What is O-cymene-5-ol?
O-cymene-5-ol is used as a preservative and anti-acne agent in cosmetics. This ingredient is an antifungal preservative that can extend the shelf life of the product. The upper limit of the ingredient addition is 0.1%.
It has significant acidity and good chemical stability. It is difficult to dissolve in water but soluble in common organic solvents, especially in alcoholic organic solvents. 3-Methyl-4-isopropylphenol is a phenol derivative, mainly used as a phenolic preservative, bactericide, etc., and has good applications in the cosmetics production industry. In addition, there are reports in the literature that this substance can also be used as a synthetic intermediate for the synthesis of matrix metalloproteinase inhibitors.
Background Art
3-Methyl-4-isopropylphenol, also known as cymene-5-ol, is a very safe, broad-spectrum, highly effective antifungal bactericide that can contact mucous membranes. It has been proven to have excellent efficacy in various skin care products and can inhibit product oxidation. It has the characteristics of safety, low toxicity, easy degradation, and low environmental pollution. It has been widely adopted by major cosmetics companies. Its scope of application is gradually expanding and its usage is increasing year by year. However, there has been no industrial production in China. How to simply prepare high-purity substances is still a problem encountered in the development and promotion of this product.
The most common method for preparing 3-methyl-4-isopropylphenol is to use m-cresol as a raw material for isopropylation. Isopropylation agents include propylene, isopropanol, isopropyl chloride, etc. Common catalysts include Lewis acids such as aluminum chloride, zirconium chloride, zinc chloride, etc., and also include inorganic acids such as sulfuric acid and phosphoric acid. However, the result of this direct isopropylation is that the product contains a large amount of isomers of thymol. For example, DE2139622 obtains a product with a content of 19.5% by reacting m-cresol with propylene under a zinc catalyst, and DE2528303 obtains a product with a content of only 2% by reacting m-cresol with propylene under an aluminum salt catalyst. It is difficult to obtain a high-purity substance in this way.
Synthesis method
1. Add 46g of sodium hydroxide to a 250ml three-necked flask, add 280g of water to dissolve, cool to 10℃, slowly add 108g of m-cresol, stir for half an hour until all the reactants are dissolved, add 1g of triethylamine, adjust the pH value to 9, dissolve 51g of triphosgene in 250g of dichloromethane, slowly add it to the above mixture, add it in 1 hour, heat it to 40℃ and reflux it for 1 hour, cool it to room temperature and separate the organic phase, wash the organic phase with dilute hydrochloric acid and pure water until neutral, dry it with anhydrous magnesium sulfate, evaporate the dichloromethane and use 90% ethanol water to crystallize and dry to obtain 115g of product, with a yield of 95%.
2. Add 48.4 g of bis(m-cresol) carbonate obtained in step 1 to a 250 ml three-necked flask, add 150 g of trichloroethylene to dissolve, add 53.2 g of aluminum chloride, cool to 5 ° C, add 31.4 g of isopropyl chloride dropwise under stirring, continue to react at 10 ° C for 2 hours after the addition is complete, slowly pour it into ice water after the reaction is completed, wash the solution to neutrality with 5wt% sodium hydroxide aqueous solution, dry the organic phase with anhydrous calcium chloride, evaporate the solvent to obtain 61.1 g of crude product with a yield of 93.2%, which is directly used for the next step reaction.
3. Add 27 g of the intermediate obtained in step 2 to a 250 ml three-necked flask, add 7 g of sodium hydroxide, 150 g of methanol, and 15 g of water in turn, stir at 20 ° C for 3 hours, evaporate the methanol, and use 90-120 ° C boiling point petroleum ether to recrystallize the remaining viscous material to obtain 10.3 g of 3-methyl-4-isopropylphenol white powder product with a content of 97.4% and a yield of 83.7%.
Company Introduction And Certificates Obtained
YTBIO mainly supplies O-cymene-5-ol etc. The company was established in 2014 and has many years of R&D and production experience. We are committed to the research and development, production and sales of raw materials for the 21st century health industry. The certificates obtained so far include ISO9001, ISO22000, HALAL, KOSHER, HACCP, FDA,etc. We always maintain the highest requirements for product quality.
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