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 |
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. |
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 |
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