2-(3,5-ジ-tert-アミル-2-ヒドロキシフェニル)ベンゾトリアゾール

Nitrogen Compounds -> Triazoles

UV filter

White to yellow powder or crystals

Powder

Dry Powder; Large Crystals; CBI; Dry Powder; Other Solid

Solid; [Sigma-Aldrich MSDS]

This chemical does not meet GHS hazard criteria for 4.5% (74 of 1647) of reports.

Warning

H373 (85.7%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]

P260, P273, P319, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1647 reports by companies from 45 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H413: May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]

Chemical: Phenol, 2-(2H-benzotriazol-2-yl)-4,6-bis(1,1-dimethylpropyl)-

Hazard Traits - Bioaccumulation; Environmental Persistence

Phenol, 2-(2H-benzotriazol-2-yl)-4,6-bis(1,1-dimethylpropyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phenol, 2-(2H-benzotriazol-2-yl)-4,6-bis(1,1-dimethylpropyl)- 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)

Status: Active Update: 28-01-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/5280

Substance: 2-(2H-benzotriazol-2-yl)-4,6-ditertpentylphenol (UV-328)

Substance: 2-(2H-benzotriazol-2-yl)-4,6-di-tert-pentylphenol

Causes fatty liver degeneration, changes in liver weight, and multiple enzyme effects in 90-day constant oral studies of dogs; Causes changes in liver and kidney weights and normocytic anemia in 90-day constant oral studies of rats; [RTECS] Prolonged or repeated oral exposure may cause damage to the liver and kidney; [ECHA REACH Registrations] A skin and strong eye irritant; Targets the liver, kidney, and reproductive system; [Sigma-Aldrich MSDS]

Residues of 2-(2'-hydroxy-3',5'-di-tert-amylphenyl) benzotriazole are exempted from the requirement of a tolerance when used in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops only. Use: Ultraviolet (UV) stabilizer. Limit: Maximum concentration of 0.6% in insecticide formulations applied to adzuki beans, canola, chickpeas, cotton, faba beans, field peas, lentils, linola, linseed, lucerne, lupins, mung beans, navy beans, pigeon peas, safflower, sunflower, and vetch.

STOT RE 2 (85.7%)

Specific target organ toxicity (repeated exposure) - category 2

Hazardous to the aquatic environment (Long-term) - Category 4

Specific target organ toxicity - Repeated exposure - Category 1 (liver), Category 2 (kidney)

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contaminated packaging: Dispose of as unused product.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.

Precautions for safe handling: Further processing of solid materials may result in the formation of combustible dusts. The potential for combustible dust formation should be taken into consideration before additional processing occurs. Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed.

Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.

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.

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.

Residues of 2-(2'-hydroxy-3',5'-di-tert-amylphenyl) benzotriazole are exempted from the requirement of a tolerance when used in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops only. Use: Ultraviolet (UV) stabilizer. Limit: Maximum concentration of 0.6% in insecticide formulations applied to adzuki beans, canola, chickpeas, cotton, faba beans, field peas, lentils, linola, linseed, lucerne, lupins, mung beans, navy beans, pigeon peas, safflower, sunflower, and vetch.

Eye/face protection: Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).

Skin protection: Handle with gloves.

Body Protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.

Respiratory protection: For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator. For higher level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 450,000(SRC), determined from a structure estimation method(2), indicates that UV-328 is expected to be immobile in soil(SRC). Volatilization of UV-328 from moist soil surfaces is not expected(SRC) given an estimated Henry's Law constant of 6.5X10-13 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). UV-328 is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.9X10-10 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Biodegradation data in soil were not available(SRC, 2018).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 450,000(SRC), determined from a structure estimation method(2), indicates that UV-328 is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 6.5X10-13 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). UV-328 is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). According to a classification scheme(4), an estimated BCF of 6000(SRC), from an estimated log Kow of 7.25(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is very high, provided the compound is not metabolized by the organism(SRC). Biodegradation data in water were not available(SRC, 2018).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), UV-328, which has an estimated vapor pressure of 1.9X10-10 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase UV-328 may be removed from the air by wet or dry deposition(SRC). UV-328 absorbs light at wavelengths >290 nm(3) but is resistant to deterioration by sunlight(4).

IDENTIFICATION AND USE: 2-(2H-Benzotriazol-2-yl)-4,6-di-tert-pentylphenol is used as a UV absorber in plastics applications. It is particularly recommended for polyolefins, polyurethanes, PVC, polyacrylate, epoxy, and elastomers. It offers strong intensity and broad UV absorption with a fairly sharp wavelength cutoff close to the visible region. HUMAN STUDIES: In vitro studies demonstrated antiandrogenic activity of human CYP3A4 enzyme-mediated hydroxylated metabolites. ANIMAL STUDIES: Rats were administered 2-(2H-benzotriazol-2-yl)-4,6-di-tert-pentylphenol via oral gavage at doses of 1392, 1800, 2325 mg/kg test-substance-basis for 14 days. Within 2 hours after treatment the rats in all dosage groups showed sedation, dyspnea, curved position and ruffled fur. The animals recovered within 8 to 9 days. Beagle dogs were fed with a diet containing 0, 15, 30, 60, 120 and 240 mg/kg body weight for 3 months. One male from the high dose group died on the 8th week of treatment. Toxicity was more pronounced in the males than in the females. Body weight loss and depression of food consumption occurred in the high dose group. Hematological analysis revealed signs of anemia at the two highest dose groups. The data from blood chemistry revealed slight increased bilirubin, GTP, GOT and alkaline phosphatase activity in the serum. There were increased liver weights associated with severe liver damage including icterus (jaundice) in a few dogs in the 120 and 240 mg/kg groups. In rats fed for 90 days, hematological analysis revealed a treatment-related decrease of hemoglobin content and packed cell volume in males at 200 ppm and above. In females, this effect was less pronounced. The data from clinical chemistry revealed an increase of glucose-6-phosphatase at lower dose groups with a steady-state level at about 200 ppm. The liver, kidney, spleen and testes weights were increased. There were also some hints for increased thyroid weights in the higher dose groups. The liver was identified as the main target organ in rats. The chemical tested negative for mutagenic effects in Salmonella typhimurium strains: TA 98, TA 100, TA 1535 and TA 1537 with or without metabolic activation. ECOTOXICITY STUDIES: Daphnia magna growth, reproduction, and gene transcription were not impacted by 21-d exposure. In the algae, results showed increased ROS production in response to the chemical exposure. The transcription of superoxide dismutase (SOD), catalase (CAT), and ascorbic peroxidase (APX) was also regulated in the green algae, most likely as a result of ROS production and lipid peroxidation.

Based on house dust concentrations measured in Malate and Payatas, Phillippines, the mean and high average daily intake of UV-328 from dust was reported as 0.15-0.34 and 0.37-0.85 ng/day for adults, and 0.5-1.2 and 2.0-4.6 ng/day for toddlers(1).

/AQUATIC SPECIES/ Benzotriazole ultra violet stabilizers (BZT-UVs) are compounds used in many applications and products to prevent photochemical degradation. Despite their widespread presence in aquatic ecosystems and persistence in the environment, there are very limited data on their effects and toxicity, and their modes of action remain largely unknown. The objectives of the present study were to evaluate the chronic effects of 2 BZT-UVs, 2-(2H-benzotriazol-2-yl)-4,6-bis(1-methyl-1-phenylethyl)phenol (UV-234) and 2-(2H-benzotriazol-2-yl)-4,6-di-tert-pentylphenol (UV-328), on the freshwater green algae Chlamydomonas reinhardtii and the freshwater crustacean Daphnia magna. Organisms were exposed to 0.01 and 10 ug/L of UV-234, UV-328, as well as a mixture of the 2 compounds. Life-history endpoints (viability, reproduction, and growth) and oxidative stress-related biomarkers (gene transcription, reactive oxygen species [ROS] production, and lipid peroxidation) were measured. Daphnia magna growth, reproduction, and gene transcription were not impacted by 21-day individual or mixed exposure. After 96-hr of exposure, no differences were observed on the cellular viability of C. reinhardtii for either of the 2 BZT-UVs. In the algae, results showed increased ROS production in response to UV-328 and lipid peroxidation following exposure to UV-234. Synergistic effects of the 2 BZT-UVs were evident at the transcriptional level with 2 to 6 times up-regulation of glutathione peroxidase (GPX) in response to the mixture for all treatment conditions. The transcription of superoxide dismutase (SOD), catalase (CAT), and ascorbic peroxidase (APX) was also regulated by UV-234 and UV-328 in the green algae, most likely as a result of ROS production and lipid peroxidation. Results from the present study suggest potential impacts of UV-234 and UV-328 exposure on the antioxidant defense system in C. reinhardtii.

EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPA; ICSS Dashboard Application; Available from, as of August 9, 2018: http://actor.epa.gov/dashboard/]

UV-328 was detected in 17.7% of 60 sewage sludge samples collected Oct 2010 to Feb 2011 from wastewater treatment plants located in 33 cities of China with a median concentration of 57.3 ng/g(1). In sludge samples collected in 2009 from five wastewater treatment plants located along the Songhua River, China, UV-328 was detected at 40.6-5920 ng/g dry weight(2).

UV-328 was reported at not detected to approximately 1000 ppm in Pawtuxet River, NJ sediment core samples collected Sep 1977 to Jun 1978(1). In sediment samples collected in 1989 from the Pawtuxet River and in 1997 from Narragansett Bay, UV-328 was detected at a trace to 2 ug/g and a trace to approximately 25 ug/g, respectively(2). UV-328 was detected at 2.6-320 ng/g dry weight in sediment samples collected 2006 to 2007 from the Ariake Sea, Japan(3). In sediment samples collected in 2009 from six locations on the Songhua River, China, UV-328 was detected at 2.06-7.12 ng/g dry weight(4). Six sediment samples collected 2002 and 1998 from the Saginaw and Detroit Rivers, US, respectively, contained 0.72-224 ng/g dry weight of UV-328(4). The concentration of UV-328 in suspended solids from the Mimico and Little Rouge Creeks, Canada following rain events that occurred Nov 2014, Mar and Oct 2015 in was 240 and 22 ng/g, respectively(5).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of UV-328 can be estimated to be 450,000(SRC). According to a classification scheme(2), this estimated Koc value suggests that UV-328 is expected to be immobile in soil(SRC).

/ENDOCRINE MODULATION/ Benzotriazole ultraviolet stabilizers (BUVSs) are prominent chemicals widely used in industrial and consumer products to protect against ultraviolet radiation. They are becoming contaminants of emerging concern since their residues are frequently detected in multiple environmental matrices and their toxicological implications are increasingly reported. We herein investigated the antiandrogenic activities of eight BUVSs prior to and after human CYP3A4-mediated metabolic activation/deactivation by the two-hybrid recombinant human androgen receptor yeast bioassay and the in vitro metabolism assay. More potent antiandrogenic activity was observed for the metabolized UV-328 in comparison with UV-328 at 0.25 uM ((40.73 +/- 4.90)% vs. (17.12 +/- 3.00)%), showing a significant metabolic activation. In contrast, the metabolized UV-P at 0.25 uM resulted in a decreased antiandrogenic activity rate from (16.08 +/- 0.95)% to (6.91 +/- 2.64)%, indicating a metabolic deactivation. Three mono-hydroxylated (OH) and three di-OH metabolites of UV-328 were identified by ultra-performance liquid chromatography quadrupole time of flight mass spectrometry (UPLC-Q-TOF-MS/MS), which were not reported previously. We further surmised that the hydroxylation of UV-328 occurs mainly at the alicyclic hydrocarbon atoms based on the in silico prediction of the lowest activation energies of hydrogen abstraction from C-H bond. Our results for the first time relate antiandrogenic activity to human CYP3A4 enzyme-mediated hydroxylated metabolites of BUVSs. The biotransformation through hydroxylation should be fully considered during the health risk assessment of structurally similar analogs of BUVSs and other emerging contaminants.

Residues of 2-(2'-hydroxy-3',5'-di-tert-amylphenyl) benzotriazole are exempted from the requirement of a tolerance when used in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops only. Use: Ultraviolet (UV) stabilizer. Limit: Maximum concentration of 0.6% in insecticide formulations applied to adzuki beans, canola, chickpeas, cotton, faba beans, field peas, lentils, linola, linseed, lucerne, lupins, mung beans, navy beans, pigeon peas, safflower, sunflower, and vetch.

Benzotriazole ultraviolet stabilizers (BUVSs) are prominent chemicals widely used in industrial and consumer products to protect against ultraviolet radiation. They are becoming contaminants of emerging concern since their residues are frequently detected in multiple environmental matrices and their toxicological implications are increasingly reported. We herein investigated the antiandrogenic activities of eight BUVSs prior to and after human CYP3A4-mediated metabolic activation/deactivation by the two-hybrid recombinant human androgen receptor yeast bioassay and the in vitro metabolism assay. More potent antiandrogenic activity was observed for the metabolized UV-328 in comparison with UV-328 at 0.25 uM ((40.73 +/- 4.90)% vs. (17.12 +/- 3.00)%), showing a significant metabolic activation. In contrast, the metabolized UV-P at 0.25 uM resulted in a decreased antiandrogenic activity rate from (16.08 +/- 0.95)% to (6.91 +/- 2.64)%, indicating a metabolic deactivation. Three mono-hydroxylated (OH) and three di-OH metabolites of UV-328 were identified by ultra-performance liquid chromatography quadrupole time of flight mass spectrometry (UPLC-Q-TOF-MS/MS), which were not reported previously. We further surmised that the hydroxylation of UV-328 occurs mainly at the alicyclic hydrocarbon atoms based on the in silico prediction of the lowest activation energies of hydrogen abstraction from C-H bond. Our results for the first time relate antiandrogenic activity to human CYP3A4 enzyme-mediated hydroxylated metabolites of BUVSs. The biotransformation through hydroxylation should be fully considered during the health risk assessment of structurally similar analogs of BUVSs and other emerging contaminants.

Used to make paints-coatings-thinners, polymers, flexible and rigid foams, adhesives-sealants, and plastic products; [ECHA REACH Registrations] Permitted for use as an inert ingredient in non-food pesticide products; [EPA]

Painting (Pigments, Binders, and Biocides) [Category: Paint]

UV stabilizer in polyolefin films, outdoor furniture and clear coat automotive finishes.

Used as a UV absorber in plastics applications. Particularly recommended for polyolefins, polyurethanes, PVC, polyacrylate, epoxy, and elastomers. Offers strong intensity and broad UV absorption with a fairly sharp wavelength cutoff close to the visible region.

2023: 850,000 - <1,000,000 lb

Non-confidential 2016 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Phenol, 2-(2H-benzotriazol-2-yl)-4,6-bis(1,1-d imethylpropyl)-:

Plastics Material and Resin Manufacturing

Phenol, 2-(2H-benzotriazol-2-yl)-4,6-bis(1,1-dimethylpropyl)-: ACTIVE