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P4405

Sigma-Aldrich

Podophyllotoxin

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About This Item

Empirical Formula (Hill Notation):
C22H22O8
CAS Number:
518-28-5
Molecular Weight:
414.41
Beilstein/REAXYS Number:
99163
EC Number:
208-250-4
MDL number:
MFCD00075290
UNSPSC Code:
12352200
PubChem Substance ID:
24277731
NACRES:
NA.77

assay

≥98%

Quality Level

200

form

powder

mp

183-184 °C (lit.)

storage temp.

2-8°C

SMILES string

COc1cc(cc(OC)c1OC)[C@H]2C3C(COC3=O)[C@@H](O)c4cc5OCOc5cc24

InChI

1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19-,20-/m0/s1

InChI key

YJGVMLPVUAXIQN-XVVDYKMHSA-N

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Application

Podophyllotoxin has been used as a reference compound for evaluating the cytotoxicity in VERO cells. It has also been used as a reference standard in high-performance liquid chromatography (HPLC).

Biochem/physiol Actions

Podophyllotoxin is a naturally occurring lignan obtained from resin podophyllin present in the genus Podophyllum. It exhibits antiviral and antimitotic properties. Podophyllotoxin may be used to treat anogenital warts in children and dermatological conditions caused by psoriasis vulgaris. It may also be used as a therapeutic agent to treat genital tumors, Wilms tumors, lung cancer, and lymphomas.
Inhibits microtubule assembly; antineoplastic.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Y Damayanthi et al.
Current medicinal chemistry, 5(3), 205-252 (1998-07-01)
Podophyllotoxin is a natural product isolated from Podophyllum peltatum and Podophyllum emodi and has long been known to possess medicinal properties. Etoposide (VP-16), a podophyllotoxin derivative, is currently in clinical use in the treatment of many cancers, particularly small cell
Diterpenoids as potential anti-malarial compounds from Andrographis paniculata
Dwivedi M, et al.
Beni-Suef University Journal of Basic and Applied Sciences, 10(1), 1-16 (2021)
Svetlana M Bakunova et al.
Journal of medicinal chemistry, 50(23), 5807-5823 (2007-10-24)
Forty three cationic bisbenzofurans were synthesized either by interaction of o-hydroxyaldehydes with alpha-halogenated ketones followed by intramolecular ring closure or by a copper- or palladium-mediated heteroannulation of substituted o-iodophenols with terminal acetylenes. In vitro antiprotozoal activities of compounds 1-43 against
Jean Fotie et al.
Journal of medicinal chemistry, 53(3), 966-982 (2010-01-06)
The current chemotherapy for second stage human African trypanosomiasis is unsatisfactory. A synthetic optimization study based on the lead antitrypanosomal compound 1,2-dihydro-2,2,4-trimethylquinolin-6-yl 3,5-dimethoxybenzoate (TDR20364, 1a) was undertaken in an attempt to discover new trypanocides with potent in vivo activity. While
Patrick Hochegger et al.
Molecules (Basel, Switzerland), 26(18) (2021-09-29)
A new series of compounds was prepared from 6-methoxyquinolin-8-amine or its N-(2-aminoethyl) analogue via Ugi-azide reaction. Their linkers between the quinoline and the tert-butyltetrazole moieties differ in chain length, basicity and substitution. Compounds were tested for their antiplasmodial activity against
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