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Epipodophyllotoxin

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Epipodophyllotoxin Basic information

Product Name:
Epipodophyllotoxin
Synonyms:
  • Eipodophyllotoxin
  • (-)-Epipodophyllotoxin
  • (5R)-5,5aα,8aβ,9-Tetrahydro-9α-hydroxy-5β-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxole-6(8H)-one
  • (5R)-5,8,8aβ,9-Tetrahydro-9α-hydroxy-5β-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxole-(5aαH)-one
  • (5R)-5β-(3,4,5-Trimethoxyphenyl)-7α-(hydroxymethyl)-8α-hydroxy-5,6,7,8-tetrahydronaphtho[2,3-d]-1,3-dioxole-6β-carboxylic acid 6,7-lactone
  • (5R,5aR,8aR,9S)-5,8,8a,9-Tetrahydro-5-(3,4,5-trimethoxyphenyl)-9-hydroxyfuro[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one
  • Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-, (5R,5aR,8aR,9S)-
  • Epipodophyllotoxin
CAS:
4375-07-9
MF:
C22H22O8
MW:
414.41
Product Categories:
  • Aromatics, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
Mol File:
4375-07-9.mol
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Epipodophyllotoxin Chemical Properties

Melting point:
160.3°C
Boiling point:
453.31°C (rough estimate)
Density 
1.2649 (rough estimate)
refractive index 
1.4480 (estimate)
storage temp. 
Hygroscopic, -20°C Freezer, Under inert atmosphere
solubility 
Chloroform (Slightly), Methanol (Slightly)
form 
Solid
pka
13.26±0.40(Predicted)
color 
White to Off-White
Stability:
Hygroscopic
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Epipodophyllotoxin Usage And Synthesis

Uses

Epipodophyllotoxins is a naturally occuring antitumors agent extracted from Mayapple plant.

Mechanism of action

Epipodophyllotoxin is a highly effective anticancer drug. Its mechanism of action may be to inhibit topoisomerase II, which in turn prevents the replication of DNA in tumour cells.

Anticancer Research

It is a lignan compound; podophyllotoxin is isolated from the roots of Podophyllumpeltatum and P. emodi. Teniposide and etoposide are the semisynthetic derivativesof epipodophyllotoxin, and they are used for lymphomas and bronchial and testicularcancers (Shoeb 2006). These compounds break DNA molecules during the G2/Mphase in cell cycle by binding to tubulin and irreversibly inhibiting DNAtopoisomerase II (Balunas and Kinghorn 2005). Podophyllotoxin prevents thebreast cancer cell growth by modifying checkpoint kinase 2 (Chk2) signalingpathway and also induces apoptosis in non-small cell lung cancer by cell cyclearrest, autophagy, and ER stress (Singh et al. 2016b).

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