アリザリン
アリザリンIe · 1,2-ジヒドロキシ-9,10-アントラキノン · 1,2-ジヒドロキシ-9,10-アントラセンジオン · 1,2-ジヒドロキシアントラキノン · アリザリンB · 9,10-ジヒドロ-9,10-ジオキソアントラセン-1,2-ジオール · C.I.モルダントレッド11 · 1,2-ジヒドロキシアントラセン-9,10-ジオン
識別子と物理属性
| CAS No. | 72-48-0 |
|---|---|
| 分子式 | C14H8O4 |
| 平均分子量 | 240.21 g/mol |
| 単同位体質量 | 240.04225874 g/mol |
| SMILES | O=C1c2ccccc2C(=O)c2c1ccc(O)c2O |
| InChIKey | RGCKGOZRHPZPFP-UHFFFAOYSA-N |
| PubChem CID | 6293 |
| ChEMBL | CHEMBL1206015 |
| ChEBI | CHEBI:16866 |
| EC No. | 200-782-5 |
| DTXSID | DTXSID5045960 |
| 現地名 | アリザリン |
化学・物理的性質
| XLogP | 3.2 |
|---|---|
| 極性表面積 | 74.6 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 4 |
| 回転可能結合数 | 0 |
| 重原子数 | 18 |
| 形式電荷 | 0 |
| 複雑度 | 378 |
| 物質分類 | Dyes -> Anthraquinone Dyes |
| 化粧品 | Hair dyeingCosmetic colorant |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| LogP（分配係数） | 2.34 |
| 密度 | 1.54 @ 20°C1.06 g/mL at 20 °C |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| 沸点 | 430 °C @760 [mm Hg] |
| 融点 | 289 °C287 °C |
| Physical Description | Red-orange crystals slightly soluble in water[Sax] |
| Collision Cross Section | 141.4 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| 屈折率 | 1.5190 (estimate) |
| 引火点 | 430°C subl. |
| 貯蔵条件 | Inert atmosphere,Room Temperature |
| 溶解度 | 水にほとんど溶けず、エタノールに溶けにくく、ベンゼン、トルエン、キシレン、ピリジン、酢酸に溶ける。ヘキサン、クロロホルムに可溶。水にわずかに溶ける。 |
| 外観・状態 | 微粉 |
| pKa（酸解離定数） | 6.77(at 25℃) |
| 色 | オレンジからオレンジブラウン |
| pH | 5.5~7.2 |
| Merck | 14,251 |
| BRN | 1914037 |
| 安定性 | 安定。強酸化剤、強塩基とは相容れない。 |
| 主な用途 | プラズマディスプレイ、反射防止コーティング、化学機械研磨、光受容体、ガラスコーティング、塗料、防錆コーティング、熱可塑性樹脂、木材着色剤、繊維、pHセンサー装置、洗剤、染毛剤、皮膚の黒ずみ防止剤、化粧品、殺寄生虫剤、抗真菌剤 |
| 化粧品成分の機能 | ヘアカラーリング着色剤 |
| InChI | 1S/C14H8O4/c15-10-6-5-9-11(14(10)18)13(17)8-4-2-1-3-7(8)12(9)16/h1-6,15,18H |
| InChIKey | RGCKGOZRHPZPFP-UHFFFAOYSA-N |
| SMILES | Oc1ccc2C(=O)c3ccccc3C(=O)c2c1O |
| LogP（分配係数） | 2.479 (est) |
| CAS データベース | 72-48-0(CAS DataBase Reference) |
| NISTの化学物質情報 | Alizarin(72-48-0) |
| EPAの化学物質情報 | Alizarin (72-48-0) |
化学的特性
orange-red crystals or powder
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 10.8% (8 of 74) of reports.WarningH302 (55.4%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 74 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Chemical: 9,10-Anthracenedione, 1,2-dihydroxy-Status: Cease Manufacture Update: 15-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/237969,10-Anthracenedione, 1,2-dihydroxy-: Does not have an individual approval but may be used under an appropriate group standard |
| 有害性の概要 | Anthraquinones are toxic by ingestion: vomiting, diarrhea, kidney and liver damage, and comaDeaths have been reported after children ingested Rhamnus berries[HSDB] Toxic by ingestionAn eye irritant[Sax] An irritantHarmful by ingestion, inhalation, or skin absorptionToxic if swallowed[Aldrich MSDS] |
| Hazard Classes and Categories | Acute Tox. 4 (55.4%) |
| Protective Action Criteria (PAC) | 1.2 [mg/m3]13 [mg/m3]79 [mg/m3] |
| 有害作用 | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | YO8300000 |
| 輸送番号（UN） | UN3077 |
| 税関コード | 29146990 |
| 危険文句（R） | 36/38-36/37/38 |
| 化審法 | (4)-704 |
| 安衛法 | 変異原性物質 |
| 危険表示 | Xi |
| 安全措置（S） | 26-36-24/25-22 |
| 危険等級 | 9Aquatic Chronic 1Eye Dam. 1Skin Sens. 1A |
| 貯蔵分類 | 11 - Combustible Solids |
用途
解説
アリザリン，橙黄色の板状または針状晶．融点290 ℃，沸点430 ℃．水に難溶，熱メタノール，エーテルに易溶，有機溶媒に可溶．アルカリ性で紫色，濃硫酸で赤褐色を呈する．硝酸酸化でフタル酸を，亜鉛末還元でアントラセンを生成する．媒染剤により種々の色に染色される．森北出版「化学辞典（第2版）
用途
染料、顔料の原料。
来歴
In ancient times, alizarin was the preferred red dye. Cloth dyed with it has been found in Egyptian tombs dating 6000 years ago. The dye is found in the madder plant, a member of the Rubiaceae family. In 1944 about 35 species of this plant were known, but the use of more sophisticated analytical methods led to the detection of many more species; by 1984 the number had increased to 50. Alizarin is a mordant dye forming various colored coordination complexes with different metallic salts.
使用
Alizarin is used widely as a prominent red dye for textile facbrics. Alizarin red is now used in biochemical assay to determine quantitatively by colorimetry, the presence of calcific deposition by ce lls of the osteogenic lineage. Alzarine derivatives was evaluated as new inhibitors of the HIV-1 reverse transcriptase associated DNA polymerase and RNase H. Alizarin was also shown to inhibit prolife ration, tumor growth and suppress tumorigenesis in human osteosarcoma and breast cancer cell representative for bone metastasis.
製法・合成法
製造方法
(a) 2 – Bromoanthraquinone and Potassium hydroxide heating; (b) 9,10-Dioxo-9,10-dihydroanthracene-2-sulfonic acid (Sodium) and Sodium hydroxide and Sodium nitrate and Sodium chlorate heating; (C) Anthracene-9,10-dioneand Sodium hydroxide and Sodium chlorate and Sodium nitrate heating (GP 186526); (d) in the presence of Sodium nitrite and Sodium hydroxide and Anthracene-9,10-dioneand Sodium nitrate heating (GP 241806245 987); (e) in the Oxidant and Sodium sulfite and the presence of lime, anthracene in a nitrocellulose derivatives and Sodium hydroxide heating (GP 292247); (f) 2 – Anthraquinonesulfonic acid in the presence of air, with the Sodium hydroxide Etanol wetting treatment (GP 287270); (g) 2-Chloroanthracene-9,10-dione Sodium chlorate in the presence of alkali fusion for (USP 1744815); (h) 2-Methylanthracene-9,10-dione in the presence of Oxidant, with Sodium hydroxide treatment (BP 293328).
純化方法
Alizarin crystallises from glacial acetic acid or 95% EtOH. It can also be sublimed at 110o/2mm. It is an indicator with max at 452nm (pH 5.8) and 520nm (pH 7.2). [Beilstein 8 IV 3256.]