esculetin
Esculetine
CAS: 305-01-1
Molecular Formula: C9H6O4
esculetin - Names and Identifiers
| Name | Esculetine |
| Synonyms | esculetin ESCULETOL ESCULETIN AESCULETIN Aesculetin Esculetine AKOS 215-98 CICHORIGENIN CICHERINGENIN 6,7-Dihydroxycoumarin LABOTEST-BB LT00233229 6,7-DIHYDROXY-CHROMEN-2-ONE (2-chlorophenyl)(phenyl)methanone |
| CAS | 305-01-1 |
| EINECS | 206-161-5 |
| InChI | InChI=1/C13H9ClO/c14-12-9-5-4-8-11(12)13(15)10-6-2-1-3-7-10/h1-9H |
| InChIKey | ILEDWLMCKZNDJK-UHFFFAOYSA-N |
esculetin - Physico-chemical Properties
| Molecular Formula | C9H6O4 |
| Molar Mass | 178.14 |
| Density | 1.3431 (rough estimate) |
| Melting Point | 271-273°C(lit.) |
| Boling Point | 270.35°C (rough estimate) |
| Flash Point | 175.2°C |
| Water Solubility | slightly soluble |
| Solubility | Soluble in ethanol and dilute alkali solution, slightly soluble in water, ethanol and ethyl acetate, insoluble in ether and chloroform. |
| Vapor Presure | 0.000164mmHg at 25°C |
| Appearance | White or yellowish needle crystals |
| Color | Light yellow |
| Merck | 14,3697 |
| BRN | 152788 |
| pKa | 1.71(at 25℃) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.4500 (estimate) |
| MDL | MFCD00006874 |
| Physical and Chemical Properties | White or yellowish needle-like crystals. Melting point 270 °c. Soluble in ethanol and dilute alkali solution, slightly soluble in water, ethanol and ethyl acetate, insoluble in ether and chloroform. No odor, slightly bitter taste. |
| Use | Used as a drug Intermediate |
| In vitro study | Escuetin reduces cell proliferation by inducing cell cycle G1 arrest, which is associated with down-regulation of cyclin D1/CDK4 and cyclin E/CDK2 complexes. Esculetin significantly inhibited the proliferation of HCC cells in a dose-dependent and time-dependent manner, with an IC50 of 2.24 mM. In SMMC-7721 cells, it arrested the cell cycle in S phase, increased the activity of caspase-3 and caspase-9 and induced apoptosis, but had no effect on the activity of caspase-8. In both in vivo and in vitro experiments, escuetin causes a collapse of the mitochondrial membrane potential, accompanied by an increase in Bax expression and a decrease in Bcl-2 expression. Esculetin has anti-proliferative activity in hepatocellular carcinoma in vitro and in vivo, and its mechanism of action is related to the mitochondrial-mediated caspase-dependent apoptosis pathway. |
| In vivo study | Esculetin significantly reduced tumor growth in tumor-bearing mice (Hepa1-6 cells). Tumor weight was reduced by 20.33, 40.37, and 55.42 percent with the dose of escuetin, without apparent toxic side effects. In an experimental rat model of trinitrobenzenesulfonic acid-induced inflammatory bowel disease, esculetin at 5 mg/kg had intestinal anti-inflammatory activity. |
esculetin - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S37/39 - Wear suitable gloves and eye/face protection |
| WGK Germany | 3 |
| RTECS | GN6382500 |
| HS Code | 29322090 |
esculetin - Reference
| Reference Show more | 1. Wan, Qi, Zhen, Shi, Cui, MA, Gui-Zhi. Determination of aesculetin in Mongolian medicine digeda-4 decoction by HPLC [J]. Northwest Pharmaceutical Journal, 2019 034(003):31-316. 2. Yan Xiao, Lu, Guo, Qiaosheng, Shihong, et al. Effects of light intensity on growth, physiology and chemical composition of Viola yedoensis Makino [J]. Chinese Journal of Traditional Chinese Medicine, 2019 044(006):1119-1125. 3. Wu Ruihuan, Zhang Zhenling, Wang Ruisheng, et al. Determination of four effective components in Qianjin decoction [J]. Chinese Journal of Information on traditional Chinese medicine 2015(07):89-92. 4. Wu Ruihuan, Zhang Zhenling, are looking forward to, Liang Jun, Wang Juanjuan, Shi Lianlian. A comparative study on the effect of flooding on the content of esculetin in meganejin [J]. Chinese medical journal, 2016,31(12):1943-1946. 5. Xu ran-da, Shao Tianyu, Jia Shaohua. Effect of esculetin on erythrocyte immune function in tumor-bearing mice [J]. Journal of Harbin University of Commerce: natural science edition, 2016. 6. Shao Tianyu, Li Sumei, Xu Ran da, etc. Esculetin regulates Smac, the mechanism of Survivin protein on SGC-7901 cell apoptosis [J]. Heilongjiang Medicine, 2016(1):21-24. 7. Wang Chunfang, ran Xin, Ma Guizhi. Study on improving the quality standard of Mongolian medicine al-el-shek decoction [J]. Northwest Pharmaceutical Journal, 2020, 035(001):14-18. 8. Xuelian Wang, Minmin Li, Hu Junhua, et al. Inhibitory effects of 18 coumarins on Colletotrichum gloeosporioides in Citrus [J]. Southern China fruit trees, 2013, 42(004):73-74. 9. Ran Xin, LV Shunzhong, Teng Liang, etc. Qualitative identification and content determination of Mongolian medicine zhuangkun-5 powder [J]. Northwest Pharmaceutical Journal, 2019, 034(006):731-735. 10. Jiang Sisi, Ma Guizhi. TLC identification and content determination of berberine hydrochloride and aesculetin in Mongolian medicine digeda-8 powder [J]. Journal of Xinjiang Medical University, 2020,43(10):1369-1373. 11. [IF = 4.411] Liang Yang et al."New Insights into the Antibacterial Activity of Hydroxycoumarins against Ralstonia solanacearum." Molecules. 2016 Apr;21(4):468 12. [IF = 1.902] Zhi Rao et al."Multicomponent determination of traditional Chinese medicine preparation yin-zhi-huang injection by LC-MS/MS for screening of its potential bioactive candidates using HepaRG cells."Biomed Chromatogr. 2018 Feb;32(2):e4057 13. [IF=4.845] Liang Yang et al."Sustainable natural bioresources in crop protection: antimicrobial hydroxycoumarins induce membrane depolarization-associated changes in the transcriptome of Ralstonia solanacearum."Pest Manag Sci. 2021 Nov;77(11):5170-5185 14. [IF=3.935] Yong-Sheng Wu et al."Chemical profiling of Callicarpa nudiflora and its effective compounds identification by compound-target network analysis."J Pharmaceut Biomed. 2020 Apr;182:113110 15. [IF=3.411] Shi Guiqin et al."UPLC-ESI-MS/MS Analysis and Evaluation of Antioxidant Activity of Total Flavonoid Extract from Paeonia lactiflora Seed Peel and Optimization by Response Surface Methodology (RSM)."Biomed Res Int. 2021;2021:7304107 16. [IF=7.514] Jie Meng et al."Conduction of a chemical structure-guided metabolic phenotype analysis method targeting phenylpropane pathway via LC-MS: Ginkgo biloba and soybean as examples."FOOD CHEMISTRY. 2022 Oct;390:133155 |
esculetin - Reference Information
| pH indicator color change ph range | Weak blue uorescence (1.5) to strong blue uorescence (2.0) |
| main applications | antiinflammatory, Herbicides, cosmetics, teth whitening agent, antifungal, neurodegenerative andfungal, antibacterial, antiviral, treating drug-induced weight gain, neurodegenerative and blood coagulation disorders, cancer, amyloidosis, skin impairments and baldness |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| biological activity | Esculetin (Cichorigenin, Aesculetin) is a coumarin derivative found in many natural plant products. it has biological and pharmacological properties of anti-edema, anti-inflammatory and anti-tumor, and can inhibit lipoxygenase. |
| Target | Value |
| use | this product is an intermediate of the drug pingchuanning. 6, 7-dihydroxycoumarin is methylated with dimethyl sulfate to obtain Pingchuanning (dimethoxycoumarin). This is an antiasthmatic medicine with obvious antiasthmatic effect and expectorant and antitussive effects. Ecupietin itself is an antibacterial drug, which has an inhibitory effect on Shigella. It can be used to treat acute bacillary dysentery, and has anti-asthma and expectorant effects. It can also be used to treat chronic bronchitis. Used as a pharmaceutical intermediate |
| Production method | It is obtained by acylation and cyclization of benzoquinone. |
Last Update：2024-04-09 02:00:08
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