알리자린
1,2-다이하이드록시안트라퀴논 · 알리자린 · 1,2-다이하이드록시안트라퀴논(안료적색83호 · CI58000) · CI58000),염모제로사용될때 · Alizarin Red · TURKEY RED OIL · Alizarine
식별자 및 물리적 특성
| CAS No. | 72-48-0 |
|---|---|
| 분자식 | C14H8O4 |
| 평균 분자량 | 240.21 g/mol |
| 단동위원소 질량 | 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 |
| 현지명 | 알리자린 |
화학 및 물리적 성질
| XLogP | 3.2 |
|---|---|
| 극성 표면적 | 74.6 |
| 수소 결합 공여자 수 | 2 |
| 수소 결합 수용자 수 | 4 |
| 회전 가능 결합 수 | 0 |
| 무거운 원자 수 | 18 |
| 형식 전하 | 0 |
| 복잡도 | 378 |
| 물질 분류 | Dyes -> Anthraquinone Dyes |
| 화장품 | Hair dyeingCosmetic colorant |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| LogP(분배 계수) | 2.34 |
| 밀도 | 1.54 @ 20°C1.06 g/mL at 20 °C |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| 끓는 점 | 430 °C @760 [mm Hg] |
| 녹는점 | 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] |
| 굴절률 | 1.5190 (estimate) |
| 인화점 | 430°C subl. |
| 저장 조건 | Inert atmosphere,Room Temperature |
| 용해도 | 용해도 물에 거의 녹지 않습니다. 에탄올에 적당히 용해되고 벤젠, 톨루엔, 익실렌, 피리딘, 아세트산에 용해됩니다. |
| 물리적 상태 | 고운 가루 |
| pKa(산도 계수) | 6.77(at 25℃) |
| 색상 | 주황색에서 주황색 갈색까지 |
| pH | 5.5~7.2 |
| 용해도 | 헥산과 클로로포름에 용해됩니다. 물에 약간 용해됩니다. |
| Merck | 14,251 |
| BRN | 1914037 |
| 안정성 | 안정적인. 강한 산화제, 강한 염기와 호환되지 않습니다. |
| 주요 응용 | 플라즈마 디스플레이, 반사 방지 코팅, 화학 기계적 연마, 광수용체, 유리 코팅, 페인트, 부식 방지 코팅, 열가소성 수지, 목재 착색제, 섬유, pH 센서 장치, 세제, 염색약, 피부 착색제, 화장품, 구충제, 항진균제 |
| 화장품 원료 기능 | 머리 염색색소 |
| 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(분배 계수) | 2.479 (est) |
| NIST | Alizarin(72-48-0) |
| EPA | Alizarin (72-48-0) |
화학적 성질
orange-red crystals or powder
안전 및 규제
| GHS 분류 | 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. |
|---|---|
| 규제 정보 | 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 |
| 유해성 요약 | 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] |
| 유해 작용 | 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. |
| 수질 위해 등급(WGK) | 3 |
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | YO8300000 |
| 운송 번호(UN) | UN3077 |
| 관세 코드 | 29146990 |
| 위험 문구(R) | 36/38-36/37/38 |
| 위험 표시 | Xi |
| 안전 문구(S) | 26-36-24/25-22 |
| 위험 등급 | 9Aquatic Chronic 1Eye Dam. 1Skin Sens. 1A |
| 기존화학 물질 | KE-10780 |
| 저장 분류 | 11 - Combustible Solids |
용도
역사
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.
용도
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.
제조 및 합성 방법
제조 방법
(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).