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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:
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

Signal Word

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 Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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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)
High-elevation cultivation increases anti-cancer podophyllotoxin accumulation in Podophyllum hexandrum
Li M, et al.
Industrial Crops and Products, 121, 33-344 (2018)
Ronald W Brown et al.
RSC medicinal chemistry, 11(12), 1413-1422 (2021-06-08)
African sleeping sickness is a potentially fatal neglected disease affecting sub-Saharan Africa. High-throughput screening identified the thiazolyl-benzothiophenamide 1 to be active against the causative parasite, Trypanosoma brucei. This work establishes structure-activity relationships of 1, guiding the design of second generation
Theresa Hermann et al.
Pharmaceuticals (Basel, Switzerland), 14(11) (2021-11-28)
The 2-phenoxybenzamide 1 from the Medicines for Malaria Venture Malaria Box Project has shown promising multi-stage activity against different strains of P. falciparum. It was successfully synthesized via a retrosynthetic approach. Subsequently, twenty-one new derivatives were prepared and tested for
Podophyllotoxin: current perspectives
Qian L, et al.
Current Bioactive Compounds, 3(1), 37-66 (2007)
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