Description
Homosalate is an organic compound that belongs to a class of chemicals called salicylates. Salicylates prevent direct skin exposure to the sun’s harmful rays by absorbing ultraviolet (UV) light. Homosalate specifically absorbs short-wave UVB rays, associated with DNA damage and an increased risk of skin cancer. It is a widely used chemical in sunscreens and skin care products with SPF. However, Homosalate is a potential endocrine disruptor and studies in cells suggest it may impact hormones. In addition to direct health concerns following homosalate exposure, the chemical may also enhance the absorption of pesticides in the body.
Chemical Properties
Liquid.
Uses
homosalate is a chemical uVB absorber included in the FDA’s Category I Sunscreen Chemical list. Its approved usage level is 4 to 15 percent by the FDA and 10 percent by the european union’s Cosmetic Directive.
Uses
UV screen, analgesic
Uses
Homosalate used as a UV filter in various personal skin care formulations and cosmetics.
Definition
A homolog of menthyl salicylate.
brand name
Eusolex (Rona
Laboratories, Great Britain); Heliophan (Greeff).
General Description
Viscous or light yellow to slightly tan liquid or oil.
Air & Water Reactions
Homosalate will hydrolyze under basic conditions. . Insoluble in water.
Reactivity Profile
An ester and a phenol. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.
Fire Hazard
Homosalate is probably combustible.
Flammability and Explosibility
Non flammable
Side effects
Similar to oxybenzone, homosalate affects hormone activity once absorbed. Skin rashes, acne and skin irritation are rare side effects of the toxic chemical. Estrogen, androgen and progesterone have all been found to be disrupted when the body is exposed to homosalate.
Synthesis
In a 250 mL three-necked flask, 10.0 g of methyl salicylate and 23.3 g of 3,3,5-trimethylcyclohexanol were added as reaction feedstock, followed by 0.50 g of potassium carbonate as a catalyst and 0.1 g of ammonium bromide as a co-catalyst. The reaction mixture was heated to 180 °C and the reaction was continued at this temperature for 13 hours. The conversion of methyl salicylate was monitored by gas chromatography during the reaction. Upon completion of the reaction, the products were separated using a vacuum distillation unit, and the fore grade fractions were recycled. Finally, 13.98 g of 3,3,5-trimethylcyclohexyl 2-hydroxybenzoate was obtained as a colorless liquid with a yield of 81.1%, and the purity was analyzed by gas chromatography to be greater than 99%.
References
[1] Patent: CN105541634, 2016, A. Location in patent: Paragraph 0023; 0024
