WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 526338

CAS#: 6559-91-7

Description: 4'-Demethylepipodophyllotoxin is a potent inhibitor of microtubule assembly.

Chemical Structure

CAS# 6559-91-7

Theoretical Analysis

MedKoo Cat#: 526338
Name: 4'-Demethylepipodophyllotoxin
CAS#: 6559-91-7
Chemical Formula: C21H20O8
Exact Mass: 400.1158
Molecular Weight: 400.383
Elemental Analysis: C, 63.00; H, 5.04; O, 31.97

Price and Availability

Size Price Availability Quantity
1.0g USD 235.0 2 Weeks
5.0g USD 500.0 2 Weeks
10.0g USD 835.0 2 Weeks
25.0g USD 1550.0 2 Weeks
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Synonym: 4'-Demethylepipodophyllotoxin

IUPAC/Chemical Name: (5R-(5alpha,5abeta,8aalpha,9beta))-5,8,8a,9-Tetrahydro-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one


InChi Code: InChI=1S/C21H20O8/c1-25-15-3-9(4-16(26-2)20(15)23)17-10-5-13-14(29-8-28-13)6-11(10)19(22)12-7-27-21(24)18(12)17/h3-6,12,17-19,22-23H,7-8H2,1-2H3/t12-,17+,18-,19+/m0/s1

SMILES Code: O=C1OC[C@]2([H])[C@H](O)C3=C(C=C4OCOC4=C3)[C@@H](C5=CC(OC)=C(O)C(OC)=C5)[C@]21[H]

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 400.383 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Zhou M, Li J, Li C, Guo L, Wang X, He Q, Fu Y, Zhang Z. Tertiary amine mediated targeted therapy against metastatic lung cancer. J Control Release. 2016 Nov 10;241:81-93. doi: 10.1016/j.jconrel.2016.09.013. Epub 2016 Sep 14. PubMed PMID: 27639682.

2: Tang ZB, Chen YZ, Zhao J, Guan XW, Bo YX, Chen SW, Hui L. Conjugates of podophyllotoxin and norcantharidin as dual inhibitors of topoisomeraseⅡ and protein phosphatase 2A. Eur J Med Chem. 2016 Nov 10;123:568-76. doi: 10.1016/j.ejmech.2016.07.031. Epub 2016 Jul 18. PubMed PMID: 27517805.

3: Li JL, Zhao W, Zhou C, Zhang YX, Li HM, Tang YL, Liang XH, Chen T, Tang YJ. Comparison of carbon-sulfur and carbon-amine bond in therapeutic drug: 4β-S-aromatic heterocyclic podophyllum derivatives display antitumor activity. Sci Rep. 2015 Oct 7;5:14814. doi: 10.1038/srep14814. PubMed PMID: 26443888; PubMed Central PMCID: PMC4595834.

4: Zi CT, Yang D, Dong FW, Li GT, Li Y, Ding ZT, Zhou J, Jiang ZH, Hu JM. Synthesis and antitumor activity of novel per-butyrylated glycosides of podophyllotoxin and its derivatives. Bioorg Med Chem. 2015 Apr 1;23(7):1437-46. doi: 10.1016/j.bmc.2015.02.021. Epub 2015 Feb 24. PubMed PMID: 25744190.

5: Kuo YC, Lee CH. Inhibition against growth of glioblastoma multiforme in vitro using etoposide-loaded solid lipid nanoparticles with p-aminophenyl-α-D-manno-pyranoside and folic acid. J Pharm Sci. 2015 May;104(5):1804-14. doi: 10.1002/jps.24388. Epub 2015 Feb 18. PubMed PMID: 25694089.

6: Xiao L, Zhao W, Li HM, Wan DJ, Li DS, Chen T, Tang YJ. Design and synthesis of the novel DNA topoisomerase II inhibitors: esterification and amination substituted 4'-demethylepipodophyllotoxin derivates exhibiting anti-tumor activity by activating ATM/ATR signaling pathways. Eur J Med Chem. 2014 Jun 10;80:267-77. doi: 10.1016/j.ejmech.2014.03.082. Epub 2014 Mar 30. PubMed PMID: 24793877.

7: Zhao W, Chen L, Li HM, Wang DJ, Li DS, Chen T, Yuan ZP, Tang YJ. A rational design strategy of the novel topoisomerase II inhibitors for the synthesis of the 4-O-(2-pyrazinecarboxylic)-4'-demethylepipodophyllotoxin with antitumor activity by diminishing the relaxation reaction of topoisomerase II-DNA decatenation. Bioorg Med Chem. 2014 Jun 1;22(11):2998-3007. doi: 10.1016/j.bmc.2014.03.048. Epub 2014 Apr 13. PubMed PMID: 24775914.

8: Zhi X, Yu X, Yang C, Ding G, Chen H, Xu H. Synthesis of 4β-acyloxypodophyllotoxin analogs modified in the C and E rings as insecticidal agents against Mythimna separata Walker. Bioorg Med Chem Lett. 2014 Feb 1;24(3):765-72. doi: 10.1016/j.bmcl.2013.12.105. Epub 2014 Jan 3. PubMed PMID: 24412075.

9: Sang CY, Liu JF, Qin WW, Zhao J, Hui L, Jin YX, Chen SW. Synthesis and evaluation of the apoptosis inducing and CT DNA interaction properties of a series of 4β-carbamoyl 4'-O-demethylepipodophyllotoxins. Eur J Med Chem. 2013;70:59-67. doi: 10.1016/j.ejmech.2013.09.053. Epub 2013 Oct 6. PubMed PMID: 24140948.

10: Li WQ, Wang XL, Qian K, Liu YQ, Wang CY, Yang L, Tian J, Morris-Natschke SL, Zhou XW, Lee KH. Design, synthesis and potent cytotoxic activity of novel podophyllotoxin derivatives. Bioorg Med Chem. 2013 Apr 15;21(8):2363-9. doi: 10.1016/j.bmc.2013.01.069. Epub 2013 Feb 17. PubMed PMID: 23490151.

11: Zhang F, Koh GY, Hollingsworth J, Russo PS, Stout RW, Liu Z. Reformulation of etoposide with solubility-enhancing rubusoside. Int J Pharm. 2012 Sep 15;434(1-2):453-9. doi: 10.1016/j.ijpharm.2012.06.013. Epub 2012 Jun 12. PubMed PMID: 22698860.

12: Bai JK, Zhao W, Li HM, Tang YJ. Novel biotransformation process of podophyllotoxin to 4 β-sulfur-substituted podophyllum derivates with anti-tumor activity by Penicillium purpurogenum Y.J. Tang. Curr Med Chem. 2012;19(6):927-36. PubMed PMID: 22214458.

13: Zhao W, Li HM, Wan DJ, Tang YJ. Manipulation of heterogeneity product in 4'-demethylepipodophyllotoxin biotransformation process by using yeast extract as nitrogen source. Appl Microbiol Biotechnol. 2012 Jan;93(1):107-15. doi: 10.1007/s00253-011-3424-y. Epub 2011 Jun 25. PubMed PMID: 21706170.

14: Tang YJ, Zhao W, Li HM. Novel tandem biotransformation process for the biosynthesis of a novel compound, 4-(2,3,5,6-tetramethylpyrazine-1)-4'-demethylepipodophyllotoxin. Appl Environ Microbiol. 2011 May;77(9):3023-34. doi: 10.1128/AEM.03047-10. Epub 2011 Mar 11. PubMed PMID: 21398491; PubMed Central PMCID: PMC3126428.

15: Zhang JQ, Zhang ZW, Hui L, Chen SW, Tian X. Novel semisynthetic spin-labeled derivatives of podophyllotoxin with cytotoxic and antioxidative activity. Bioorg Med Chem Lett. 2010 Feb 1;20(3):983-6. doi: 10.1016/j.bmcl.2009.12.048. Epub 2009 Dec 22. PubMed PMID: 20053564.

16: Li X, Choi JS. Effects of quercetin on the pharmacokinetics of Etoposide after oral or intravenous administration of etoposide in rats. Anticancer Res. 2009 Apr;29(4):1411-5. PubMed PMID: 19414395.

17: Tang YJ, Xu XL, Zhong JJ. A novel biotransformation process of 4'-demethylepipodophyllotoxin to 4'-demethylepipodophyllic acid by Bacillus fusiformis CICC 20463, Part II: process optimization. Bioprocess Biosyst Eng. 2010 Feb;33(2):237-46. doi: 10.1007/s00449-009-0317-x. Epub 2009 Apr 25. PubMed PMID: 19396467.

18: Chen SW, Xiang R, Liu J, Tian X. Synthesis and biological evaluation of novel conjugates of podophyllotoxin and 5-FU as antineoplastic agents. Bioorg Med Chem. 2009 Apr 15;17(8):3111-7. doi: 10.1016/j.bmc.2009.03.009. Epub 2009 Mar 12. PubMed PMID: 19324555.

19: Bender RP, Jablonksy MJ, Shadid M, Romaine I, Dunlap N, Anklin C, Graves DE, Osheroff N. Substituents on etoposide that interact with human topoisomerase IIalpha in the binary enzyme-drug complex: contributions to etoposide binding and activity. Biochemistry. 2008 Apr 15;47(15):4501-9. doi: 10.1021/bi702019z. Epub 2008 Mar 21. PubMed PMID: 18355043; PubMed Central PMCID: PMC2737519.

20: Yang TM, Guo SF, Chen CR, Zhang XY, Li WG. Anti-osteosarcoma effects and mechanisms of 4-O-amino-phenol-4'-demethylepipodophyllotoxin ether. J Pharm Pharmacol. 2008 Feb;60(2):179-88. doi: 10.1211/jpp.60.2.0006. PubMed PMID: 18237465.