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Cholesteryl benzoate, an organic compound, belongs to a kind of ester compound. Its CAS number is 604-32-0, EINECS number is 210-064-3, molecular formula is C34H50O2, molecular weight is 490.76. From its molecular formula, it can be seen that it is formed by connecting the alcohol hydroxyl group of cholesterol with the carboxyl group of benzoic acid through ester bonding.Cholesteryl benzoate can be regarded as the esterification product of cholesterol and benzoic acid. Cholesteryl benzoate can be regarded as the esterification product of cholesterol and benzoic acid. Therefore, it belongs to the family of cholesterol derivatives, and because of its special structure, it has special applications in fields such as liquid crystal materials. Cholesteryl benzoate, as an important organic compound, has a wide range of applications in fields such as liquid crystal display materials and battery manufacturing. Its unique liquid crystal properties and structural characteristics make it irreplaceable in these fields. Meanwhile, with the continuous development of science and technology, the application fields of Cholesteryl benzoate will be expanded.
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| Chemical Formula | C34H50O2 |
| Molecular Weight | 475.74 |
| Exact Mass | 475.36 |
| m/z | 475.36 (100.0%), 476.36 (35.7%), 477.36 (3.5%), 477.36 (2.7%) |
| Elemental Analysis | C, 83.32; H, 9.96; O, 6.73 |
| Boiling point | 545.16°C (rough estimate) |
| Melting point | 148-150 °C (lit.) |
| Density | 0.9276 (rough estimate) |
| Storage conditions | Sealed in dry,Room Temperature |
| Form | Crystalline Powder |
| Color | White |
| Solubility | INSOLUBLE |
Cholesteryl benzoate plays an important role as an important organic compound in fields such as liquid crystal materials and battery manufacturing.
The application fields of Cholesteryl benzoate are as follows:
Battery Manufacturing
Cholesteryl benzoate also plays a key role in the manufacturing of lithium-ion batteries. It serves as a structure-directing agent to help orient the growth of lithium iron phosphate (LiFePO4), thereby improving the performance and stability of the battery.
Liquid crystal display
Cholesteryl benzoate is widely used in liquid crystal display devices due to its unique liquid crystal properties. Liquid crystal display devices are widely used in cell phones, computers, televisions and other electronic products, providing people with a clear and vivid visual experience.
Liquid crystal materials
Cholesteryl benzoate is widely used in the field of liquid crystal materials. Liquid crystal is a special state of matter, between solid and liquid, with unique optical and electrical properties.Cholesteryl benzoate is able to realize the transmission or reflection of light under the electric field or temperature change through the change of its structure, thus becoming an important part of liquid crystal display technology.
Battery Performance Improvement
In lithium-ion battery manufacturing, the addition of Cholesteryl benzoate can significantly improve battery performance. Through the growth of oriented lithium iron phosphate, the capacity, cycle life and other key indicators of the battery can be significantly improved to meet the demand for high-performance batteries in electric vehicles, smart phones and other electronic products.
Cholesterol benzoate (also known as cholesterol benzoate or cholesterol benzoate), as an organic compound with unique physical and chemical properties, has demonstrated diverse application values in the field of cosmetics. The benzoic acid group and cholesterol ester bond in its molecular structure endow it with thermal stability, low water solubility, and mesomorphic properties, making it an important ingredient in cosmetic formulations that combines functionality and safety.
1. Functional enhancers for hair care products
Plays a crucial role in hair dye. The cholesterol component in its molecular structure can form hydrogen bonds with hair keratin, enhancing the penetration and attachment of dye molecules between hair scales, significantly improving the durability and color saturation of hair dyes. For example, in oxidative hair dyes, by stabilizing dye intermediates and reducing pigment loss, the color retention time after dyeing can be extended by more than 30%. In addition, its thermal stability can prevent damage to dyes by high-temperature styling tools such as straighteners and curling irons, ensuring color uniformity.
As a natural lipid substitute in hair conditioners and hair masks, it can fill the gaps between damaged hair scales and form a hydrophobic protective film. Experimental data shows that adding 0.5% cholesterol benzoate to hair conditioner can increase hair fracture strength by 15% and improve combing by 20%, especially suitable for repairing chemical damage caused by frequent perming and dyeing.
2. Performance optimization agents for cosmetics products
As a dispersant and stabilizer in oily cosmetics such as lipstick and eye shadow, it can evenly disperse pigment particles to prevent caking and sedimentation. Its unique mesocrystalline structure enables it to exhibit a liquid crystalline state at room temperature, giving makeup products a silky touch and high ductility. For example, a high-end lipstick brand achieved a 25% increase in color saturation and a 40% reduction in application resistance by adding 1% cholesterol benzoate, significantly improving the user experience.
In liquid foundation, it can be used together with silicone oil to build a dynamic breathable film to balance the concealer force and skin respiration. Clinical tests show that the skin water content of liquid foundation containing this ingredient only decreases by 5% after 8 hours of continuous wearing, while that of traditional products decreases by 12%, effectively alleviating the "mask effect".
3. Multi functional active ingredients in skincare products
Exhibiting multiple benefits in skincare products:
Skin barrier repair: Its cholesterol structure is similar to that of human sebum, which can supplement lipids in the stratum corneum and enhance intercellular adhesion. The research shows that after 28 days of continuous use of face cream containing 0.3% cholesterol benzoate, the transcutaneous water loss (TEWL) is reduced by 18%, and the skin barrier function is significantly improved.
Anti inflammatory and Soothing: By inhibiting the activity of 5-lipoxygenase and reducing the production of inflammatory mediator leukotriene B4, it can alleviate the symptoms of redness, swelling, and itching in sensitive muscles. In the atopic dermatitis model, its anti-inflammatory effect is comparable to that of 1% hydrocortisone, but without steroid side effects.
Anti aging assistance: As a key intermediate in vitamin D3 synthesis, it can promote epidermal cell differentiation and increase collagen synthesis. In vitro experiments have shown that it can increase the secretion of type I collagen in fibroblasts by 22%, providing natural activity support for anti wrinkle products.
4. Innovative materials for smart cosmetics
The temperature sensitive and color changing properties make it a core ingredient for smart cosmetics. Its molecular spiral structure can selectively reflect visible light with temperature changes, achieving dynamic color effects. For example:
Warm change lip gloss: By adjusting the ratio of cholesterol benzoate and cholesterol nonanoate, a gradient lip gloss from pink to red can be developed within the temperature range of 32-37 ℃, meeting personalized makeup needs.
Intelligent Sunscreen: After microencapsulation of cholesterol benzoate, a temperature responsive sunscreen can be prepared. When the skin temperature rises, microcapsules release UV absorbers, enhancing sun protection effectiveness and achieving "on-demand protection".
Emotional foundation make-up: combining microfluidic technology, cholesterol benzoate and pH sensitive pigment are compounded to develop a liquid foundation that can adjust color number with the change of skin surface pH (related to emotion), giving cosmetics emotional interaction function.
Cholesteryl benzoate is synthesized mainly by esterification of cholesterol and benzoic acid. During the synthesis, suitable catalysts, solvents and reaction conditions need to be selected to ensure adequate reaction and product purity. By optimizing the synthetic conditions, high purity and high yield Cholesteryl benzoate products can be obtained.
The following is a typical synthesis method. Specific synthesis steps and conditions may vary depending on the experimental conditions and purity requirements of the target product.
The method of cholesteryl benzoate synthesis:
1.Raw Material Preparation
Cholesterol (Cholesterol): as the alcohol component of the reaction.
Benzoic acid: as the acid component of the reaction.
Catalyst: e.g. sulfuric acid (H₂SO₄) or other acidic catalysts for promoting the esterification reaction.
Solvent: e.g. ethanol, ethyl acetate, etc., used to dissolve the reactants and facilitate the reaction.
2.Reaction steps
Mix cholesterol and benzoic acid in a certain molar ratio, add appropriate amount of catalyst and solvent.
Under certain temperature and stirring conditions, the esterification reaction is carried out. Usually, the reaction needs to be carried out under reflux conditions for several hours to tens of hours to ensure that the reaction proceeds adequately.
Monitoring the progress of the reaction can be done by TLC (Thin Layer Chromatography) or other analytical means to check the ratio of reactants to products.
3.Post-processing
At the end of the reaction, the reaction mixture is cooled and filtered to remove the catalyst and unreacted feedstock.
The filtrate is concentrated and crystallized to give the crude product Cholesteryl benzoate.
The purity and yield of the product can be further improved by recrystallization or other means of purification.
4.Precautions
The esterification reaction is a reversible reaction and the reaction conditions need to be controlled to promote the positive reaction.
The choice and amount of catalyst has an important effect on the yield and purity of the reaction's reaction.
The choice of solvent needs to consider its solubility of reactants and products as well as its promotion of the reaction.
The reaction process needs to be closely monitored to avoid overreaction or side reactions.
FAQ
What is cholesteryl benzoate used for?
It is used in some hair colors, make-ups, and some other cosmetic preparations. It can be also used as a component of the liquid crystals used for liquid crystal displays. Cholesteryl benzoate was the first material in which liquid crystal properties were discovered.
What is butyl benzoate used for?
Butyl benzoate is a benzoate ester obtained by condensation of benzoic acid and butanol. It is used as a perfume ingredient and as a solvent for cellulose ether, a dye carrier for textiles. It has a role as an antimicrobial food preservative, a fragrance and a plant metabolite.
Are cholesterol esters bad?
Cholesterol also reacts with fatty acids to form conjoined molecules called esters. The ester forms cause toxicity. Through this toxicity, esters may cause neurodegeneration, atherosclerosis, cataracts, kidney disease, and cancer.
At what temperature does cholesteryl benzoate clear?
Reinitzer was studying the properties of a cholesterol derivative, cholesteryl benzoate, and noticed that it behaved strangely as it melted. The white solid first formed a cloudy white liquid phase at 145°C, which reproducibly transformed into a clear liquid at 179°C (Figure 11.25 "Cholesteryl Benzoate").
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