16481-54-2

Basic information

• Product Name: Podophyllotoxin glucoside
• Synonyms: Podophyllotoxin glucoside;9-(β-D-Glucopyranosyloxy)-5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one;(5R,5aR,8aR,9R)-9-(beta-D-Glucopyranosyloxy)-5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)-furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one;Podophyllotoxin 4-O-glucoside;Podophyllotoxin 7'-O-beta-D-glucopyranoside;Podophyllotoxin-7-O-glucoside
• CAS NO: 16481-54-2
• Molecular Formula: C₂₈H₃₂O₁₃
• Molecular Weight: 664.656
• Mol File: 16481-54-2.mol
• Article Data: 1

Chemical Properties

• Melting Point: 152-154℃
• Boiling Point: 781.3±60.0 °C(Predicted)
• Appearance: /
• Density: 1.55
• PKA: 12.84±0.70(Predicted)
• CAS DataBase Reference: Podophyllotoxin glucoside(CAS DataBase Reference)
• NIST Chemistry Reference: Podophyllotoxin glucoside(16481-54-2)
• EPA Substance Registry System: Podophyllotoxin glucoside(16481-54-2)

Safety Data

• Hazardous Substances Data: 16481-54-2(Hazardous Substances Data)

Usage

Description

Podophyllotoxin glucoside, also known as Podophyllotoxin 4-O-glucoside, is a glucoside derivative of Podophyllotoxin (P681000). It is a naturally occurring compound with significant medicinal properties, derived from the Podophyllum plant species. The molecule exhibits various biological activities, making it a valuable compound in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
Podophyllotoxin glucoside is used as an active pharmaceutical ingredient for the treatment of genital warts caused by certain types of human papillomaviruses (HPVs). It demonstrates antiviral properties that help in the management and elimination of genital warts, providing relief to affected individuals.
Used in Skin Treatment Applications:
In the field of dermatology, Podophyllotoxin glucoside is utilized as a therapeutic agent for skin conditions related to HPV infections. Its application in topical formulations allows for targeted treatment, reducing the spread of the virus and promoting the healing of affected areas.
Used in Anticancer Research:
Although not explicitly mentioned in the provided materials, Podophyllotoxin glucoside, like its parent compound Podophyllotoxin, has potential applications in cancer research. It may be investigated for its ability to inhibit cell division and proliferation in cancer cells, making it a candidate for the development of novel anticancer drugs.

Synthetic route

diazomethane (186581-53-3, 908094-01-9) + O9-β-D-glucopyranosyl-O4'-demethyl-podophyllotoxin → podophyllotoxin-7′-O-β-D-glucopyranoside (16481-54-2)

Conditions	Yield
With methanol; diethyl ether at 0℃;

UDP-glucose (133-89-1) + podofilox (518-28-5) → podophyllotoxin-7′-O-β-D-glucopyranoside (16481-54-2)

Conditions	Yield
With diothiothreitol In various solvents at 25℃; pH=8.5; Enzyme kinetics;

podophyllotoxin-7′-O-β-D-glucopyranoside (16481-54-2) + acetic anhydride (108-24-7) → O-(Tetra-O-acetyl-β-D-glucopyranosyl)-podophyllotoxin (20254-45-9, 22154-65-0, 22154-66-1)

Conditions	Yield
With pyridine

podophyllotoxin-7′-O-β-D-glucopyranoside (16481-54-2) → L-picropodophillotoxin 7'-O-β-D-glucopyranoside (1400-92-6)

Conditions	Yield
With methanol; ammonium hydroxide

podophyllotoxin-7′-O-β-D-glucopyranoside (16481-54-2) → podofilox (518-28-5)

Conditions	Yield
With emulsin-substance

podophyllotoxin-7′-O-β-D-glucopyranoside (16481-54-2) → podophyllotoxone (477-48-5, 477-49-6, 55515-07-6, 60660-51-7, 64550-42-1, 64937-82-2, 86594-36-7, 130322-38-2) + podofilox (518-28-5)

Conditions	Yield
In dimethyl sulfoxide for 72h; Forsythia intermedia; Yield given. Yields of byproduct given;

podophyllotoxin-7′-O-β-D-glucopyranoside (16481-54-2) + diethyl acetal (105-57-7) → (5R,5aR,8aR,9R)-9-((2R,4aR,6R,7R,8R,8aS)-7,8-Dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-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

Conditions	Yield
With toluene-4-sulfonic acid In nitromethane for 6h;	1.1 g

podophyllotoxin-7′-O-β-D-glucopyranoside (16481-54-2) → (5aR,8aS,9R)-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5,8-dione (477-48-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethylsulfoxide / 72 h / Forsythia intermedia 2: dimethylsulfoxide / other conditions: Forsythia intermedia; substrate concentration; incubation time; stage of growth; feeding period View Scheme

podophyllotoxin-7′-O-β-D-glucopyranoside (16481-54-2) → podophyllotoxone (477-48-5, 477-49-6, 55515-07-6, 60660-51-7, 64550-42-1, 64937-82-2, 86594-36-7, 130322-38-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethylsulfoxide / 72 h / Forsythia intermedia 2: dimethylsulfoxide / other conditions: Forsythia intermedia; substrate concentration; incubation time; stage of growth; feeding period View Scheme

podophyllotoxin-7′-O-β-D-glucopyranoside (16481-54-2) → podophyllotoxinyl acetate (1180-34-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: emulsin-substance View Scheme

podophyllotoxin-7′-O-β-D-glucopyranoside (16481-54-2) → O-(Tetra-O-acetyl-β-D-glucopyranosyl)-picropodophyllin (20254-45-9, 22154-65-0, 22154-66-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol; aqueous ammonia 2: pyridine View Scheme

Upstream product

• 133-89-1 UDP-glucose 
• 518-28-5 podofilox 
• 186581-53-3 diazomethane 

Downstream Products

• 20254-45-9 O-(Tetra-O-acetyl-β-D-glucopyranosyl)-podophyllotoxin 
• 1400-92-6 L-picropodophillotoxin 7'-O-β-D-glucopyranoside 
• 518-28-5 podofilox 
• 20254-45-9 O-(Tetra-O-acetyl-β-D-glucopyranosyl)-picropodophyllin 
• 1180-34-3 podophyllotoxinyl acetate 
• 477-48-5 podophyllotoxone 
• 477-48-5 (5aR,8aS,9R)-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5,8-dione 

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