WILFORLIDE A

Base Information

• Chemical Name: WILFORLIDE A
• CAS No.: 84104-71-2
• Molecular Formula: C₃₀H₄₆O₃
• Molecular Weight: 454.693
• European Community (EC) Number: 683-224-7
• UNII: JW7QMP68BC
• DSSTox Substance ID: DTXSID601004388
• Nikkaji Number: J712.464C
• Wikidata: Q72516557
• Metabolomics Workbench ID: 138336
• ChEMBL ID: CHEMBL484424
• Mol file: 84104-71-2.mol

Synonyms:(-)-Abruslactone A;Abruslactone A;Regelide;Wilforlide A;

Chemical Property of WILFORLIDE A

Chemical Property:

• Vapor Pressure: 1.24E-14mmHg at 25°C
• Melting Point: 318-320 °C
• Refractive Index: 1.563
• Boiling Point: 555 °C at 760 mmHg
• PKA: 15.17±0.70(Predicted)
• Flash Point: 208.6 °C
• PSA: 46.53000
• Density: 1.12 g/cm³
• LogP: 6.68430
• XLogP3: 6.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 454.34469533
• Heavy Atom Count: 33
• Complexity: 935

Purity/Quality:

99% ^*data from raw suppliers

Wilforlide A ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2CCC3(C(C2(CCC1O)C)CC=C4C3(CCC5(C4CC6(CC5OC6=O)C)C)C)C)C
• Isomeric SMILES: C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4C[C@]6(C[C@@H]5OC6=O)C)C)C)C)(C)C)O
• Uses: Wilforlide A is a terpenoid found in tissue cultures of tripterygium wilfordii.

Technology Process of WILFORLIDE A

There total 4 articles about WILFORLIDE A 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:

(2R,4R,4aR,6aS,6bR,8aR,10S,12aR,14bS)-4-Acetoxy-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydro-picene-2-carboxylic acid methyl ester (118525-45-4) → deoxoglabrolide (10379-62-1,84104-71-2)

Guidance literature:

With sulfuric acid; In water;

DOI:10.1248/cpb.36.3710

Reference yield:

(2R,4R,4aR,6aS,6bR,8aR,10S,12aR,14bS)-4-Acetoxy-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydro-picene-2-carboxylic acid (118525-50-1) → deoxoglabrolide (10379-62-1,84104-71-2)

Guidance literature:

Multi-step reaction with 2 steps

2: 10 percent H₂SO₄-50 percent MeOH / H₂O

With sulfuric acid; In water;

DOI:10.1248/cpb.36.3710

Reference yield:

licorice-saponin D3 (118536-87-1) → deoxoglabrolide (10379-62-1,84104-71-2)

Guidance literature:

Multi-step reaction with 3 steps

1: methanolysis

3: 10 percent H₂SO₄-50 percent MeOH / H₂O

With sulfuric acid; In water;

DOI:10.1248/cpb.36.3710

upstream raw materials:

(2R,4R,4aR,6aS,6bR,8aR,10S,12aR,14bS)-4-Acetoxy-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydro-picene-2-carboxylic acid methyl ester

(2R,4R,4aR,6aS,6bR,8aR,10S,12aR,14bS)-4-Acetoxy-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydro-picene-2-carboxylic acid

licorice-saponin D₃

3β,22α-dihydroxy-olean-12-en-29α-oic acid

Downstream raw materials:

3β,22α-dihydroxy-olean-12-en-29α-oic acid

Refernces

• 1、 Kitagawa,Zhou,Sakagami,Taniyama,Yoshikawa. "Licorice-saponins A3, B2, C2, D3, and E2, five new oleanene-type triterpene oligoglycosides from Chinese glycyrrhizae radix". . p. 3710 - 3713. Retrieved 2007/10/02.