2-Ethylhexyl 4-methoxycinnamate

290.4

290.40

226-775-7

DTXSID1025302

Pale yellow liquid|Colorless to light yellow viscous liquid

D - Dermatologicals

29189090

35.53000

5.66

Clear colorless to yellow Liquid

1.0±0.1 g/cm3

less than -13 °F (NTP, 1992)

140-150 °C @ Press: 0.076 Torr

193°C

1.515

H2O: <0.1 g/100 mL at 27 ºC

2-8°C

2.3X10-5 mm Hg at 25 °C (est)

Practically odorless

Henry's Law constant = 8.5X10-6 atm-cu m/mol at 25 °C (est)

log Kow: >6 at 23 C OECD Guideline 117 (Partition Coefficient (n-octanol / water), HPLC Method)|Hydroxyl radical reaction rate constant = 5.3X10-11 cu cm/molecule-sec at 25 °C (est)

Insoluble in water.

Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters

NONH for all modes of transport

nwg

24/25

UD3392732

Stable. Incompatible with strong oxidizing agents.

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.

Strong oxidizing agents

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.

Flash point data for this compound are not available, however, it is probably combustible. (NTP, 1992)

Not Classified

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. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)

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)

Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide|Wear self contained breathing apparatus for fire fighting if necessary.

Hazardous decomposition products formed under fire conditions. - Carbon oxides

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.

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.

Derivatives of PABA, benzophenone, cinnamic acid, and salicylate and 2-phenylbenzimidazole-5-sulfonic acid have caused skin irritation including burning, stinging, pruritus, and erythema on rare occasions. /Sunscreens/

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).

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.

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.

LD50 Rat oral >20 mL/kg b.w.|LD50 Mouse oral >8 g/kg b.w.

/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.

Because the absorptive characteristics of skin of children younger than 6 months of age may differ from those of adults and because the immaturity of metabolic and excretory pathways of these children may limit their ability to eliminate any percutaneously absorbed sunscreen agent, sunscreen products should be used in children younger than 6 months of age only as directed by a clinician. It is possible that the characteristics of geriatric skin also differ from those of skin in younger adults, but these characteristics and the need for special considerations regarding use of sunscreen preparations in this age group are poorly understood. /Sunscreens/

Octinoxate (2-ethylhexyl p-methoxycinnamate) does not occur naturally(1).

Octinoxate's production and use as an ingredient in sunscreens and cosmetics(1,2) may result in its release to the environment through various waste streams(SRC).

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).

The rate constant for the vapor-phase reaction of octinoxate with photochemically-produced hydroxyl radicals has been estimated as 5.3X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 7.2 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 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(1). This corresponds to an atmospheric half-life of about 20 hours at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(1). Using OECD Guideline 111 (Hydrolysis as a Function of pH), the hydrolysis half-life of octinoxate at 20 °C was determined to be greater than one year at pH 4, pH 7 and pH9(2). Octinoxate absorbs light at wavelength 310 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). Using EPA Guideline Subdivision N 161-2 (Photodegradation Studies in Water), the direct photolysis half-life of octinoxate in aqueous solution was found to range from 5-9 days when irradiation levels were orrected to 40 degrees N latitude sunlight(2). When exposed to natural sunlight (mid-September in Schenectady, NY in 2007 and 2008), octinoxate in aqueous solution was found to have direct photolysis half-lives of 0.8 and 1.3 hours, respectively, for the trans and cis-isomers of octinoxate(4); dimerization was found to occur as a result of direct photolysis in aqueous solution(4); in addition to various dimers, photodegradation products included 4-methoxybenzaldehyde and 2-ethylhexanol(4). Other photodegradation studies exposing octinoxate to sunlight irradiation have detected degradation products including cis-octyl-p-methoxycinnamate, cinnamate dimers and substituted oxopentanoates and oxobutaneoates(5-7).

Using OECD Guideline 305 (Bioconcentration: Flow-through Fish Test) and a 5-day exposure period, whole body BCF values of 433 and 174 were determined for octinoxate in rainbow trout (Oncorhynchus mykiss) at respective concentrations of 70 ug/L and 700 ug/L(1). According to a classification scheme(2), these BCF values suggest the potential for bioconcentration in aquatic organisms is high(SRC).

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.

The Henry's Law constant for octinoxate is estimated as 8.5X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that octinoxate is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 7.6 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 60 days(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(3). Octinoxate's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC), but volatilization may be attenuated by adsorption to 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(1).

DRINKING WATER: Octinoxate was detected at a concentration of 0.45 ug/L in one of 15 finished drinking water samples collected in San Diego County, CA during 2001-2002 monitoring(1).|SURFACE WATER: The concentration of octinoxate ranged from <2 to 7 ng/L in samples collected from 4 lakes in Switzerland during summer 2002 monitoring(1). In surface seawater samples collected from Folly Beach, South Carolina in the summer of 2010, sulisobenzone was not detected in any samples from four sites (detection limit 1 ng/L) while other UV filter compounds (avobenzone, octocrylene, octinoxate, and padimate-O) were detected at concentrations ranging from 10 to 2013 ng/L(2).

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.

Occupational exposure to octinoxate may occur through dermal contact with this compound at workplaces where octinoxate is produced or used. The general population may be exposed to octinoxate via dermal contact with this compound in consumer products such as cosmetics and sunscreens. (SRC)

Octinoxate was detected in humans tested during a monitoring study of sunscreen agents in the area of Lake Meerfelder Maar/Eifel in Germany in the early 1990s(1). Concentrations were not reported.

Ultraviolet /UVB/ screen|/The authors/ tested the sun protection factor of a hydroquinone formulation (Lustra-Ultra, TaroPharma, Hawthorne, NY) containing avobenzone 3%, and octinoxate 7.5% according to the FDA Sunscreen Monograph on 20 volunteer subjects. We also determined the UVR absorbance spectrum of the preparation. ... The mean sun protection factor (SPF) of 21.7 satisfied labeling requirements for SPF 20. The formulation exhibited strongest photoprotection near the wavelengths of peak sun burning effectiveness in the UVB region and maintains significant UVR absorbance through the entire UVA region. Avobenzone 3% and octinoxate 7.5% provide broad spectrum UV protection. Incorporating these sunscreens into a hydroquinone preparation simplifies the treatment regimen while providing significant photoprotection for patients being treated for dyschromia.|Sunscreens capable of inhibiting erythema are assumed to protect against UV-induced carcinogenesis as well. However, the correlation between inflammation and carcinogenesis is uncertain, and the prevention of UV-induced erythema might in fact be biologically irrelevant as an indicator of protection against UV-induced skin cancer. Ultraviolet-B radiation promotes cutaneous immunosuppression by the release of immunoregulatory cytokines and by depletion of Langerhans cells. /The authors/ investigated the ability of two different sunscreens to inhibit UVB-induced expression of epidermal interleukin (IL)-10 and depletion of Langerhans cells. Chemical and physical sunscreens were applied to the forearms of volunteers 15 min prior to 4 minimal erythemal doses of UVB exposure. Suction blisters were induced 24 hr after irradiation, and RNA was extracted from the blister roofs. Reverse transcription polymerase chain reaction was performed using primers for IL-10 and CD1a. A chemical sunscreen containing octyl methoxycinnamate (12 sun protection factor (SPF)) and a physical sunscreen containing zinc oxide (16 SPF) were assayed: UVB-induced IL-10 mRNA expression was nearly totally inhibited by both sunscreens (median protection for chemical and physical sunscreens was 95% and 78%, respectively), whereas UVB-induced Langerhans cell depletion was partially prevented (47% and 50% for chemical and physical sunscreens, respectively). Langerhans cell protection by sunscreens was confirmed by estimation of cell density after ATPase staining. In contrast, both sunscreens effectively prevented the induction of UVB-induced erythema. /The authors/ believe this to be the first demonstration that sunscreens can prevent the induction of cutaneous mediators of immunosuppression, and that the results indicate that the immunoprotection offered by the sunscreens is significantly lower than their ability to prevent erythema.|Daily use of a sunscreen with a high SPF (greater than 15) on usually exposed skin is recommended for residents of areas of high ... /solar radiation/ who work outdoors or ... /enjoy/ regular outdoor recreation. Daily use of a sunscreen can reduce the cumulative ... /solar/ exposure that causes actinic keratoses and squamous-cell carcinoma.|Sunscreen agents are indicated for the prevention of sunburn. In addition to limiting the skin's exposure to the sun, using sunscreen agents regularly when in the sun may help reduce long-term sun damage such as premature aging of the skin and skin cancer. /Sunscreen agents, topical; Included in US product labeling/

The manufacturers of sunscreen preparations with propellants warn that concentrating and subsequently inhaling the fumes from these preparations may be harmful or fatal. /Propellants/|Because the absorptive characteristics of skin of children younger than 6 months of age may differ from those of adults and because the immaturity of metabolic and excretory pathways of these children may limit their ability to eliminate any percutaneously absorbed sunscreen agent, sunscreen products should be used in children younger than 6 months of age only as directed by a clinician. It is possible that the characteristics of geriatric skin also differ from those of skin in younger adults, but these characteristics and the need for special considerations regarding use of sunscreen preparations in this age group are poorly understood. /Sunscreens/|Little information is available regarding the safety of chronic sunscreen usage, but commercially available physical and chemical sunscreens appear to have a low incidence of adverse effects. Derivatives of PABA, benzophenone, cinnamic acid, and salicylate and 2-phenylbenzimidazole-5-sulfonic acid have caused skin irritation including burning, stinging, pruritus, and erythema on rare occasions. /Sunscreens/|Sunscreens should not be used as a means of extending the duration of solar exposure, such as prolonging sunbathing, and should not be used as a substitute for clothing on usually unexposed sites, such as the trunk and buttocks. /Sunscreens/|For more Drug Warnings (Complete) data for OCTINOXATE (11 total), please visit the HSDB record page.

Chemical or physical agents that protect the skin from sunburn and erythema by absorbing or blocking ultraviolet radiation. (See all compounds classified as Sunscreening Agents.)

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.|For more Absorption, Distribution and Excretion (Complete) data for OCTINOXATE (19 total), please visit the HSDB record page.

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.

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/

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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/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.

2-ethylhexyl-4-methoxycinnamate

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

Fragrances|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.

Simultaneous determination for 9 ultraviolet absorbers those set a limit to the amount in cosmetics was performed. Ultraviolet absorbers were extracted from cosmetics with tetrahydrofuran (THF) by ultrasonication. After centrifugation, the supernatant was collected, and the sample solution was injected into the HPLC. Separation was archived using an ODS column with the mixture of THF and water as the mobile phase. Detection wavelength was set at 310 nm. The linearity was obtained between the peak areas and the concentrations of each ultraviolet absorber in the range of 5 - 100 ug/mL. In 70 commercial cosmetic products, such as sunscreen, face powder, foundation, massage cream, moisture lotion, lip balm and essence, 2-ethylhexyl-p-methoxycinnamate (EMC), 2-hydroxy-4-methoxybenzophenone (HMB), 4-tert-butyl-4'-methoxydibenzoylmethane (BMB) and 2-ethylhexyl salicylate (ES) were detected.|Simultaneous determination of six internationally authorized organic UV-filters in sunscreen formulations was performed by HPLC with UV spectrophotometric detection. The filters determined were: sulisobenzone, oxybenzone, octyl dimethyl PABA, octyl methoxycinnamate, octyl salicylate and homosalate. A C18 stationary phase and a mobile phase of ethanol water acetic acid (70:29.5:0.5) were used with a flow rate of 0.5 mL/min. UV measurements were carried out at 313 nm. The time required for the analysis was 25 min and the limits of detection were between 0.2 and 2 mg/L, except for sulisobenzone, which gave a limit of detection of 20 mg/L. The procedure proposed provides an accurate, fast and green analytical method, that does not involve toxic organic solvents.|Simultaneous determination of organic UV filters worldwide authorised in sunscreen formulations was performed by HPLC with UV spectrophotometric detection. The filters determined were: benzophenone-4, benzophenone-3, butyl methoxydibenzoylmethane, octyl dimethyl PABA, octyl methoxycinnamate, homosalate and octyl salicylate. A C18 stationary phase and an isocratic mobile phase of ethanol-water-acetic acid (70:29.5:0.5) containing 65.4 mM of hydroxypropyl-beta-cyclodextrin, were used with a flow-rate of 0.6 mL/min. UV measurements were carried out at 313 nm. The time required for the analysis was 20 min and the limits of detection were between 1.5 and 2.3 mg/L. The procedure proposed provides a green analytical method with a basic instrumental configuration, it is fast and accurate and does not involve highly toxic organic solvents.|A method for quantitative determination of eleven sunscreen agents (benzophenone-4,p-amino-benzoic acid, salicylic acid, benzophenone-3,phenyl salicylate, 4-methylbenzylidene camphor, octyl dimethyl p-amino-benzoate, isopropyl dibenzoylmethane, butyl methoxydibenzoylmethane, octyl methoxycinnamate, octyl salicylate) in cosmetic products is described. It was based on a high performance liquid chromatographic separation under the condition of isocratic elution with a mixture solution of methanol-THF-water-70% perchloric acid (200:200:160:0.1) by using a column packed with 10 microns YWG-C15 and UV detection. The recoveries (n = 6) were 94.1%-101% and the relative standard deviations(n = 6) for all eleven sunscreen agents were less than 5%. In addition, the results of analysis of 30 samples out of 103 samples of commercial suntan cosmetics performed are reported in this paper.|For more Analytic Laboratory Methods (Complete) data for OCTINOXATE (8 total), please visit the HSDB record page.

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Cosmetics -> Uv absorber; Uv filter