SML3418

Xanthatin

≥98% (HPLC)

• Synonym(s): (-)-Xanthatin, (3aR,​7S,​8aS)​-3,​3a,​4,​7,​8,​8a-​hexahydro-​7-​methyl-​3-​methylene-​6-​[(1E)​-​3-​oxo-​1-​buten-​1-​yl]​-​2H-​cyclohepta[b]​furan-​2-​one, CID 5281511
• Empirical Formula (Hill Notation): C₁₅H₁₈O₃
• CAS Number: 26791-73-1
• Molecular Weight: 246.30
• UNSPSC Code: 12352200
• NACRES: NA.77
• MDL number: MFCD17214852
• Assay: ≥98% (HPLC)
• Form: powder

Properties

• Quality Segment: 100
• assay: ≥98% (HPLC)
• form: powder
• color: white to beige
• solubility: DMSO: 2 mg/mL, clear
• storage temp.: -10 to -25°C
• SMILES string: O1[C@@H]2[C@H](CC=C([C@H](C2)C)\C=C\C(=O)C)C(=C)C1=O
• 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
• InChI key: RBRPTFMVULVGIC-ZTIIIDENSA-N

Description

Biochem/physiol Actions

Potent anticancer agent that induces cell cycle arrest at the G2/M phase.

Xanthatin, a sesquiterpene lactone isolated from Xanthium plants (Asteraceae), is a potent anticancer agent that induces cell cycle arrest at the G2/M phase in hepatocellular carcinoma and colon cancer cells. Xanthatin induces apoptosis in numerous cancer cell lines including colon, breast, lung, cervix, and skin cancers, while apparently spearing human normal LO2 hepatocytes. It appears to activate endoplasmic reticulum stress through activation of the PERK/eIF-2α/ATF4 axis in hepatocellular carcinoma cells. Also, xanthatin exhibit potent phytotoxic activity, which suppressed root growth of receiver plants.

Safety Information

• Storage Class: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point (°F): Not applicable
• Flash Point (°C): Not applicable