1,3-ジフェニル-1,3-プロパンジオン
1,3-ジフェニル-1,3-プロパンジオン · ω-ベンゾイルアセトフェノン · ジベンゾイルメタン · フェナシルフェニルケトン · 1,3-ジフェニルプロパン-1,3-ジオン · α-ベンゾイルアセトフェノン · 1,1'-(メチレンビスカルボニル)ビスベンゼン · γ-ヒドロキシカルコン
識別子と物理属性
| CAS No. | 120-46-7 |
|---|---|
| 分子式 | C15H12O2 |
| 平均分子量 | 224.25 g/mol |
| 単同位体質量 | 224.08372962 g/mol |
| SMILES | O=C(CC(=O)c1ccccc1)c1ccccc1 |
| InChIKey | NZZIMKJIVMHWJC-UHFFFAOYSA-N |
| PubChem CID | 8433 |
| ChEMBL | CHEMBL371523 |
| ChEBI | CHEBI:75417 |
| EC No. | 204-398-9 |
| DTXSID | DTXSID3041247 |
| 現地名 | 1,3-ジフェニル-1,3-プロパンジオン |
化学・物理的性質
| XLogP | 3.1 |
|---|---|
| 極性表面積 | 34.1 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 4 |
| 重原子数 | 17 |
| 形式電荷 | 0 |
| 複雑度 | 243 |
| Physical Description | Large CrystalsDry PowderSolid[Merck Index] Light yellow crystalline powder[Alfa Aesar MSDS] |
| Collision Cross Section | 165.9 Ų [M+Na]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: TOXCASTSource Identifier: DTXSID3041247]154.4 Ų [M-H]- [CCS Type: DTIonization: ESI- |
| 融点 | 77-79 °C(lit.) |
| 沸点 | 219-221 °C18 mm Hg(lit.) |
| 密度 | 0.800 g/cm3 |
| 蒸気圧 | 0.01Pa at 20℃ |
| 屈折率 | 1.6600 (estimate) |
| 引火点 | 219-221°C/18mm |
| 貯蔵条件 | Store below +30°C. |
| 溶解度 | クロロホルム（わずかに）、メタノール（わずかに、超音波処理）エーテル、クロロホルム、水酸化ナトリウム水溶液に可溶。水に不溶。 |
| pKa（酸解離定数） | 8.95±0.10(Predicted) |
| 外観・状態 | クリスタル |
| 色 | 薄黄色～黄色 |
| Merck | 14,3009 |
| BRN | 514910 |
| ヘンリー定数 | 7.5×103 mol/(m3Pa) at 25℃, Zhang et al. (2010) |
| 安定性 | 安定。強力な酸化剤とは相容れない。 |
| InChI | 1S/C15H12O2/c16-14(12-7-3-1-4-8-12)11-15(17)13-9-5-2-6-10-13/h1-10H,11H2 |
| InChIKey | NZZIMKJIVMHWJC-UHFFFAOYSA-N |
| SMILES | O=C(CC(=O)c1ccccc1)c2ccccc2 |
| LogP（分配係数） | 4.59 at 25℃ |
| CAS データベース | 120-46-7(CAS DataBase Reference) |
| NISTの化学物質情報 | 1,3-Propanedione, 1,3-diphenyl-(120-46-7) |
| EPAの化学物質情報 | 1,3-Propanedione, 1,3-diphenyl- (120-46-7) |
化学的特性
Dibenzoylmethane (DB), a minor constituent of the root extract of licorice, belongs to the flavonoid family. It is a colorless rhombus flake crystal or yellowish-white powder. soluble in chlorohydrin and chloroform, soluble in sodium hydroxide solution, insoluble in sodium carbonate solution, and very slightly soluble in water. It is used as a colorimetric reagent for the determination of uranium.
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 32.7% (84 of 257) of reports.WarningH317 (66.1%): May cause an allergic skin reaction [Warning Sensitization, Skin]P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 257 reports by companies from 6 notifications to the ECHA C&L Inventory.Reported as not meeting GHS hazard criteria per 84 of 257 reports by companies.There are 5 notifications provided by 173 of 257 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| 規制情報 | Chemical: 1,3-Propanedione, 1,3-diphenyl-1,3-Propanedione, 1,3-diphenyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3-Propanedione, 1,3-diphenyl- 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: 13-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/113711,3-Propanedione, 1,3-diphenyl-: Does not have an individual approval but may be used under an appropriate group standard |
| 有害性の概要 | Causes changes in liver and uterine weights in 2-week constant oral studies of mice[RTECS] May cause irritation[Alfa Aesar MSDS] |
| Hazard Classes and Categories | Skin Sens. 1 (66.1%) |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | TZ1930000 |
| 毒性 | rat,LD,oral,> 500mg/kg (500mg/kg),National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 28, 1953. |
| 税関コード |
用途
解説
ジベンゾイルメタン略称DBM．エノール形，ケト形が存在する．カルコンの二臭化物にナトリウムメトキシドを作用させ，ついで塩酸と加熱すると得られる．ケト形は融点81 ℃．エノール形は融点72 ℃(Z形)および78 ℃(E形)がある．沸点219～221 ℃(2.4 kPa)．種々の金属イオンとキレート錯イオンを生じ，これらの抽出剤として使用できる．とくにEDTAと併用してウラン(Ⅵ)の選択的抽出や，Cdの分離に用いられる．
用途
有機合成原料、金属の抽出，分離用キレート剤、ウランの吸光光度法による発色試薬。
天然物の起源
Dibenzoylmethane(DBM) is a 1,3-diketone derivative of acetylacetone that has both methyl groups replaced with phenyl groups.Although smaller in size and lacking hydroxyl and methoxy groups，DBM resembles the turmeric spice curcumin (CUR),a diferuloylmethane. Both molecules are metal-chelating agents，contain a B-diketone flanked by two aryl groups,and exhibit anti-proliferative and anticarcinogenic activity. In addition to sharing structural similarity with DBM,CUR,which is also a naturally occurring compound is found in the plant Curcuma longa and has numerous medicinal uses.DBM and its many naturally occurring derivatives are minor constituentsof licorice. DBM has been isolated from licorice root extracts and otherspecies of Glycyrrhiza.
使用
Dibenzoylmethane is a new kind of PVC heat stabilizer, it has better transparency, nontoxic and odorless. In case of combined use with Calcium/Zinc, Barium/Zin and other heat stabilizer, it can greatly improve the initial color, transparency, long term stability of PVC, and also can improve the precipitation and “zinc burning” problem during the process. It has very good synergy with zinc soaps, and can protect the PVC color. This material can absorb UV at 290nm, which has the effect as light stabilizer and act as long term stabilizer for PVC products.
製法・合成法
製造方法
dibenzoylmethane is prepared by condensation of ethyl benzoate with acetophenone.
純化方法
Dibenzoylmethane (1,3-diphenyl-1,3-propanedione) [120-46-7] M 224.3, m 8 0o. Crystallise dibenzoylmethane from pet ether or MeOH. [Beilstein 7 IV 2512.]