Description
Diethylamino hydroxybenzoyl hexyl benzoate is an organic compound belonging to the class of benzophenones, commercially used as UVA filter and is anticipated to provide reliable protection against free radicals and premature skin aging, mainly caused by shortwave UVA radiations.
Uses
Diethylamino hydroxybenzoyl hexyl benzoate is a UV filter with high absorption in the UV-A range. Minimizing the overexposure of human skin to ultraviolet radiation that may lead to acute and chronic photodamage, diethylamino hydroxybenzoyl hexyl benzoate is an oil-soluble UV filter that may be incorporated in the oil phase of emulsions. Diethylamino hydroxybenzoyl hexyl benzoate was approved in Europe in 2005, and is also marketed in the U.S., South America, Mexico, Japan and Taiwan. It has a chemical structure similar to the classical benxophoenone drug class, and displays good photostability. It is used in concentrations up to 10% in sunscreen products, either alone or in combination with other UV absorbers.
Application
Hexyl 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoate may be used as a test material in investigating the structural elucidation of its transformation products in chlorinated water using liquid chromatography coupled to mass spectrometry.
Definition
ChEBI: Diethylamino hydroxybenzoyl hexyl benzoate is a member of benzophenones.
Flammability and Explosibility
Nonflammable
Safety Profile
Diethylamino Hydroxybenzoyl Hexyl Benzoate is generally regarded as safe for cosmetic use. It has a low likelihood of causing skin irritation or allergies. Concerns about cancer risk due to its use in cosmetics are largely unsubstantiated, but research is ongoing. However, pregnant individuals should consult with a healthcare professional before use.
Synthesis
Expose
3 mL of a 0.018 mg/mL solution of 3-diethylaminophenyl
2-hexanoxycarbonylbenzoate in methanol to UV-B radiation in a Luzchem
LZC-4 photoreactor equipped with 16 broad band UV-B lamps (LES-UVB-01)
at 35 °C to obtain Diethylamino hydroxybenzoyl hexyl benzoate.
in vitro
Diethylamino hydroxybenzoyl hexyl benzoate (DHHB) absorbs UV-A radiation with a peak at 354 nm. The molar absorption coefficient of Diethylamino hydroxybenzoyl hexyl benzoate in EtOH at 25°C is obtained to be 39 000 mol/dm 3 /cm at 354 nm. The emission spectrum of Diethylamino hydroxybenzoyl hexyl benzoate in EtOH is dependent on the excitation wavelength.
References
[1] Panduo Shan . “Transformation and toxicity studies of UV filter diethylamino hydroxybenzoyl hexyl benzoate in the swimming pools.” Science of the Total Environment 881 (2023): Article 163498.
[2] A. Sobańska, E. Brzezińska. “Simultaneous NP TLC Analysis of the Sunscreens Diethylamino Hydroxybenzoyl Hexyl Benzoate and Octyl Methoxycinnamate.” Jpc-journal of Planar Chromatography-modern Tlc 14 1 (2011): 227–231.
Research
In recent years, research involving DHHB in the environmental area has included mass spectrometry studies of its chlorination products, chlorination kinetics, and pathways; detection of the metabolites in humans; degradation under UV/H2O2 treatment, including the effects of pH and DHHB initial concentrations. Since UV filters, such as DHHB, may result in adverse environmental impacts, it is essential to examine processes, such as the Chlorination and Solar/Chlorine processes, that the UV filters are exposed to in swimming pools. This examination should include the UV filter degradation rates and its degradation mechanism, including the effects of various matrix components in swimming pool waters[1].
