69222-20-4

Basic information

• Product Name: deoxypodophyllotoxin
• Synonyms: deoxypodophyllotoxin
• CAS NO: 69222-20-4
• Molecular Formula: C₂₂H₂₂O₇
• Molecular Weight: 398.41
• Mol File: 69222-20-4.mol
• Article Data: 41

Chemical Properties

• Boiling Point: 564.5±50.0 °C(Predicted)
• Appearance: /
• Density: 1.304±0.06 g/cm3(Predicted)
• CAS DataBase Reference: deoxypodophyllotoxin(CAS DataBase Reference)
• NIST Chemistry Reference: deoxypodophyllotoxin(69222-20-4)
• EPA Substance Registry System: deoxypodophyllotoxin(69222-20-4)

Safety Data

• Hazardous Substances Data: 69222-20-4(Hazardous Substances Data)

Usage

General Description

Deoxypodophyllotoxin is a chemical compound found in the plant species Podophyllum. It is a lignan with potential antineoplastic and cytotoxic properties, making it a promising candidate for cancer treatment. Deoxypodophyllotoxin has been shown to inhibit the growth of cancer cells by interfering with the normal function of microtubules, which are essential for cell division. deoxypodophyllotoxin has also been reported to induce apoptosis, or programmed cell death, in cancer cells. Additionally, deoxypodophyllotoxin has exhibited anti-inflammatory and immunomodulatory effects, making it a versatile compound with potential for various therapeutic applications. Its promising pharmacological properties have garnered attention for further research and development in the field of oncology and other diseases.

Upstream product

• 75-11-6 diiodomethane 
• 1173-42-8 6,7-demethylenedeoxypodophyllotoxin 
• 6258-32-8 (dl)-5-(3,4,5-trimethoxyphenyl)-8a,9-dihydrofuro[3′,4’:6,7]-naphtho[2,3-d][1,3]dioxol-6(8H)-one 
• 1254-07-5 7-Hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic 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 
• 1643-12-5 (5S,6R,7R)-7-Hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester 
• 58095-76-4 (E)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-ol 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 1643-12-5 (5S,6S,7S)-7-Hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester 
• 116097-18-8 6,7-methylenedioxy-1-(3',4',5'-trimethoxyphenyl)-2-benzopyran-3-one 
• 477-47-4 (+/-)-epi-picropodophyllin 
• 120-57-0 piperonal 
• 74879-22-4 6-bromobenzo-1,3-dioxole-5-carboxaldehyde dimethyl acetal 
• 74879-25-7 -3,4-methylenedioxybenzaldehyde dimethyl acetal 

Downstream Products

• 24150-39-8 deoxypicropodophyllin 
• 60073-37-2 2'-bromo-dehydrodesoxypodophyllotoxin 
• 139219-13-9 (5S,6S,7S)-5-(2-Bromo-3,4,5-trimethoxy-phenyl)-7-hydroxymethyl-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl 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 
• 321747-09-5 deoxyanhydro-4-isopodophyllol 
• 321747-15-3 C₂₂H₂₄O₇ 
• 25088-82-8 9-deoxyanhydropodophyllol 
• 106636-74-2 4-bromo-4-deoxypodophyllotoxin 
• 1014671-34-1 (-)-podophyllotoxin 
• 1445712-18-4 C₃₃H₂₅N₃O₆ 
• 1445712-19-5 C₃₃H₂₄IN₃O₆ 
• 1445712-20-8 C₃₄H₂₇N₃O₇ 
• 1445712-21-9 C₃₄H₂₇N₃O₇ 

Relevant articles and documents

Chemoenzymatic Total Synthesis of Deoxy-, epi-, and Podophyllotoxin and a Biocatalytic Kinetic Resolution of Dibenzylbutyrolactones

Podophyllotoxin is probably the most prominent representative of lignan natural products. Deoxy-, epi-, and podophyllotoxin, which are all precursors to frequently used chemotherapeutic agents, were prepared by a stereodivergent biotransformation and a biocatalytic kinetic resolution of the corresponding dibenzylbutyrolactones with the same 2-oxoglutarate-dependent dioxygenase. The reaction can be conducted on 2 g scale, and the enzyme allows tailoring of the initial, “natural” structure and thus transforms various non-natural derivatives. Depending on the substitution pattern, the enzyme performs an oxidative C?C bond formation by C?H activation or hydroxylation at the benzylic position prone to ring closure.

Divergent Asymmetric Syntheses of Podophyllotoxin and Related Family Members via Stereoselective Reductive Ni-Catalysis

A nickel-catalyzed reductive cascade approach to the efficient construction of diastereodivergent cores embedded in podophyllum lignans is developed for the first time. Their gram-scale access paved the way for unified syntheses of naturally occurring podophyllotoxin and other members.

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.