PHENOL, 2-METHOXY-5-[2-(3,4,5-TRIMETHOXYPHENYL)ETHYL]- Chemical Properties

Boiling point:

439.1±40.0 °C(Predicted)

Density 

1.147

storage temp. 

2-8°C

solubility 

DMSO:PBS (pH 7.2) (1:8):0.11(Max Conc. mg/mL);0.35(Max Conc. mM)
DMF:30.0(Max Conc. mg/mL);94.23(Max Conc. mM)
Ethanol:5.0(Max Conc. mg/mL);15.71(Max Conc. mM)

form 

A crystalline solid

pka

9.99±0.10(Predicted)

color 

White to off-white

InChI

InChI=1S/C18H22O5/c1-20-15-8-7-12(9-14(15)19)5-6-13-10-16(21-2)18(23-4)17(11-13)22-3/h7-11,19H,5-6H2,1-4H3

InChIKey

UXDFUVFNIAJEGM-UHFFFAOYSA-N

SMILES

C1(O)=CC(CCC2=CC(OC)=C(OC)C(OC)=C2)=CC=C1OC

Safety Information

HS Code 

29089990

PHENOL, 2-METHOXY-5-[2-(3,4,5-TRIMETHOXYPHENYL)ETHYL]- Usage And Synthesis

Chemical Properties

White or off-white powder

Uses

Erianin acts as a promising anticancer agent. Cytotoxic compound strongly inhibits tubulin polymerization in cell mitosis.

Synthesis

General procedure for the synthesis of 2-methoxy-5-(3,4,5-trimethoxyphenethyl)phenol (SIT-1) from the compound (CAS:117048-62-1): compound CA-4 (1.0 g, 3.16 mmol) and 10% palladium-carbon catalyst (0.1 g) were dissolved in methanol (20 mL) and the reaction was stirred for 2 h at room temperature under hydrogen atmosphere. . Upon completion of the reaction, the palladium-carbon catalyst was removed by filtration and the filtrate was dried with anhydrous sodium sulfate and concentrated to afford the target product SIT-1 in 91% yield. The product was characterized by 1H NMR (500 MHz, CDCl3): δ 6.81 (d, 1H, J=3.0 Hz), 6.77 (d, 1H, J=8.0 Hz), 6.64-6.66 (m, 1H), 6.38 (s, 2H), 5.61 (s, 1H), 3.87 (s, 3H), 3.83 (s, 9H), 2.82 (s 4H).

References

[1] Journal of Medicinal Chemistry, 1995, vol. 38, # 10, p. 1666 - 1672
[2] Chinese Chemical Letters, 2015, vol. 26, # 8, p. 993 - 999
[3] Journal of Chemical Research, 2008, # 6, p. 354 - 356
[4] ChemMedChem, 2011, vol. 6, # 3, p. 488 - 497

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