Picropodophyllic acid

Base Information

• Chemical Name: Picropodophyllic acid
• CAS No.: 477-67-8
• Molecular Formula: C22H24 O9
• Molecular Weight: 432.427
• UNII: T264PGD64X
• Nikkaji Number: J6.139E
• Wikidata: Q27289560
• Mol file: 477-67-8.mol

Synonyms:Picropodophyllic acid;UNII-T264PGD64X;T264PGD64X;477-67-8;Naphtho(2,3-d)-1,3-dioxole-6-carboxylic acid, 5,6,7,8-tetrahydro-8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-, (5R,6S,7R,8R)-;Picropodophyllinic acid;Q27289560

Chemical Property of Picropodophyllic acid

Chemical Property:

• Melting Point: 150-155° and 200-232°
• Boiling Point: 632.8°Cat760mmHg
• Flash Point: 220.2°C
• PSA: 123.91000
• Density: 1.388g/cm³
• LogP: 1.92930
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 432.14203234
• Heavy Atom Count: 31
• Complexity: 616

Purity/Quality:

PODOPHYLLIC ACIDS-2,3-CIS-HYDROXY ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1OC)OC)C2C(C(C(C3=CC4=C(C=C23)OCO4)O)CO)C(=O)O
• Isomeric SMILES: COC1=CC(=CC(=C1OC)OC)[C@H]2[C@@H]([C@@H]([C@H](C3=CC4=C(C=C23)OCO4)O)CO)C(=O)O

Technology Process of Picropodophyllic acid

There total 60 articles about Picropodophyllic acid 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: 63.0%

(+/-)-methyl epipodophyllate (1256-91-3,55515-12-3,75171-58-3,78216-03-2,86334-69-2,116180-67-7,122871-76-5,127126-86-7) → epipicropodophyllic acid (477-67-8,477-68-9,518-48-9,1853-37-8,4354-75-0,79355-65-0,86334-72-7,100896-01-3,112068-24-3,113565-15-4,122871-78-7,122871-80-1,130981-13-4)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; for 4h; Heating;

DOI:10.1021/jo00279a011

Reference yield: 58.0%

epipodophyllic acid 4,11-acetonide (79289-93-3,86334-71-6) → epipodophyllic acid (477-67-8,477-68-9,518-48-9,1853-37-8,4354-75-0,79355-65-0,86334-72-7,100896-01-3,112068-24-3,113565-15-4,122871-78-7,122871-80-1,130981-13-4)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 25 ℃; for 24h;

DOI:10.1021/jo00279a011

Reference yield:

(+/-)-methyl epipodophyllate (1256-91-3,55515-12-3,75171-58-3,78216-03-2,86334-69-2,116180-67-7,122871-76-5,127126-86-7) → epipodophyllic acid (477-67-8,477-68-9,518-48-9,1853-37-8,4354-75-0,79355-65-0,86334-72-7,100896-01-3,112068-24-3,113565-15-4,122871-78-7,122871-80-1,130981-13-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / p-toluenesulfonic acid

2: 82 percent / NaOH / H₂O; dioxane / 6 h / Heating

3: 45 percent / dilute acid / H₂O; dioxane / 24 h / Ambient temperature

With sodium hydroxide; dilute acid; toluene-4-sulfonic acid; In 1,4-dioxane; water;

DOI:10.1021/ja00410a038

upstream raw materials:

acetyl-epipicropodophyllotoxin

epipodophyllotoxin acetate

epipicropodophyllotoxin

epipodophyllotoxin

Downstream raw materials:

epipicropodophyllotoxin

(5R,6S,7R,8R)-8-Hydroxy-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

Refernces

• 1、 Castro, Ma. ángeles,Miguel Del Corral, José Ma.,García, Pablo A.,Rojo, Ma. Victoria,De La Iglesia-Vicente, Janis,Mollinedo, Faustino,Cuevas, Carmen,San Feliciano, Arturo. "Synthesis and biological evaluation of new podophyllic aldehyde derivatives with cytotoxic and apoptosis-inducing activities". experimental part. p. 983 - 993. Retrieved 2010/07/16.
• 2、 Gordaliza, Marina,Faircloth, Glynn T.,Castro, Ma. Angeles,Miguel Del Corral, José M.,López-Vázquez, Ma. Luisa,San Feliciano, Arturo. "Immunosuppressive cyclolignans". . p. 2865 - 2868. Retrieved 2007/10/03.