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Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
8-Epixanthatin is a potential colchicine binding site inhibitor isolated from Xanthium chinese Mill. 8-Epixanthatin can inhibit the activation of STAT3 , induce apoptosis , and has anti-tumor activity.
In Vitro
8-Epixanthatin(2-20 μM, 12 h) inhibits DU145 cell proliferation and p-STAT3 levels of DU145 cell in a dose-dependent manner with an IC 50 value of 3.2 μM. 8-Epixanthatin can inhibit STAT3 activation and cell proliferation by inducing ROS production in DU145 cancer cells. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Cell Proliferation AssayCell Line: DU145 cell Concentration: 2, 5, 10, and 20 μM Incubation Time: 12 h or 48 h Result: Reduced STAT3 phosphorylation by 90% at a concentration of 20 μM but not p-JAK2-Y1007/1008. Significantly reduced the amount of BCL-2 and BCL-xL, and induces BCL-xL PARP cleavage, the percentage of cells in G0/G1 phase decreased.
In Vivo
8-Epixanthatin (i.p., 50 mg/kg, 5 days per week for 25 days) can inhibit tumor growth through STAT3 inactivation, the tumor volume of mice was reduced by 40.1%, the tumor weight was reduced by 40.0%, and the p-STAT3 level in the tumor was significantly reduced in the mouse xenograft model of DU145 cells . MCE has not independently confirmed the accuracy of these methods. They are for reference only.
Form:Solid
| Canonical Smiles | CC1CC2C(CC=C1C=CC(=O)C)C(=C)C(=O)O2 |
|---|---|
| IUPAC Name | (3aR,7S,8aR)-7-methyl-3-methylidene-6-[(E)-3-oxobut-1-enyl]-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one |
| InChIKey | RBRPTFMVULVGIC-MDKNCZOUSA-N |
| INCHI | 1S/C15H18O3/c1-9-8-14-13(11(3)15(17)18-14)7-6-12(9)5-4-10(2)16/h4-6,9,13-14H,3,7-8H2,1-2H3/b5-4+/t9-,13+,14+/m0/s1 |
| Isomeric SMILES | C[C@H]1C[C@@H]2[C@H](CC=C1/C=C/C(=O)C)C(=C)C(=O)O2 |
| Alternate CAS | 30890-35-8 |
| PubChem CID | 11694445 |
| MeSH Entry Terms | 8-epi-xanthatin;xanthatin |
| Molecular Weight | 246.30 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Lipids and lipid-like molecules |
| Class | Prenol lipids |
| Subclass | Terpene lactones |
| Intermediate Tree Nodes | Sesquiterpene lactones |
| Direct Parent | Xanthanolides |
| Alternative Parents | Sesquiterpenoids Gamma butyrolactones Oxolanes Enones Enoate esters Acryloyl compounds Ketones Oxacyclic compounds Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives |
| Molecular Framework | Aliphatic heteropolycyclic compounds |
| Substituents | Xanthanolide-skeleton - Sesquiterpenoid - Xanthane sesquiterpenoid - Gamma butyrolactone - Acryloyl-group - Enone - Oxolane - Enoate ester - Alpha,beta-unsaturated carboxylic ester - Alpha,beta-unsaturated ketone - Lactone - Ketone - Carboxylic acid ester - Monocarboxylic acid or derivatives - Oxacycle - Carboxylic acid derivative - Organoheterocyclic compound - Organic oxide - Carbonyl group - Organooxygen compound - Organic oxygen compound - Hydrocarbon derivative - Aliphatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as xanthanolides. These are sesquiterpenoids with a structure based on the xanthanolide skeleton consistsing of a cycloheptane ring usually attached to a four-carbon chain (at carbon 1 ) and a methyl group (at carbon 10), and fused to a five-member lactone ring (sharing carbons 7 and 8). The lactone ring can be conjugated with a methyl or methylene group at position 11. |
| External Descriptors | Not available |
| Molecular Weight | 246.300 g/mol |
|---|---|
| XLogP3 | 2.100 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 2 |
| Exact Mass | 246.126 Da |
| Monoisotopic Mass | 246.126 Da |
| Topological Polar Surface Area | 43.400 Ų |
| Heavy Atom Count | 18 |
| Formal Charge | 0 |
| Complexity | 456.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 3 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 1 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 1 |
| Covalently-Bonded Unit Count | 1 |