p-Hydroxyacetophenone, normally referred to as piceol, is a white needle-like crystal at area temperature level, combustible, comfortably soluble in hot water, methanol, ethanol, ether, acetone, as well as likewise benzene, as well as also insoluble in oil ether. It is normally existing in the stems as well as leaves of Artemisia chinensis of Asteraceae, and the origins of Artemisia chinensis and Panax ginseng of Radish household. This product is utilized in the manufacture of choleretic medicines and also various other raw materials for natural synthesis. This product is medically made use of to deal with liver disease and also has particular alleviative effect on jaundice. It has anti-oxidation, anti-irritation, solution stabilization and broad-spectrum disinfectant capabilities. Since its molecule includes hydroxyl as well as ketone groups on the benzene ring, it is usually used as an intermediate in natural synthesis to react with various other compounds to manufacture lots of vital materials.
147-148 °C3 mm Hg(lit.)
0.002Pa at 20℃
Store below +30°C.
methanol: 0.1 g/mL, clear
Almost white to beige
10 g/L (22 ºC)
Application and Development Prospect of P-Hydroxyacetophenone
1. Utilized as a preservative
For a lot of cosmetics, to ensure sanitary security within the duration of use, chemicals might not be added, but disinfectant systems should be made use of, as well as the problem of anti-bacterial should be thought about. P-Hydroxyacetophenone is generally used as a preservative in cosmetics. It additionally has anti-oxidation, relaxing and calming functions. It is also a synergistic result when compounded with other preservatives. It is a multi-functional cosmetic basic material. The duty of chemicals is primarily utilized to keep the quality of the product as well as avoid microorganisms as well as fungis from attacking and infecting. Poor quality preservatives are harmful to the skin, and frequent get in touch with will certainly trigger allergic reactions, so the preservatives used in our skin care items as well as cosmetics need to be moderate in nature and also stable in structure.
P-Hydroxyacetophenone is presently the best high-temperature auxiliary active stabilizer in the clinical area. It is commonly utilized as a preservative in cosmetics and also has no harm to body or skin.
P-Hydroxyacetophenone is presently the safest high-temperature supporting energetic stabilizer in the clinical area. It is usually used as a preservative in cosmetics as well as has no injury to human body or skin. Several cosmetics or skin treatment products claim to not include any kind of preservatives, yet as a matter of fact they make use of p-hydroxyacetophenone rather than chemicals.
2. Utilized as medication and organic synthesis intermediate
P-Hydroxyacetophenone is commonly made use of in medicine, cosmetics and industrial fields. It is a sort of all-natural plant remove, which normally exists in the stems and leaves of Artemisia chinensis of Compositae, Artemisia capriculum, Asclepiaceae, Panax ginseng and various other plants. It has a great medicinal impact on yellow eyes brought on by hepatitis and also various other conditions, as well as additionally has a great complementary result on yellow eyes triggered by various reasons. p-Hydroxyacetophenone is also a choleretic drug, ideal for adjuvant therapy of cholecystitis as well as intense as well as persistent jaundice hepatitis.
Due to weak molecular task, heat resistance, melting point of 95-97 ° C and also boiling point of 296 ° C, it is commonly utilized in various fluid medications and can extend the service life of various other active ingredients under heat problems. At the same time, it is likewise an intermediate of natural synthesis, utilized in the manufacturing of seasonings.
Preparation of P-Hydroxyacetophenone
A kind of synthetic method of p-hydroxyacetophenone, carries out according to the following steps:
(1) Esterification reaction: Put 60g (0.63mol) of phenol and 70.0g (0.68mol) of acetic anhydride into a 500ml reaction bottle, stir and cool to 10°C, add the first drop of concentrated sulfuric acid dropwise, wait for the reaction to cool down to room temperature Then add the second drop of concentrated sulfuric acid dropwise. The amount of concentrated sulfuric acid added dropwise is 0.5g; Pour the solution into 3 times the amount of water, adjust the pH to 8-9 with 5% sodium hydroxide, extract 3 times with ethyl acetate, combine the extracts, dry with anhydrous magnesium sulfate, filter, and concentrate to obtain phenyl acetate liquid 84.3 g, yield 94.6%; be divided into three standby;
(2) Fries rearrangement: Take 27.2g (0.2mol) of phenyl acetate obtained in step (1), put it in a 250ml reaction bottle, add 30ml of o-dichlorobenzene under stirring conditions, and slowly add it under the condition of lower than 10°C 40.0g (0.3mol) of aluminum trichloride, after adding, heat up to 80°C and react for 3.5 hours until HPLC detects that all the raw materials have reacted; then drop to 50-60°C, slowly add water for steam distillation; the distillate is separated , the o-dichlorobenzene layer containing o-hydroxyacetophenone was obtained, dried, filtered, and used for subsequent feeding; the raffinate was added with active carbon and filtered while hot, cooled and crystallized, filtered to obtain 11.8 g of p-hydroxyacetophenone white solid, Purity 99.3%, yield 43.3%;
(3) first circulation: get the phenyl acetate 27.2g (0.2mol) of step (1) gained, add the ortho-dichlorobenzene dry liquid that contains o-hydroxyacetophenone of step (2) gained under stirring condition, in Slowly add 40.0g (0.3mol) of aluminum trichloride at a temperature lower than 10°C. After the addition, heat up to 80°C and react for 3.5 hours until the reaction of all the raw materials is detected by HPLC; Steam distillation; the distillate is separated into layers to obtain the o-dichlorobenzene layer containing o-hydroxyacetophenone, dried, filtered, and used for subsequent feeding; the raffinate is added with activated carbon to filter while it is hot, concentrated, cooled and crystallized, and filtered to obtain p-Hydroxyacetophenone white solid 14.1g, purity 99.6%, yield 51.9%;
(4) The second cycle: the operation process is the same as the first cycle, and 27.2g (0.2mol) of phenyl acetate obtained in step (1) is taken, and the o-hydroxyacetophenone containing o-hydroxyacetophenone layered after the first cycle is added. The dichlorobenzene layer was dried and the liquid was reacted to obtain 14.8 g of p-hydroxyacetophenone as a white solid with a purity of 99.7% and a yield of 54.3%;
(5) Combine the white solids obtained from the three reactions of steps (2) to (4) to obtain the final product, i.e. 40.7 g of p-hydroxyacetophenone;
(6) The ortho-dichlorobenzene layer containing o-hydroxyacetophenone after step (4) steam distillation and stratification is extracted 2 times with 5% sodium hydroxide solution, and the layers are adjusted with 10% hydrochloric acid after the water layers are combined pH to 3-4; then extracted twice with ethyl acetate, combined and dried, concentrated by filtration, and finely evaporated to obtain 14.7 g of o-hydroxyacetophenone.
Uses of P-Hydroxyacetophenone
Prep work of 1-( 4-isopropoxyphenyl) ethanone (CAS NO.:4074 -51 -5). 4-Hydroxyacetophenone (20.3 g, 149.26 mmol, 1.00 equiv), acetonitrile (200mL), bromoisopropane (60.53 g, 496.15 mmol, 3.32 equiv) and potassium carbonate (62.15 g, 450.36 mmol, 3.02 equiv), the reaction service was warmed to 70 ° C and stirred over night. The next day, the temperature was decreased to area temperature, the inorganic salt was gotten rid of by purification, and the filtrate was focused in vacuum cleaner at around 40 ° C to obtain 26.38 g (99%) of 1-( 4-isopropoxyphenyl) ethanone as a straw yellow solid.
Prep Work of 2-iodo-4-acetylphenol (CAS NO.:62615 -24 -1). 4-Hydroxyacetophenone (2.0 g, 14.7 mmol) and ammonia water were sequentially added to a 250ml three-necked flask, stirred and dissolved, and also a solution of KI (12g, 73.5 mmol) and also I2 (3.7 g, 14.7 mmol) in water (200mL) was slowly added dropwise, the dropwise addition was complete, as well as the response mix was mixed overnight at area temperature, then filteringed system. The filtrate was acidified with hydrochloric acid to pH 2.0-3.0, filtered to obtain a crude yellow solid, which was recrystallized and also detoxified with methanol: water (7:3) to acquire a yellow strong (return: 81%), 1H NMR (400 MHz, CDCl3) d 8.30 (s,1 H, eOH),7.90 (d, J 8.3 Hz, 1H, ArH),7.06 (d, J 8.5 Hz, 1H, ArH), 5.99 (s, 1H, ArH), 2.57 (s, 3H, eC] OCH3).
About Products: If you need P-Hydroxyacetophenone as a cosmetic raw material, please contact our service staff directly, and we will provide you with high-quality products at the best price. As an experienced manufacturer and supplier of P-Hydroxyacetophenone, ZSpharmac will provide P-Hydroxyacetophenone raw materials for customers all over the world for a long time. Over the years, the company has been adhering to the spirit of “integrity management, strict quality control, customer first”, and has won unanimous praise from domestic and foreign customers.
Company Profile and Corporate Culture
ZhiShang Chemical is owned by ZhiShang Group is a professional new-type chemicals enterprise combined into research and development, production and sales .
The company’s competitive product is pharmaceutical raw materials and intermediates (especially carbohydrate derivatives Series), In recent years, the company has made a major breakthrough in food and feed additives, plant extraction, industrial chemicals industry .
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The production base is located in Zhangqiu chemical industry park and Tai’an high-tech chemical industry park. laboratory and workshop in strict accordance with the GMP standard and the product fit national ISO9001 and ISO2000 standards.
“Zhishang” products are exported to Europe, North and South America, the Middle East, Asia Pacific and Africa area, so as to establish a long-term and stable cooperation relationship with customer in the world.
Business Type: Manufacturer
Product Range: Cosmetic raw materials
Products/Service:Cosmetic raw materials (flavors and fragrances,antioxidant products, moisturizing and hydrating, whitening agents, cosmetic additives)
Factory Location : Diao Town Industry Park, Zhangqiu City, Jinan City, Shandong Province, China.
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