化工社化工社 化学情報印刷レポート · 研究参考用
2,2'-ジヒドロキシ-4,4'-ジメトキシベンゾフェノン
2,2'-ジヒドロキシ-4,4'-ジメトキシベンゾフェノン · 2,2-ジ-ヒドロキシ-4,4-ジ-メトキシベンゾフェノン · オキシベンゾン－６ · 2，2’-ジヒドロキシ-4，4’-ジメトキシベンゾフェノン · UVINUL® 3049 · UVINUL® 3049 (1000 ΜG/ML IN HEXANE:ACETONE 8:2 ) · ビス(2-ヒドロキシ-4-メトキシフェニル)メタノン · 2,2'-ジヒドロキシ-4,4'-ジメトキシベンゾフェノン, 98%
識別子と物理属性
| CAS No. | 131-54-4 |
|---|---|
| 分子式 | C15H14O5 |
| 平均分子量 | 274.27 g/mol |
| 単同位体質量 | 274.08412355 g/mol |
| SMILES | COc1ccc(C(=O)c2ccc(OC)cc2O)c(O)c1 |
| InChIKey | SODJJEXAWOSSON-UHFFFAOYSA-N |
| PubChem CID | 8570 |
| ChEMBL | CHEMBL1598017 |
| ChEBI | CHEBI:229993 |
| EC No. | 205-027-3 |
| DTXSID | DTXSID6038875 |
| 現地名 | 2,2'-ジヒドロキシ-4,4'-ジメトキシベンゾフェノン |
化学・物理的性質
| XLogP | 3.3 |
|---|---|
| 極性表面積 | 76 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 5 |
| 回転可能結合数 | 4 |
| 重原子数 | 20 |
| 形式電荷 | 0 |
| 複雑度 | 302 |
| 化粧品 | Cosmetic ingredients (Benzophenone-6) -> CIR (Cosmetic Ingredient Review)Uv absorber |
| SpringerMaterials Properties | Boiling point |
| Color/Form | Crystals |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| 融点 | 139.1 °CMP: 139-149 °C133-136 °C(lit.) |
| 沸点 | 377.26°C (rough estimate) |
| 密度 | 1.2662 (rough estimate) |
| 屈折率 | 1.5000 (estimate) |
| 貯蔵条件 | 2-8°C(protect from light) |
| 溶解度 | クロロホルム（微量）、メタノール（微量、加温）無視できる |
| 外観・状態 | 個体 |
| pKa（酸解離定数） | 6.81±0.35(Predicted) |
| 色 | 淡黄色～淡黄色 |
| Merck | 14,1099 |
| BRN | 1887087 |
| 安定性 | Hygroscopic |
| 化粧品成分の機能 | 香料紫外線吸収剤 |
| InChI | 1S/C15H14O5/c1-19-9-3-5-11(13(16)7-9)15(18)12-6-4-10(20-2)8-14(12)17/h3-8,16-17H,1-2H3 |
| InChIKey | SODJJEXAWOSSON-UHFFFAOYSA-N |
| SMILES | COc1ccc(c(O)c1)C(=O)c2ccc(OC)cc2O |
| LogP（分配係数） | 3.9-4.1 |
| CAS データベース | 131-54-4(CAS DataBase Reference) |
| NISTの化学物質情報 | 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone(131-54-4) |
| EPAの化学物質情報 | Methanone, bis(2-hydroxy-4-methoxyphenyl)- (131-54-4) |
化学的特性
Yellow crystalline powder
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 29% (65 of 224) of reports.WarningH315 (20.1%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 224 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Chemical: Methanone, bis(2-hydroxy-4-methoxyphenyl)-Status: Active Update: 30-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/255922,2-Dihydroxy-4,4-dimethoxybenzophenone: Does not have an individual approval but may be used under an appropriate group standard |
| Special Reports | Cosmetic Ingredient ReviewAnnual Review of Cosmetic Ingredient Safety Assessments - 2002-2003. Int J Toxicol 24 (Suppl 1): 1-102 (2005)[Available from, as of November 21, 2018: https://www.cir-safety.org/ingredients] |
| Hazard Classes and Categories | Skin Irrit. 2 (20.1%) |
| 処分方法 | 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 qualitypotential migration in air, soil or watereffects on animal, aquatic and plant lifeand 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. |
| 体内負荷 | 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone was present at a mean concentration of 0.11 ng/mL in 2 of 34 urine samples from Tunisian women, collected from May to October 2012(1). The compound was tested for but not detected in urine samples from the general population in Seoul and Gyeonggi province, Koreasampling was conducted between July and August, 2014(2).Biomonitoring of human exposure to bisphenol A diglycidyl ethers (BADGEsresin coating for food cans), p-hydroxybenzoic acid esters (parabenspreservatives), benzophenone-type UV filters (BP-UV filterssunscreen agents), triclosan (TCSantimicrobials), and triclocarban (TCCantimicrobials) has been investigated in western European countries and North America. Nevertheless, little is known about the exposure of Greek populations to these environmental chemicals. In this study, 100 urine samples collected from Athens, Greece, were analyzed by liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) for the determination of total concentrations of five derivatives of BADGEs, six parabens and their metabolite (ethyl-protocatechuate), five derivatives of BP-UV filters, TCS, and TCC. Urinary concentrations of BADGEs, parabens, ethyl-protocatechuate, BP-UV filters, TCS and TCC (on a volume basis) ranged 0.3-20.9 (geometric mean: 0.9), 1.6-1010 (24.2), <2-71.0 (2.1), 0.5-1120 (4.4), <0.5-2580 (8.0) and <0.5-1.9 (0.6) ng/mL, respectively. All 19 target chemicals were found in urine, and the highest detection rates were observed for methyl paraben (100%), bisphenol A bis (2,3-dihydroxypropyl) ether (90%), ethyl paraben (87%), 2,4-dihydroxybenzophenone (78%), propyl paraben (72%), and TCS (71%). Estimated daily intakes (EDIurine), calculated on the basis of the measured urinary concentrations, ranged from 0.023 ug/kg bw/day for sum5BADGEs to 31.4 ug/kg bw/day for sum6Parabens. /Benzophenones/ |
| 生態毒性値 | LC50Species: Dugesia japonica (Flatworm)Conditions: freshwater, staticConcentration: 35 mg/L for 24 hr />99% purity/Concentration: 14 mg/L for 48 hr (95% confidence interval: 10.9-17.9 mg/L) />99% purity/Concentration: 2.1 mg/L for 96 hr (95% confidence interval: 1.7-2.7 mg/L) />99% purity/ |
| 環境中動態 | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 800(SRC), determined from a structure estimation method(2), indicates that 2,2'-dihydroxy-4,4'-dimethoxybenzophenone is expected to have low mobility in soil(SRC). Volatilization of 2,2'-dihydroxy-4,4'-dimethoxybenzophenone from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.2X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.4X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Utilizing the Modified MITI test, 0% of the Theoretical BOD was reached in 4 weeks(3) indicating that biodegradation is not an important environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 800(SRC), determined from a structure estimation method(2), indicates that 2,2'-dihydroxy-4,4'-dimethoxybenzophenone 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 1.2X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). According to a classification scheme(4), an estimated BCF of 45(SRC), from an estimated log Kow of 3.90(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Utilizing the Modified MITI test, 0% of the Theoretical BOD was reached in 4 weeks(5) indicating that biodegradation is not an important environmental fate process in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, which has an estimated vapor pressure of 7.4X10-9 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 2,2'-dihydroxy-4,4'-dimethoxybenzophenone may be removed from the air by wet and dry deposition(SRC). 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone absorbs UV light at wavelengths of 284 and 340 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). |
| 毒性の概要 | Safe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.orgIDENTIFICATION AND USE: 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone (Benzophenone-6) is used as a cosmetic ingredient in a range of cosmetic products. HUMAN STUDIES: There are no data available. ANIMAL STUDIES: Benzophenone-6 was hepatotoxic in guinea pigs when given i.p. for 15 days at 5 mg/kg. Benzophenone-6 was nonmutagenic when assayed directly and was mutagenic with metabolic activation in Salmonella strain TA1537. Benzophenone-6 did not induce sister chromatid exchanges in vivo in the bone marrow of Chinese hamsters. |
| Ongoing Test Status | 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/[USEPAICSS Dashboard ApplicationAvailable from, as of February 4, 2019: http://actor.epa.gov/dashboard/] |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc of 2,2'-dihydroxy-4,4'-dimethoxybenzophenone can be estimated to be 800(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2,2'-dihydroxy-4,4'-dimethoxybenzophenone is expected to have low mobility in soil(SRC). |
| Artificial Pollution Sources | 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone's production and use as a ultraviolet light absorber with special applications in paints and plastics(1) and limited use as a cosmetic ingredient(2) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | AEROBIC: 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone, present at 100 mg/L, reached 0% of its theoretical BOD in 28 days using an activated sludge inoculum at 30 mg/L in the Modified MITI test (OECD Guideline 301C)(1). |
| Environmental Bioconcentration | An estimated BCF of 45 was calculated in fish for 2,2'-dihydroxy-4,4'-dimethoxybenzophenone(SRC), using an estimated log Kow of 3.90(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for 2,2'-dihydroxy-4,4'-dimethoxybenzophenone is estimated as 1.2X10-10 atm-cu m/mole(SRC) developed using a fragment constant estimation method(1). This Henry's Law constant indicates that 2,2'-dihydroxy-4,4'-dimethoxybenzophenone is expected to be essentially nonvolatile from water and moist soil surfaces(2). 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.4X10-9 mm Hg(SRC), determined from a fragment constant method(1). |
| Non-Human Toxicity Excerpts | /LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ The hepatotoxicity of benzophenone /-6/ was studied in guinea-pigs. Male guinea-pigs were injected intraperitoneally with 5 mg/kg benzophenone every day for 15 days and were killed 24 hours after the last injection. Liver sections were examined for histopathological changes. Hepatic glycogen and DNA concentrations were determined by histochemical techniques. Changes in hepatocellular DNA content were used as a marker of mitotic activity. Benzophenone /-6/ induced slight hepatomegaly and nodular cirrhotic lesions. The lobular architecture and hepatic cords were disrupted. The cirrhotic lesions which occurred in the perilobular and centrilobular regions consisted of hepatocellular degeneration, mild fatty changes, and replacement of hepatocytes with connective tissue. Hepatocellular necrosis, seen primarily in the periportal region, also contained areas of regeneration. Proliferation of bile duct epithelial cells was observed. Fibrinous thrombi with significant amounts of leukocyte infiltration were seen in the blood vessels. Macrophages and Kupffer cells containing bile pigments were observed frequently in the sinusoids. Significant depletion of glycogen stores occurred. Biliary epithelial cells showed significantly increased mitotic activity. The authors conclude that benzophenone /-6/ causes unequivocal hepatotoxicity. The increased mitotic activity seen in biliary epithelial cells could indicate incipient hepatocarcinogenesis. Since benzophenone /-6/ is widely used in the perfume industry, long term toxicity studies are needed./GENOTOXICITY/ The mutagenicity of Benzophenones-2, -6, and -8 was investigated with the Ames mammalian-microsomal assay. Salmonella typhimurium strains TA98, TA100, TA1535, TA1537, and TA1538 were usedall tests were performed. in the presence and absence of Aroclor-induced rat liver microsomal S-9 cell fraction to observe the mutagenic effect of each compound following metabolic activation. Preliminary cytotoxicity studies determined the dose range of each compound to be used. Benzophenones-2, -6, and -8 were nonmutagenic when assayed directly and were mutagenic with metabolic activation in Salmonella strain TA1537. Benzophenone-8 was weakly mutagenic in Salmonella strain TA1537, whereas Benzophenone-6 was determined to be mutagenic at three doses in the same strain./GENOTOXICITY/ Female Chinese hamsters were orally administered 62.5-500 mg/kg Benzophenones-2 and -6 in a 10% aqueous acacia solution. The animals were sacrificed, and the frequency of bone marrow SCE exchange was determined. Benzophenones-2 and -6 did not induce SCE in vivo in the bone marrow of Chinese hamsters. Cytotoxicity was not observed with either chemical./GENOTOXICITY/ The gradient plate test of McMahon et al., a modification of the Ames test, was used to investigate the effects of Benzophenone-2 and -6 on bacterial mutation. The chemicals were dissolved in DMSO and tested at concentrations of 0.1-1000 ug/mL with and without rat liver S-9 metabolic activation. Benzophenones-2 and -6 were tested with Salmonella typhimurium strains G46, TA1535, TAlOO, C3076, TA1537, D3052, TA1538, and TA98 (histidine auxotrophs) and Escherichia co/i strains WP2 and WP2 uvrA-(tryptophan auxotrophs). Benzophenone-2 inhibited the growth of all the bacterial strains but did not induce mutations with or without metabolic activation. Benzophenone-6 did not inhibit bacterial growth and did not produce mutations in any of the bacterial strains with or without metabolic activation. The induction of unscheduled DNA synthesis (repair synthesis) in primary cultures of adult rat hepatocytes was studied after exposure of the cultures to Benzophenones-2 and -6 dissolved in DMSO and at concentrations of 0.5-1000 nmoles/mL. Cytotoxicity was observed at the 500 and 100 nmoles/mL concentrations of both chemicals. Benzophenones-2 and -6 did not induce DNA repair synthesis. |
| Environmental Abiotic Degradation | 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(1). 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone absorbs UV light at wavelengths of 284 and 340 nm(2) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | DJ0900000 |
| 税関コード | 29145090 |
| 危険文句（R） | 36/37/38 |
| 化審法 | (3)-1261, (4)-158 |
| 危険表示 | Xi |
| 安全措置（S） | 26-37/39-22 |
| 危険等級 | Aquatic Chronic 2 |
| 貯蔵分類 | 11 - Combustible Solids |
| 有害物質データ | 131-54-4(Hazardous Substances Data) |
用途
用途
紫外線吸収剤、有機合成原料。
使用
As ultraviolet light absorber, especially in paints, plastics.
製法・合成法
製造方法
preparation by reaction of 2-hydroxy-4-methoxy-benzoic acid with resorcinol monomethyl ether in the presence of zinc chloride and phosphorous oxychloride at 7075° for 2.