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podophyllotoxin
[5R-(5a,5ab,8aa,9a)]-5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one

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CAS Number: 518-28-5Picture of molecule3D/inchi
Other(deleted CASRN):11016-28-7
ECHA EINECS - REACH Pre-Reg:208-250-4
FDA UNII: L36H50F353
Nikkaji Web:J6.582J
Beilstein Number:0099163
MDL:MFCD00075290
XlogP3:2.00 (est)
Molecular Weight:414.41094000
Formula:C22 H22 O8
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
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Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Appearance:white crystalline powder (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 183.00 °C. @ 760.00 mm Hg
Boiling Point: 597.00 to 598.00 °C. @ 760.00 mm Hg (est)
Flash Point: 410.00 °F. TCC ( 210.20 °C. ) (est)
logP (o/w): 2.010
Soluble in:
 water, 154.9 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Podophyllotoxin 98%
AuNutra® Industries
Podophyllatoxin P.E.
BOC Sciences
For experimental / research use only.
Podophyllotoxin > 95%
Odor: characteristic
Use: Podophyllotoxin, a kind of non-alkaloid toxin lignan extracted from the roots and rhizomes of Podophyllum plant, has been shown to inhibit the growth of various carcinoma cells. It is a potent inhibitor of microtubule assembly and DNA topoisomerase II
Coompo
For experimental / research use only.
Podophyllotoxin from Plants ≥98%
Odor: characteristic
Use: Among the plethora of physiological activities and potential medicinal and agricultural applications, the antineoplastic and antiviral properties of podophyllotoxin congeners and their derivatives are arguably the most eminent from a pharmacological perspective. Podophyllotoxin is an antimitotic. It acts by preventing viral wart cells from dividing and multiplying. Eventually all the wart cells die and new healthy cells grow in their place. In the 1930s, doctors in New Orleans started using podophyllotoxin for the treatment of genital warts. By 1942 the first description of this practice was published in medical literature.
ExtraSynthese
For experimental / research use only.
(-)-Podophyllotoxin (HPLC) ≥99%
Glentham Life Sciences
Podophyllotoxin
Shaanxi Y-Herb Biotechnology
Pure Podophyllotoxin Monomer Powder Podophyllum Peltatum Podophyllum Hexandrum Extract
Sigma-Aldrich: Sigma
For experimental / research use only.
Podophyllotoxin
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intravenous-rat LD50 8.70 mg/kg
LUNGS, THORAX, OR RESPIRATION: DYSPNEA GASTROINTESTINAL: NAUSEA OR VOMITING BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 7, Pg. 249, 1948.

intraperitoneal-rat LD50 15 mg/kg
LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: NAUSEA OR VOMITING
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 7, Pg. 249, 1948.

intravenous-rabbit LD50 5 mg/kg
LUNGS, THORAX, OR RESPIRATION: DYSPNEA SKIN AND APPENDAGES (SKIN): CUTANEOUS SENSITIZATION (EXPERIMENTAL): AFTER TOPICAL EXPOSURE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 7, Pg. 249, 1948.

oral-mouse LD50 100 mg/kg
PCT Vol. #86-04062

intravenous-mouse LD50 56 mg/kg
U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#01679

intraperitoneal-mouse LD50 30 mg/kg
Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 327, 1961.

intramuscular-cat LD50 4 mg/kg
SKIN AND APPENDAGES (SKIN): CUTANEOUS SENSITIZATION (EXPERIMENTAL): AFTER TOPICAL EXPOSURE LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 7, Pg. 249, 1948.

intravenous-cat LD50 1700 ug/kg
GASTROINTESTINAL: NAUSEA OR VOMITING LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 7, Pg. 249, 1948.

parenteral-frog LDLo 152 mg/kg
BEHAVIORAL: STIFFNESS
Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 28, Pg. 32, 1891.

intramuscular-rat LD50 3 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: NAUSEA OR VOMITING LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 7, Pg. 249, 1948.

intravenous-rat LD50 8700 ug/kg
LUNGS, THORAX, OR RESPIRATION: DYSPNEA GASTROINTESTINAL: NAUSEA OR VOMITING BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 7, Pg. 249, 1948.

Dermal Toxicity:
subcutaneous-rat LD50 8 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Proceedings of the Society for Experimental Biology and Medicine. Vol. 77, Pg. 269, 1951.

skin-rat LD50 500 mg/kg
PCT Vol. #86-04062

skin-rabbit LD50 200 mg/kg
PCT Vol. #86-04062

subcutaneous-cat LDLo 300 ug/kg
GASTROINTESTINAL: NAUSEA OR VOMITING BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 28, Pg. 32, 1891.

subcutaneous-chicken LDLo 6250 ug/kg
GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 28, Pg. 32, 1891.

subcutaneous-dog LDLo 1 mg/kg
GASTROINTESTINAL: NAUSEA OR VOMITING BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 28, Pg. 32, 1891.

subcutaneous-mouse LDLo 24600 ug/kg
Toxicon. Vol. 8, Pg. 85, 1970.

Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for podophyllotoxin usage levels up to:
 not for fragrance use.
 
Recommendation for podophyllotoxin flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
ClinicalTrials.gov:search
Daily Med:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA GENetic TOXicology:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :10607
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(5R,5aR,8aR,9R)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
Chemidplus:0000518285
RTECS:LV2500000 for cas# 518-28-5
 
References:
 (5R,5aR,8aR,9R)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):10607
Pubchem (sid):134976487
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C10874
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2932.90.4100
MedlinePlusSupp:View
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
EFSA Update of results on the monitoring of furan levels in food:Read Report
EFSA Previous report: Results on the monitoring of furan levels in food:Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food:Read Report
Formulations/Preparations:
topical: gel: 0.5%, condylox, (watson); solution: 0.5%, condylox (with alcohol 95% lactic acid and sodium lactate), (watson).
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 
Synonyms:
 condyline
 condylox
(10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.03,7.011,15]hexadeca-1(9),2,7-trien-12-one
(5R,5aR,8aR,9R)-9-hydroxy-5-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one
(5R,5aR,8aR,9R)-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one
(5R,5aR,8aR,9R)-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one
(5R,9R,5aR,8aR)-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,8,9,5a,8a-pentahydro-2H-isobenzofurano[5',6'-2,1]benzo[4,5-d]1,3-dioxolan-6-one
(5R,5aR,8aR,9R)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
 podofilox
 podophilox
 podophyllinic acid lactone
 podophyllotoxin (8CI)
 podophyllotoxin 7
(5R,5aR,8aR,9R)-5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-furo(3',4':6,7)naphtho[2,3-d]-1,3-dioxol-6(5aH)-one
(5R,5aR,8aR,9R)-5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one
(5R,5aR,8aR,9R)-5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one
[5R-(5a,5ab,8aa,9a)]-5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one
 warticon
 

Articles:

PubMed:Podophyllotoxin and 6-methoxy podophyllotoxin Production in Hairy Root Cultures of Liunm mucronatum ssp. mucronatum.
PubMed:Stereoselective synthesis of 2α-Chloropicropodophyllotoxins and insecticidal activity of their esters against oriental armyworm, Mythimna separata walker.
PubMed:Synthesis of novel 4α-(acyloxy)-2'(2',6')-(di)halogenopodophyllotoxin derivatives as insecticidal agents.
PubMed:Production of podophyllotoxin from roots and plantlets of Hyptis suaveolens cultivated in vitro.
PubMed:Synthesis and insecticidal activity of new deoxypodophyllotoxin-based phenazine analogues against Mythimna separata Walker.
PubMed:Synthesis and quantitative structure-activity relationship (QSAR) study of novel 4-acyloxypodophyllotoxin derivatives modified in the A and C rings as insecticidal agents.
PubMed:Synthesis and quantitative structure-activity relationship (QSAR) study of novel isoxazoline and oxime derivatives of podophyllotoxin as insecticidal agents.
PubMed:Podophyllotoxin and deoxypodophyllotoxin in Juniperus bermudiana and 12 other Juniperus species: optimization of extraction, method validation, and quantification.
PubMed:Seasonal variations in the deoxypodophyllotoxin content and yield of Anthriscus sylvestris L. (Hoffm.) grown in the field and under controlled conditions.
PubMed:Plant-derived bioactive compounds produced by endophytic fungi.
PubMed:Warts (genital).
PubMed:Semisynthesis and quantitative structure-activity relationship (QSAR) study of novel aromatic esters of 4'-demethyl-4-deoxypodophyllotoxin as insecticidal agents.
PubMed:Modulation of gamma radiation-inflicted damage in Swiss albino mice by an alcoholic fraction of Podophyllum hexandrum rhizome.
PubMed:Replacement of the lactone moiety on podophyllotoxin and steganacin analogues with a 1,5-disubstituted 1,2,3-triazole via ruthenium-catalyzed click chemistry.
PubMed:Warts (genital).
PubMed:Frequency and timing of leaf removal affect growth and podophyllotoxin content of Podophyllum peltatum in full sun.
PubMed:Biologically active components against Drosophila melanogaster from Podophyllum hexandrum.
PubMed:Mandrake toxicity. A case of mistaken identity.
PubMed:Human papillomavirus infection and genital warts: update on epidemiology and treatment.
PubMed:The effect of food and concurrent chemotherapy on the bioavailability of oral etoposide.
PubMed:Etoposide: a semisynthetic epipodophyllotoxin. Chemistry, pharmacology, pharmacokinetics, adverse effects and use as an antineoplastic agent.
PubMed:Review of etoposide.
 
Notes:
a lignan (lignans) found in podophyllin resin from the roots of podophyllum plants. it is a potent spindle poison, toxic if taken internally, and has been used as a cathartic. it is very irritating to skin and mucous membranes, has keratolytic actions, has been used to treat warts and keratoses, and may have antineoplastic properties, as do some of its congeners and derivatives.
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