Dihydroxyacetone is aOrganic compound, the molecular formula is CthreeHsixOthree, is polyhydroxyKetoseIs the simplest ketose.The appearance is white powder crystal, easily soluble in waterethanol、Etherandacetoneetc.Organic solvent, melting point is 75-80 ℃,Water solubility＞ 250g/L (20 ℃), sweet, stable at pH 6.0.
with1,3-Dichloroacetone、glycolAs the main raw material, 1,3-dihydroxyacetone was synthesized through carbonyl protection, etherification, hydrogenolysis and hydrolysis.1,3-Dichloroacetone and ethylene glycol are heated and refluxed to dehydrate in toluene to generate 2,2-dichloromethyl-1,3-dioxolane ring, and then react with sodium benzylate in N, N-dimethylformamide to generate 2,2-dibenzyloxy-1,3-dioxolane ring. 1,3-dioxolane cyclo-2,2-dimethanol is synthesized by hydrogenolysis under the catalysis of Pd/C, and then hydrolyzed in hydrochloric acid to generate 1,3-dihydroxyacetone.The raw material for the synthesis of 1,3-dihydroxyacetone by this method is easy to obtain, the reaction conditions are mild, and the Pd/C catalyst can be recycled, which has important application value.[3]
two
1,3-Dihydroxyacetone was synthesized from 1,3-dichloroacetone and methanol through carbonyl protection, etherification, hydrogenolysis and hydrolysis.1,3-Dichloroacetone reacts with excess anhydrous methanol in the presence of water absorbent to generate 2,2-dimethoxy-1,3-dichloropropane, and then reacts with sodium benzylate in N, N-dimethylformamide to generate 2,2-dimethoxy-1,3-dibenzyloxypropane, hydrogenolysis under Pd/C catalyst to generate 2,2-dimethoxy-1,3-propanediol, and then hydrolyzes in hydrochloric acid to generate 1,3-dihydroxyacetone.This route changes the carbonyl protector from ethylene glycol to methanol, making the product 1,3-dihydroxyacetone easier to separate and purify, which has important development and application value.[3]
three
withacetone, methanol and chlorine orbromine 1,3-dihydroxyacetone was synthesized as the main raw material.Acetone, anhydrous methanol and chlorine or bromine“One pot method”Generate 2,2-dimethoxy-1,3-dichloropropane or 1,3-dibromo-2,2-dimethoxypropane, and then combine withSodium benzyl alcoholThe etherification reaction is carried out to generate 2,2-dimethoxy-1,3-dibenzyloxypropane, which is hydrogenated and hydrolyzed to generate 1,3-dihydroxyacetone.This route has mild reaction conditions. The "one pot" reaction avoids the use of high cost and irritating 1,3-Dichloroacetone, which makes this route low cost and has high development value.[3]
Safety terminology
Announce
edit
Avoid contact with skin and eyes.
purpose
Announce
edit
Dihydroxyacetone is an important chemical raw materialpharmaceutical intermediates And functional additives.Its uses are mainly divided into two categories: direct use and indirect use (chemical intermediate).
Direct use
Dihydroxyacetone is a naturalKetose, withBiodegradabilityIt is edible and harmless to human body and environment. It is a multifunctional additive and can be used in cosmetics, medicine and food industries.
Used in cosmetics industry
Dihydroxyacetone is mainly used as the ingredient of cosmetics, especially assunscreen creamyesSpecial effects, can prevent excessive evaporation of skin moisture, and play a role in moisturizing, sunscreen and preventionultraviolet radiationRole of.In addition,DHAKetone infunctional groupMay contact skinKeratinOfamino acidandaminoThe group reacts to form a brown polymer, which makes people's skin produce an artificial brown. Therefore, it can also be used as a skin tone simulator to get the appearance and long-term exposure tosunlightThe brown or tan skin with the same result as that obtained below makes it look beautiful.
Dihydroxyacetone isCarbohydrate metabolismOfIntermediate product, plays an important role in the process of sugar metabolism, has the role of reducing pig body fat and improving lean meat rate.Japanscientific and technical personnelIt has been proved by test thatPig feedA certain amount of DHA andPyruvate(Calcium salt）The fat content of pig back meat can be reduced by 12%~15%, and the fat content of leg meat and the longest muscle of back can also be reduced accordingly,protein content increase.
Dihydroxyacetone can also be directly used as aantiviralReagent, such as in chickenEmbryo cultureThe use of DHA can greatly inhibitChicken plagueViruses51%~100% of the fowl plague virus were killed.stayTanning industryDHA can be used as theProtective agent。In addition, DHA basedPreservativeIt can be used for preservation of fruits and vegetables, aquatic products and meat products.
Indirect use
Dihydroxyacetone molecule contains 3 functional groups (2 hydroxyl groups, 1carbonyl) ,chemical propertyIt is active and can widely participate in such reactions as polymerization and condensation. It is an important intermediate for pharmaceutical and pesticide synthesis.And amidineImineThe reaction of ethers and other substances can produceimidazole、furanetc.Heterocyclic compound;adoptesterificationVarious products can be madetriglyceride; Ketone substituted compounds can also be synthesized.Its derivatives are also a class of very important intermediates in organic synthetic chemistry, with extremely wide applications:Chemical methodRestore to getOptical activityOfSecondary alcohol;be used forAldol condensation reactionPrepare variousChiral compound;Directly used forPhotochemical reactionDiels Alder inAddition reactionPreparation of saccharides;Preparation by interaction with 2,2-dialoxycyclopropane derivativeslactone。In addition, some compounds synthesized with its derivatives as intermediates also have therapeutic effectsCardiovascular disease、diabetesAnd antiviral activity (such as AIDS).
