4'-Demethylepipodophyllotoxin

Modify Date: 2026-06-30 17:49:30

4'-Demethylepipodophyllotoxin structure	Common Name	4'-Demethylepipodophyllotoxin
	CAS Number	6559-91-7	Molecular Weight	400.379
	Density	1.4±0.1 g/cm3	Boiling Point	626.5±55.0 °C at 760 mmHg
	Molecular Formula	C₂₁H₂₀O₈	Melting Point	246-248ºC
	MSDS	N/A	Flash Point	224.4±25.0 °C

Use of 4'-Demethylepipodophyllotoxin

4'-Demethylepipodophyllotoxin(4'-DMEP) is a key intermediate compound for the preparation of podophyllotoxin-type anti-cancer drugs; a potent inhibitor of microtubule assembly.IC50 Value: 0.31uM(EC5 0in HL60 cell, MTT assay, 48h); 0.37uM(EC50 in HepG2 cell, MTT assay, 48h) [1]Target: microtubulein vitro: 4-TMP-DMEP showed strong cytotoxicity activity against the above-mentioned five tumor cell lines. The EC50s of 4-TMP-DMEP against these tumor cell lines ranged from 0.24 to 0.11 μM, which were 0.29 to 3618 times lower than that of DMEP [1].in vivo: Treatment of animals with DMEP (until the end of the experiment), 30 min before TPA treatment, significantly reduced the tumor incidence, tumor volume and the conversion efficiency of papillomas to squamous cell carcinomas. The tumor formation and growth was also delayed by DMEP pre-treatment [2].

Name	4'-demethylepipodophyllotoxin
Synonym	More Synonyms

Description	4'-Demethylepipodophyllotoxin(4'-DMEP) is a key intermediate compound for the preparation of podophyllotoxin-type anti-cancer drugs; a potent inhibitor of microtubule assembly.IC50 Value: 0.31uM(EC5 0in HL60 cell, MTT assay, 48h); 0.37uM(EC50 in HepG2 cell, MTT assay, 48h) [1]Target: microtubulein vitro: 4-TMP-DMEP showed strong cytotoxicity activity against the above-mentioned five tumor cell lines. The EC50s of 4-TMP-DMEP against these tumor cell lines ranged from 0.24 to 0.11 μM, which were 0.29 to 3618 times lower than that of DMEP [1].in vivo: Treatment of animals with DMEP (until the end of the experiment), 30 min before TPA treatment, significantly reduced the tumor incidence, tumor volume and the conversion efficiency of papillomas to squamous cell carcinomas. The tumor formation and growth was also delayed by DMEP pre-treatment [2].
Related Catalog	Signaling Pathways >> Cell Cycle/DNA Damage >> Microtubule/Tubulin Signaling Pathways >> Cytoskeleton >> Microtubule/Tubulin Research Areas >> Cancer
References	[1]. 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. [2]. Dhawan D, Balasubramanian S, Amonkar AJ, Chemopreventive effect of 4'-demethyl epipodophyllotoxin on DMBA/TPA-induced mouse skin carcinogenesis. Carcinogenesis. 1999 Jun;20(6):997-1003.

Description

Related Catalog

Signaling Pathways >> Cell Cycle/DNA Damage >> Microtubule/Tubulin

Signaling Pathways >> Cytoskeleton >> Microtubule/Tubulin

Research Areas >> Cancer

References

[1]. 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.

[2]. Dhawan D, Balasubramanian S, Amonkar AJ, Chemopreventive effect of 4'-demethyl epipodophyllotoxin on DMBA/TPA-induced mouse skin carcinogenesis. Carcinogenesis. 1999 Jun;20(6):997-1003.

Density	1.4±0.1 g/cm3
Boiling Point	626.5±55.0 °C at 760 mmHg
Melting Point	246-248ºC
Molecular Formula	C₂₁H₂₀O₈
Molecular Weight	400.379
Flash Point	224.4±25.0 °C
Exact Mass	400.115814
PSA	103.68000
LogP	0.71
Vapour Pressure	0.0±1.9 mmHg at 25°C
Index of Refraction	1.638
InChIKey	YVCVYCSAAZQOJI-JHQYFNNDSA-N
SMILES	COc1cc(C2c3cc4c(cc3C(O)C3COC(=O)C23)OCO4)cc(OC)c1O
Storage condition	-20°C Freezer

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LV2476200

CAS REGISTRY NUMBER :: 6559-91-7

BEILSTEIN REFERENCE NO. :: 1358259

LAST UPDATED :: 199612

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C21-H20-O8

MOLECULAR WEIGHT :: 400.41

WISWESSER LINE NOTATION :: T E5 C665 FVO NO PO OHTT&&J DR DQ CO1 EO1& JQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Human HeLa cell

DOSE/DURATION :: 10 umol/L

REFERENCE :: BICHAW Biochemistry. (American Chemical Soc., Distribution Office Dept. 223, POB 57136, West End Stn., Washington, DC 20037) V.1- 1962- Volume(issue)/page/year: 15,5443,1976

Precursor 4
CAS#:518-28-5 Podophyllotoxin CAS#:746639-24-7 (5R,5aR,8aR,9S)... CAS#:1185862-69-4 7-chlorodeoxypo... CAS#:64-19-7 acetic acid
DownStream 10
CAS#:33419-42-0 Etoposide CAS#:23363-35-1 Lignan P CAS#:127882-59-1 ethyl 4-[[(5R,9... CAS#:127882-83-1 (5S,5aR,8aR,9R)...
CAS#:3590-93-0 4-Demethyldeoxy... CAS#:138355-94-9 (3aS,4S,9R,9aR)... CAS#:138456-91-4 (3aR,4S,9R,9aR)... CAS#:138355-95-0 ethyl 4-[[(3aS,...
CAS#:125830-36-6 NPF-etoposide CAS#:138355-93-8 (3aS,4S,9R,9aR)...

Name: Compound tested for ability to form a cellular covalent topoisomerase II-DNA complex.
Source: ChEMBL
Target: DNA topoisomerase 2-beta
External Id: CHEMBL809380

Name: ERK5 transcriptional activity HTS
Source: 24565
Target: N/A
External Id: ERK5 transcriptional activity-HTS

Name: Inhibition of human DNA topoisomerase 2 assessed as bacteriophage P4 DNA unknotting a...
Source: ChEMBL
Target: DNA topoisomerase 2-alpha
External Id: CHEMBL981359

Name: Inhibition of DNA topoisomerase 2 in human KB cells assessed as enzyme-[methyl-3H]thy...
Source: ChEMBL
Target: DNA topoisomerase 2-alpha
External Id: CHEMBL981362

Name: Cytotoxicity against human KB cells assessed as reduction in cell number after 3 days...
Source: ChEMBL
Target: KB
External Id: CHEMBL981361

Name: Cytotoxicity against human HepG2 cells after 48 hrs by MTT assay
Source: ChEMBL
Target: HepG2
External Id: CHEMBL3267476

Name: Cytotoxicity against human A549 cells after 48 hrs by MTT assay
Source: ChEMBL
Target: A549
External Id: CHEMBL3267478

Name: Cytotoxicity against human HeLa cells after 48 hrs by MTT assay
Source: ChEMBL
Target: HeLa
External Id: CHEMBL3267477

Name: Cytotoxicity against human HL-7702 cells after 48 hrs by MTT assay
Source: ChEMBL
Target: N/A
External Id: CHEMBL3267480

Name: Cytotoxicity against human BGC823 cells after 48 hrs by MTT assay
Source: ChEMBL
Target: NON-PROTEIN TARGET
External Id: CHEMBL3267479

Total 104, Current Page 1 of 11

(5R,5aR,8aR,9S)-9-Hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one

4'-DMEP

4'-Demethylepipodophyllotoxin

4-DEMETHYL EIPODOPHYLLOTOXIN

4-Domethylpodophyllotoxin,4'-demethyl-epi-Podophyllotoxin

4'-demethyl-9-epipodophyllotoxin

4'-demethyl-epipodophyllotoxin

4'-demethyl-4-epipodophyllotoxin

4'-O-demethyl-4-epipodophyllotoxin

4'-DEMETHYLEPIPODOPHYLLOTOXINE

DMEP

MFCD00189421

4'-O-demethylepipodophyllotoxin

etoposide aglycone

4-Demethylepipodo phyllotoxin

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4'-Demethylepipodophyllotoxin

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