Deoxypodophyllotoxin

Base Information

• Chemical Name: Deoxypodophyllotoxin
• CAS No.: 19186-35-7
• Molecular Formula: C22H22O7
• Molecular Weight: 398.4059
• NSC Number: 403148
• UNII: 45NR8XYU1L
• DSSTox Substance ID: DTXSID701019944
• Nikkaji Number: J16.374K
• Wikidata: Q27106380
• Metabolomics Workbench ID: 143423
• ChEMBL ID: CHEMBL63970
• Mol file: 19186-35-7.mol

Synonyms:deoxypicropodophyllin;deoxypodophyllotoxin;deoxypodophyllotoxin, (5alpha,5aalpha,8aalpha)-(+-)-isomer;deoxypodophyllotoxin, (5alpha,5aalpha,8abeta)-(+-)-isomer;deoxypodophyllotoxin, (5R-(5alpha,5aalpha,8aalpha))-isomer;deoxypodophyllotoxin, (5R-(5alpha,5aalpha,8abeta))-isomer;deoxypodophyllotoxin, (5R-(5alpha,5abeta,8aalpha))-isomer;deoxypodophyllotoxin, (5R-(5alpha,5abeta,8abeta))-isomer;isoanthricin;isodeoxypodophyllotoxin

Chemical Property of Deoxypodophyllotoxin

Chemical Property:

• Melting Point: 168 °C
• Boiling Point: 564.5°Cat760mmHg
• Flash Point: 247°C
• PSA: 72.45000
• Density: 1.304g/cm³
• LogP: 2.91830
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 398.13655304
• Heavy Atom Count: 29
• Complexity: 598

Purity/Quality:

≥98% ^*data from raw suppliers

4-Deoxypodophyllotoxin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1OC)OC)C2C3C(CC4=CC5=C(C=C24)OCO5)COC3=O
• Isomeric SMILES: COC1=CC(=CC(=C1OC)OC)[C@H]2[C@@H]3[C@@H](CC4=CC5=C(C=C24)OCO5)COC3=O
• Uses: 4-Deoxypodophyllotoxin is a medicinal herb product isolated from Anthriscus sylvestris Hoffm. It is well known for its antitumor, antiviral, and anti-inflammatory activities. 4-Deoxypodophyllotoxin wa s also shown to inhibit the passive cutaneous anaphylaxis reaction.

Technology Process of Deoxypodophyllotoxin

There total 168 articles about Deoxypodophyllotoxin 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: 95.0%

yatein (40456-50-6,17301-91-6,61091-56-3,72690-16-5,96745-44-7,119066-80-7,128049-89-8,139560-31-9) → deoxypodophyllotoxin (477-51-0,6258-33-9,17187-81-4,17301-90-5,19186-35-7,24150-39-8,31892-96-3,55568-81-5,64550-41-0,69222-20-4,75171-57-2,83023-41-0,100348-38-7)

Guidance literature:

With ferrous(II) sulfate heptahydrate; ATGGGCAGCACCGCGCCGCTGCGTTTCCCGGTTATCGATTTGAGCATGAAGAACCTGAAACCTGGAACCACATCATGGAACAGCGTACGCACTCAGGTGCGTGAAGCTTTGGAAGAATATGGTTGCTTTGAAGCCGTTATTGATGCGGTTTCCCCAGAGTTGCAAAAAGCTGTCTGCAACAAGGGGCACGAACTGTTAAATTTACCGCTGGAGACCAAGATGCTTAATGGTAATAAGCCGGAGTACGATGGATTTACATCAATCCCGAACCTTAACGAAGGTATGGGTGTTGGCCGCATCACTGACTTAGAGAAGGTCGAACGTTTCACTAATCTGATGTGGCCTGAGGGGAACAAGGATTTTTGCGAAACAGTTTACTCCTATGGTAAGCGCATGGCAGAGGTTGACCATATTCTGAAGATGATGGTATTCGAATCTTTTGGTATGGAGAAACATTTTGACTCCTTCTGCGAAAGTACAAATTACTTGCTGCATTTCATGCGCTATCAACAACCCGGCAAAGACGGTCGCTCTCCCGCATTGAGTTTACACAAAGATAAATCTATCCTTACGATCGTCAACCAAAACGATGTAAAAGGACTGGAGTTCGAAACAAAGGATGGCGAATGGATTTTGCCAACAGCCGATAACCACATCGTATTACTTGGAGATTGCTTCATGGCTTGGAGTAACGGTCGCCTGCACTCTCCACTGCACCGTGTGACATTAGTGGCAAATCAGGCACGTTTGAGTACCTCCTCATTTAGCTTCCCAAAAGATATTATTGAGACACCGGCGGAATTGGTGGACGAGGAACATCCGCTTTTATTCAATCCCTTCGAGATCACCGAGCTTTTAGCCTACTGTTTTACAAAAGAAGGAGCCAAGGCGGTTTGCGATTTAAAGCAGTATAAAGCGTACACTGGAGCATGA; α-ketoglutaric acid disodium salt; ascorbic acid; In dimethyl sulfoxide; at 23 ℃; for 20h;

DOI:10.1002/anie.201904102

Reference yield: 45.0%

3-methyl-butan-2-one (563-80-4) + 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) → 7α-[(2R)-2-hydroxy-3-methylbut-2-yl]epi-podophyllotoxin + 7α-[(2S)-2-hydroxy-3-methylbut-2-yl]epi-podophyllotoxin + deoxypodophyllotoxin (477-51-0,6258-33-9,17187-81-4,17301-90-5,19186-35-7,24150-39-8,31892-96-3,55568-81-5,64550-41-0,69222-20-4,75171-57-2,83023-41-0,100348-38-7) + podofilox (518-28-5)

Guidance literature:

With titanium tetrachloride; zinc; In tetrahydrofuran; at -20 - -10 ℃; for 4h; Inert atmosphere;

DOI:10.1021/jm2017573

Reference yield: 45.0%

acetone (67-64-1) + 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) → 7α-(2-hydroxyprop-2-yl)podophyllotoxin + 7β-(2-hydroxyprop-2-yl)podophyllotoxin + deoxypodophyllotoxin (477-51-0,6258-33-9,17187-81-4,17301-90-5,19186-35-7,24150-39-8,31892-96-3,55568-81-5,64550-41-0,69222-20-4,75171-57-2,83023-41-0,100348-38-7) + podofilox (518-28-5)

Guidance literature:

With titanium tetrachloride; zinc; In tetrahydrofuran; at -20 - -10 ℃; for 4h; optical yield given as %de; Inert atmosphere;

DOI:10.1021/jm2017573

upstream raw materials:

diiodomethane

6,7-demethylenedeoxypodophyllotoxin

(+)-γ-apopodophyllic acid

(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

Downstream raw materials:

deoxypicropodophyllin

5-methoxypodophyllotoxin

5-methoxypodophyllotoxin-4-O-β-D-glucoside

5-(3,4,5-Trimethoxy-phenyl)-8H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one

Refernces

• 1、 Lazzarotto, Mattia,Hammerer, Lucas,Hetmann, Michael,Borg, Annika,Schmermund, Luca,Steiner, Lorenz,Hartmann, Peter,Belaj, Ferdinand,Kroutil, Wolfgang,Gruber, Karl,Fuchs, Michael. "Chemoenzymatic Total Synthesis of Deoxy-, epi-, and Podophyllotoxin and a Biocatalytic Kinetic Resolution of Dibenzylbutyrolactones". . p. 8226 - 8230. Retrieved 2019/05/21.
• 2、 Saavedra, Diana I.,Rencher, Benjamin D.,Kwon, Doo-Hyun,Smith, Stacey J.,Ess, Daniel H.,Andrus, Merritt B.. "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". . p. 2018 - 2026. Retrieved 2018/02/23.