Orcinol monohydrate is a chemical substance, also known as moss black phenol or 3,5-dihydroxytoluene monohydrate. Molecular formula C7H8O2 · H2O, CAS 6153-39-5, white to beige crystalline powder, sometimes appearing as white diamond shaped crystals. Its high solubility in water makes its treatment and application in aqueous solutions relatively easy. Easy to dissolve in alcohols and ethers, indicating good miscibility with alcohol and ether solvents. Slightly soluble in benzene, with relatively low solubility in benzene, but still possessing a certain degree of solubility. Slightly soluble in chloroform and carbon disulfide, with lower solubility in chloroform and carbon disulfide, indicating poor solubility in these two solvents. Commonly used in laboratory research and scientific experiments, especially in organic synthesis and drug development. Due to its pharmaceutical grade purity, it also has applications in the pharmaceutical field, including drug synthesis or as a drug ingredient.
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Chemical Formula |
C7H10O3 |
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Exact Mass |
142.06 |
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Molecular Weight |
142.15 |
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m/z |
142.06 (100.0%), 143.07 (7.6%) |
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Elemental Analysis |
C, 59.15; H, 7.09; O, 33.76 |
3,5-dihydroxytoluene (Orcinol monohydrate), chemical formula C7H10O3, molecular weight 142.15, CAS number 6153-39-5, also known as moss black phenol monohydrate or lichen phenol monohydrate. Its molecular structure contains two phenolic hydroxyl groups and one methyl group, with unique chemical properties such as sensitivity to light and oxygen, easy solubility in water, alcohol, and ether, and easy oxidation to turn red in air.
It is an important detection reagent in analytical chemistry, and its phenolic hydroxyl structure enables it to undergo color or complexation reactions with specific substances, providing reliable basis for qualitative and quantitative analysis of substances.
1. Metal ion detection
In heavy metal detection, it can undergo specific reactions with metal ions such as antimony and chromium to form colored complexes. For example, in antimony ion detection, a red complex is formed by reacting with antimony ions under specific conditions. By using colorimetric or spectrophotometric methods, the antimony ion content can be accurately determined by comparing the color depth with the standard curve. This method is easy to operate, highly sensitive, and widely used in environmental monitoring, industrial wastewater treatment, and other fields to ensure that heavy metal content meets environmental standards.
2. Sugar substance detection
In carbohydrate analysis, it has unique advantages. Its concentrated sulfuric acid solution can decompose monosaccharides and polysaccharides in cotton fibers into sugar aldehyde derivatives, which form obvious red complexes with 3,5-dihydroxytoluene (monohydrate), and the degree of color development is linearly related to the sugar concentration. The industry standard SN/T 0311.1-94 "Quantitative Method for Testing Sugar Content in Cotton Fibers for Import and Export" and the national standard GB/T 16258-2008 "Quantitative Method for Testing Sugar Content in Cotton Fibers" in China are both based on this principle. By using colorimetric or spectrophotometric methods, the sugar content in cotton fibers can be quickly and accurately determined, providing important data for textile quality control.
3. Nitrate and nitrite detection
Nitrate and nitrite content are important indicators in food and environmental monitoring. Reacts with nitrate and nitrite to produce specific colored products. For example, under acidic conditions, nitrite reacts with 3,5-dihydroxytoluene (monohydrate) to produce orange red compounds, and the nitrite content can be determined by measuring the absorbance. This method has high sensitivity and good selectivity, and is widely used for detecting nitrate and nitrite in drinking water and food, ensuring food safety and human health.
Organic synthesis field: Building the 'key puzzle' of complex molecules
As an important intermediate in organic synthesis, the phenolic hydroxyl and methyl structures of 3,5-dihydroxytoluene (monohydrate) make it a key raw material for the synthesis of various organic compounds, playing an important role in the synthesis of drugs, fragrances, dyes, and more.
1. Drug synthesis
It is an important raw material for synthesizing various drugs. For example, in the synthesis of phenemode ((E) -3,5-dihydroxy-4-isopropylstilbene), the final phenemode is synthesized through reaction steps such as bromination, isopropylation, and Witting Homer condensation. Phenemode is a pioneering new drug that has obtained clinical approval for the treatment of various major autoimmune diseases, such as psoriasis, eczema, ulcerative colitis, and various allergic diseases. The use provides a new source of drugs for the treatment of these diseases, improving the quality of life of patients.
2. Spice synthesis
In the spice industry, it is an important precursor for synthesizing various spices. Moscin monomethyl ether is a essence with the aroma of oak moss resin and fruit flavor, which naturally exists in oak moss resin. Chlorophenol monomethyl ether can be synthesized through reactions such as methylation. In the formula of daily chemical essence, 25 parts of lanolin monomethyl ether and 75 parts of 2,4-dihydroxy-3,6-dimethylbenzoic acid methyl ester are usually used together. The compound perfume has a vivid natural oak moss fragrance, which is widely used in perfume, cosmetics, soap essence and other fields, adding unique fragrance to the product and improving the competitiveness of the product.
3. Dye synthesis
Orcinol monohydrate also plays an important role in dye synthesis. Its phenolic hydroxyl group can react with other functional groups in the dye molecule to form stable chemical bonds, thereby synthesizing dyes with specific colors and properties. For example, in the synthesis of certain azo dyes, 3 can be used as a diazo component or coupling component to participate in diazotization and coupling reactions, generating brightly colored and colorfast dyes that are widely used in industries such as textiles and leather dyeing.
In the field of medicine, it has biological activities such as antibacterial, antifungal, and anti radiation, providing strong support for disease treatment and health protection.
1. Antibacterial and antifungal effects
Its phenolic hydroxyl structure has the ability to damage bacterial and fungal cell membranes, inhibit cell respiration and metabolism, and has a significant inhibitory effect on various fungi. It has been widely used in clinical practice to treat superficial fungal infections and fungal vaginitis. When treating fungal vaginitis, it is made into an external preparation that directly acts on the affected area, inhibits the growth and reproduction of mold, relieves symptoms such as itching and burning, promotes vaginal mucosal repair, and improves the quality of life of patients.
2. Anti radiation effect
In terms of radiation protection, it has also shown certain potential. Research has shown that it can eliminate free radicals generated by radiation, reduce the damage of free radicals to biomolecules such as DNA, proteins, and lipids in cells, and protect the normal structure and function of cells. In radiation therapy and emergency response to nuclear radiation accidents, it can be used as an auxiliary drug to reduce the harm of radiation to the human body, improve the survival rate and quality of life of patients.
In the food industry, it has become an important substance for ensuring food safety and extending the shelf life of food due to its antioxidant and preservative effects.
1. Antioxidant effect
Its phenolic hydroxyl structure gives it strong antioxidant capacity, which can eliminate free radicals in food, inhibit oil oxidation and rancidity, and prevent food from changing color, taste, and spoilage. Adding an appropriate amount to oily foods can effectively extend their shelf life, maintain their flavor and nutritional value. For example, adding this substance to edible oil can inhibit the production of peroxides and free radicals from oil oxidation, reduce oil rancidity, and improve the quality and safety of edible oil.
3. Preservation function
It also has certain applications in the preservation of fruits and vegetables. It can inhibit the respiration and microbial growth and reproduction of fruits and vegetables, delay their aging and decay. Make it into a preservative, spray it on the surface of fruits and vegetables or soak them to form a protective film, reduce water loss and oxygen contact, and maintain the freshness and quality of fruits and vegetables. For example, in strawberry preservation, the use of this preservative can extend the shelf life of strawberries, reduce the rate of strawberry decay, and increase the commercial value of strawberries.
It is an important raw material in the spice industry, providing rich possibilities for spice synthesis and making spice aromas more diverse.
1. Synthetic natural flavors
Many natural flavors contain 3,5-dihydroxytoluene (monohydrate) or its derivative structures. By using chemical synthesis methods, this substance can be used as a raw material to synthesize fragrances with natural aroma. For example, synthesizing certain spices with floral, fruity, or woody aromas to meet people's demand for natural fragrances. These synthetic fragrances are widely used in daily chemical products such as perfume, cosmetics, soap, etc., to improve the aroma quality and attractiveness of products.
2. Blending essence
In essence blending, it can be used as an important flavoring component to coordinate with other spices to blend essence with unique aroma style. According to different product needs and aroma characteristics, a reasonable adjustment of the dosage of 3,5-dihydroxytoluene (monohydrate) and the proportion of other spices can be made to produce a variety of fragrance essence, such as flower flavor, fruit flavor, wood flavor, oriental flavor, which are widely used in food, beverage, tobacco, washing products and other industries, adding unique charm to the products.
In the field of scientific research, it is an important organic compound for the study of biological dyes and proteomics, providing powerful tools for scientific research.
1. Biological dyes
In biological research, staining technology is an important means of observing and studying the structure of cells and tissues. Can be used as a biological dye to stain cells and tissues. It can bind with specific components in cells and tissues, producing different color reactions, thus clearly displaying the structure of cells and tissues. For example, in cell staining, different structures such as the nucleus and cytoplasm can be colored differently, making it easier to observe and study cell morphology and function.
2. Proteomic research
In proteomics research, it can be used for protein separation and identification. It can have specific interactions with proteins, and different proteins can be separated through separation methods such as chromatography and electrophoresis. Combined with identification methods such as mass spectrometry, the protein type and structure can be determined. This provides important technical means for in-depth research on protein functions, interactions, and regulatory mechanisms, and promotes the development of the field of life sciences.
Orcinol monohydrate, as an important fine chemical intermediate, has a wide range of applications in various fields such as pharmaceuticals, dyes, fragrances, and food additives. There are various synthesis methods, and the following are several common synthesis methods. The specific steps and reaction conditions of these methods will be introduced in detail.
The following are detailed introductions of two synthesis methods for 3,5-dihydroxytoluene, namely microbial fermentation and enzyme catalysis:
Microbial fermentation
Microbial fermentation is the process of using the metabolic activity of microorganisms to produce useful substances. In the synthesis of 3,5-dihydroxytoluene, certain specific microorganisms have the potential to convert precursor substances into the compound.
Select microbial strains from nature that can efficiently convert precursor substances into 3,5-dihydroxytoluene through natural screening or genetic engineering methods.
Further improve the selected bacterial strains to enhance their conversion efficiency, tolerance, and product purity.
Fermentation conditions include temperature, pH value, dissolved oxygen concentration, nutrient ratio, etc. These factors have a significant impact on the growth of microorganisms and the accumulation of products.
By finely regulating these conditions, the metabolic pathways of microorganisms can be optimized, thereby increasing the yield and purity of 3,5-dihydroxytoluene.
After fermentation, it is necessary to separate 3,5-dihydroxytoluene from the fermentation broth. This usually involves steps such as filtration, extraction, crystallization, etc.
The separated product may require further purification to remove impurities and improve purity.
At present, the method of synthesizing 3,5-dihydroxytoluene through microbial fermentation is still in the laboratory research stage and has not yet been industrialized.
The main challenges include unstable yield, difficulty in product separation and purification, and high production costs.
Enzyme catalysis
Enzymatic catalysis is the process of using enzymes purified from within or outside the body as catalysts to accelerate chemical reactions. Enzyme catalysis has the advantages of high efficiency, strong specificity, and mild reaction conditions in the synthesis of 3,5-dihydroxytoluene.
By carefully selecting or designing enzymes with specific catalytic activity, efficient synthesis of 3,5-dihydroxytoluene can be achieved.
These enzymes may originate from microorganisms, plants, or animals in nature, or may be modified and optimized through genetic engineering methods.
The conditions for enzyme catalyzed reactions are usually mild, such as room temperature, atmospheric pressure, and pH values close to neutral.
By optimizing the composition, pH value, temperature and other conditions of the reaction medium, the efficiency of enzyme catalysis and product yield can be further improved.
Compared to microbial fermentation, the products of enzyme catalyzed reactions are usually easier to separate and purify.
This is mainly because enzyme catalyzed reactions have higher specificity and product purity.
Although enzyme catalysis has shown promising application prospects in the synthesis of 3,5-dihydroxytoluene, it still faces some technical challenges.
For example, the stability and reusability of enzymes, the selection of reaction media, and the inhibitory effects of products all need to be improved and optimized through enzyme engineering strategies.
With the continuous development and improvement of enzyme engineering technology, it is believed that enzyme catalysis will play an increasingly important role in the synthesis of 3,5-dihydroxytoluene.
In summary, microbial fermentation and enzyme catalysis are both promising methods for the synthesis of 3,5-dihydroxytoluene. However, both require further exploration and optimization at the technical level to achieve more efficient and economical production processes.
Frequently Asked Questions
What is the positive result of Orcinol test?
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Bial's test detects pentoses and pentosans by hydrolyzing them into pentoses, which are then dehydrated to form furfural and condense with orcinol to produce a blue-green precipitate, indicating a positive result. A bluish color with xylose confirmed it contains pentoses.
What is orcinol monohydrate used for?
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Orcinol is a phenolic compound occurring in lichens. It is used in the detection of pentoses as part of Bial's reagent, which forms a green product upon reaction. Storage/Handling: Store at room temperature and protect from light.
Is orcinol a phenol?
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Resorcinol and orcinol are simple members of the family of phenolic compounds present in particulate matter in the atmosphere; they are amphiphilic in nature and thus surface active in aqueous solution.
Is orcinol light sensitive?
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Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Air and light sensitive. Store under inert gas.
What is the Bial orcinol reagent?
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Bial's reagent consists of 0.4 g orcinol, 200 ml of concentrated hydrochloric acid and 0.5 ml of a 10% solution of ferric chloride. Bial's test is used to distinguish pentoses from hexoses; this distinction is based on the color that develops in the presence of orcinol and iron (III) chloride.
Is orcinol toxic?
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Hazard class: Acute toxicity, oral (Category 4). Harmful if swallowed (H302). Do not eat, drink or smoke when using this product (P270). Hazard class: Skin and serious eye damage, corrosion or irritation (Category 2, 2A).
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