CHEMICAL AND PHYSICAL PROPERTIES
| Physical Description | Light-brown to greenish-yellow powder; Commercial resin preparations contain 5-25% podophyllum. [INCHEM] |
|---|---|
| Color/Form | Solvated crystals |
| Melting Point | 228 °C |
| Solubility | 100 mg/L (at 25 °C) |
| Vapor Pressure | 8.3X10-15 mm Hg at 25 °C /Estimated/ |
| LogP | 1.5 |
| Henry's Law Constant | Henry's Law constant = 3.8X10-18 atm-cu m/mol at 25 °C /Estimated/ |
| Optical Rotation | Hygroscopic amorphos white flakes, mp = 152-154 °C. Specific optical rotation = -76.4 deg (c=0.576 in methanol); specific optical rotation = -117.0 deg (c=0.668 in pyridine) /Podophyllotoxin-beta-D-glucoside/ |
| Collision Cross Section | 190.1 Ų [M+H-H2O]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards] |
| Other Experimental Properties | Several polymorphic modifications. After drying up: mp = 183.3-184.0 °C. Specific optical rotation = -132.7 deg @ 20 °C/D (chloroform). Solubility in water at 23 °C = 12- mg/L. Soluble in alcohol, chloroform, acetone, warm benzene, glacial acetic acid. |
| Chemical Classes | Other Uses -> Pharmaceuticals |
SAFETY INFORMATION
| Signal word | Danger |
|---|---|
| Pictogram(s) |
 Skull and Crossbones Acute Toxicity GHS06 |
| GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
| Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P280:Wear protective gloves/protective clothing/eye protection/face protection. P301+P310:IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
COMPUTED DESCRIPTORS
| Molecular Weight | 414.4 g/mol |
|---|---|
| XLogP3 | 2 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 4 |
| Exact Mass | 414.13146766 g/mol |
| Monoisotopic Mass | 414.13146766 g/mol |
| Topological Polar Surface Area | 92.7 Ų |
| Heavy Atom Count | 30 |
| Formal Charge | 0 |
| Complexity | 629 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 4 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 1 |
| Compound Is Canonicalized | Yes |
PRODUCT INTRODUCTION
description
Podophyllotoxin is an organic heterotetracyclic compound that has a furonaphthodioxole skeleton bearing a 3,4,5-trimethoxyphenyl substituent. It is found in the roots and rhizomes of Podophyllum species and is used for the topical treatment of genital warts. It has a role as an antineoplastic agent, a keratolytic drug, a tubulin modulator, a microtubule-destabilising agent, an antimitotic and a plant metabolite. It is a furonaphthodioxole, a lignan and an organic heterotetracyclic compound.