4'-Demethylepipodophyllotoxin Chemical Properties

Melting point:

246-248°C

Boiling point:

626.5±55.0 °C(Predicted)

Density 

1.446±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

9.94±0.40(Predicted)

color 

White to Off-White

InChIKey

YVCVYCSAAZQOJI-JHQYFNNDSA-N

SMILES

O1C2=CC3=C(C=C2OC1)[C@@H](C1=CC(OC)=C(O)C(OC)=C1)[C@@]1([H])C(=O)OC[C@]1([H])[C@@H]3O

Safety Information

HS Code 

29349990

4'-Demethylepipodophyllotoxin Usage And Synthesis

Chemical Properties

Off-White Solid

Uses

A potent inhibitor of microtubule assembly.

Definition

ChEBI: An organic heterotetracyclic compound that is the 9- epimer of 4'-demethylpodophyllotoxin.

Synthesis

(5R,5aR,8aR,9R)-9-Hydroxy-5-(3,4,5-trimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one (onychocercazylidene, 2.1 g, 5.0 mmol) was used as a raw material and dissolved in anhydrous dichloromethane. Sodium iodide (2.3 g, 15.0 mmol) was added to this solution and stirred for 5 min. The reaction mixture was cooled to 0°C (ice-water bath) and methanesulfonic acid (1.48 mL, 15.0 mmol) was added slowly dropwise, after which stirring was continued and gradually brought to room temperature. The reaction was continued at room temperature for 5 hours, during which time nitrogen was introduced to remove the HI gas generated from the reaction. After completion of the reaction, the solvent was removed by concentration under reduced pressure. The crude product was dissolved in a solvent mixture of acetone-water (25 mL-25 mL), barium carbonate (2.0 g, 10.0 mmol) was added, and the reaction was carried out at 40 °C for 30 min. The reaction solution was diluted with dichloromethane (100 mL), poured into 500 mL of 10% aqueous sodium thiosulfate solution and extracted with dichloromethane. The organic phases were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (eluent: chloroform:methanol=92:8) to afford the target product (5R,5aR,8aR,9S)-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxolan-6(8H)-one ( VII, 1.8g, 90% yield), as white solid.

in vivo

References

[1] Synthetic Communications, 2012, vol. 42, # 18, p. 2780 - 2789
[2] Patent: CN104098594, 2016, B. Location in patent: Paragraph 0040-0041
[3] European Journal of Medicinal Chemistry, 2011, vol. 46, # 3, p. 901 - 906
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 11, p. 4851 - 4856
[5] Journal of Medicinal Chemistry, 1998, vol. 41, # 23, p. 4475 - 4485

4'-Demethylepipodophyllotoxin(6559-91-7)Related Product Information

• Podophyllotoxin
• Norandrostenedione
• CHLOROPHOSPHONAZO III
• 4’-demethylepipodophyllotoxin-β-D-glucoside,4'-demethylepipodophyllotoxin-9 beta-glucopyranoside
• Etoposide
• 4'-deMethylpodophyllotoxin
• 4'-Demethylpodophyllotoxin
• Etoposide Impurity B
• α-Etoposide
• Etoposide EP Impurity J
• Etoposide EP Impurity A
• Etoposide EP Impurity H
• 4'-deMethyldehydropodophyllotoxin
• Etoposide EP Impurity Q
• Etoposide EP Impurity I
• Etoposide impurity O
• Etoposide phosphate
• 4’-demethylepipodophyllotoxin9-(4,6-o-2-thenylidene-beta-d-glucopyranoside