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Homosalate

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Related articles

Homosalate Basic information
Product Name:Homosalate
Synonyms:Benzoic acid, 2-hydroxy-, 3,3,5-trimethylcyclohexyl ester;Benzoicacid,2-hydroxy-,3,3,5-trimethylcyclohexylester;component of Coppertone;Coppertone;Filtersol ''A'';Filtrosol A;Heliopan;Homosalat
CAS:118-56-9
MF:C16H22O3
MW:262.34
EINECS:204-260-8
Product Categories:EUSOLEX
Mol File:118-56-9.mol
Homosalate Structure
Homosalate Chemical Properties
Boiling point 161-165°C (12 torr)
density 1.05
vapor pressure 0.015Pa at 25℃
refractive index n20 1.516 to 1.518
Fp 169 - 173℃
storage temp. Inert atmosphere,Room Temperature
solubility Chloroform (Slightly), DMSO (Slightly)
form Liquid
pka8.10±0.30(Predicted)
color Colourless
Odorat 100.00?%. mild menthol
Water Solubility <0.1 g/100 mL at 26 ºC
BRN 2731604
Cosmetics Ingredients FunctionsFRAGRANCE
UV ABSORBER
UV FILTER
LogP6.27 at 25℃
CAS DataBase Reference118-56-9(CAS DataBase Reference)
NIST Chemistry ReferenceHomosalate(118-56-9)
EPA Substance Registry System3,3,5-Trimethylcyclohexyl salicylate (118-56-9)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36/39
WGK Germany 2
TSCA TSCA listed
HS Code 29182300
MSDS Information
Homosalate Usage And Synthesis
DescriptionHomosalate 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 PropertiesLiquid.
UsesHomosalate used as a UV filter in various personal skin care formulations and cosmetics.
UsesUV screen, analgesic
Useshomosalate 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.
DefinitionA homolog of menthyl salicylate.
Brand nameEusolex (Rona Laboratories, Great Britain); Heliophan (Greeff).
General DescriptionViscous or light yellow to slightly tan liquid or oil.
Air & Water ReactionsHomosalate will hydrolyze under basic conditions. . Insoluble in water.
Reactivity ProfileAn 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 HazardHomosalate is probably combustible.
Flammability and ExplosibilityNon flammable
Side effectsSimilar 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
3,3,5-Trimethylcyclohexanol

116-02-9

Methyl salicylate

119-36-8

Homosalate

118-56-9

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
Homosalate Preparation Products And Raw materials
Raw materialsMethyl salicylate-->3,3,5-Trimethylcyclohexanol
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