Dehydro Cholesterol 

What is Dehydrocholesterol?

Dehydro Cholesterol is a steroid substance that exists in the sebaceous glands and their secretions in the skin of animals. As a precursor of cholesterol, it plays a key role in the body. It is not only an important precursor of vitamin D3, but also has the function of protecting cells from oxidative damage. It is of great significance to human health and disease treatment. It can be converted from cholesterol in the human body. It is stored under the skin and can be converted into vitamin D3 under sunlight or ultraviolet rays. It has biological activity in regulating calcium and phosphorus metabolism. It is not only an important biologically active substance, but also has broad application prospects in the fields of medicine and health.

Characteristics

Solubility: Insoluble in water, easily soluble in ethanol, ether, chloroform or acetone, slightly soluble in vegetable oil.
Stability: Stable at room temperature and pressure, but avoid contact with light and air to prevent deterioration. Reacts with strong oxidants.

Functions

Precursor of vitamin D synthesis
It is an important precursor for the synthesis of vitamin D3, which is essential for the absorption of calcium and phosphorus, two minerals that are key components for maintaining bone health. Therefore, proper sunlight exposure helps ensure that there is enough vitamin D3 synthesis in the body, thereby supporting bone health.

Antioxidant protection
It can act as an antioxidant to protect cells from ferroptosis. This protective function helps cells maintain stability in the face of oxidative stress, thereby preventing cell death.

Cell membrane stability
Dehydrocholesterol plays a role in the composition of cell membranes, increases cell membrane stability, reduces the permeability of water-soluble substances, and plays an important role in maintaining the basic structure of cell membranes.

Participate in cholesterol metabolism
It is an intermediate product in the cholesterol metabolism process and plays a role in cholesterol balance in the body. By converting into vitamin D3, it may affect the distribution and metabolism of cholesterol, reduce the accumulation of excess cholesterol in the body, and help reduce the risk of cardiovascular disease.

Protect cardiovascular health
It has anti-inflammatory effects and helps reduce the risk of atherosclerosis. It can remove necrotic cells caused by inflammation, enhance heart and blood vessel function, and improve blood circulation, thereby having a positive impact on cardiovascular health.

Applications

Food
Nutritional supplements: As a precursor of vitamin D3, it is used as a nutritional supplement to help supplement vitamin D for people who cannot get enough vitamin D through daily diet or sunlight exposure.
Functional foods: It is also added to some functional foods, such as fortified milk, yogurt and juice, to provide additional vitamin D.

Cosmetics
Skin care: Due to its ability to convert into vitamin D3, it is also used in some skin care products, such as sunscreen and repair cream, to help protect the skin from UV damage and promote skin health.

Medicine
Vitamin D3 synthesis: It is a key precursor for the synthesis of vitamin D3 and is converted into vitamin D3 by ultraviolet radiation. Therefore, it is often used in the pharmaceutical industry as a raw material for the production of vitamin D3 to support bone health, calcium absorption and the normal function of the immune system.

Preparation Method

1) Take 5g of cholesterol and add it to 40ml of acetyl chloride, reflux at 100°C for 8h, and react to generate cholesterol acetate. The purity of cholesterol acetate generated by the reaction was determined by the internal standard method to be 94%, and the yield was 90%.

2) Take 5g of cholesterol acetate and dissolve it in 70ml of cyclohexanone, shake it at room temperature, and heat it to 50°C. Take 0.3g of selenium dioxide and add it to the reaction solution in batches, and add it in 30min. React at 80°C for 8h, cool it to room temperature, and then cool it with 3°C water. Crystals precipitate, filter it, and vacuum dry it at 50°C for 6h. The purity of 7-carbonyl cholesterol acetate obtained by testing is 86%, and the yield is 65%.

3) Take 5g of 7-carbonyl cholesterol acetate and 8g of p-toluenesulfonyl hydrazide and dissolve them in 50ml of anhydrous ethanol, stir at room temperature and monitor it by thin layer chromatography, stop the reaction after 15h, and concentrate to obtain the product 7-p-toluenesulfonyl hydrazone cholesterol acetate. The purity was 96% and the yield was 98%.

4,5) 5 g of 7-p-methylbenzenesulfonyl hydrazone cholesterol acetate was dissolved in 50 ml of chlorobenzene, and 0.4 g of lithium amide was added in batches at 100 ° C and stirred for 5 h. Cool to room temperature, wash with 10 ml of glacial acetic acid until weakly acidic, and then wash with deionized water until neutral. The concentrated product obtained 7-dehydrocholesterol as a pale yellow solid. The purity of 7-dehydrocholesterol was 57% and the yield was 75%.

Certificates

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