Octinoxate

1.01 to 1.02 at 68 °F (NTP, 1992)

Specific gravity = 1.01 - 1.02

Pale yellow liquid

Colorless to light yellow viscous liquid

less than 1 mg/mL at 81 °F (NTP, 1992)

<0.1 g/100 mL at 27°C

In water, 0.22 to 0.75 mg/L at 21 °C; 0.041 mg/L at 24 °C and pH 7.1

In water, 0.2 mg/L at 20 °C

Miscible in alcohols, propylene glycol monomyristate, and various oils

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

388 to 392 °F at 3 mmHg (NTP, 1992)

185-195°C at 1mbar

382 °C at 760 mm Hg

Boiling point = 185-195 °C at 1 mbar and 140-150 °C at 0.1 mbar

less than -13 °F (NTP, 1992)

-25°C

-68.3 °C using OECD Guideline 102 (Melting point/Melting Range)

This chemical does not meet GHS hazard criteria for 92.2% (1853 of 2010) of all reports.

Not Classified

Aggregated GHS information provided per 2010 reports by companies from 6 notifications to the ECHA C&L Inventory.

This chemical does not meet GHS hazard criteria for 46.6% (88 of 189) of reports.

Warning

H315 (20.1%): Causes skin irritation [Warning Skin corrosion/irritation]

Chemical: 2-Propenoic acid, 3-(4-methoxyphenyl)-, 2-ethylhexyl ester

2-Propenoic acid, 3-(4-methoxyphenyl)-, 2-ethylhexyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 3-(4-methoxyphenyl)-, 2-ethylhexyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

REACH registered substance: 2-ethylhexyl (2E)-3-(4-methoxyphenyl)acrylate (EC: 629-661-9)

2-Ethylhexyl-p-methoxycinnamate: Does not have an individual approval but may be used under an appropriate group standard

May cause photoallergic contact dermatitis in certain individuals; [HSDB] It is patch tested at 7.5% concentration in petrolatum; It is a very low-level sensitizer: 1/108 patients tested photo-patch test positive; In another series, 1/280 and 1/280 tested positive for patch or photo patch, respectively; Octinoxate may be found in cosmetics, shampoos, and lip balms; [Marks, p. 219] May cause photosensitivity and irritation; [MSDSonline]

The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed over-the-counter drug products, including octinoxate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

Sunscreen active ingredients. The active ingredient of the product consists of any of the following, within the concentration specified for each ingredient, and the finished product provides a minimum SPF value of not less than 2 as measured by the testing procedures established in subpart D of this part: Octyl methoxycinnamate up to 7.5 percent is included on this list.

Not Classified

Skin Irrit. 2 (20.1%)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide

Wear self contained breathing apparatus for fire fighting if necessary.

Keep container tightly closed in a dry and well-ventilated place. Light sensitive.

Store below 40 °C (104 °F), preferably between 15 and 30 deg. C (59 and 86 deg. F), unless otherwise specified by manufacturer. /Sunscreen agents, topical/

Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Keep in suitable, closed containers for disposal.

SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Respiratory protection not required. For nuisance exposures use type OV/AG (US) or type ABEK (EU EN 14387) respirator cartridges. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.

Skin and body protection: impervious clothing, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Agricultural workers are encouraged to use sunscreen to decrease the risk of UV-related skin cancer. ... Previous studies have shown certain commercial sunscreens to be penetration enhancers. The focus of this project is to determine whether active ingredients in sunscreen formulations (i.e., the UV absorbing components and insect repellants for the sunscreen/bug repellant combinations) also act as dermal penetration enhancers for herbicides in vitro. The total percentages of 2,4-dichlorophenoxyacetic acid (2,4-D) penetrating through hairless mouse skin in 24 hr ranged from 54.9 +/- 4.7 for the no sunscreen control to 86.9 +/- 2.5 for padimate-O. Of the active ingredients tested (7.5% octyl methoxycinnamate, 7% octocrylene, 0.6% oxybenzone, 5% homosalate, 5% octyl salicylate, 8% padimate-o, 10% sulisobenzone, and 9.5% and 19% N,N-diethyl-m-toluamide (DEET)), all but octocrylene led to a significant increase in total 2,4-D penetration as compared to the control (P < 0.05), and only octocrylene and oxybenzone did not significantly decrease the corresponding lag time. Octyl salicylate (P < 0.01) and octyl methoxycinnimate (P < 0.05) significantly increased the 3H2O penetration across mouse skin, indicating physical damage to the stratum corneum. Additional studies demonstrated that the penetration enhancement seen across hairless mouse skin also occurred with human skin. Thus, the active ingredients of sunscreen formulations enhance dermal penetration of the moderately lipophilic herbicide 2,4-D.

/The authors/sought to determine whether the effect of preapplication of a sun protection factor (SPF) 29 sunscreen (containing octyl methoxycinnamate, oxybenzone, and octyl salicylate) could prevent local UVB-induced suppression of contact hypersensitivity to dinitrochlorobenzene (DNCB). Nineteen subjects received either three minimal erythema doses of UVB daily on three consecutive days (UVB group) or sunscreen followed by this same dose of UVB irradiation (sunscreen plus UVB group) to a 16-sq cm area of the buttock. One day after completion of irradiation, DNCB was applied to this buttock site, and 2 weeks later, forearm challenge with four different concentrations of DNCB was performed. A control group of 10 subjects underwent DNCB testing as above, but with no prior exposure to UVB (no-UVB group). ... The UVB group had a reduced response rate to all challenge doses of DNCB (3.125, 6.25, and 8.8 ug), except for the highest dose (12.5 ug) compared with the no-UVB control group (Fisher's Exact test, P < or = 0.008), and compared with the sunscreen plus UVB group (P < or = 0.02). The no-UVB and sunscreen plus UVB groups showed no significant differences in response rates to any of the doses of DNCB tested (P > or = 0.53). ... These results indicate that application of a sunscreen with over ninefold greater protection than that needed to prevent erythema prior to localized UVB radiation prevents localized UVB-induced suppression of contact hypersensitivity...

The influence of sucrose laureate and sucrose oleate on the in vivo percutaneous penetration of octyl methoxycinnamate (OMC) formulated in i) colloidal suspensions (nano-emulsions and nanocapsules), and ii) conventional o/w emulsions was evaluated. The results showed that nano-emulsions formulated with sucrose laureate exhibited the highest penetration in the stratum corneum compared to the other formulations. A two-fold increase in OMC skin deposition was observed with the nano-emulsion containing sucrose laureate when compared to the control. The data obtained suggest that the total amount of OMC detected in the stratum corneum and the penetration depth are strongly dependent upon the formulation's nature, the particle size, and the type of enhancer.

Hairless mice were exposed to repeated doses of UV simulating the solar energy spectrum. After a rest period, 3 applications a week were made to an area of skin of 12-o-tetradecanoyl phorbol-13-acetate ... Suitable controls were used. The test group was completely protected by 50 % a.i., and 7.5 % gave an effect equivalent to reducing the insolation four-fold. It had been suggested that the a.i. could itself have been a promoter, but there was no evidence of this.

For more Interactions (Complete) data for OCTINOXATE (7 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 8,600(SRC), determined from a structure estimation method(2), indicates that octinoxate is expected to be immobile in soil(SRC). Volatilization of octinoxate from moist soil surfaces is expected to be an important fate rocess(SRC) given an estimated Henry's Law constant of 8.5X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(2). However, adsorption to soil is expected to attenuate volatilization from moist soil(SRC). Octinoxate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.3X10-5 mm Hg(SRC), determined from a fragment constant method(2). Octinoxate absorbs light at wavelengths greater than 310 nm(3) and has been shown to photodegrade readily in aqueous solutions exposed to sunlight(4); therefore, octinoxate may be susceptible to direct photolysis by sunlight on soil surfaces(SRC). Octinoxate was found to be readily biodegradable using OECD Guideline 301 F (Ready Biodegradability: Manometric Respirometry Test) with a 78% degradation over a 28-day exposure period using a non-adapted activated sludge inoculum(5).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 8,600(SRC), determined from a structure estimation method(2), indicates that octinoxate is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 8.5X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 7.6 and 60 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 6 years if adsorption is considered(4). According to a classification scheme(5), measured BCF values of 174 and 433 in rainbow trout (Oncorhynchus mykiss)(6), suggest the potential for bioconcentration in aquatic organisms is high(SRC). In one photodegradation study, the direct photolysis half-life of octinoxate in aqueous solution was found to range from 5-9 days when irradiation levels were corrected to 40 degrees N latitude sunlight(6). In another aqueous study, exposure to natural sunlight (mid-September in Schenectady), octinoxate was found to have direct photolysis half-lives of 0.8 and 1.3 hours respectively for the trans and cis-isomers of octinoxate(7); dimerization was found to occur as a result of direct photolysis in aqueous solution(7); in addition to various dimers, photodegradation products included 4-methoxybenzaldehyde and 2-ethylhexanol(7). The hydrolysis half-life of octinoxate at 20 °C was determined to be greater than one year at pH 4, pH 7 and pH 9(6). Octinoxate was found to be readily biodegradable using OECD Guideline 301 F (Ready Biodegradability: Manometric Respirometry Test) with a 78% degradation over a 28-day exposure period using a non-adapted activated sludge inoculum(6).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), octinoxate, which has an estimated vapor pressure of 2.3X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Octinoxate has been detected in atmospheric aerosol particulates(3). Vapor-phase octinoxate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 7.2 hours(SRC), calculated from its rate constant of 5.3X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). The rate constant for the vapor-phase reaction of octinoxate with ozone has been estimated as 1.6X10-17 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2); this corresponds to an atmospheric half-life of about 20 hours(SRC). Particulate-phase octinoxate may be removed from the air by wet or dry deposition(SRC). Octinoxate absorbs light at wavelengths greater than 310 nm(4) and has been shown to photodegrade readily in aqueous solutions exposed to sunlight(5); therefore, octinoxate may be susceptible to direct photolysis by sunlight in the atmosphere(SRC).

Gas chromatography with mass spectrometry was used to assess the presence of five sunscreen ingredients- iso amyl-para-methoxycinnamate, benzophenone-3, 4-methylbenzylidene camphor, ethyl dimethyl PABA and ethyl hexyl methoxycinnamate--in the breast milk of six women who had used sunscreens or skin-care products or used public swimming pools. ... Two samples contained ethylhexyl methoxycinnamates at concentrations of 28 and 47 ng/g of fat.

Researchers in Europe analyzed samples of human milk for the presence of sunscreens and other chemicals with possible endocrine activity. Mothers were asked about their use of sunscreens and cosmetics that contained sunscreen ingredients (benzophenone 2, benzophenone 3, 3-benzylidene camphor, 4-MBC, OMC, homosalate, octocrylene, and octyl-dimethyl PABA). Responding to questionnaires, 78.8% of the women reported using products that contained sunscreens; 76.5% of human milk samples contained these chemicals. There was a high correlation reported between mothers' use of these chemicals and their concentrations in human milk. The authors concluded that except for lipsticks (the ingestion of which is probably important), their results agree with studies in animals and humans showing dermal absorption of sunscreens. Given that some of these chemicals have endocrine activity in animals, the authors suggested that exposure could be lessened if mothers abstained from using these products during their children's sensitive life stages.

/AQUATIC SPECIES/ There is increasing evidence indicating that several UV filters might have endocrine disruptive effects. Numerous studies have evaluated hormonal effects in vertebrates, mainly reporting estrogenic and androgenic activities in mammals and fishes. There is only limited knowledge about potential endocrine activity in invertebrate hormonal systems. In this work, the effects on endocrine signaling genes of six frequently used UV filters were investigated in Chironomus riparius, a reference organism in aquatic toxicology. The UV filters studied were: octyl-p-methoxycinnamate (OMC) also called 2-ethylhexyl-4-methoxycinnamate (EHMC); 4-methylbenzylidene camphor (4-MBC); benzophenone-3 (BP-3); 4-hidroxybenzophenone (4-HB); octocrylene (OC); and octyldimethyl-p-aminobenzoate (OD-PABA). After in vivo exposure at different dosages, expression levels of the genes coding for the ecdysone receptor (EcR), the ultraspiracle (usp, ortholog of the RXR) and the estrogen-related receptor (ERR) were quantified by Real Time PCR. The EcR gene was significantly upregulated by 4-MBC, OMC/EHMC and OD-PABA, with a dose-related response following 24 hr exposure. In contrast, the benzophenones, BP-3 and 4-HB, as well as OC did not alter this gene at the same exposure conditions. The transcription profiles of the usp and ERR genes were not significantly affected, except for BP-3 that inhibited the usp gene at the highest concentration. To our knowledge, this is the first experimental evidence in invertebrates of a direct effect of UV filters on endocrine-related genes, and is consistent with the known effects on vertebrate hormonal receptor genes. The capability of 4-MBC, OMC/EHMC and OD-PABA to stimulate the expression of the ecdysone receptor, a key transcription factor for the ecdysone-genomic response in arthropods, suggests the possibility of a broad and long-term effect on this hormonal pathway. These findings strengthen the need for further research about the ecotoxicological implications of chronic exposure to these compounds in aquatic invertebrates.

/AQUATIC SPECIES/ ... The aim of the study was to determine effects of four frequently used UV filters on primary aquatic producers and consumers, the green alga Desmodesmus subspicatus and the crustacean Daphnia magna. Exposure to benzophenone 3 (BP3), ethylhexyl methoxycinnamate (EHMC), 3-benzylidene camphor (3-BC) and 3-(4'-methylbenzylidene)-camphor (4-MBC) resulted in growth inhibition of D. subspicatus with 72 h IC(10) values of 0.56 mg/L (BP 3), 0.24 mg/L (EHMC), 0.27 mg/L (3-BC) and 0.21 mg/L (4-MBC). EC(50) concentrations in the acute test with D. magna were 1.67, 0.57, 3.61 and 0.80 mg/L for BP3, EHMC, 3-BC and 4-MBC, respectively. Chronic exposure of D. magna resulted in NOECs of 0.04 mg/L (EHMC) and 0.1 mg/L (3-BC and 4-MBC). BP 3 showed no effects on neonate production or the length of adults. Rapid dissipation of these substances from the water phase was observed indicating the need for more frequent test medium renewal in chronic tests or the use of flow-through test systems.

Gray water (any washwater that has been used in the home, except water from toilets) collected from 32 homes in the Netherlands contained an average octinoxate concentration of 15.5 ug/L with a range of 3.9 to 67.7 ug/L(1). The concentration of octinoxate ranged from <0.01 to 1.0 ug/L in effluent samples from 11 wastewater treatment plants in Switzerland during 2002-2003 monitoring(2).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of octinoxate can be estimated to be 8,600(SRC). According to a classification scheme(2), this estimated Koc value suggests that octinoxate is expected to be immobile in soil.

RURAL/REMOTE: Octinoxate was detected in 87% of organic aerosol samples collected at the lighthouse of Fajardo, Puerto Rico(1). It was also detected in the atmosphere above the open ocean at locations around the island(1). Concentrations were not reported.

/HUMAN EXPOSURE STUDIES/ In 10 subjects, patches were applied for 24 hours and the areas then exposed to a suberythematous dose of UV irradiation. There was no evidence of phototoxicity.

/HUMAN EXPOSURE STUDIES/ A 10 % solution of a.i. in dimethylphthalate was used. A total of 58 subjects were recruited, 12 males and 46 females, aged 18-63. Of these, 6 subjects failed to complete the test for reasons unconnected with the experimental procedure. Induction applications were made on the skin of the back, for 24 hours with occlusion, 3 times a week for 9 applications. Following a rest period of 2 weeks, a further patch was now applied to a new site on the back for 24 hours with occlusion. The area was inspected at 0, 24 and 48 hours after removal of the patch. No adverse reaction was noted at any stage of the experiment.

/HUMAN EXPOSURE STUDIES/ A Draize repeated insult patch test was carried out at a concentration of 2 % in 53 subjects. There was no sensitization. In 54 subjects, a formulation of 7.5 % a.i. in petrolatum was applied for 48 hours under occlusion for 11 applications. After a 14 day rest, a challenge application of a single dose was made. There was no adverse reaction. In an extensive series of patch tests carried out in man, the a.i. was found to be very rarely responsible for allergic contact effects.

/HUMAN EXPOSURE STUDIES/ In 53 subjects, a Draize repeated insult patch test at a concentration of 2 % caused no irritation. In 54 subjects, a Draize repeated insult patch test of a 7.5 % dilution of a.i. in petrolatum caused no irritation.

For more Human Toxicity Excerpts (Complete) data for OCTINOXATE (19 total), please visit the HSDB record page.

Octinoxate was detected in fish (concentrations were not reported) tested during a monitoring study of sunscreen agents in the area of Lake Meerfelder Maar/Eifel in Germany in the early 1990s(1). The concentration of octinoxate ranged from <2 to 72 ng/g lipid-wt in fish collected from 5 lakes in Switzerland during 2002 monitoring(2).

The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed over-the-counter drug products, including octinoxate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

Sunscreen active ingredients. The active ingredient of the product consists of any of the following, within the concentration specified for each ingredient, and the finished product provides a minimum SPF value of not less than 2 as measured by the testing procedures established in subpart D of this part: Octyl methoxycinnamate up to 7.5 percent is included on this list.

D - Dermatologicals

QD - Dermatologicals

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.

Absorbs UV-B (predominantly) and UV-A rays while accumulating in the outermost layer of the epidermis. Like any other photoprotective agents, octinoxate prevents the damage to cells and deoxyribonucleic acid (DNA) by reducing the p53 protein expression following UV exposure and also increases the skin's tolerability to UV rays.

Diminish the penetration of ultraviolet (UV) light through the epidermis by absorbing UV radiation within a specific wavelength range. The amount and wavelength of UV radiation absorbed are affected by the molecular structure of the sunscreen agent. /Sunscreen agents, topical/

Radiation is absorbed by chemical sunscreens when the electron energy level of the drug is raised from its ground state to a higher energy level or excited state. Chromophore groups (C=C, C=O, O-N=O) with loosely held electrons are easily excited by radiation. Compounds which have several chromophore groups in optimal positions have high absorbance over a broad range of wavelengths. Chemical sunscreens are usually agents that absorb not less than 85% of UVB radiation (thus preventing burning) but may permit transmission of UVA radiation (thus allowing tanning). Some sunscreens may absorb wavelengths over a range that is slightly wider or narrower than that of UVB. All PABA derivatives absorb wavelengths of approximately 290-320 nm, benzophenone derivatives absorb wavelengths of approximately 250-360 nm, cinnamic acid derivatives absorb wavelengths of 280-320 nm, and salicylate derivatives and other miscellaneous chemical sunscreens absorb wavelengths of about 270-320 nm.

The wavelength to which the skin is maximally sensitive had been accepted for many years to be 296.7 nm; however, recent evidence suggests that the most erythemogenic UVB wavelength may be slightly lower (e.g., somewhere in the range of 292-295 nm). In addition, of the stronger burning wavelengths that reach the earth's surface, most are approximately 310 nm. Therefore, sunscreens that maximally absorb UVB radiation near either of these wavelengths are particularly effective at preventing sunburn. Maximum absorbance occurs at about 290 nm for PABA, at about 295 nm for glyceryl-p-aminobenzoate, and at about 310 nm for the remaining PABA derivatives. Maximum absorbance occurs at 280-290 nm for benzophenone derivatives, at 310 nm for cinnamic acid derivatives with the exception of diethanolamine-p-methoxycinnamate which has its maximum absorbance at 290 nm, and at 300-305 nm for salicylate derivatives and other miscellaneous sunscreens. /Sunscreens/

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.

As a lipophilic substance, the a.i. is very likely to be metabolized; it is known in any case to be hydrolyzed by plasma esterases, although slowly.

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.

Can be detected in urine in unchanged form.

Naked rat skin. This was studied in a chamber experiment. Most of the material was found in the stripped skin; there was less in the stratum corneum, and least in the chamber. The approximate amounts found in the chamber were: after 6 hrs, 1.13 %; after 16 hrs, 11.4 %; and at 24 hrs 17,9 %. The figures for the horny layer and the strippings combined were, respectively, 31.4 %, 44.4 % and 45.7 % (percentages of applied doses). Solutions of 3% and 20 % of a.i. gave similar results.

Eight healthy volunteers had small amounts of radioactive a.i. applied to the interscapular region. One group of 4 had the material applied under a watch glass; the other 4 had it applied on gauze, with occlusion in one case. Tests for absorption of a.i. were negative except for about 0.2 % in urine. The concentrations used were not stated.

In a preliminary experiment, a capsule containing 100 mg of a.i. was taken orally. ... The cumulative excretion of 4methoxycinnamate in the urine over 24 hours was studied by GC/MS of the methyl ester derivative. (This method would also detect 4-hydroxycinnamic acid). Over 24 hours, 13.2 % of the amount ingested was recovered, equivalent to 21.5 % of the amount that would be expected if the a.i. were completely absorbed. In the main part of the experiment, an o/w cream containing 10 % a.i. was used. Applications of 2 grams of this material (= 200 mg a.i.) were made to the interscapular area of each of 5 male subjects, aged 29 to 46. The area of skin covered was 25x30 cm. After application, the area was covered with 3 layers of gauze, left in place for 12 hours. Blood was taken at times 0, 0.5, 1, 2, 3, 5, 7, and 24 hours. Urine was collected at 0, 1, 2, 3, 4, 5, 6, 7, 12, 24, 48, 72 and 96 hours. The control plasma samples showed a level equivalent to about 10 ng/ml before any application had been made. There was no evidence of any rise in plasma levels during the experiment. The urine showed a "physiological" level of 100 to 300 ng/ml. No significant increase in this amount was found in any sample. The authors conclude that very little, if any, of the compound was absorbed under the conditions of the experiment.

The objective of this study was to determine the influence of vehicles on the penetration of octyl methoxycinnamate (OMC), as a UV absorber, to the stratum corneum by the stripping method. The experimental formulations consisted of a conventional o/w emulsion and multilamellar and small unilamellar liposomes (MLVs and SUVs) containing OMC. MLVs containing OMC were prepared by the fusion method and then converted to SUVs by probe sonication. Various formulations were then applied onto the midvolar forearms of six volunteers at a dose of 2 mg/sq cm. After determined timepoints, the stripping method was conducted whereby 22 tape strips were applied and subsequently divided into different stripping groups. The sunscreen agent was assessed by HPLC while the SPF (sun protection factor) of the formulations was determined in human volunteers in accordance with the Australian standard. Overall the results indicate that skin accumulation of OMC in MLVs was significantly greater than in the o/w emulsion and SUVs. Furthermore, SUV's penetration into the deeper skin layers was significantly greater than MLV's and that of a conventional o/w emulsion. Also, higher amounts of OMC were recovered from the upper layers of the stratum corneum than from the deeper layers in all the formulations tested. Finally, the SPF of the liposomes containing OMC was slightly greater than that of the control lotions at a similar concentration of OMC. In conclusion, the result of this study indicates that an MLV prepared by the fusion method could be a better vehicle for OMC as a sunscreen since it has a slightly better SPF compared to a conventional formulation and more remains in the stratum corneum, reducing its penetration to the deeper layers.

Used as ultraviolet sunscreen; [Merck Index]

For octinoxate (USEPA/OPP Pesticide Code: 088407) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

The most widely used sunscreen ingredient in the United States, octyl methoxycinnamate is thought to be the UVB filter in 90% of sun lotions

Used as an ultraviolet absorber in US cosmetics.

Ultraviolet screen

For more Uses (Complete) data for OCTINOXATE (6 total), please visit the HSDB record page.

2023: 8,269,659 lb

2-Propenoic acid, 3-(4-methoxyphenyl)-, 2-ethylhexyl ester is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR ) (40 CFR part 710 subpart B; 51FR21438).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#7117]

The insertion reaction of ketene with p-methoxybenzaldehyde is used to produce 2-ethylhexyl p-methoxycinnamate.

Using Novozym 435 as catalyst, the syntheses of ... octyl methoxycinnamate (OMC) from p-methoxycinnamic acid and 2-ethyl hexanol /was/ successfully carried out in this study... For the synthesis of OMC at 80 degrees C, 90% conversion can be obtained within 1 day. The use of solvent and high reaction temperature resulted in better conversion for the synthesis of cinnamic acid derivatives. Some cinnamic acid esters could also be obtained with higher conversion and shorter reaction times in comparison to other methods reported in the literature. The enzyme can be reused several times before significant activity loss was observed.

Manufacturing process and purification: P. Schudel et al, United States of America 4713473 (1987 to Givaudan)

Uvinul MC 80: stabilized with 0.07+/-0.02% BHT and Uvinul MC 80 N: unstabilized

SHADE UVAGUARD: avobenzone 3%, octinoxate 7.5%, oxybenzone 3% over the counter sunscreen topical lotion

Fragrance Ingredients

Cosmetics -> Uv filter; Uv absorber

All Other Chemical Product and Preparation Manufacturing

2-Propenoic acid, 3-(4-methoxyphenyl)-, 2-ethylhexyl ester: ACTIVE

This study investigates the different nanocapsules (NCs) made of poly-epsilon-caprolactone (PCL) containing the lipophilic sunscreen Escalol 557 (octyl methoxycinnamate (OMC)) and analyzes the influence of nanoparticle-based systems on light-induced decomposition of the sunscreen agent. ... The PCL nanoparticles loaded with OMC were effective in reducing light-induced degradation of the sunscreen agent.