Periplogenin

Base Information

• Chemical Name: Periplogenin
• CAS No.: 514-39-6
• Molecular Formula: C₂₃H₃₄O₅
• Molecular Weight: 390.52
• UNII: B6808P7IY9
• DSSTox Substance ID: DTXSID50965711
• Nikkaji Number: J6.288J
• Wikidata: Q27274425
• Metabolomics Workbench ID: 135940
• ChEMBL ID: CHEMBL460768
• Mol file: 514-39-6.mol

Synonyms:3 beta,5,14-trihydroxy-5 beta-card-20(22)-enolide;5 beta-hydroxydigitoxigenin;periplogenin

Chemical Property of Periplogenin

Chemical Property:

• Vapor Pressure: 5.06E-16mmHg at 25°C
• Melting Point: 245-248℃
• Boiling Point: 583°Cat760mmHg
• PKA: 14.60±0.70(Predicted)
• Flash Point: 200.4°C
• PSA: 86.99000
• Density: 1.32g/cm³
• LogP: 2.71920
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 390.24062418
• Heavy Atom Count: 28
• Complexity: 733

Purity/Quality:

≥98% ^*data from raw suppliers

Periplogenin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(CC1(CCC3C2CCC4(C3(CCC4C5=CC(=O)OC5)O)C)O)O
• Isomeric SMILES: C[C@]12CC[C@@H](C[C@]1(CC[C@@H]3[C@@H]2CC[C@]4([C@@]3(CC[C@@H]4C5=CC(=O)OC5)O)C)O)O

Technology Process of Periplogenin

There total 33 articles about Periplogenin 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: 37.0%

Sucrose (57-50-1) + (+)-digitoxigenin (143-62-4) → 3-epi-periplogenin (71884-72-5) + digitoxigenin 3-O-β-D-glucoside (17059-16-4) + periplogenin glucoside (18531-44-7) + 4-[(3S,5S,8R,9S,10R,13R,14S,17S)-5,14-Dihydroxy-10,13-dimethyl-3-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-5H-furan-2-one + (17β)-H-periplogenin (4433-58-3) + periplogenin (514-39-6,4433-58-3,71884-72-5,107596-70-3,117020-71-0)

Guidance literature:

With Tween 80; F₈ cells; In various solvent(s); at 25 ℃; for 360h; Product distribution; other reagents, reaction time;

DOI:10.1016/S0031-9422(97)00748-6

Reference yield: 17.9%

(+)-digitoxigenin (143-62-4) → digitoxigenin 3-O-β-D-glucoside (17059-16-4) + periplogenin glucoside (18531-44-7) + 3α,14-dihydroxy-5β,14β-card-20(22)-enolide (545-52-8) + periplogenin (514-39-6,4433-58-3,71884-72-5,107596-70-3,117020-71-0)

Guidance literature:

With B₂K agar medium; Panax ginseng C_. A_. Meyer cells; In various solvent(s); at 25 ℃; for 456h; Further byproducts given;

DOI:10.1016/0031-9422(96)00079-9

Reference yield: 17.9%

(+)-digitoxigenin (143-62-4) → digitoxigenin 3-O-β-D-glucoside (17059-16-4) + digitoxigenin β-D-sorphoroside + 3α,14-dihydroxy-5β,14β-card-20(22)-enolide (545-52-8) + periplogenin (514-39-6,4433-58-3,71884-72-5,107596-70-3,117020-71-0)

Guidance literature:

With B₂K agar medium; Panax ginseng C_. A_. Meyer cells; In various solvent(s); at 25 ℃; for 456h; Further byproducts given;

DOI:10.1016/0031-9422(96)00079-9

upstream raw materials:

neridiginoside

(+)-digitoxigenin

Sucrose

digitoxigenin

Downstream raw materials:

14-hydroxy-14β-carda-3,5,20(22)-trienolide

periplogenin glucoside