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4-Hydroxycoumarin, white needle like crystal. Industrial products are white or light yellow solid powders. Slightly soluble in cold water, soluble in hot water, ethanol, ether and other organic solvents. There are many synthetic routes for 4-hydroxycoumarin. The common production methods in industry include: the Clausen condensation of methyl acetylsalicylate under the condition of basic catalyst; Acetoacetate reacts with acetylsalicylyl chloride and condenses. Coumarins are widely distributed in the plant kingdom. It is mainly used for the synthesis of antithrombotic drugs and 4-hydroxycoumarin type anticoagulant rodenticides (warfarin, Dalong, etc.).
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Chemical Formula |
C9H6O3 |
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Exact Mass |
162 |
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Molecular Weight |
162 |
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m/z |
162 (100.0%), 163 (9.7%) |
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Elemental Analysis |
C, 66.67; H, 3.73; O, 29.60 |
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4-hydroxycoumarin, with the chemical formula C9H6O3, is a white needle shaped crystal or white to light yellow solid powder with a melting point typically between 210 and 216 ℃. It is slightly soluble in cold water, but soluble in various organic solvents such as hot water, ethanol, and ether. 4-hydroxycoumarin can emit a floral like fragrance, which is not only pleasant but also harmless to human health. Therefore, it is widely used in the field of spices and flavorings.
Cosmetics and perfume fixatives
As a perfume, 4-hydroxycoumarin is widely used to prepare cosmetics and cosmetics perfume. Its unique aroma can add long-lasting fragrance to cosmetics, making the product more attractive. In perfume, 4-hydroxycoumarin, as a fixative, can enhance the durability and stability of perfume, making the fragrance more lasting and charming. For example, some high-end perfume brands use 4-hydroxycoumarin as one of their fragrance fixing ingredients to provide consumers with a lasting and elegant fragrance experience.
Soap and detergent fragrances
In the fields of soap and detergent, 4-hydroxycoumarin also plays an important role. As a spice ingredient, it can give soap and detergent a pleasant aroma, enhancing the product's user experience. Meanwhile, 4-hydroxycoumarin also has antibacterial and antioxidant properties, which help maintain the cleanliness and stability of the product. Therefore, adding 4-hydroxycoumarin to soap and detergent can not only enhance the fragrance of the product, but also improve its cleaning effect and service life.
Food and candy additives
4-hydroxycoumarin is also used as an additive in food and candy. In food, it can add unique aroma and taste, enhancing the attractiveness of food. In candy, 4-hydroxycoumarin, as one of the flavoring ingredients, can add long-lasting aroma and taste to candy, making consumers more fond of it. However, it should be noted that when used as a food additive, relevant regulations and standards must be strictly followed to ensure the safety and health of the food.
Rubber and plastic product fragrance enhancers
In addition to cosmetics, soap, and food industries, 4-hydroxycoumarin is also used as a fragrance enhancer for rubber and plastic products. Adding 4-hydroxycoumarin to rubber and plastic products can give them a pleasant aroma, enhance their added value and market competitiveness. For example, some rubber and plastic products such as automotive interior parts and household items use 4-hydroxycoumarin as one of their fragrance enhancing ingredients, providing consumers with a more comfortable and enjoyable user experience.
Specific examples
Application in high-end perfume
High end perfume brands often pursue unique fragrance and lasting fragrance effect. 4-hydroxycoumarin is widely used in high-end perfume formulations because of its unique fragrance and durability. For example, a well-known perfume brand uses 4-hydroxycoumarin as one of its fragrance fixing ingredients, which cooperates with other fragrance ingredients to form the unique fragrance of the perfume. This perfume not only has a lasting and charming fragrance, but also has an elegant and elegant temperament, which is deeply loved by consumers.
Enhanced fragrance in soap and detergent
In the soap and detergent industry, 4-hydroxycoumarin is also used as a fragrance enhancer. By adding 4-hydroxycoumarin, soap and detergent can be endowed with a more intense and long-lasting aroma. For example, a well-known detergent brand uses 4-hydroxycoumarin as one of its aroma enhancing ingredients, which, when combined with other fragrance components, together form the unique aroma of the detergent. This detergent not only has excellent cleaning effect, but also has a long-lasting and pleasant aroma, providing consumers with a more pleasant user experience.ble.
Aroma enhancement in food and candy
In the fields of food and candy, 4-hydroxycoumarin also plays an important role. By adding 4-hydroxycoumarin, food and candy can be endowed with a more unique and long-lasting aroma and taste. For example, some high-end chocolate brands use 4-hydroxycoumarin as one of their aroma enhancing ingredients, which, when combined with other spice components, create the unique aroma and taste of the chocolate. This type of chocolate not only has a delicate and rich taste, but also has a long-lasting and charming aroma, which is deeply loved by consumers.
Fragrance enhancement applications in rubber and plastic products
In the field of rubber and plastic products, 4-hydroxycoumarin is also used as a fragrance enhancer. By adding 4-hydroxycoumarin, rubber and plastic products can be endowed with a more pleasant and long-lasting aroma. For example, some car interior brands use 4-hydroxycoumarin as one of their fragrance enhancing ingredients, which, when combined with other spice components, create the unique aroma of the car interior. This type of car interior not only has excellent comfort and aesthetics, but also has a long-lasting and pleasant aroma, providing consumers with a more pleasant and comfortable driving experience.
Advantage
(1) Unique and persistent aroma:
4-hydroxycoumarin has a unique aroma and persistence, which can add unique and long-lasting fragrance effects to spice and flavoring products.
(2) High safety:
4-hydroxycoumarin is harmless to human health and meets the requirements of relevant regulations and standards, so it can be safely used in the field of fragrances and flavorings.
(3) Widely used:
4-hydroxycoumarin can be used not only in cosmetics, soap, detergents and other fields, but also in food, candy, rubber, plastic products and other fields, with broad application prospects.
challenge
(1) Complex synthesis process:
Currently, there are many methods for synthesizing 4-hydroxycoumarin, but they all have some shortcomings and drawbacks, such as expensive raw material prices and complex synthesis processes. This limits the large-scale production and application of 4-hydroxycoumarin.
(2) Intense market competition:
With the continuous development of the spice and fragrance market, competition is becoming increasingly fierce. In order to stand out in the market, it is necessary to continuously develop new spice ingredients and formulas, improve product quality and competitiveness.
(3) Environmental requirements are increasing:
With the continuous improvement of environmental awareness, the environmental requirements for spice and fragrance products are also becoming higher and higher.
Synthesis of 4-hydroxycoumarin: obtained by cyclization of methyl acetylsalicylate.
Specific steps:
1. Put sodium carbonate and liquid paraffin into the reaction pot, heat and stir in an airtight manner, and gradually increase the temperature to 240 ° C. add the dissolved methyl acetylsalicylate. When the temperature drops for about 10min, it gradually rises again and remains at 240-260 ° C. After addition, reflux for 1H.
2. Discharge, filter, discard the filtrate, dissolve the solid in water, heat it to about 70 ℃, separate a small amount of oil layer in the upper layer, add salt and acid to adjust the pH to 6, and add activated carbon to decolorize. After filtration, the filtrate is acidified with hydrochloric acid to pH 1, i.e. 4-hydroxycoumarin is precipitated. Ice is added to complete the precipitation. After filtration, water is washed until the washing solution is neutral. After the filter cake is dried, 4-hydroxycoumarin is obtained. The yield was 15.21%.
3. In production, acetylsalicylyl chloride can be used as raw material, condensed with ethyl acetoacetate to form ethyl a - (2-hydroxybenzoyl) acetoacetate, and hydrolyzed with sodium hydroxide solution to obtain sodium a - (2-hydroxybenzoyl) acetoacetate. Then, in 92% sulfuric acid, cyclization was carried out at 110-115 ℃ to produce 3-acetyl-4-hydroxycoumarin, which was then hydrolyzed to obtain 4-hydroxycoumarin. The yield of this method is about 64%.
FAQ
What is 4-hydroxycoumarin used for?
Most 4-hydroxycoumarin derivatives showed representative anticoagulant effects, while compounds 3, 5, 30, 40, 46, and 64 exhibit a wide variety of activities including antiarthritis, anti-inflammatory, anticancer, antithrombosis, teratogenic, antibacterial, and photoaffinity effects.
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