Podophyllotoxin, glucoside

Base Information

• Chemical Name: Podophyllotoxin, glucoside
• CAS No.: 16481-54-2
• Molecular Formula: C28H32 O13
• Molecular Weight: 576.554
• NSC Number: 163024
• DSSTox Substance ID: DTXSID80936999
• Wikidata: Q72501176
• Mol file: 16481-54-2.mol

Synonyms:Podophyllotoxin, glucoside;Podophyllotoxin glucoside;16481-54-2;Podophyllotoxin, .beta.-D-glucopyranoside;Compound NP-008106;Picropodopyllotoxin glycoside;DTXSID80936999;CHEBI:181284;Podophyllotoxin-.beta.-D-glucoside;Podophyllotoxin, .beta.-D-glucoside;NSC163024;NSC401593;ZINC05022629;AKOS040739377;NSC-163024;FT-0697790;Podophyllotoxin, 3-.beta.-D-glucopyranoside;5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzouro[6,5-][1,3]benzodioxol-8-one;8-Oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydro-2H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl hexopyranoside;Furo[3',7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 9-(.beta.-D-glucopyranosyloxy)-5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)-, [5R-(5.alpha.,5a.beta.,8a.alpha.,9.alpha.)]-;NCGC00385164-01!5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one

Chemical Property of Podophyllotoxin, glucoside

Chemical Property:

• Melting Point: 152-154℃
• Boiling Point: 781.3±60.0 °C(Predicted)
• PKA: 12.84±0.70(Predicted)
• Flash Point: 258.2oC
• PSA: 171.83000
• Density: 1.55
• LogP: 0.23340
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 7
• Exact Mass: 576.18429107
• Heavy Atom Count: 41
• Complexity: 907

Purity/Quality:

98%,99%, ^*data from raw suppliers

Podophyllotoxin 4-O-Glucoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Moderately toxic by ingestion.
• Hazard Codes: Moderately toxic by ingestion.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1OC)OC)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)OC6C(C(C(C(O6)CO)O)O)O
• Uses: Podophyllotoxin 4-O-glucoside is the glucoside derivative of Podophyllotoxin (P681000), a skin treatment for genital warts caused by some types of HPVs.

Technology Process of Podophyllotoxin, glucoside

There total 2 articles about Podophyllotoxin, glucoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) → podophyllotoxin-7′-O-β-D-glucopyranoside (16481-54-2)

Guidance literature:

With methanol; diethyl ether; at 0 ℃;

DOI:10.1002/hlca.19560390402

Reference yield:

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

Guidance literature:

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

DOI:10.1016/j.phytochem.2007.07.030

Reference yield:

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

Guidance literature:

With emulsin-substance;

DOI:10.1002/hlca.19540370620

upstream raw materials:

diazomethane

UDP-glucose

podofilox

Downstream raw materials:

O-(Tetra-O-acetyl-β-D-glucopyranosyl)-podophyllotoxin

L-picropodophillotoxin 7'-O-β-D-glucopyranoside

podofilox

podophyllotoxone

Refernces

• 1、 Berim, Anna,Ebel, Rainer,Schneider, Bernd,Petersen, Maike. "UDP-glucose:(6-methoxy)podophyllotoxin 7-O-glucosyltransferase from suspension cultures of Linum nodiflorum". . p. 374 - 381. Retrieved 2008.