Xanthotoxol
9-hydroxy- · NSC 401269 · XANTHOTOXOL · AKOS 210-08 · Xanthotoxol-RM · Xanthotoxol(AS) · Xanthotoxol?, BR · 8-HYDROXYPSORALEN
식별자 및 물리적 특성
| CAS No. | 2009-24-7 |
|---|---|
| 분자식 | C11H6O4 |
| 평균 분자량 | 202.16 g/mol |
| 단동위원소 질량 | 202.02660867 g/mol |
| SMILES | O=c1ccc2cc3ccoc3c(O)c2o1 |
| InChIKey | JWVYQQGERKEAHW-UHFFFAOYSA-N |
| PubChem CID | 65090 |
| ChEMBL | CHEMBL1192 |
| ChEBI | CHEBI:15709 |
| EC No. | 217-923-1 |
| DTXSID | DTXSID50173910 |
화학 및 물리적 성질
| XLogP | 1.6 |
|---|---|
| 극성 표면적 | 59.7 |
| 수소 결합 공여자 수 | 1 |
| 수소 결합 수용자 수 | 4 |
| 회전 가능 결합 수 | 0 |
| 무거운 원자 수 | 15 |
| 형식 전하 | 0 |
| 복잡도 | 312 |
| 녹는점 | 251 - 252 °C250°C |
| Physical Description | Solid |
| 끓는 점 | 428.1±45.0 °C(Predicted) |
| 밀도 | 1.526±0.06 g/cm3(Predicted) |
| 저장 조건 | 2-8°C |
| 용해도 | DMSO(약간 용해됨), 메탄올(약간 용해됨) |
| 물리적 상태 | 고체 |
| pKa(산도 계수) | 5.74±0.20(Predicted) |
| 색상 | 라이트 베이지부터 다크 브라운까지 |
| 주요 응용 | 음식 및 음료 |
| InChI | InChI=1S/C11H6O4/c12-8-2-1-6-5-7-3-4-14-10(7)9(13)11(6)15-8/h1-5,13H |
| InChIKey | JWVYQQGERKEAHW-UHFFFAOYSA-N |
| SMILES | C1(=O)OC2=C(O)C3OC=CC=3C=C2C=C1 |
| LogP(분배 계수) | 1.405 (est) |
화학적 성질
Dark Brown Solid
안전 및 규제
| GHS 분류 | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P270, P272, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 3 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| 수질 위해 등급(WGK) | WGK 3 |
| 운송 번호(UN) | 2810 |
| 관세 코드 | 29329990 |
| 위험 문구(R) | 25 |
| 안전 문구(S) | 20-45-24/25 |
| 위험 등급 | Acute Tox. 4 OralSkin Sens. 1 |
| 저장 분류 | 11 - Combustible Solids |
용도
개요
Xanthotoxol is a coumarin and a major component in C. monnieri that has diverse biological activities. It inhibits proliferation of HeLa and HepG2 cells in vitro (IC50s = 23.59 and 15.57 μM, respectively). Xanthotoxol increases histamine release from mast cells and decreases secretion of TNF-α, IL-4, and IL-1β from RBL-2H3 cells induced by DNP-human serum albumin (DNP-HSA). It is nematocidal against M. incognita (IC50 = 68 mg/L). In vivo, xanthotoxol inhibits predatory mouse and rat killing behavior in dogs and cats when administered at doses ranging from 3 to 100 mg/kg and 5 to 20 mg/kg, respectively. It reduces amphetamine-induced hypermobility in mice and hamsters. Xanthotoxol (5 and 10 mg/kg) reduces brain edema, neutrophil infiltration, blood-brain barrier disruption, production of IL-1β, TNF-α, IL-8, and nitric oxide (NO), and levels of intercellular adhesion molecule-1 (ICAM-1) and E-selectin in a rat model of focal cerebral ischemia.
용도
Xanthotoxol is a hydroxylated psoralen that inhibits neutrophil infiltration and brain edema induced by focal cerebral ischemia-reperfusion injury in rats. A potentially useful antiarrhythmic agent. It has been show n to be effective in the prevention of ventricular fibrillation of mice induced by chloroform, of rats induced by calcium chloride, and in treatment of rat arrhythmia induced by aconitine. Recent stud ies show that it may also have antioxidant and anticancer activities.