Octyl 4-methoxycinnamate

Description

Octinoxate, or Octyl 4-methoxycinnamate, is a more recent sunscreen component. It is marketed by Merck under the tradename Eusolex 2292 and by BASF as Uvinul MC80. It absorbs primarily in the UV-B range.

Chemical properties

colourless or pale yellow liquid

The Uses of Octyl 4-methoxycinnamate

2-Ethylhexyl 4-Methoxycinnamate is an UV induced cyclobutane pyrimidine dimer (CDP) formation inhibitior.

The Uses of Octyl 4-methoxycinnamate

octinoxate is the drug name for the sunscreen chemical generally known as octyl methoxycinnamate and ethylhexyl methoxycinnamate.

The Uses of Octyl 4-methoxycinnamate

2-Ethylhexyl-4-methoxy-cinnamate is used as UV-B-absorbing agent in sunscreens and cosmetic creams, lotions, lipsticks, sun oils, etc.

Background

Octinoxate is a cinnamate ester and common ingredient in sunscreen and other skin care products to minimize DNA photodamage. It was originally developed in 1950's as an organic UV-B filter that absorbs UV-B rays from sun. It is often combined with nanoparticles or other water-resistant liposomes in formulations to increase the localization at the epidermis and decrease the risk of percutaneous absorption. Its use in pharmaceutical and cosmetic formulations is approved by FDA.

Indications

Octinoxate is used as an active ingredient in sunscreens and lip balms. Used for protection against damaging effects of sun rays.

Definition

ChEBI: Octyl 4-methoxycinnamic acid is a cinnamate ester.

brand name

Parsol (Roche); Neo Heliopan (H & R Florasynth); Escalol (ISP Van Dyk) Note—The International Cosmetic Ingredient (INCI) name for octinoxate is octyl methoxycinnamate.

General Description

Colorless to pale yellow viscous liquid.

Air & Water Reactions

Insoluble in water.

Fire Hazard

Flash point data for Octyl 4-methoxycinnamate are not available, however, Octyl 4-methoxycinnamate is probably combustible.

Pharmacokinetics

Acts as a photoprotective agent that protects the skin by preventing and minimizing the damaging effects of ultraviolet (UV) rays of natural light. The cellular effects of UV irradiation include DNA damage, cell cycle arrest, immunological depression, apoptosis, and transcriptional changes .

Preparation

Octyl 4-methoxycinnamate is formed by combining methoxycinnamic acid and 2-ethylhexanol.

Absorption

Can be systemically absorbed after skin application, being found in the deeper layers of the stratum corneum as well as urine, plasma, and breast milk . The mean maximum plasma concentration detected after application of 2mg/cm2 sunscreen was 7ng/mL in women and 16ng/mL in men .

Metabolism

Can undergo hepatic metabolism when systematically absorbed. Can be enzymatically degraded by lipases in the stratum corneum where esters undergo hydrolysis . Degrade into photoproducts when exposed to sunlight, which leads to a decrease in UV absorption efficiency .

Toxicity

Slightly hazardous in case of skin contact, eye contact, ingestion and inhalation. Octinoxate may form reactive singlet oxygen species and induce anti-estrogenic effects . UV-induced molecular breakdown of octinoxate may interfere with cellular processes or induce oxidative damage in human skin . The NOAEL (no observed adverse effect level) is 450 mg/kg bw/day for fertility and reproductive performance, for systemic parental and developmental toxicity in Wistar rats .