Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C9H6O4 |
| Molecular Weight | 178.1415 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=C(O)C=C2C=CC(=O)OC2=C1
InChI
InChIKey=ILEDWLMCKZNDJK-UHFFFAOYSA-N
InChI=1S/C9H6O4/c10-6-3-5-1-2-9(12)13-8(5)4-7(6)11/h1-4,10-11H
Esculetin (aka Aesculetin) is a derivative of coumarin. It is a naturally occurring lactone which is present in chicory and in many toxic medicinal plants; often found in a glycosidic form or conjugated to caffeic acids. It is used as an ingredient in some sunscreens, but there is evidence that it acts as a photosensitizer for DNA damage. Esculetin has been investigated in a number of cellular and animal cancer models, and for other conditions such as dry eyes.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P42574 Gene ID: 836.0 Gene Symbol: CASP3 Target Organism: Homo sapiens (Human) |
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Target ID: P55211|||Q9UEQ3 Gene ID: 842.0 Gene Symbol: CASP9 Target Organism: Homo sapiens (Human) |
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Target ID: P12527 Gene ID: 25290.0 Gene Symbol: Alox5 Target Organism: Rattus norvegicus (Rat) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Structural insights into hydroxycoumarin-induced apoptosis in U-937 cells. | 2008-03-01 |
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| Induction of apoptosis by esculetin in human leukemia U937 cells through activation of JNK and ERK. | 2008-03-01 |
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| Eicosanoids mediate melanotic nodulation reactions to viral infection in larvae of the parasitic wasp, Pimpla turionellae. | 2008-01 |
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| Inhibitory effect of natural coumarin compounds, esculetin and esculin, on oxidative DNA damage and formation of aberrant crypt foci and tumors induced by 1,2-dimethylhydrazine in rat colons. | 2007-11 |
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| Anti-oxidative and photo-protective effects of coumarins isolated from Fraxinus chinensis. | 2007-10 |
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| Modulation of hypericin photodynamic therapy by pretreatment with 12 various inhibitors of arachidonic acid metabolism in colon adenocarcinoma HT-29 cells. | 2007-09-21 |
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| Micelle-mediated extraction and cloud point preconcentration for the analysis of aesculin and aesculetin in Cortex fraxini by HPLC. | 2007-08-15 |
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| [Study on the extracting and dried process of Qinxiangzhixie enteric-coated tablet]. | 2007-08 |
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| Biosynthesis and functions of eicosanoids generated by the coelomocytes of the starfish, Asterias rubens. | 2007-08 |
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| The transfer of VLDL-associated phospholipids to activated platelets depends upon cytosolic phospholipase A2 activity. | 2007-07 |
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| Eicosanoid biosynthesis inhibitors increase the susceptibility of Lymantria dispar to nucleopolyhedrovirus LdMNPV. | 2007-06 |
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| Fluorescent dyes of the esculetin and alizarin families respond to zinc ions ratiometrically. | 2007-05-21 |
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| A rapid TLC autographic method for the detection of glucosidase inhibitors. | 2007-05-16 |
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| 12S-lipoxygenase protein associates with alpha-actin fibers in human umbilical artery vascular smooth muscle cells. | 2007-05-11 |
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| [Studies on constitutes from Taraxacum mongolicum]. | 2007-05 |
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| Method development for the determination of coumarin compounds by capillary electrophoresis with indirect laser-induced fluorescence detection. | 2007-04-27 |
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| Kinetic characterization of the oxidation of esculetin by polyphenol oxidase and peroxidase. | 2007-02 |
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| Enterohaemorrhagic Escherichia coli O157 and non-O157 serovars differ in their mechanisms for iron supply. | 2007-02 |
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| [Simultaneous determination of multi-components in Chinese herbal medicine with UV spectrometry by virtual components-artificial neural network]. | 2007-01 |
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| Eicosanoid biosynthesis inhibitors influence mortality of Pieris brassicae larvae co-injected with fungal conidia. | 2006-11 |
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| Analysis of ultraviolet absorption spectrum of Chinese herbal medicine-Cortex Fraxini by double ANN. | 2006-11 |
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| Esculetin induces apoptosis and inhibits adipogenesis in 3T3-L1 cells. | 2006-10 |
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| Anticancer activity of extracts derived from the mature roots of Scutellaria baicalensis on human malignant brain tumor cells. | 2006-08-16 |
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| Bacillus pasteurii urease shares with plant ureases the ability to induce aggregation of blood platelets. | 2006-08-15 |
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| Esculetin induces mitochondria-mediated apoptosis in 3T3-L1 adipocytes. | 2006-08 |
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| Production of three O-methhylated esculetins with Escherichia coli expressing O-methyltransferase from poplar. | 2006-05 |
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| Characterization of an O-methyltransferase from soybean. | 2006-04 |
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| Binding investigation of human 5-lipoxygenase with its inhibitors by SPR technology correlating with molecular docking simulation. | 2006-04 |
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| Enhancement of esculetin on Taxol-induced apoptosis in human hepatoma HepG2 cells. | 2006-01-01 |
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| Determination of the hydrolysis rate constants and activation energy of aesculin with capillary electrophoresis end-column amperometric detection. | 2005-12-09 |
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| Lipoxygenase pathway of arachidonic acid metabolism in growth control of tumor cells of different type. | 2005-12 |
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| Dynamic ultrasound-assisted extraction of polyphenols in tobacco. | 2005-12 |
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| Non-aqueous capillary electrophoresis for separation and simultaneous determination of fraxin, esculin and esculetin in Cortex fraxini and its medicinal preparations. | 2005-11 |
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| Separation and simultaneous determination of rutin, puerarin, daidzein, esculin and esculetin in medicinal preparations by non-aqueous capillary. | 2005-09-01 |
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| Inhibition of P-glycoprotein transport function and reversion of MDR1 multidrug resistance by cnidiadin. | 2005-08 |
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| ROS mediates 4HPR-induced posttranscriptional expression of the Gadd153 gene. | 2005-06-15 |
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| Immunomodulatory effects of esculetin (6,7-dihydroxycoumarin) on murine lymphocytes and peritoneal macrophages. | 2005-06 |
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| Eicosanoids mediate the laminarin-induced nodulation response in larvae of the flesh fly, Neobellieria bullata. | 2005-05 |
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| Isolation and purification of coumarin compounds from Cortex fraxinus by high-speed counter-current chromatography. | 2005-04-29 |
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| Analysis of ADAMTS4 and MT4-MMP indicates that both are involved in aggrecanolysis in interleukin-1-treated bovine cartilage. | 2005-04 |
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| Protective effect of epigallocatechin gallate and esculetin on oxidative DNA damage induced by psoralen plus ultraviolet-A therapy. | 2005-03 |
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| Solid-phase extraction of esculetin from the ash bark of Chinese traditional medicine by using molecularly imprinted polymers. | 2005-01-07 |
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| Oxidation of ethanol to acetaldehyde and free radicals by rat testicular microsomes. | 2005-01 |
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| Removal of phenolic compounds in water by ultrafiltration membrane treatments. | 2005 |
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| Evidence for the existence of PAH-quinone reductase and catechol-O-methyltransferase in Mycobacterium vanbaalenii PYR-1. | 2004-12 |
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| Glucosylation of phenolic compounds by Pharbitis nil hairy roots: I. Glucosylation of coumarin and flavone derivatives. | 2004-10 |
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| Dietary antioxidant compounds and liver health. | 2004 |
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| Natural and synthetic coumarin derivatives with anti-inflammatory/ antioxidant activities. | 2004 |
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| Studies on coumarins and coumarin-related compounds to determine their therapeutic role in the treatment of cancer. | 2004 |
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| Effect of BN 52256 and other mediator antagonists on ouabain-induced ventricular fibrillation in sensitized guinea-pigs and on ischemia-induced fibrillation in rats. | 1992 |
Patents
Sample Use Guides
In a study of acute non-inflammatory pain and acute inflammatory pain. Rats were given 1.25 - 20 mg/kg esculetin by intraperitoneal injection. Esculetin was found to dose-dependently alleviate hyperalgesia and exhibit antinociceptive effects in both experimental models.
Route of Administration:
Intraperitoneal
Human hepatocellular carcinoma cells SMMC-7721 were maintained in DMEM supplemented with 10% heat-inactivated fetal bovine serum at 37 deg-C in a 5% CO2 atmosphere. Cells were seeded onto 96 well plates ata density of 1x10^4 cells/mL in 0.1 mL medium an cultured for 24 hours. Cells were treated with various concentrations of esculetin (0 - 5 mM) for 24, 48 and 72 hours. Cell proliferation was assessed using the MTT assay method. Esculetin significantly inhibited the viability of hepatocellular carcinoma cells in a dose- and time-dependent manner. The IC50 values of esculetin against SMMC-7721 cells at 72 h was 2.24 mM.
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206-161-5
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305-01-1
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5281416
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m5022
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490095
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DTXSID3075383
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C007628
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Esculetin
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26428
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SM2XD6V944
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PRODRUG (METABOLITE ACTIVE)
SUBSTANCE RECORD
