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1,3-Dihydroxyacetone is an organic compound with sweet white powder crystal. Its molecular formula is C3H6O3, CAS C3H6O3. It is a polyhydroxyketose and the simplest ketose. The appearance is white powder crystal, which is easily soluble in organic solvents such as water, ethanol, ether and acetone. The water solubility is > 250G / L (20 ℃), with a lovelytaste, and is stable at pH 6.0. It is the main active ingredient in sun-free tanning skincare products and an important precursor for the synthesis of various fine chemicals. It is produced on an industrial scale by microbial fermentation of glycerol by Gluconobacter oxydans.
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Chemical Formula |
C3H6O3 |
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Exact Mass |
90 |
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Molecular Weight |
90 |
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m/z |
90 (100.0%), 91 (3.2%) |
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Elemental Analysis |
C, 40.00; H, 6.71; O, 53.28 |
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Melting point 75 – 80 °C , Boiling point 107.25 ° C ( rough estimate ) , Density 1.1385 ( rough estimate ) , FEMA 4033 | DIHYDROXYACETONE , Refractive index 1.4540 ( estimate ) , Storage conditions Store at + 2 ° C to + 8 ° C. , morphological powder , Acidity coefficient ( pKa ) 12.45 ± 0.10 ( Predicted ) , Color White , Water solubility > 250 g / L ( 20 oC ) , JECFA Number1716 , Stable. Combustible. Hygroscopic.
DHA is a naturally occurring ketose with the molecular formula C3H6O3 and a molecular weight of 90.07. Its appearance is white powdery crystals with a sweet taste, melting point of 75-80 ℃, easily soluble in organic solvents such as water, ethanol, ether, and acetone. Its water solubility exceeds 250g/L at 20 ℃, and its stability is optimal under pH 6.0 conditions. This compound is biodegradable, non-toxic to humans and the environment, and can be produced through microbial fermentation or chemical synthesis. Its molecular structure contains two hydroxyl groups and one carbonyl group, and its chemical properties are active. It can participate in various reactions such as condensation, esterification, and polymerization, and is known as a "green platform compound".
1,3-dihydroxyacetone is widely used in the cosmetics industry, with core functions including tanning, sun protection, and moisturizing.
1. Tanning agent
The ketone functional groups in DHA can undergo non enzymatic browning reactions with the amino acids and amino groups of skin keratin, generating brown polymers that simulate the skin tone effect after sun exposure. This tanning method does not require UV exposure, avoiding the risk of skin damage, and the effect can last for several days. The US FDA has approved DHA as the only legal non tanning skin tanning agent ingredient and included it in the US Pharmacopeia. DHA is the core ingredient of most tanning spray, lotion and other products on the market, and the addition amount is usually 1% -10%.
2. Sunscreen and Moisturizing
DHA can form a transparent film on the surface of the skin, reflecting sunlight and blocking ultraviolet rays, while preventing excessive evaporation of skin moisture. Research has shown that sunscreen containing DHA can significantly reduce skin redness and dryness caused by ultraviolet radiation. In addition, DHA can be compounded with components such as erythritol to enhance the tanning effect and strengthen the skin barrier function.
3. Hair dye adjuvants
The reducibility of DHA makes it suitable for use in hair dye products, helping pigment molecules penetrate hair strands better and improving hair dye uniformity and durability.
The applications of 1,3-dihydroxyaceton in the pharmaceutical field include intermediate synthesis and direct therapeutic effects.
1. Pharmaceutical intermediates
DHA is a key raw material for the synthesis of cardiovascular disease drugs (such as some statins and lipid lowering drugs) and diabetes drugs. Its derivatives can be chemically modified to obtain specific biological activities, such as generating optically active secondary alcohols through reduction reactions for chiral drug synthesis. In addition, DHA can also participate in aldol condensation reactions to prepare carbohydrate compounds and lactone structures, which are of great value in the development of antibiotics and anti-tumor drugs.
2. Antiviral activity
DHA directly exhibits antiviral properties. For example, in chicken embryo culture experiments, DHA can inhibit chicken plague virus infection with a killing rate of 51% -100%. The compounds synthesized with DHA derivatives as intermediates also have anti AIDS virus activity, providing a direction for the development of new antiviral drugs.
3. Metabolic regulation effect
Research has shown that DHA can regulate the metabolic rate of the body. Obese women who supplemented DHA with a low calorie diet showed significantly higher weight and body fat loss compared to the control group (weight loss 6.5kg vs. 5.6kg, body fat loss 4.3kg vs. 3.5kg), indicating its potential application in weight management.
The application of 1,3-dihydroxyacetone in the food and feed industry is mainly based on its non-toxic and metabolic regulatory functions.
1. Food additive
DHA can be used as a functional food ingredient to enhance the health attributes of products. For example, adding DHA to sports nutrition supplements can assist in energy metabolism and fat oxidation. In addition, the sweetness of DHA makes it a potential alternative to low calorie sweeteners.
2. Feed additive
Adding a mixture of DHA and pyruvate (calcium salt) to pig feed (in a 3:1 weight ratio) can significantly reduce pork fat content and increase lean meat percentage. The experiments conducted by Japanese scientists have proven that this formula can effectively improve meat quality and meet the market's demand for low-fat meat. Meanwhile, DHA can also serve as an energy supplement for ruminant animal feed, enhancing animal growth performance.
The application of 1,3-dihydroxyaceton in industrial and scientific fields reflects the diversity of its chemical properties.
1. Organic synthesis intermediates
DHA can be synthesized into chiral compounds through aldol condensation reaction for asymmetric synthesis. For example, reacting with 2,2-dialkoxycyclopropane derivatives can generate lactone compounds, which have important value in the synthesis of fragrances and drugs. In addition, DHA can also participate in Diels Alder addition reactions, constructing carbohydrate compounds and cyclic structures.
2. Materials Science
The reducibility of DHA makes it suitable for the preparation of functional materials.
For example, polymer materials with specific physical properties can be obtained by reducing butadiene styrene composites. In addition, DHA can also serve as a catalyst to promote the condensation reaction of formaldehyde to aldehydes and ketones, thereby improving the efficiency of chemical production.
3. Research reagents
DHA is commonly used in cell culture and virus suppression experiments in biomedical research. For example, in chicken embryo culture, DHA can significantly reduce the infection rate of chicken plague virus, providing a model for screening antiviral drugs. In addition, DHA can also be used to prepare optically active secondary alcohols as ligands for chiral catalysts.
The application of 1,3-dihydroxyaceton has also extended to multiple sub fields.
1. Leather protectant
DHA can form a protective film on the surface of leather, preventing aging caused by moisture and ultraviolet rays, and extending the service life of leather products.
2. Fruit and vegetable preservatives
Preservatives mainly composed of DHA can inhibit the respiration of fruits and vegetables, delay decay, and maintain freshness. For example, DHA treatment can significantly extend the shelf life of perishable fruits and vegetables such as strawberries and tomatoes during storage.
3. Vitiligo treatment adjuvant
Research has shown that applying a 0.2% -0.5% DHA alcohol solution to vitiligo affected areas can bring them closer to normal skin color. In addition, DHA complex solution (containing vitamin B and dimethyl sulfoxide) combined with He Ne laser irradiation has a better therapeutic effect on vitiligo and white spots.
Synthesis of 1,3-Dihydroxyacetone:
Dihydroxyacetone is an important chemical raw material, pharmaceutical intermediate and functional additive. Its uses are mainly divided into two categories: direct use and indirect use (chemical intermediate).
1: Direct use
Which is biodegradable, edible and harmless to human body and environment. It is a multifunctional additive and can be used in cosmetics, medicine and food industries.
Dihydroxyacetone is mainly used as a formula material for cosmetics, especially as a sunscreen, which has special effects, can prevent excessive evaporation of skin moisture, and plays a role in moisturizing, sunscreen and ultraviolet radiation protection. In addition, the ketone functional group in DHA can react with the amino acid and amino group of skin keratin to form a brown polymer, which can make people's skin produce an artificial brown color. Therefore, it can also be used as a simulator for sunning skin to obtain brown or tan skin that looks the same as the result of long-term exposure to sunlight, making it look beautiful.
Dihydroxyacetone is the intermediate product of sugar metabolism and plays an important role in the process of sugar metabolism. It can reduce the body fat of pigs and improve the lean meat rate. Japanese scientists and technicians have proved through experiments that adding a certain amount of mixture of DHA and pyruvate (calcium salt) (in a 3:1 weight ratio) to pig feed can reduce the fat content of pig back meat by 12%~15%, and the fat content of leg meat and the longest muscle of the back also decreases correspondingly, and the protein content increases.
Dihydroxyacetone supplementation (especially in combination with pyruvate) can improve the metabolism rate and fatty acid oxidation of the body, potentially effectively burn fat, reduce body fat and delay weight gain (weight loss effect), reduce the incidence of related diseases, improve insulin sensitivity and reduce plasma cholesterol level caused by high cholesterol diet, and long-term supplementation can increase the utilization rate of blood glucose and save muscle glycogen, For athletes, it can improve aerobic endurance performance.
Dihydroxyacetone can also be directly used as an anti-virus agent. For example, in chicken embryo culture, the use of DHA can greatly inhibit the infection of chicken plague virus and kill 51%~100% of chicken plague virus. In the leather industry, DHA can be used as a protective agent for leather products. In addition, the preservative with DHA as the main component can be used for the preservation of fruits and vegetables, aquatic products, meat products, etc.
2. Indirect use:
Dihydroxyacetone molecule contains three functional groups (two hydroxyl groups and one carbonyl group), which is active in chemical properties and can widely participate in such reactions as polymerization and condensation. It is an important intermediate for the synthesis of medicine and pesticide. Reacting with amidines, imino ethers and other substances, heterocyclic compounds such as imidazole and furan can be prepared; Various triglycerides can be prepared by esterification reaction; Ketone substituted compounds can also be synthesized. Its derivatives are also a class of very important intermediates in organic synthetic chemistry, and have extremely wide applications: secondary alcohols with optical activity can be obtained by biological or chemical reduction; For preparing various chiral compounds by aldol condensation reaction; Diels Wider addition reaction directly used in photochemical reaction to prepare carbohydrate compounds; The lactone is prepared by reacting with 2,2-dimethoxycyclopropane derivatives. In addition, some compounds synthesized with its derivatives as intermediates also have the effects of treating cardiovascular diseases, diabetes and antiviral activities (such as AIDS).
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