GRAVEOLINE Chemical Properties

Melting point:

204-205 °C

Boiling point:

436.7±45.0 °C(Predicted)

Density 

1.327±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

1.74±0.70(Predicted)

color 

White to Off-White

GRAVEOLINE Usage And Synthesis

Uses

Graveoline is an apoptosis and autophagy inducer in skin melanoma cancer cells.

Definition

ChEBI: Graveoline is a member of quinolines.

Synthesis

Under nitrogen protection, 2-benzo[1,3]dioxol-5-yl-1H-quinolin-4-one (100 mg, 0.37 mmol) was dissolved in anhydrous N,N-dimethylformamide (5 mL) and stirred at room temperature. Potassium carbonate (156 mg, 1.1 mmol) and iodomethane (80 mg, 0.56 mmol) were added sequentially, and the reaction mixture was heated to 80 °C and stirred for 5 hours. The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction was quenched with ice water and extracted with dichloromethane (315 mL). The organic phase was dried with anhydrous sodium sulfate and the solvent was concentrated under reduced pressure to give the crude product. The crude product was purified by recrystallization from ethyl acetate to give an off-white solid (100 mg, 95% yield). Melting point: 188.6-191.4°C. IR (KBr, cm?1): 1621, 1599, 1490, 1446, 1251, 1032, 751. mass spectrum (ESI): m/z 280.3 [M+H]? 1H NMR (400 MHz, CDCl?) δ (ppm): 3.60 (s, 3H), 5.99 (s, 1H), 6.14 (s, 2H), 7.02 (d, 1H, J=7.2 Hz), 7.08 (d, 1H, J=8.0 Hz), 7.17 (s, 1H), 7.42-7.46 (m, 1H), 7.79 ( d, 2H, J=3.6 Hz), 8.22 (d, 1H, J=8.0 Hz).13C NMR (100 MHz, CDCl?) δ (ppm): 37.35, 101.72, 108.64, 109.00, 112.64, 116.04, 122.76, 123.68, 126.68, 126.81, 129.43, 132.81 129.43, 132.37, 141.97, 147.94, 148.77, 154.44, 177.59.The 1H and 13C NMR data of the obtained products are in agreement with literature reports.

References

[1] Synthetic Communications, 2018, vol. 48, # 20, p. 2635 - 2641
[2] Synthetic Communications, 1996, vol. 26, # 3, p. 495 - 501

GRAVEOLINE(485-61-0)Related Product Information

• METANIL YELLOW
• METHYLENECYCLOHEXANE
• 2-PHENYL-1H-QUINOLIN-4-ONE
• 4-HYDROXY-2-METHYLQUINOLINE
• GRAVEOLINE