8-dihydroxynaphthalene is a precursor for the synthesis of DHN melanin (1,8-dihydroxynaphthalene melanin). DHN melanin is an important component of the cell wall of many plant pathogenic fungi, such as rice blast fungus and wheat blast fungus, endowing them with stress resistance (such as UV resistance and enzymatic hydrolysis resistance).
Plant defense strategy: Plants may competitively inhibit or degrade 1,8-dihydroxynaphthalene, block the synthesis of melanin by pathogenic fungi, and weaken their infectivity. For example, melanin degrading enzymes or chelating agents produced by plants can interfere with fungal metabolism.
Case support: Studies have shown that certain plants synthesize compounds similar to 1,8-dihydroxynaphthalene structures when infected by pathogens, which inhibit fungal melanin deposition and limit its expansion.
Synthesize antibacterial active molecules to directly inhibit pathogens
Derivative synthesis: 1,8-dihydroxynaphthalene can generate antibacterial derivatives such as naphthoquinone compounds through oxidation, cyclization, and other reactions. These derivatives can damage pathogen cell membranes, inhibit respiratory chains, or interfere with DNA synthesis.
Experimental evidence: In vitro experiments have shown that certain derivatives of 1,8-dihydroxynaphthalene have inhibitory effects on bacteria (such as Escherichia coli, Staphylococcus aureus) and fungi (such as Candida albicans), suggesting that they may play a similar role in plants.
Metabolic pathway association: Compounds with naphthalene like structures (such as naphthols and naphthoquinones) in plants are often reported to have antibacterial activity, supporting the hypothesis that 1,8-dihydroxynaphthalene serves as a precursor for defense substances.
Participate in plant microbe interactions and regulate defense signals
Signal molecule function: 1,8-dihydroxynaphthalene may act as a signal molecule to trigger the expression of plant defense related genes. For example, its oxidation products may activate the jasmonic acid (JA) or salicylic acid (SA) signaling pathways, inducing systemic acquired resistance (SAR).
Microbial induced synthesis: Infection by pathogenic bacteria or colonization by beneficial microorganisms may induce plant synthesis of 1,8-dihydroxynaphthalene as a local or systemic defense signal. For example, rhizosphere bacteria can stimulate the synthesis of phenolic compounds in plant roots, enhancing disease resistance.
Research gap: Currently, there is no direct evidence to suggest that 1,8-dihydroxynaphthalene is involved in plant signal transduction, but its chemical structure similarity to known signaling molecules such as salicylic acid and chlorogenic acid suggests this possibility.
Metal ion chelation inhibits pathogen enzyme activity
Metal dependent enzyme inhibition: Many pathogenic bacteria 'enzymes (such as proteases and chitinase) rely on metal ions (such as Fe ² ⁺, Zn ² ⁺) to exert their activity. The coordination ability of 1,8-dihydroxynaphthalene may enable it to chelate these ions and inhibit enzyme function.
Defense case: Plant produced iron chelators (such as iron carriers) can deprive pathogenic bacteria of essential iron ions, limiting their growth. 1,8-dihydroxynaphthalene may interfere with pathogen metabolism through a similar mechanism, combining with copper and zinc ions.
Experimental support: Synthetic metal chelating agents (such as EDTA) are used in agriculture to inhibit pathogens, suggesting that natural chelating agents (such as 1,8-dihydroxynaphthalene) may have similar functions.
Synergistic effect with other defense mechanisms
Synergistic effect with phenolic compounds
1,8-dihydroxynaphthalene may interact with other phenols (such as chlorogenic acid and tannins) to enhance antibacterial efficacy. For example, phenolic compounds can damage pathogen cell membranes, while 1,8-dihydroxynaphthalene derivatives may further inhibit their repair mechanisms.
Complementarity with terpenes
Terpenes (such as phytohormones) are often used as constitutive defense substances, while 1,8-dihydroxynaphthalene derivatives may act as inducible substances, rapidly synthesizing and forming multi-level defense after invasion occurs.
Coordination with physical barriers
By inhibiting the synthesis of melanin by pathogenic bacteria, 1,8-dihydroxynaphthalene may weaken its ability to penetrate plant cell walls and work synergistically with physical defense mechanisms such as lignin deposition.
Research Status and Future Directions
Current research limitations
The natural existence and synthetic pathway of 1,8-dihydroxynaphthalene in plants are not yet clear, and most studies focus on its chemical synthesis or in vitro activity.
Lack of in vivo functional validation experiments in plants, such as gene editing and metabolomics analysis.
Future research focus
Metabolomics analysis: Identify the accumulation patterns of 1,8-Naphthalenediol and its derivatives in plants infected with pathogens.
Gene function research: Knocking out or overexpressing related synthetic genes using CRISPR/Cas9 and other technologies to observe changes in defense phenotypes.
Interaction mechanism analysis: Using yeast two hybrid or immunoprecipitation techniques, screen plant or pathogen proteins that bind to 1,8-dihydroxynaphthalene.
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