| Identification | Back Directory | [Name]
xanthatin | [CAS]
26791-73-1 | [Synonyms]
( - ) - xanthatin
(3aR)-3,3aα,4,7,8,8aβ-Hexahydro-7β-methyl-3-methylene-6-(3-oxo-1-butenyl)-2H-cyclohepta[b]furan-2-one
(3aR)-3-Methylene-7β-methyl-6-(3-oxo-1-butenyl)-3,3aα,4,7,8,8aβ-hexahydro-2H-cyclohepta[b]furan-2-one
(3aR,7S,8aS)-7-methyl-3-methylidene-6-[(E)-3-oxobut-1-enyl]-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one
2H-Cyclohepta[b]furan-2-one,3,3a,4,7,8,8a-hexahydro-7-Methyl-3-Methylene-6-(3-oxo-1-buten-1-yl)-,(3aR,7S,8aS)-
(3aR,7S,8aS)-7-methyl-3-methylidene-6-[(1E)-3-oxobut-1-en-1-yl]-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one
2H-Cyclohepta[b]furan-2-one, 3,3a,4,7,8,8a-hexahydro-7-methyl-3-methylene-6-[(1E)-3-oxo-1-buten-1-yl]-, (3aR,7S,8aS)- | [Molecular Formula]
C15H18O3 | [MDL Number]
MFCD17214852 | [MOL File]
26791-73-1.mol | [Molecular Weight]
246.3 |
| Chemical Properties | Back Directory | [Melting point ]
114.5-115° | [alpha ]
D30 -20° (ethanol) | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
DMSO: 2mg/mL, clear | [Boiling point ]
444.3±45.0 °C(Predicted) | [density ]
1.10±0.1 g/cm3(Predicted) | [form ]
powder | [color ]
white to beige |
| Hazard Information | Back Directory | [Definition]
ChEBI: Xanthatin is a sesquiterpene lactone. | [Biological Activity]
Potent anticancer agent th at induces cell cycle arrest at the G2/M phase.
Xanthatina sesquiterpene lactone isolated from Xanthium plants (Asteraceae)is a potent anticancer agent th at 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 colonbreastlungcervixand skin cancerswhile 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. Alsoxanthatin exhibit potent phytotoxic activitywhich suppressed root growth of receiver plants. | [Purification Methods]
Crystallise xanthatin from MeOH, aqueous MeOH, EtOH or aqueous EtOH. UV: 213 and 275nm (max 7300). The 2,4-dinitrophenylhydrazone has m 240o(dec) (twice recrystallised from CHCl3/MeOH). [Geissman et al. J Am Chem Soc 76 685 1954, Deuel & Geissman J Am Chem Soc 79 3778 1957, Beilstein 17 III/IV 6221, 17/1 V 305.] |
|
|