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

CAS: 518-28-5 C22 H22 O8 MW: 414.41094000

Identification

Namepodophyllotoxin
CAS Number518-28-5
EINECS208-250-4
FDA UNIIL36H50F353
Molecular FormulaC22 H22 O8
Molecular Weight414.41094000
MDL NumberMFCD00075290
Nikkaji NumberJ6.582J
Beilstein0099163
XlogP32.00 (est)

Regulatory

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)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityintravenous-rat LD50 8.70 mg/kg
Dermal Toxicitysubcutaneous-rat LD50 8 mg/kg
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements', 'U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#01679']

Safety in Use

Categorynatural substances and extractives
Recommendation for podophyllotoxin usage levels up tonot for fragrance use.
Recommendation for podophyllotoxin flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

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 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.