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Avobenzone powder is a common UV absorber, usually a white to light yellow powder or crystal, with a core component of an oil soluble substance that can be used in sunscreen products to absorb full wave UVA. The molecular formula is C20H22O3, CAS 70356-09-1, which contains a benzene ring and a ketone group in its molecular structure. It is a synthesized organic compound. It is a derivative of dibenzoylmethane. It is a synthetic derivative of dibenzoylmethane, also known as butylmethoxydibenzoylmethane, or bason 1789. It is a synthetic sunscreen ingredient that can better absorb most of the wavelength range of UVA and block the full wavelength of UV UVA. It is an anhydride type UV absorbent that can undergo isomerization reactions under light, generating molecular structures with stronger absorption capacity. Chemical sunscreen ingredients have less irritation. Store in a sealed container in a cool, dry place. Keep away from oxidants during storage.
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Chemical Formula |
C20H22O3 |
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Exact Mass |
310 |
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Molecular Weight |
310 |
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m/z |
310 (100.0%), 311 (21.6%), 312 (2.2%) |
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Elemental Analysis |
C, 77.39; H, 7.14; O, 15.46 |
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Melting point 81-84 ° C, Boiling point 463.6 ± 35.0 ° C (predicted), Density 1.079, Storage conditions: insert atmosphere, room temperature, Morphological neat, Acidity coefficient (PKA) 9.74 ± 0.13 (predicted), Maximum wavelength( λ max)356nm(EtOH)(lit.), InChIKeyGTIRDWBOUTYFQO-UHFFFAOYSA-N, Warning word, Hazard description H410, Precautions p273-p501, Dangerous goods sign n, Hazard category code 50 / 53, Safety instructions 60-61, Dangerous goods transport No.: un3077 9 / PG 3, WGK Germany 2.
We are the supplier of Avobenzone powder.
Remark: BLOOM TECH(Since 2008), ACHIEVE CHEM-TECH is our subsidiary of us.
A common method for synthesizing Avobenzone is as follows:
C11H14O+Methoxyacetophenone → Condensation reaction → Imine compounds
Imine compounds+oxidants → oxidation reaction → C20H22O3
The detailed steps for synthesizing Avobenzone are as follows:
1.
Prepare tert butyl benzaldehyde and methoxy acetophenone as raw materials. Ensure the purity and quality of raw materials.
2.
In a dry, anhydrous reaction vessel, add an appropriate amount of sodium ethanol solution or sodium methanol solution as an alkaline catalyst. This catalyst will promote the condensation reaction.
3.
Add tert butyl benzaldehyde and methoxy acetophenone in molar ratio to the reaction vessel. Usually, 1.2-1.5 moles of benzaldehyde and 1 mole of acetophenone can be used.
4.
Stir the reaction mixture at room temperature and observe the progress of the reaction. Reactions usually take several hours to several days.
5.
When the reaction is complete, the progress of the reaction can be monitored by thin-layer chromatography (TLC). When TLC shows that the reactants have been consumed, the reaction can be stopped.
6.
Transfer the reaction mixture to a separating funnel and wash the reaction mixture with a dilute hydrochloric acid solution. Then, wash the organic phase with a saturated sodium chloride solution.
7.
Collect the organic phase and treat it with a desiccant to remove moisture and impurities. Common desiccants include anhydrous sodium chloride or anhydrous sulfuric acid.
8.
Remove the solvent from the collected organic phase by rotary evaporation or other appropriate methods to obtain imine compounds.
9.
Conduct oxidation reactions on imine compounds to convert tert butyl and methoxy functional groups into ketone and alcohol functional groups. Common oxidants include hydrogen peroxide (H2O2) or benzoyl peroxide (BPO).
10.
Conduct oxidation reactions under appropriate conditions, such as in appropriate solvents, temperatures, and reaction times. Reactions usually take several hours to several days.
11.
After the oxidation reaction is completed, TLC or other analytical methods can be used to check the purity and yield of the reaction.
12.
Purify the reaction mixture through appropriate column chromatography or crystallization techniques to obtain a high-purity product of Avobenzone.
This preparation method is simple and feasible, with few reaction steps, mild and easy to control preparation conditions. The resulting product has light color, good quality, and a pure odor, strong market competitiveness, and is easy to industrialize and promote.
Avobenzone powder is an oil-soluble sunscreen. It is classified as a "chemical" sunscreen because it works by absorbing a wide wavelength of UV rays and converting them into less harmful infrared radiation (heat). It is defined on the market as a "broad-spectrum" sunscreen because it can resist full-band UVA rays. It is one of the few sunscreen agents with a wide range of UV protection, so it is widely used in sunscreen products.
The main uses of Avobenzone in leather processing are reflected in the following aspects:
1. Dyeing Aids:
Can be used as dyeing aids to help leather better absorb dyes, improve dyeing effects and uniformity. By using Avobenzone, the color brightness and durability of leather can be improved.
2. Coating Agent:
Can be used as a coating agent for the surface finishing of leather. It can form a uniform film, increasing the waterproof, wear-resistant, and aesthetic properties of leather. This helps to improve the quality and service life of leather.
3. Anti UV Agent:
Due to its ability to absorb ultraviolet rays, it can be used as an anti UV agent in leather processing. By absorbing ultraviolet rays, Avobenzone can prevent leather from fading, cracking, and other problems caused by ultraviolet radiation, extending the service life of leather.
4. Softening Agent:
Can be used as a softening agent to make leather softer and more comfortable, improving the touch and texture of leather. Softeners can make leather easy to process and shape, while improving the texture and appearance of the leather.
5. Antibacterial Agent:
It can be used as an antibacterial agent to inhibit the growth of bacteria and mold on leather, prevent leather from becoming moldy and producing odors. This helps to maintain the cleanliness and hygiene of leather, improving its comfort during use.
6. Antioxidants:
They can also act as antioxidants to slow down the aging process of leather caused by oxidation. By inhibiting oxidation reactions, Avobenzone can extend the service life of leather and maintain its good appearance and quality.
Avobenzone, also known as Butylmethoxydibenzoylmethane in Chinese, is one of the few organic sunscreens that can absorb UVA1, which is the largest wavelength range in the ultraviolet spectrum and cannot be blocked by most UV absorbers: 340-400 nanometers.
The significance of protecting against UVA is quite significant, possibly more important than sun protection: UVA reaching the Earth's surface accounts for 95% of total ultraviolet radiation , and it was only recently discovered that UVA is not only the main cause of skin photoaging, but also participates in the process of sun induced cancer. Compared to only 10% of UVB that can reach the top layer of the dermis, 20% -30% of UVA can reach the dermis.
The signs of photoaging, including pigmentation, wrinkles, sagging, and dry skin, are all the original intention of our sunscreen to prevent aging. Speaking of which, the special feature of avobenzone is that it can provide strong protection in the UVA1 range, and when combined with other UVB absorbers, the entire formula can provide broad-spectrum UVA/UVB protection. But it has a huge flaw - it is very light unstable:
Without stabilization, avobenzone can lose 36% of its absorption capacity after one hour of sunlight exposure.
This is because the principle of all sunscreens (including inorganic sunscreens) absorbing ultraviolet radiation is simply that important molecules in the skin, after absorbing the light energy of ultraviolet radiation, will undergo photoexcitation reactions to varying degrees. On the one hand, they may produce photosensitive reactions, and on the other hand, they may produce free radicals; The principle of sunscreen is to sacrifice oneself and replace the cells in the skin to absorb the energy of ultraviolet rays, converting excess energy into other forms such as heat energy. However, for example, for avobenzone, after absorbing ultraviolet rays, enol molecules are converted into ketone molecules, and the triplet state formed by light excitation is one of the reasons for its photodegradation.
Returning to the above figure, it can also be seen that in the experiment, when only 1% of avobenzone was used and exposed to 10 times the minimum erythema dose (MED) of ultraviolet radiation, the remaining amount of avobenzone was only over 20% of the original [8]. It can be said that the higher the intensity of ultraviolet rays, the more severe the exposure to sunlight, and the less UVA protection you will receive.
Mixing titanium dioxide with avobenzone can also accelerate the decomposition of avobenzone. When OMC (Ethylhexyl Methoxycinnamate), a common UVB absorber, is mixed with avobenzone, it can cause both molecules to disintegrate and perish together. Of course, there is also a solution: formulas containing avobenzone can achieve stability by adding other sunscreen agents, such as Tinosorb S (Bemotrizinol in the picture) or Octocrylene (Octocrylene in the picture), and the stability effect is still significant (refer to the green and orange lines in the line chart above), although there is still a corresponding decrease. Later, it was discovered that certain lubricants, solvents (such as Butyloctyl Salicylate, Polyester-8), and antioxidants (such as vitamin E, vitamin C, and coenzyme Q10) can stabilize avobenzone.
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