19186-35-7

Basic information

• Product Name: Desoxypodophyllotoxin
• Synonyms: Desoxypodophyllotoxin;4-Deoxypodophyllotoxin;Furo[3',4':6,7]naphtho[2,3-D]-1,3-dioxol-6(5ah)-one, 5,8,8A,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)-,(5R,5ar,8ar)-;Nsc403148;anthric;Anthricin/Deoxypodophyllotoxin
• CAS NO: 19186-35-7
• Molecular Formula: C22H22O7
• Molecular Weight: 398.40588
• Mol File: 19186-35-7.mol
• Article Data: 39

Chemical Properties

• Melting Point: 168 °C
• Boiling Point: 564.5°Cat760mmHg
• Flash Point: 247°C
• Appearance: /
• Density: 1.304g/cm³
• CAS DataBase Reference: Desoxypodophyllotoxin(CAS DataBase Reference)
• NIST Chemistry Reference: Desoxypodophyllotoxin(19186-35-7)
• EPA Substance Registry System: Desoxypodophyllotoxin(19186-35-7)

Safety Data

• Hazardous Substances Data: 19186-35-7(Hazardous Substances Data)

Usage

Description

DESOXYPODOPHYLLOTOXIN, also known as 4-Deoxypodophyllotoxin, is a compound belonging to the class of furonaphthodioxoles. It is characterized by its unique structure, featuring a 5,8,8a,9-tetrahydro-2H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one framework, with a 3,4,5-trimethoxyphenyl group substitution at the 5-position. DESOXYPODOPHYLLOTOXIN is derived from the medicinal herb Anthriscus sylvestris Hoffm and has been recognized for its diverse biological activities, including antitumor, antiviral, and anti-inflammatory properties.

Uses

Used in Pharmaceutical Industry:
DESOXYPODOPHYLLOTOXIN is used as an active pharmaceutical ingredient for its antitumor properties. It has been found to exhibit significant activity against various types of cancer, making it a valuable compound in the development of cancer treatments.
Used in Antiviral Applications:
DESOXYPODOPHYLLOTOXIN is used as an antiviral agent due to its ability to inhibit viral replication and reduce the severity of viral infections.
Used in Anti-Inflammatory Applications:
DESOXYPODOPHYLLOTOXIN is used as an anti-inflammatory agent to alleviate inflammation and reduce the associated pain and swelling.
Used in Allergy Treatment:
DESOXYPODOPHYLLOTOXIN is used as a therapeutic agent for the treatment of allergic reactions, such as passive cutaneous anaphylaxis, by inhibiting the immune response involved in these reactions.

Upstream product

• 75-11-6 diiodomethane 
• 1173-42-8 6,7-demethylenedeoxypodophyllotoxin 
• 128014-53-9 (+)-γ-apopodophyllic acid 
• 1254-07-5 (5S,6S,7R)-7-Hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid 
• 74-95-3 1,1-dibromomethane 
• 160869-33-0 (5R,5aR,8aR)-5-(3,4,5-Trimethoxy-phenyl)-5,5a,8a,9-tetrahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-6,8-dione 
• 518-28-5 podofilox 
• 477-48-5 podophyllotoxone 
• 68415-05-4 α-(3,4,5-trimethoxyphenyl)-α-morpholinoacetonitrile 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 134454-88-9 1-(3',4',5'-trimethoxyphenyl)-1,2-dihydro-4,5-methylenedioxybenzocyclobuten-1-ol 
• 134454-84-5 1-(3,4,5-trimethoxyphenyl)-2-(2'-iodo-4',5'-methylenedioxyphenyl)ethanone 
• 160823-61-0 (5R,6R,7R)-5-(3,4,5-Trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6,7-dicarboxylic acid 
• 160823-58-5 (5R,6S,7R)-5-Hydroxy-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6,7-dicarboxylic acid bis-((S)-methoxycarbonyl-phenyl-methyl) ester 

Downstream Products

• 24150-39-8 deoxypicropodophyllin 
• 3590-93-0 4'-demethyl-4-deoxypodophyllotoxin 
• 105608-71-7 3',4'-didemethoxy-4-deoxy-3',4'-dihydro-3',4'-dioxopodophyllotoxin 
• 93108-13-5 2′-bromodeoxypodophyllotoxin 
• 477-48-5 podophyllotoxone 
• 518-28-5 podofilox 
• 4375-07-9 epipodophyllotoxin 
• 128443-52-7 5-methoxypodophyllotoxin 
• 119188-52-2 5-methoxypodophyllotoxin-4-O-β-D-glucoside 
• 6258-41-9 5-(3,4,5-Trimethoxy-phenyl)-8H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one 
• 78215-95-9 desoxypodophyllinic acid ethyl ester 
• 1173-42-8 6,7-demethylenedeoxypodophyllotoxin 
• 3590-88-3 6,7-dihydroxy-9-(3,4,5-trimethoxy-phenyl)-3a,4,9,9a-tetrahydro-3H-naphtho[2,3-c]furan-1-one 
• 518-29-6 β-peltatin 

Relevant articles and documents

Asymmetric Chemoenzymatic Synthesis of (?)-Podophyllotoxin and Related Aryltetralin Lignans

(?)-Podophyllotoxin is one of the most potent microtubule depolymerizing agents and has served as an important lead compound in antineoplastic drug discovery. Reported here is a short chemoenzymatic total synthesis of (?)-podophyllotoxin and related aryltetralin lignans. Vital to this approach is the use of an enzymatic oxidative C?C coupling reaction to construct the tetracyclic core of the natural product in a diastereoselective fashion. This strategy allows gram-scale access to (?)-deoxypodophyllotoxin and is readily adaptable to the preparation of related aryltetralin lignans.

Synthesis and Computational Studies Demonstrate the Utility of an Intramolecular Styryl Diels-Alder Reaction and Di-t-butylhydroxytoluene Assisted [1,3]-Shift to Construct Anticancer dl-Deoxypodophyllotoxin

Deoxypodophyllotoxin is a secondary metabolite lignan possessing potent anticancer activity with potential as a precursor for known anticancer drugs, but its use is limited by scarcity from natural sources. We here report the total synthesis of racemic de

Design and synthesis of novel 4'-demethyl-4-deoxypodophyllotoxin derivatives as potential anticancer agents

A group of podophyllotoxin (PPT) derivatives (7a-j) were synthesized by conjugating aryloxyacetanilide moieties to the 4'-hydroxyl of 4'-demethyl-4-deoxypodophyllotoxin (DDPT), and their anticancer activity was evaluated. It was found that the most potent compound 7d inhibited the proliferation of three cancer cell lines with sub to low micromolar IC50 values. Furthermore, it was demonstrated that 7d induced cell cycle arrest in G2/M phase in MGC-803 cells, and regulated the expression of cell cycle check point proteins, such as cyclin A, cyclin B, CDK1, cdc25c, and p21. Finally, 4 mg/kg of 7d reduced the weights and volumes of HepG2 xenografts in mice. Our findings suggest that 7d might be a potential anticancer agent.