NSC 646568
1,8-Dihydroxyanthraquinone
CAS: 117-10-2
Molecular Formula: C14H8O4
NSC 646568 - Names and Identifiers
| Name | 1,8-Dihydroxyanthraquinone |
| Synonyms | dantron Dionone Dorbane Dorbanex Danthron NSC 7210 NSC 38626 NSC 646568 Chrysazine 1,8-Dihydroxyanthraquinone 1,4,5,8-tetroxyantraquinone 1,8-dihydroxyanthracene-9,10-dione Danthron1,8-DihydroxyanthraquinoneIstizine |
| CAS | 117-10-2 |
| EINECS | 204-173-5 |
| InChI | InChI=1/C14H8O4/c15-9-5-1-3-7-11(9)14(18)12-8(13(7)17)4-2-6-10(12)16/h1-6,15-16H |
NSC 646568 - Physico-chemical Properties
| Molecular Formula | C14H8O4 |
| Molar Mass | 240.21 |
| Density | 1.3032 (rough estimate) |
| Melting Point | 191-193 °C (lit.) |
| Boling Point | 342.92°C (rough estimate) |
| Flash Point | >200°C |
| Water Solubility | insoluble |
| Solubility | Soluble in hot glacial acetic acid, slightly soluble in ether and chloroform, very slightly soluble in alkali hydroxide, almost insoluble in water and ethanol |
| Vapor Presure | 8.21E-09mmHg at 25°C |
| Appearance | Orange powder |
| Color | Orange-brown or brown |
| Merck | 14,2815 |
| BRN | 2054727 |
| pKa | 6.27±0.20(Predicted) |
| Storage Condition | Sealed in dry,2-8°C |
| Sensitive | Sensitive to light |
| Refractive Index | 1.5430 (estimate) |
| MDL | MFCD00001211 |
| Physical and Chemical Properties | Orange needle Crystal, soluble in methanol, ethanol, ethyl acetate, ethyl ether, chloroform, almost insoluble in water, derived from Tripterygium wilfordii, Salvia miltiorrhiza. |
| In vitro study | Danthron (0.1, 1, and 10 μM) dose-dependently promotes the phosphorylation of AMPK and acetyl-CoA carboxylase (ACC) in both HepG2 and C2C12 cells. Meanwhile, Danthron treatment significantly reduces the lipid synthesis related sterol regulatory element-binding protein 1c (SREBP1c) and fatty acid synthetase (FAS) gene expressions, and the total cholesterol (TC) and triglyceride (TG) levels. In addition, Danthron treatment efficiently increases glucose consumption. Danthron effectively reduces intracellular lipid contents and enhances glucose consumption in vitro via activation of AMPK signaling pathway. 10 μM Danthron/24 h is safe for HepG2 cells. With 80% confluence, HepG2 cells are incubated with Danthron (0.1-10 μM) in FBS-Free media for 8 h. Subsequently, cells are harvested for Western blot assay. Danthron increases the p-AMPK protein in a dose-dependent manner, and no changes in t-AMPK protein are observed. Danthron inhibits 9-cis retinoic acid (9cRA)-induced retinoic X receptor α (RXRα) transactivation by IC 50 at 0.11 μM. To further clarify the stoichimetric ratio of Danthron binding to RXRα-ligand-binding domain (LBD), isothermal titration calorimetry (ITC) experiment is performed. The K D value of Danthron binds to RXRα-LBD by ITC experiment is determined at 7.5 μM. |
| In vivo study | Danthron functions as an insulin sensitizer in vivo. Danthron improves insulin sensitivity in diet-induced obese (DIO) mice. The insulin tolerance test result shows that Danthron (5 mg/kg) treated diet-induced obesity mice exhibit lower glucose levels after insulin challenge, compared with the control vehicle-treated group. |
NSC 646568 - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 40 - Limited evidence of a carcinogenic effect |
| Safety Description | S36/37 - Wear suitable protective clothing and gloves. S36 - Wear suitable protective clothing. S22 - Do not breathe dust. |
| UN IDs | 2811 |
| WGK Germany | 1 |
| RTECS | CB6650000 |
| TSCA | Yes |
| HS Code | 29146990 |
| Hazard Class | IRRITANT |
| Toxicity | LD50 orally in mice: <7 g/kg (Case) |
NSC 646568 - Reference
| Reference Show more | 1. Lin Shui Hua Huang Youxia Huang Xiaoyi, etc. Comparison of anthraquinone compounds content and antioxidant activity in different cassia seed processed products [J]. Fujian Traditional Chinese Medicine 2019 v.50;No.327(02):43-44 52. 2. Lu Jinfeng, Pei Jihua Wang Xiaoming. Inhibitory Effect of Dananthraquinone on MCF-7 Proliferation, Invasion and Metastasis of Breast Cancer Cells and Its Mechanism [J]. Drug Evaluation Research 2019 42(10):1950-1954. 3. Liu Quande, Tang Shirong, Song Hui, Wang Ying, Xing Hongwei. Ultrasonic Extraction and Antioxidant Activity of Anthraquinone Compounds from Aloe [J]. Food and machinery, 2011,27(05):68-71. 4. Xie, Li, et al. "Development of an UHPLC-MS/MS method for comparative pharmacokinetics of nine anthraquinones in rats and application to dosage conversion between different Semen Cassiae forms." Journal of pharmaceutical and biomedical analysis 174 (2019): 5. Zhang, Guoying, and Xiaofeng Chi. "A green strategy for obtaining anthraquinones from Rheum tanguticum by subcritical water." Open Chemistry 18.1 (2020): 702-710. 6. [IF = 3.935] Li Xie et al. "Development of an UHPLC-MS/MS method for comparative pharmacokinetics of nine anthraquinones in rats and application to dosage conversion between different Semen Cassiae forms." J Pharmaceut Biomed. 2019 Sep;174:696 7. [IF = 1.902] Chenxi Wang et al. "Multiple component-pharmacokinetic studies on 10 bioactive constituents of Peiyuan Tongnao capsule using parallel reaction monitoring mode." Biomed Chromatogr. 2021 Oct;35(10):e5153 8. [IF = 1.554] Guoying Zhang et al. "A green strategy for obtaining anthraquinones from Rheum tanguticum by subcritical water." Open Chem. 2020 Jan;18(1): 702-710 |
NSC 646568 - Reference Information
| (IARC) carcinogen classification | 2B (Vol. 50) 1990 |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Biological activity | Danthron (Chrysazin, Antrapurol) regulates glucose and lipid metabolism by activating AMPK. Danthron is a natural product extracted from traditional Chinese medicine rhubarb. Once a laxative, Danthron is now used as an antioxidant in synthetic lubricants, synthesis of experimental antitumor agents, fungicides and intermediates in the manufacture of dyes. |
| use | verify beryllium. Dye intermediates. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-10 22:29:15
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